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Title:
ACYLATED SACCHARIDES AND PROCESS FOR PRODUCTION THEREOF
Document Type and Number:
WIPO Patent Application WO/2006/029453
Kind Code:
A1
Abstract:
A surface active material including an acylated saccharide, processes for the production thereof and uses thereof.

Inventors:
MAILVAGANAM PILLAI THAVALINGAM (MY)
Application Number:
PCT/AU2005/001392
Publication Date:
March 23, 2006
Filing Date:
September 13, 2005
Export Citation:
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Assignee:
IP ORGANISERS (AU)
MAILVAGANAM PILLAI THAVALINGAM (MY)
International Classes:
A61K31/7024; A61K31/722; A61P17/06; A61P17/10; A61P31/12; B01F17/06; B01F17/22; B01F17/56; C07H13/06; C07H5/06; C08B37/08; (IPC1-7): C07H5/06; A61K31/7024; A61K31/722; A61P17/06; A61P17/10; A61P31/12; B01F17/06; B01F17/22; B01F17/56; C07H13/06; C08B37/08
Domestic Patent References:
WO2004026912A12004-04-01
WO2002094224A12002-11-28
Foreign References:
EP0413307A11991-02-20
EP0507323B11997-01-29
US6197942B12001-03-06
Other References:
DATABASE MEDLINE [online] DUFES C ET AL: "Niosomes and polymeric chitosan based vesicles bearing transferrin and glucose ligands for drug targeting.", accession no. STN Database accession no. (2001129520)
DATABASE MEDLINE [online] YOSHIOKA H ET AL: "Chitosan-derived polymer-surfactants and their micellar properties.", accession no. STN Database accession no. (96068937)
DATABASE MEDLINE [online] LEE M Y ET AL: "Synthesis of chitosan-based polymeric surfactants and their adsorption properties for heavy metals and fatty acids.", accession no. STN Database accession no. (2005412922)
DATABASE CA [online] SHINOHARA S ET AL: "Development of water resistant O/W sun care products using polymer-surfactant derived chitosan.", accession no. STN Database accession no. (142:225092)
DATABASE CAPLUS [online] accession no. STN Database accession no. (138:289387)
DATABASE CA [online] accession no. STN Database accession no. (132:23483)
DATABASE CA [online] accession no. STN Database accession no. (131:273369)
DATABASE CA [online] accession no. STN Database accession no. (127:253221)
DATABASE CA [online] accession no. STN Database accession no. (114:99987)
DATABASE CA [online] accession no. STN Database accession no. (110:141226)
DATABASE WPI Week 200256, Derwent World Patents Index; AN 2005-522610
DATABASE WPI Week 199108, Derwent World Patents Index; AN 1991-054729
PATENT ABSTRACTS OF JAPAN vol. 013, no. 056
PATENT ABSTRACTS OF JAPAN vol. 1997, no. 11
PATENT ABSTRACTS OF JAPAN vol. 1997, no. 10
PATENT ABSTRACTS OF JAPAN vol. 014, no. 077
UCHEGBU I F ET AL: "Polymeric chitosan-based vesicles for drug delivery.", J PHARM PHARMACOL., vol. 50, no. 5, May 1998 (1998-05-01), pages 453 - 458
CERCHIARA T ET AL: "Physically cross-linked chitosan hydrogels as topical vehicles for hydrophilic drugs.", J PHARM PHARMACOL., vol. 54, no. 11, November 2002 (2002-11-01), pages 1453 - 1459
CHEN X G ET AL: "O/W emulsification for the self-aggregation and nanoparticle formation of linoleic acid-modified chitosan in the aqueous system.", J AGRIC FOOD CHEM., vol. 51, no. 10, 7 May 2003 (2003-05-07), pages 3135 - 3139
ODA K.: "Separation and characterization of adjuvant oligosaccharide oleate ester derived from product mixture of mannitol-oleic acid esterification.", VACCINE., vol. 22, no. 21-22, 29 July 2004 (2004-07-29), pages 2812 - 2821
Attorney, Agent or Firm:
PHILLIPS ORMONDE & FITZPATRICK (367 Collins Street Melbourne, Victoria 3000, AU)
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Claims:
Claims
1. A surface active material including an acylated saccharide.
2. A material according to claim 1 wherein the acylated saccharide is an acylated polysaccharide.
3. A material according to claim 2 wherein the polysaccharide is chitosan.
4. A material according to claim 3 wherein the chitosan is Nacylated.
5. A material according to any one of claims 1 to 4 wherein the material includes more than one acylated saccharide.
6. A material according to any one of claims 1 to 4 wherein the material includes a plurality of acylated saccharides.
7. A material according to claim 5 or 6 wherein each acylated saccharide is an acylated polysaccharide.
8. A material according to claim 7 wherein the polysaccharide is chitosan.
9. A material according to any one of the preceding claims wherein the acylated saccharide(s) include acyl components derived from fatty acids selected from the group consisting of capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and αlinoleic acid.
10. A material according to any one of the preceding claims wherein the saccharide is polyacylated.
11. A material according to claim 10 including at least one acyl group derived from a C8Cu fatty acid and at least one acyl group derived from a C12C15 fatty acid.
12. A material according to any one of the preceding claims wherein the acyl component material has the following free fatty acid profile upon GC MS analysis of the material: Fatty Acid Percentage of Acyl Component C6:0 0.0 to 0.3% C8:0 0.0 to 5.0% C10.0 0.0 to 5.0% C12:0 10.0 to 60% C14:0 5.0 to 20.0% C16:0 5.0 to 15.0% C18:0 0.0 to 4.0% C18:1 10.0 to 30.0% C18:2 0.0 to 25.0% C18:3 0.0 to 1.0% C20:0 0.0 to 1.0% C22:0 0.0 to 1.0%.
13. A material according to claim 12 wherein the acyl component of the material has one of the free fatty acid profiles provided in table 4 upon hydrolysis.
14. A method of producing a surface active material that includes an acylated saccharide, the method including: (a) providing a glyceride hydrolysate containing one or more free fatty acids or derivatives thereof, and (b) allowing the free fatty acids or derivatives thereof to react with a saccharide or a saccharide containing material.
15. A method according to claim 14 wherein the step of providing a glyceride hydrolysate includes at least partially hydrolysing a glyceride containing material to form free fatty acids or derivatives thereof.
16. A method according to claim 15 wherein the glyceride containing material is selected from the group consisting of fats and oils and mixtures thereof.
17. A method according to claim 15 or 16 wherein the glyceride containing material is selected from the group consisting of beef tallow, human butter fat, beef butter fat, canola oil, cocoa butter, cod liver oil, coconut oil, com oil, cotton seed oil, flax seed oil, grape seed oil, pork fat, linseed oil, olive oil, palm oil, palm kernel oil, peanut oil, safflower oil, sesame oil, soy bean oil, sunflower oil and mixtures thereof.
18. A method according to claim 15 wherein the glyceride containing material is palm oil.
19. A method according to any one of claims 15 to 18 wherein the hydrolysis is carried out in a solvent.
20. A method according to any one of claims 15 to 19 wherein the solvent is a hydroxylic organic solvent.
21. A method according to claim 19 or 20 wherein the solvent is tertiary butyl alcohol.
22. A method according to any one of claims 15 to 21 wherein the hydrolysis step includes addition of a lipolytic material to the glyceride containing material.
23. A method according to claim 22 wherein the lipolytic material is a lipase.
24. A method according to claim 23 wherein the lipase is derived from Candida antarctica or Thermomyces lanuginorus.
25. A method according to any one of claims 15 to 24 wherein the hydrolysis occurs in the presence of a base.
26. A method according to claim 25 wherein the base is sodium acetate.
27. A method according to any one of claims 15 to 26 wherein the hydrolysis is carried out at a temperature of 200C to 600C.
28. A method according to any one of claims 15 to 27 wherein the hydrolysis is carried out at a temperature of 3O0C to 500C.
29. A method according to claim any one of claims 15 to 28 wherein the hydrolysis is carried out at a temperature of 35°C to 44°C.
30. A method according to any one of claims 15 to 29 wherein the hydrolysis is carried out for a period of from 3 to 24 hours.
31. A method according to any one of claims 15 to 30 wherein the hydrolysis is carried out for a period of from 6 to 15 hours.
32. A method according to any one of claims 15 to 31 wherein the hydrolysis is carried out for a period of from 8 to 11 hours.
33. A method according to any one of claims 15 to 32 wherein the saccharide containing material includes more than one saccharide.
34. A method according to one of claims 15 to 32 wherein the saccharide is a polysaccharide.
35. A method according to one of claims 15 to 34 wherein the saccharide is chitosan.
36. A method according to any one of claims 15 to 35 wherein the hydrolysis is conducted in the presence of the saccharide or saccharide containing material.
37. A method according to any one of claims 15 to 35 wherein the saccharide or saccharide containing material is added after the completion of the hydrolysis.
38. A method of treatment or prevention of a biological condition of a subject the method including administration of an effective amount of a surface active material including an acylated saccharide.
39. A method according to claim 38 wherein the biological condition is caused by a living organism.
40. A method according to claim 38 or 39 wherein the biological condition is selected from the group consisting of a fungal infection, a scale infection, a bacterial infection, a viral infection and insect infestation.
41. A method according to claim 38 wherein the biological condition is a skin condition.
42. A method according to claim 41 wherein the skin condition is selected from the group consisting of acne, eczema, psoriasis and skin wrinkling.
43. A method according to claim 41 or 42 wherein the surface active material is applied topically to the skin.
44. A method according to any one of claims 41 to 43 wherein the surface active material is applied as a composition having a concentration of from 1 % to 2% by weight of surface active agent.
45. A method according to claim 38 wherein the condition is a bacterial or viral infection.
46. A method according to claim 45 wherein the condition is a viral infection.
47. A method according to claim 46 wherein the viral infection is HIVAIDS.
48. A method according to claim 38 wherein the subject is a fish and the condition is a bacterial or parasitic infection of the fish.
49. A method according to claim 48 wherein the condition is a protozoa infection.
50. A method according to claim 49 wherein the protozoa is Trichodina sp.
51. A method according to any one of claims 48 to 50 wherein the surface active agent is administered by contacting the fish with a composition containing the surface active agent.
52. A method according to claim 51 wherein the concentration of the surface active agent in the composition is greater than 2000 ppm.
53. A method according to claim 52 wherein the concentration is 4000 ppm.
54. A method according to any one of claims 51 to 53 wherein the fish is contacted with the composition for more than 30 seconds.
55. A method according to any one of claims 38 to 40 wherein the subject is a plant.
56. A method according to claim 55 wherein the biological condition is a fungal infection.
57. A method according to claim 56 wherein the fungal infection is selected from the group consisting of Powdery Mildew, Anthracnose, Plumier Rust, Fig Rust, Rice Blast Fungus and Black Spot.
58. A method according to claim 55 wherein the biological condition is a scale infection.
59. A method according to claim 58 wherein the scale infection is selected from the group consisting of Florida red Scale, False Oleander Scale, Soft Green Scale, Snot Scale, San Jose Scale and Torpedo Scale.
60. A method according to claim 55 wherein the biological condition is a bacterial infection.
61. A method according to claim 57 wherein the bacterial infection is Asiatic citrus Psyllid.
62. A method according to claim 55 wherein the biological condition is a viral infection.
63. A method according to claim 62 wherein the viral infection is Aphid Citrus Tristeza virus.
64. A method according to claim 55 wherein the biological condition is an insect infestation.
65. A method according to claim 64 wherein the insect is selected from the group consisting of Mealy bugs, Aphids, Leaf Hoppers, White Flies and Thrips.
66. A method according to any one of claims 55 to 65 wherein the administration includes applying a composition containing the surface active agent to the plant.
67. A method according to claim 66 wherein the concentration of surface active agent in the composition is from 0.001 % to 1 % by weight.
68. A method according to claim 66 wherein the concentration of surface active agent in the composition is from 0.005% to 0.04% by weight.
69. A method according to claim 66 wherein the concentration of surface active agent in the composition is 0.02%.
70. A method according to any one of claims 66 to 69 wherein the composition is applied at a rate of between 40 and 200 ml_ per square metre.
71. A method according to any one of claims 38 to 47 wherein the subject is a human.
72. A method according to any one of claims 38 to 47 wherein the subject is an animal selected from the group consisting of pigs, cattle, sheep, horses, goats, cats, dogs, chickens and ducks.
73. Use of a surface active material including an acylated saccharide in the preparation of a medicament for the treatment or prevention of a biological condition of a subject.
74. A use according to claim 73 wherein the biological condition is caused by a living organism.
75. A use according to. claim 73 or 74 wherein the biological condition is selected from the group consisting of a fungal infection, a scale infection, a bacterial infection, a viral infection and insect infestation.
76. A use according to claim 73 wherein the biological condition is a skin condition.
77. A use according to claim 76 wherein the skin condition is selected from the group consisting of acne, eczema, psoriasis and skin wrinkling.
78. A use according to claim 76 or 77 wherein the medicament is adapted to be applied topically to the skin.
79. A use according to claim 73 wherein the condition is a bacterial or viral infection.
80. A use according to claim 79 wherein the condition is a viral infection.
81. A use according to claim 80 wherein the viral infection is HIVAIDS.
82. A use according to any one of claims 73 to 81 wherein the subject is a human.
83. A use according to any one of claims 73 to 81 wherein the subject is an animal selected from the group consisting of pigs, cattle, sheep, horses, goats, cats, dogs, chickens and ducks.
84. A composition including a surface active agent including an acylated saccharide.
85. A method according to any one of claims 38 to 72, a use according to any one of claims 73 to 83 or a composition according to claim 84 wherein the acylated saccharide is an acylated polysaccharide.
86. A method, use or composition according to claim 85 wherein the polysaccharide is chitosan.
87. A method, use or composition according to claim 86 wherein the chitosan is Nacylated.
88. A method, use or composition according to any one of claims 85 to 87 wherein the material includes more than one acylated saccharide.
89. A method, use or composition according to any one of claims 85 to 87 wherein the material includes a plurality of acylated saccharides.
90. A method, use or composition according to claim 88 or 89 wherein each acylated saccharide is an acylated polysaccharide.
91. A method, use or composition according to claim 90 wherein the polysaccharide is chitosan.
92. A method, use or composition according to any one of claims 85 to 91 wherein the acylated saccharide(s) include acyl components derived from fatty acids selected from the group consisting of capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and αlinoleic acid.
93. A method, use or composition according to any one of claims 85 to 92 wherein the saccharide is polyacylated.
94. A method, use or composition according to claim 93 wherein the acylated saccharide includes at least one acyl group derived from a C8Ci4 fatty acid and at least one acyl group derived from a C12C15 fatty acid.
95. A method, use or composition according to any one of claims 85 to 94 wherein the acyl component of the material has the following free fatty acid profile upon GC MS analysis of the material: Fatty Acid Percentage of Acyl Component C6:0 0.0 to 0.3% C8:0 0.0 to 5.0% C10:0 0.0 to 5.0% C12:0 10.0 to 60% C14:0 5.0 to 20.0% C16:0 5.0 to 15.0% C18:0 0.0 to 4.0% C18:1 10.0 to 30.0% C18:2 0.0 to 25.0% C18:3 0.0 to 1.0% C20:0 0.0 to 1.0% C22:0 0.0 to 1.0%.
96. A method, use or composition according to claim 95 wherein the acyl component of the material has one of the free fatty acid profiles provided in table 4 upon hydrolysis.
Description:
ACYLATED SACCHARIDES AND PROCESS FOR PRODUCTION THEREOF FIELD OF THE INVENTION The present invention relates generally to a surface active material containing acylated saccharides and a process for production thereof. In particular the invention relates to a surface active material that contains one or more acylated saccharides, particularly one or more acylated polysaccharides. The saccharide may be a mono-, di-, tri- or polyacylated saccharide, or a mixture thereof. The acylation may occur, for example, on the OH groups of the saccharide to form esters. Alternatively, if the saccharide contains amino moieties the acylation may occur on the amino groups to form amide moieties. The acids used to form the acyl moiety of the acylated saccharide are organic acids, preferably fatty acids, more preferably long and medium chain fatty acids typically derived from animal or vegetable sources. The invention also provides a process for the manufacture of materials of this type. The process is such that the materials can be produced efficiently from readily available starting materials thus providing a relatively cheap source of these materials. These materials typically are surface active agents and find use in cosmetic and pharmaceutical applications. As such the invention also relates to methods of treatment of biological conditions utilising surface active materials containing acylated saccharides.

BACKGROUND OF THE INVENTION Non-ionic surface active agents are increasingly being used in a number of commercial applications such as in the pharmaceutical, cosmetic, food, textile and paint industries. As a class of surfactants the non-ionic surfactants have a number of physical properties in relation to their mode of action that make them useful in these applications. For example in contrast to their ionic counterparts, non-ionic surfactants do not disassociate into hydrated ions in aqueous media but rather maintain their structural integrity. Accordingly the surface active properties of non-ionic surfactants are provided by hydration of hydrophilic groups such as hydroxy, ether, amine or amide groups present in the surfactant. When a sufficiently large number of these hydrophilic constituents are present the level of hydration is such that a water solubility comparable to ionic surfactants is achieved through hydrogen bonding of the non-ionic surfactant to water molecules. The oil and water solubility of non-ionic surfactants therefore depends upon the relative proportions of the hydrophilic and hydrophobic building blocks present in the surfactant. In general surfactants will form micelles in solution with a diameter of from 4 to 7 nanometres. Typically, therefore the final properties of the surfactants can be controlled by controlling the balance between the hydrophilic and hydrophobic components and allows for significant tailoring of their properties to be carried out. The molecular structure of surfactants of this type means that they have unusual properties, leading to both widespread and highly specialised applications. The properties of surfactants fall into two broad categories, namely adsorption and self-assembly. Adsorption is the tendency for a surface molecule to collect at an interface. Self-assembly is the tendency for surfactant molecules to organise themselves into extended structures in water. This includes the formation of micelles, nanoparticles, bilayers and liquid crystals. These structures are formed when the hydrophobic tails of the surfactants cluster together, forming small aggregates such as micelles, or large layer structures (bilayers) which are similar to a cell wall. It is the similarity of a surfactant bilayer to a cell membrane that provides many of the biological properties of the surfactant. For example non-ionic surfactants can disrupt the cell membrane thus leading to cell death. Many of the beneficial properties of non-ionic surfactants can be controlled/predicted based on the components of the surfactant. Where the surfactant contains an ester or amide moiety the activity of the surfactant can in part be determined from the acid constituent of the ester or amide. For example lauric acid has been recognized for its unique properties in food use, which are related to its anti-viral, anti-bacterial and anti-protozoal functions. Lauric acid is a medium-chain fatty acid which has an additional beneficial function of being formed into moήolaurin in the human body. For example Palm Kernel oil and coconut fat are known to contain a high level of lauric acid and it is believed to be this that leads to the observation that natural coconut fat in the diet leads to a normalization of body lipids, protects against alcohol damage to the liver, and improves the immune system's anti-inflammatory response. Kaunitz and Dayrit (1992) have reviewed some of the epidemiological and experimental data regarding coconut-eating groups and noted that the "available population studies show that dietary coconut oil does not lead to high serum cholesterol nor to high coronary heart disease morality or morbidity". Monolaurin is the anti-viral, anti-bacterial and anti-protozoal monoglyceride used by the human body to destroy lipid-coated viruses such as HIV, herpes, cytomegalovirus, influenza, various pathogenic bacteria such as Listeria monocytogenes and Helicobacter pylori, and protozoa such as Giardia lamblia. On a more general level: in 1993 a group of searchers at Harvard University led by Professor Walter Willett, reported a positive relationship between the dietary intake of the trans fatty acids and coronary heart disease; in the 1920s, German researchers showed that mice on a fat-free diet were practically free of cancer. Since then, many studies have demonstrated a very close association between consumption of unsaturated oils and the incidence of cancer. Capric acid is another medium-chain fatty acid that has a similar beneficial function when it is formed into monocaprin in the human body. Monocaprin has also been shown to have anti-viral effects against HIV, and is currently being tested for its anti-viral effects against herpes simplex and its anti-bacterial effects against Chlamydia and other sexually transmitted bacteria. Recognition of the anti-viral aspects, in the anti-microbial activity of monoglycerides with respect to lauric acid (monolaurin), has been reported since 1966. Some of the viruses inactivated by these lipids, in additional to HIV, are the measles virus, herpes simplex virus-1 (HS-1), vesticular stomatitis (VSV), visna virus and cytomegalovirus (CMV). Many of the pathogenic microorganisms reported to be inactivated by these anti-microbial lipids are those known to be responsible for opportunistic infections in HIV-positive individual. For example, concurrent infection with cytomegalovirus is recognized as a serious complication for HIV-positive individuals. Kabara, and others have reported that certain fatty acids (FAs) (e.g., medium-chain saturates) and their derivatives (e.g., monoglycerides (MGs)) can have adverse effects on various microorganisms: those microorganisms that are inactivated include bacteria, yeast, fungi, and enveloped viruses. Additionally, it is reported that the anti-microbial effects of the FAs and MGs are additive, and total concentration is critical for inactivating viruses. The properties that determine the anti-infective action of lipids are related to their structure e.g., monoglycerides, free fatty adds. The monoglycerides are active; diglycerides and triglycerides are inactive. Of the saturated fatty acids, lauric acid has greater anti-viral activity than either caprylic acid (C6), capric acid (Cio), or myristic acid (Cu). In general, it is reported that the fatty acids and monoglycerides produce their killing/inactivating effect by lysing the plasma membrane lipid bi-layer. The anti-viral action attributed to monolaurin is that of solubilising the lipids and phospholipids in the envelope of the virus, causing the disintegration of the virus envelope. However, there is evidence from recent studies that one anti-microbial effect in bacteria is related to monolaurin's interference with signal transduction, and another anti-microbial effect in viruses is due to lauric acid's interference with virus assembly and viral maturation. As stated, recognition of the anti-viral aspects of the anti-microbial activity of the monoglyceride of lauric acid (monolaurin) has been reported since 1966. Some of the early work by that showed virucidal effects of monolaurin on enveloped RNA and DNA viruses was done in conjunction with the Center for Disease Control of the U.S. Public Health Service. These studies were done with selected virus prototypes or recognized representative strains of enveloped human viruses. The envelope of these viruses is a lipid membrane, and the presence of a lipid membrane on viruses makes them especially vulnerable to lauric acid and its derivative monolaurin. Without wishing to be bound by theory it was felt that the mode of action of these actives was by way of the surface active properties of these glycerides. As such it was felt by the present applicants that materials based on saccharides, especially polysaccharides that were acylated such that they incorporated at least one fatty acid moiety would show interesting properties due to their structural similarity to these molecules. The present applicants therefore expected that they would have surfactant properties that would be expected to mimic the behaviour of the known monoglycerides. Not only would these types of molecules therefore be expected to be surfactants per se there was also the potential that they would demonstrate a number of other interesting properties. In recent times therefore there has been a significant amount of research carried out on producing materials of this type due to their potential to display interesting properties. In particular there has been a focus on deriving these agents from natural materials such as carbohydrates. These materials are gaining increasing exposure as raw materials for surface active agents as they are generally readily available, relatively inexpensive and easy to source. For example saccharose, glucose, maltose, lactose and fructose are typical polyhydroxy compounds with high degrees of chemical purity which can be used as starting materials. In general these can be acylated by reaction with acid sources to produce the resultant acids or esters of the polyhydroxy compound. The production of esters or amides of this type is based on transacylation of fatty acids esters with a saccharide component. Unfortunately, however, the controlled introduction of only one longer chain fatty acyl group onto the polyvalent sugar molecule typically fails to be carried out controllably. In contrast reaction products typically are complex mixtures of unconverted starting materials together with mono-, di- and higher acylated sugars. There are a number of variables have been identified that help control the reaction. Accordingly it has been found that control of the ratio of polyhydroxy compound to fatty acid ester, control of reaction time and control of rate of solvent removal are all variables that can be used to affect the ratio of fatty acid mono-, di-, tri- and fatty acylated product. Unfortunately, it is hard to obtain pure mono acyl species by this route as they tend to disproportionate to form the polyhydroxy compound and the di-acylated moiety. Another method that has been used is comproportionation of a diester and saccharose. Comproportionation of diesters with saccharose typically results in monoesters, which still contained 10% diester. The solubility of sugar monoesters depends on the carbon chain length of the acyl groups. Monoesters of fatty adds length C8--I8 form gels with water. Naturally derived sugar esters therefore demonstrate a number of desirable properties. As discussed above, however, whilst there are therefore many uses for materials of this type there are a number of difficulties in producing materials such as surface active agents containing these materials. Several methods have been used in the production of materials of this type, however, many are not commercially desirable. For example in one of the methods known the reaction takes in excess of 24 hours. Accordingly it would be desirable to provide alternative methods of producing materials containing acylated saccharides. It would also be desirable to provide alternative acylated saccharides as these would be expected to have useful properties.

SUMMARY OF THE INVENTION After significant research the applicants have found that materials that contain one or more acylated saccharides can be produced efficiently and in high yield using readily available starting materials. These materials are generally environmentally friendly typically being non-toxic to humans and biodegradable. They are also typically useful as surface active agents. In a first aspect the invention provides a surface active material including an acylated saccharide. The saccharide is preferably mono-acylated, di- acylated, tri-acylated or polyacylated. In one preferred embodiment the saccharide is mono-acylated. In another preferred embodiment the saccharide is polyacylated. In embodiments where the material is polyacylated it is preferred in one embodiment that it includes at least one acyl group derived from a Cs-Ci4 fatty acid and at least one acyl group derived from a C12-Ci5 fatty acid. In another embodiment it is preferred that it includes at least one acyl group derived from a Cs-Ci2 fatty acid and at least one acyl group derived from a Ci2-Ci5 fatty acid. The acyl component is preferably derived from an acid, preferably an organic acid, more preferably a fatty acid, particularly a fatty acid derived from fats or oils or combinations thereof, especially animal or vegetable fats or oils. Preferably the fatty acid is selected from the group consisting of capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and α-linolenic acid. In one preferred embodiment of the material of the invention the acyl component is derived from animal fats or vegetable fats or mixtures thereof. In another preferred embodiment the acyl component is derived from animal or vegetable oils or mixtures thereof. In a particularly preferred embodiment the acyl component is derived from the group consisting of beef tallow, human butter fat, beef butter fat, canoia oil cocoa butter, cod liver oil, coconut oil, com oil, cotton seed oil, flax seed oil, grape seed oil, pork fat, linseed oil, olive oil, palm oil, palm kernel oil, rice bran oil, cereal oil, peanut oil, safflower oil, sesame oil, soy bean oil, sunflower oil and mixtures thereof. It is particularly preferred that the acyl component is derived from palm oil. Any suitable saccharide or saccharide containing material may be used as the saccharide component in the material of the invention. The saccharide may be a monosaccharide but is preferably a polysaccharide. Accordingly the acylated saccharide is preferably an acylated polysaccharide. The polysaccharide may be from any suitable source such as from vegetables, fibre from bran or cereals such as rice bran or oat bran, cereals, root crops, marine based animals or plants or from flowers. The polysaccharide can be a disaccharide (such as sucrose or maltose) a tri-saccharide, a tetra- saccharide, an oligosaccharide or a higher polysaccharide, or a mixture thereof. The saccharide preferably contains one or more amine groups such that upon acylation the material contains one or more amide moieties. An example of a polysaccharide that contains one or more amine groups is chitosan. Accordingly, in one preferred embodiment the polysaccharide or polysaccharide containing material is or includes chitosan. In a particularly preferred embodiment the chitosan is N-acylated. In another preferred embodiment the polysaccharide containing material includes rice husk. In one preferred embodiment the material includes more than one acylated saccharide. In a particularly preferred embodiment the material includes a plurality of acylated saccharides. In embodiments where there is more than one acylated saccharid it is preferred that each acylated saccharide is an acylated polysaccharide. In each of these embodiments it is preferred that the polysaccharide is chitosan. The properties of the surface active agent may be controlled by varying the fatty acid used in the acylation step. For example, in order to improve anti¬ microbial properties of the surface active agent it is preferred that the fatty acid chain length is C8-Ci4. Similarly, in order to achieve a high detergency or wetting properties it is preferred that a chain length of Ci2 to C15 is used. Accordingly depending on the application it is preferred that the material include more than one different acyl group. Thus one acyl group may contain a C8-Cu fatty acid whilst another may contain a C12-C15 fatty acid. In a preferred embodiment the acyl component of the material has the following free fatty acid profile upon GC MS analysis of the material: Fatty Acid Percentage of Acyl Component C6:0 0.0 to 0.3% C8:0 0.0 to 5.0% C10:0 0.0 to 5.0% C12:0 10.0 to 60% C14:0 5.0 to 20.0% C16:0 5.0 to 15.0% C18:0 0.0 to 4.0% C18:1 10.0 to 30.0% C18:2 0.0 to 25.0% C18:3 0.0 to 1.0% C20:0 0.0 to 1.0% C22:0 0.0 to 1.0%.

In a particularly preferred embodiment the acyl component of the material has one of the free fatty acid profiles provided in table 4 upon upon GC MS analysis of the material. The materials of the invention typically have anti-microbial or anti¬ parasitic activity. As such in a further aspect the invention provides an anti¬ microbial composition including a material including one or more acylated saccharides. The material used in the composition is preferably a material of the invention as discussed above. The properties of the material may also be improved by blending it with other ingredients. Thus for example it may be blended with a fragrance to improve the organoleptic properties. In a further preferred embodiment the material of the invention is blended with rice husks. The amount of rice husks blended well depend on the desired product but is preferably from 0.5 to 15wt.%, more preferably from 1.5 to 10wt.%, even more preferably 2 to 8 wt.%, most preferably 4 to 6 wt.% of the surface active agent. The rice husk preferably has been ground to a size of from 4-25 micron, more preferably from 6-21 micron, even more preferably 8-17 micron. By incorporating an amount of rice husk in this way it is found that the anti-microbial properties of the rice husk are incorporated into the material. Accordingly in a further aspect the present invention provides an anti¬ microbial composition including: (a) a material including one or more acylated saccharides, and (b) rice husk. The material is preferably one produced by the process of the invention as described herein. In a further aspect of the present invention there is provided a method of producing a surface active material that includes an acylated saccharide, the method including: (a) providing a glyceride hydrolysate containing one or more free fatty acids or derivatives thereof, and (b) allowing the free fatty acids or derivatives thereof to react with a saccharide or a saccharide containing material. In a preferred embodiment the step of providing a glyceride hydrolysate includes at least partially hydrolysing a glyceride containing material to form free fatty acids or derivatives thereof. The glyceride containing material can be of any suitable type, however, it is preferably selected from the group consisting of fats and oils or mixtures thereof. In one preferred embodiment the fats are selected from animal fats or vegetable fats or mixtures thereof. In another preferred embodiment the oils are selected from animal or vegetable oils or mixtures thereof. In a particularly preferred embodiment the glyceride containing material is selected from the group consisting of beef tallow, human butter fat, beef butter fat, canola oil cocoa butter, cod liver oil, coconut oil, corn oil, cotton seed oil, flax seed oil, grape seed oil, pork fat, linseed oil, olive oil, palm oil, palm kernel oil, peanut oil, safflower oil, sesame oil, soy bean oil, sunflower oil and mixtures thereof. A particularly preferred glyceride containing material is palm oil. Hydrolysis (hydrolysing) of the glyceride containing material to form free fatty acids or derivatives thereof may be conducted without a solvent but is typically conducted in a non-interfering solvent as this is found to increase the rate of hydrolysis. A preferred solvent is an organic solvent, preferably a hydroxylic organic solvent, even more preferably an organic alcohol, most preferably tertiary butyl alcohol. Hydrolysis of the glyceride containing material can occur in any way well known in the art. It is preferred, however, that hydrolysis is achieved by addition of a lipolytic material to the glyceride containing material, preferably in a non-interfering solvent Any lipolytic material can be chosen with the identify of the lipolytic material used being determined based on the glyceride containing material subjected to the process. A suitable lipolytic material is a lipase. A particularly suitable lipase is a lipase derived from Candida antarctica or Thermomyces lanuginorus. The hydrolysis can be carried out only partially or may be carried out to completion. Whilst either are found to be effective it is more commercially desirable for the hydrolysis of the glyceride containing material to be almost complete. The hydrolysis of the glyceride containing material preferably occurs in the presence of a base. A number of bases are suitable for this purpose, however, a preferred base is sodium acetate preferably anhydrous sodium acetate. If sodium acetate trihydrate is used it is preferably oven dried for a period of hours to remove excess moisture prior to use. For example it may be oven treated for approximately 4 hours to remove a majority of the water. The hydrolysis can occur at any suitable temperature. It is found, however, that control of temperature is useful in order to ensure that undesirable side reactions do not occur. For example some sensitive fats with conjugated bonds or fats with four or five double bonds (polyunsaturated fats) are susceptible to side reaction occurs. The hydrolysis of the glyceride containing material preferably occurs at a temperature in the range of 200C to 600C, more preferably from 300C to 50°C, even more preferably 35°C to 440C, most preferably about 38°C. The hydrolysis is typically carried out for a period of from 3 to 24 hours, more preferably from 6 to 15 hours, even more preferably for 8 to 11 hours, most preferably for about 8 hours. Any suitable saccharide or saccharide containing material can be used in the process of the invention. . In another preferred embodiment the saccharide containing material includes more than one saccharide. The saccharide is preferably a polysaccharide or a polysaccharide containing material. The polysaccharide can be a disaccharide (such as sucrose or maltose) a tri- saccharide, a tetra-saccharide, an oligosaccharide or a higher polysaccharide, or a mixture thereof. The saccharide preferably contains one or more amine groups such that upon reaction the amino groups of the saccharide are at least partially acylated to form one or more amide moieties In one preferred embodiment the saccharide containing material includes chitosan. In a particularly preferred embodiment the saccharide material is chitosan. In another preferred embodiment the saccharide containing material is rice husk. The steps of hydrolysing the glyceride containing material to from free fatty acids and reacting the free fatty acids with a saccharide or saccharide containing material can occur sequentially or simultaneously. Thus, for example, if desired one could partially hydrolyse glyceride containing material to form a fatty acid containing solution. The fatty acids could in theory be isolated from the solution or the solution then reacted further without purification. For example following the completion of hydrolysis the solution could then be contacted with a saccharide or saccharide containing material in order to allow the free fatty acids or derivatives thereof to react with free hydroxy groups (or amino groups if present) on the saccharide. If this was done it would generally be carried out by addition of the saccharide to the hydrolysed solution. In one embodiment the hydrolysis is conducted in the presence of the saccharide or saccharide containing material. In another embodiment the saccharide or saccharide containing material is added after the completion of the hydrolysis. It is found, however, that it is not desirable to carry out the process sequentially or to isolate the free fatty acids. The step of isolation of the free fatty acids is undesirable as this is difficult and quite expensive to achieve in a cost-effective manner. The difficulty with carrying out the steps sequentially is that as the concentration of free fatty acids and glycerol increases there is the tendency for the fatty acids to react with the free hydroxy groups on the glycerol thus leading to re-esterification of the glycerol and formation of the starting glyceride. This is clearly inefficient and should therefore be avoided if possible. Accordingly it is preferred that the steps are carried out simultaneously wherein the saccharide or saccharide containing material is present when the glyceride containing material is hydrolysed and the free fatty acids liberated. This ensures that as the free fatty acids are liberated they will have the tendency to acylate the saccharide rather than re-esterifying the glycerol. Accordingly in a further aspect there is provided a method of producing a material including one or more acylated saccharides, the method including partially hydrolysing a glyceride containing material to form free fatty acids and derivatives thereof in the presence of a saccharide or saccharide containing material. This ensures that as the free fatty acids are liberated in the hydrolysis reaction they are available for reaction with free hydroxy groups (or amino groups if present) on the saccharide or saccharide containing material. In this aspect of the invention it is preferred that all components of the reaction mixture except for the lipase are combined to form a relatively homogeneous mixture. The lipase is then typically added as the last additive to the reaction mixture. Alternatively, all components of the mixture except for the solvent can be combined with the solvent being added in the last step. It has been found that by use of the method of the present invention control of the properties of the material can be achieved by control of either the saccharide component or the free fatty acid profile of the glyceride component. The materials produced by the process of the invention have a number of interesting properties. As stated above the present applicant has found that fats and oils can be utilised in the preparation of a material containing one or more acylated saccharides. In yet a further aspect the present invention provides the use of a fat or oil in the preparation of a material that contains one or more acylated saccharides. In one preferred embodiment the fats are selected from animal fats or vegetable fats or mixtures thereof. In another preferred embodiment the oils are selected from animal or vegetable oils or mixtures thereof. In a particularly preferred embodiment the glyceride containing material is selected from the group consisting of beef tallow, human butter fat, beef butter fat, canola oil cocoa butter, cod liver oil, coconut oil, corn oil, cotton seed oil, flax seed oil, grape seed oil, pork fat, linseed oil, olive oil, palm oil, palm kernel oil, peanut oil, safflower oil, sesame oil, soy bean oil, sunflower oil and mixtures thereof. A particularly preferred glyceride containing material is palm oil. The present applicants have also found that chitosan or rice husks may be used in the preparation of a material containing one or more acylated saccharides. Accordingly, in yet a further aspect the present invention provides the use of chitosan or rice husks in the preparation of a material containing one or more acylated saccharides. As stated above the materials of the invention typically have anti- microbial activity. Accordingly in yet a further aspect the invention provides a method of controlling a population of micro-organisms, the method including contacting the population with an effective amount of a material including one or more acylated saccharides of the invention as described above. In one preferred embodiment the population is on a surface such as a bench top or the like and the method includes washing the surface with a composition including the material. In another preferred embodiment the micro-organism population has infected a host and the step of contacting includes administration of an effective amount of a composition including the material to the host. The materials of the invention may also be used in the prevention or treatment of a number of biological conditions in subjects. In yet a further aspect therefore the invention provides a method of treatment or prevention of a biological condition of a subject the method including administration of an effective amount of a surface active material according to the invention. It is found that the materials are particularly applicable to those conditions caused by living organisms and so in a preferred embodiment the biological condition is caused by a living organism. In one preferred embodiment the biological condition is selected from the group consisting of a fungal infection, a scale infection, a bacterial infection, a viral infection and an insect infestation. The materials may be used in the treatment of a wide range of biological conditions in a wide range of subjects. In one preferred embodiment the subject is a human. In another preferred embodiment the subject is an animal selected from the group consisting of fish, pigs, cattle, sheep, horses, goats, cats, dogs, chickens and ducks. In yet a further preferred embodiment the subject is a plant. The materials of the invention have also been found to be useful in the treatment of skin conditions. In one embodiment the biological condition is a skin condition. It is preferred that the skin condition is selected from the group consisting of acne, eczema, psoriasis and skin wrinkling. In the treatment of skin condition of this type it is preferred that the surface active material is applied topically to the skin. A particularly preferred mode of administration is one in which the surface active material is applied as a composition having a concentration of 1 % to 2% by weight of surface active agent. In another embodiment the condition is a bacterial or viral infection, preferably a viral infection. The material may be used against a number of viral infections but it is preferred that the viral infection is HIV-AIDS. In one preferred embodiment the subject is a fish. The material has been found to be applicable to the treatment of a number of conditions of fish but is particularly applicable to bacterial or parasitic infection of fish. In one embodiment the condition is a protozoa infection. A particularly preferred protozoa infection is one where the protozoa is Trichodina sp. The material may be administered in a number of ways well known in the art but it is preferred that the surface active material is administered by contacting the fish with a composition containing the surface active material. It is preferred that the concentration of the surface active material in the composition is greater than 2000 ppm, more preferably greater than 4000 ppm. In a particularly preferred embodiment the fish is contacted with the composition for more than 30 seconds. In another preferred embodiment the subject is a plant. In one preferred form of this embodiment the biological condition is a fungal infection. In this form of the invention the fungal infection is selected from the group consisting of Powdery Mildew, Anthracnose, Plumier Rust, Fig Rust, Rice Blast Fungus and Black Spot. In another preferred embodiment the biological condition is a scale infection. In a particularly preferred embodiment the scale infection is selected from the group consisting of Florida red Scale, False Oleander Scale, Soft Green Scale, Snot Scale, San Jose Scale and Torpedo Scale. In another preferred embodiment the biological condition is a bacterial infection. In this form of the invention it is preferred that the bacterial infection is Asiatic citrus Psyllid. In another preferred embodiment the biological condition is a viral infection. A preferred viral infection is Aphid Citrus Tristeza virus. In another embodiment the biological condition is an insect infestation. In this form of the invention it is preferred that the insect is selected from the group consisting of Mealy bugs, Aphids, Leaf Hoppers, White Flies and Thrips. When the subject is a plant administration preferably includes applying a composition containing the surface active agent to the plant. It is preferred that the concentration of surface active agent is less than 0.5 %, more preferably in the range 0.001% to 0.1%, most preferably in the range 0.005% to 0.04%. In order to achieve these low concentrations the material may be diluted at such low level at first instance or it may be provided as a dilute solution which is further diluted. For example it is preferred that it is provided as a 2% solution which is then diluted by factors of 1 :50 or 1 :400 to provide the desired end point dilutions. In general the concentration will depend upon the type of infestation and whether the treatment is to treat an infected plant or whether it is a preventative treatment. In general higher concentrations are required to treat infected plants. The following provides indicative dilutions (and the resultant concentrations for a variety of plant conditions. The table lists preferred concentrations for the treatment of infected species as well as maintenance treatments.

The composition may be applied at any suitable rate to achieve the desired effect however it is preferred that the composition is applied at a rate of between 40 and 200 ml_ per square metre. In yet a further aspect the invention provides the use of a surface active material of the invention in the preparation of a medicament for the treatment or prevention of a biological condition of a subject. In a preferred form the biological condition is caused by a living organism. In a particularly preferred form the biological condition is selected from the group consisting of a fungal infection, a scale infection, a bacterial infection, a viral infection and insect infestation. In another preferred form the biological condition is a skin condition. In a preferred form the skin condition is selected from the group consisting of acne, eczema, psoriasis and skin wrinkling. In particularly preferred form the medicament is adapted to be applied topically to the skin. In another preferred form the condition is a bacterial or viral infection, preferably a viral infection, most preferably HIV-AIDS. In a preferred form the subject is a human. In another preferred form the subject is an animal selected from the group consisting of fish, pigs, cattle, sheep, horses, goats, cats, dogs, chickens and ducks. In a final form of the invention provides a composition including a surface active material of the invention.

BRIEF DESCRIPTION OF THE FIGURES Figure 1(a) This figure shows a photograph of the surface active agent of example 1 dissolved in potable water at a concentration of 10mg/ml at a magnification of 100x under polarised light and shows a unilamellar vesicle Figure 1(b) This figure shows a photograph of the surface active agent of example 1 dissolved in potable water at a concentration of 10mg/ml at a magnification of 2Ox under polarised light with a dark field and shows a multilamellar vesicle Figure 1(c) This figure shows a photograph of the surface active agent of example 1 dissolved in potable water at a concentration of 10mg/ml at a magnification of 2Ox under polarised light d shows a multilamellar vesicle Figure 1(d) This figure shows a photograph of the surface active agent of example 1 dissolved in potable water at a concentration of 10mg/ml at a magnification of 2Ox under polarised light and shows a unilamellar vesicle Figure 1(e) This figure shows a photograph of the surface active agent of example 1 dissolved in potable water at a concentration of 10mg/ml at a magnification of 2Ox under polarised light and shows a multi-lamellar vesicle. DETAILED DESCRIPTION OF THE INVENTION Various terms that will be used throughout the specification have meanings that will be well understood by a skilled addressee. However, for ease of reference some of these terms will now be defined. As used herein reference to a percentage of a component in a reaction mixture or composition refers to the percentage by weight unless otherwise specified. Acylation - this is a chemical transformation which substitutes the acyl group (RCO-) into a moiety generally for an active hydrogen. Acylation of a hydroxy group forms an ester whereas acylation of an amino group forms an amide. A molecule that has been subjected to acylation is said to have been acylated. Biological Condition - A biological condition is any condition which may afflict a living organism. Examples of a biological condition include bacterial infection, fungal infection, scale infection, viral infection and insect infestations. Therapeutically effective amount or effective amount - this is an amount sufficient to effect beneficial or desired results. An effective amount can be administered in one or more administrations. An effective amount is typically sufficient to palliate, ameliorate, stabilize, reverse, slow or delay the progression of the condition. Fats - the fats are esters of fatty acids with glycerol having the general formula (R1COO)CH2-CH(OOCR2)CH2(OOCR3). In the formula R1, R2 and R3 may be the same fatty acid member but in general the fats are mixed glycerols with each residue being different. The fatty acids present in the greatest quantity are typically oleic, palmitic and stearic acids. The fats are generally seen as having a melting point of greater than 20° atmospheric pressure. Lipolytic material - A lipolytic material has the ability to hydrolyse fats into fatty acids and glycerol. A preferred example of a lipolytic material is a lipase. Oils - these are glycerides of fatty acids as described for fats but having a melting point of less than 20° atmospheric pressure. Vegetable oil - vegetable oils are oils obtained from leaves, fruit or seeds of plants. Animal oil - oils derived from animals. Fatty acids - monobasic acids containing only the elements carbon, hydrogen and oxygen and consisting of a straight chain organic radical attached to the carboxyl group. Fatty acids may be saturated, monounsaturated, or polyunsaturated depending on the number of carbon carbon double bonds in the organic radical. The saturated fatty acids have the general formula CnHbnOa with methanoic and ethanoic (acetic) acid being the lowest members of the series which includes palmitic and stearic acid. The oleic acid series with one double bond has the general formula CnH2π-2θ2 with the acrylic acid being the lowest member. The linoleic series has two double bonds and the general formula

The linolenic series has three double bonds and the general formula

CnH2n-6θ2. Fatty acids with more than three double bonds are general classed as polyunsaturated fatty acids. Examples of fatty acids are capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid and alpha linolenic acid. Micelles -A micelle is a cluster or group of associated molecules. The micelle may be represented as a globular cylindrical or ellipsoidal cluster of individual surfactant molecules in equilibrium with its monomers. Critical Micelle Concentration (CMC) - The corresponding surfactant concentration at this discontinuity corresponds to the critical micelle concentration. At surfactant concentrations below the CMC, the surfactant molecules are loosely integrated into the water structure. In the region of the CMC, the surfactant-water structure is changed in such a way that the surfactant molecules begin to build up their own structures (micelles in the interior and monolayers at the surf ace Saccharides - These are sugars and include monosaccharides, di- saccharides, tri-saccharides, oligosaccharides and polysaccharides. Polysaccharides - A polysaccharide is any molecule that can be hydrolysed to form more than one saccharide molecule. Surface Active Materials - These are materials which contain structurally dissimilar groups with opposing solubility tendencies such as water soluble and water insoluble groups. When dissolved in water or some other solvent these materials are adsorbed at the interface between the solution and a phase in contact with it (air, another liquid, soiled material) and modify its properties. Subject- A subject is any organism that can be treated using materials of the invention. In general a subject will be selected from the group consisting of humans, fish, pigs, cattle, sheep, horses, goats, cats, dogs, chickens and ducks. As discussed the present applicants have developed an improved technique for the production of a material that contains one or more acylated saccharides. This has allowed for the production of novel materials of this type.

Surface active materials of the invention The present invention relates in one embodiment to a surface active material including one or more acylated saccharides. The saccharide may be mono-acylated, di-acylated, tri-acylated or polyacylated with a mono-acylated saccharide being particularly preferred. The material preferably contains a plurality of different acylated saccharides, preferably at least two, more preferably at least three, most preferably at least four distinct acylated saccharides. For example this may be achieved by including a plurality of saccharide components in the synthesis of the material in which case there will be at least two (and possibly more) acylated saccharides present in the final material. More typically, however, a single saccharide is used and a plurality of acylated saccharides is produced by reacting the saccharide with a plurality of different acid sources. This is especially the case where the material is produced by the process of the present invention. The acyl component of the acylated saccharide is preferably derived from an organic acid, more preferably a fatty acid, particularly a fatty acid derived from fats or oils or combinations thereof. The fatty acid preferably has from 1 to 24 carbon atoms, more preferably from 4 to 20 carbon atoms, most preferably from 8 to 16 carbon atoms. The fatty acid preferably has 0 to 4 unsaturations, more preferably 0 to 2 unsaturations, most preferably 0 or 1 unsaturations. Preferably the fatty acid is selected from the group consisting of capric acid, caproic, caprylic, lauric acid, myristic acid, palmitic acid, stearin acid, oleic acid, linoleic acid, and α-linoleic acid. In one preferred embodiment of the invention the acyl component is derived from animal fats or vegetable fats or mixtures thereof. In another preferred embodiment the oils are selected from animal or vegetable oils or mixtures thereof. In a particularly preferred embodiment the acyl component is derived from the group consisting of beef tallow, human butter fat, beef butter fat, canola oil cocoa butter, cod liver oil, coconut oil, corn oil, cotton seed oil, flax seed oil, grape seed oil, pork fat, linseed oil, olive oil, palm oil, palm kernel oil, peanut oil, safflower oil, sesame oil, soy bean oil, sunflower oil and mixtures thereof. It is particularly preferred that the acyl component is derived from palm oil and/or coconut oil or a pure source of lauric acid, caproic acid, caprylic acid, or myristic acid. In the process of manufacture of materials of this type the acyl source is typically mixed to determine the fatty acid profile of the final material. A number of different acyl sources can be used in this way in order to arrive at a plurality of acylated saccharides in the final product. Any suitable saccharide or saccharide containing material may be used as the saccharide component of the material. Preferably the saccharide is a polysaccharide or polysaccharide containing material. The polysaccharide can be a disaccharide (such as sucrose or maltose) a tri-saccharide, a tetra- saccharide or a higher polysaccharide, or a mixture thereof. Examples of polysaccharides that may be used in the surface active agent of the invention include starches and their derivatives, cellulose and its derivatives, amino sugars and the like. It is preferred that the saccharide contains one or more amino groups. In one preferred embodiment the polysaccharide containing material includes chitosan. It is particularly preferred that the material is chitosan. In another preferred embodiment the polysaccharide containing material is rice husk. These materials may be used alone or may be used in combination with other polysaccharide sources. The properties of the material may be controlled by varying the fatty acid make-up of the ester. For example, in order to improve anti-microbial properties of the material it is preferred that the fatty acid chain length is C8-Ci4. Similarly, in order to achieve a high detergency or wetting properties it is preferred that a chain length of Ci2 to C15 is used. Accordingly depending on the application it is preferred that the material include more than one acylated saccharide. Thus one acylated saccharide may contain a C8-Ci4 fatty acid whilst another may contain a Ci2-Ci5 fatty acid. Accordingly by varying the fatty acid profile of the acylated saccharide one can produce either a material with high detergency or a material with antimicrobial properties, or a material that has both these properties. In a preferred embodiment the acyl component of the material has the following free fatty acid profile upon GC MS analysis of the material: Fatty Acid Percentage of Acyl Component C6:0 0.0% to 0.3% C8:0 0.0% to 5.0% C10:0 0.0% to 5.0% C12:0 10.0% to 60% C14:0 5.0% to 20.0% C16:0 5.0% to 15.0% C18:0 0.0% to 4.0% C18:1 10.0% to 30.0% C18:2 0.0% to 25.0% C18:3 0.0% to 1.0% C20:0 0.0% to 1.0% C22:0 0.0% to 1.0%.

In a particularly preferred embodiment the acyl component of the material has one of the free fatty acid profiles provided in table 4 upon upon GC MS analysis of the material. A skilled addressee would readily be able to adjust these in order to arrive at a material having the desired properties. The properties of the material may also be improved by blending it with other ingredients. Thus for example it may be blended with a fragrance to improve the organoleptic properties, colours to provide the desired colour and the like. In addition the material may be blended with vitamins such as vitamins A, D and E. In a further preferred embodiment the material of the invention is blended with rice husks. The amount of rice husks blended well depend on the final form of the desired product but is preferably from 0.5% to 15wt.%, more preferably from 1.5% to 10wt.%, even more preferably 2% to 8 wt.%, most preferably 4% to 6 wt.% of the surface active agent. The rice husk preferably has been ground to a size of from 4-25 micron, more preferably from 6-21 micron, even more preferably 8-17 micron. By incorporating an amount of rice husk in this way it is found that the anti-microbial properties of the rice husk are incorporated into the material and complement the activity of the material. Accordingly in a further aspect the present invention provides an anti¬ microbial composition including: (a) material including one or acylated saccharides, and (b) rice husk. The material is preferably one produced by the process of the invention although a number of other processes could be used. The material of the invention may be used in a number of applications such as a pharmaceutical (anti-microbial, anti-viral, anti-fungal, anti-parasitic), a detergent and an emulsifier.

Process of production of surface active materials of the invention The invention also provides a method of producing a surface active material that includes an acylated saccharide, the method including: (a) providing a glyceride hydrolysate containing one or more free fatty acids or derivatives thereof, and (b) allowing the free fatty acids or derivatives thereof to react with a saccharide or a saccharide containing material. The glyceride hydosylate may be pre-formed or it may be prepared by at least partially hydrolysing a glyceride containing material to form free fatty acids or derivatives thereof The glyceride containing material used in the process can be of any suitable type and the glyceride containing material is chosen based on a number of factors. These include cost, availability, and the free fatty acid profile desired in the final product. The glyceride containing material is preferably selected from the group consisting of fats and oils or mixtures thereof. In one preferred embodiment the fats are selected from animal fats or vegetable fats or mixtures thereof. In another preferred embodiment the oils are selected from animal or vegetable oils or mixtures thereof. Natural fats or oils of this type typically consist of glycerol esters of linear saturated or unsaturated fatty acids with an even number of carbon atoms. The chemical nature of the glycerine ester will depend upon the material but in general these can be separated into three groups: 1. Vegetable fats and oils which principally vary in the ratio of caproic, caprylic, lauric, myristic, oleic and linolenic acid ratios. 2. Animal fats and oils composed of primarily palmitic and oleic acids. 3. Vegetable oils with a high content of lauric and myristic acid. The full acid composition of common fats and oils is given in Table 1. As can be seen the fatty acid profile of common fats and oils varies greatly. As such the identity of the glyceride containing material can be chosen to introduce certain fatty acids into the final surface active agent. For example if one wishes to incorporate a high level of oleic acid into the material a good choice of glyceride containing material is canola oil. Approximately 62% of the fatty acids in canola oil is oleic acid and so if their oil is used it is likely that oleic acid will end up in the material. In contrast, if it is determined that lauric acid is a desired free fatty acid then coconut oil or palm kernel oil, both of which are high in this fatty acid, should be used. A skilled worker could use the information in Table 1 to readily determine the appropriate glyceride or combination thereof to introduce the desired free fatty acids into the material using the process of this invention. TABLE 1 Fatty Acid Composition of Some Common Edible Fats and Oils Percent of Total Fatt Acids K In a particularly preferred embodiment the glyceride containing material is selected from the group consisting of beef tallow, human butter fat, beef butter fat, canola oil, cocoa butter, cod liver oil, coconut oil, com oil, cotton seed oil, flax seed oil, grape seed oil, pork fat, linseed oil, olive oil, palm oil, palm kernel oil, peanut oil, safflower oil, sesame oil, soy bean oil, sunflower oil, and mixture thereof. A particularly preferred glyceride containing material is palm oil. These materials are useful sources of free fatty acids as they are relatively cheap and their fatty acid analysis on hydrolysis is reasonably well understood. In general all these glyceride containing materials are readily available and may be sourced commercially. The amount of glyceride containing material used will be determined on the basis of the amount of free fatty acid required to be generated for the saccharide or saccharide containing material to be used. In general it will be readily apparent to a skilled addressee how to determine the amount of glyceride containing material. In general, however, it is preferred that the glyceride containing material is employed in slight excess of that required to produce the mono-acylated of the saccharide. In a preferred embodiment the amount of glyceride containing material constitutes between 40% to 60% of the reaction mixture, more preferably 45% to 55%, even more preferably 48% to 52% of the reaction mixture. The glyceride material can be a single fat or oil or may be a mixture of fats and oils depending on the free fatty acid profile being introduced into the surface active agent. The step of partially hydrolysing the glyceride containing material to form free fatty acids is typically conducted in a non-interfering solvent. Any of a number of solvents can be used. In general a solvent will be considered a non- interfering solvent if it does not inhibit or participate in the hydrolysis/acylation processes. It is desirable, however, that the solvent is one in which the surface active agent, once formed is not soluble. This can be determined by trial and error in each instance. A preferred solvent is an organic solvent, preferably an alcohol such as ethanol, methanol, propanol or butanol, more preferably tertiary butyl alcohol. It is found that tertiary butyl alcohol is a particularly preferred solvent as it is miscible with most fats and oils but the surface active agents once formed are not soluble in it. An advantage of this is that the product can be isolated by filtration as discussed later. The amount of solvent (if used) will vary on a case by case basis. The amount of solvent is typically from 10% to 30% of the total reaction mixture, more preferably from 14% to 26%, most preferably from 17% to 19%. As such it is typical that the fat or oil is admixed with the solvent and agitated to form a homogeneous solution or mixture (depending on the solubility of the fat or oil in the solvent) before addition of the other ingredients. Alternatively all the solid ingredients are added to the reaction vessel followed by addition of the liquid ingredients. It is preferred that the solvent is one in which the fat(s) and/or oil(s) chosen are soluble. Hydrolysis of the glyceride containing material can occur in any way well known in the art for the hydrolysis of a glyceride to form a free fatty acid or derivative thereof. It is preferred, however, that hydrolysis is achieved by addition of a lipolytic material to a glyceride containing material in the solvent chosen. Any lipolytic material can be chosen with the identify of the lipolytic material being determined based on the glyceride containing material. As would be well known to a skilled addressee different lipolytic materials have different selectivities. Some lipolytic materials have broad spectrum activity and can be used with any glyceride containing material. Other lipolytic materials have quite high selectivity and are selective for certain fatty acids. The choice of lipolytic material will thus depend on the choice of glyceride containing material and the fatty acid to be acylated onto the saccharide. In general this will cause little difficulty as commercial lipase suppliers typically provide Free Fatty Acid Profiles for their lipase products which indicate their selectivity (if any). The lipolytic material used in the present invention may be any lipolytic material well known in the art. An example of a suitable lipolytic material are enzymes that may be synthetic or derived from animal, vegetable, bacterial or mould sources. A particularly suitable lipolytic material is lipases, particularly lipases of animal, vegetable, bacterial or moulds origin. For example any commercial lipase preparation containing predominantly lipase activity may be used. These may be used either in their crude form or may be used in partially or wholly purified form. The identity of the lipolytic material will typically vary with the identity of the glyceride containing material. A skilled worker will in general be able to determine a suitable lipolytic material for the glyceride chosen as discussed above. A particularly preferred lipase is a lipase derived from Candida Antarctica of Thermomyces lanuginorus. The amount of lipase used depend on a number of factors including the nature of the glyceride containing material, the concentration of the glyceride containing material in solution, the desired temperature of the lipolytic reaction, the concentration or activity of the lipase, and the pH of the reaction mixture. In general a skilled worked will easily be able to choose a suitable amount of lipase to achieve the desired result. Nevertheless the amount of lipase is typically of the order of 4% to 17%, more preferably 6% to 15%, even more preferably 8% to 13%, most preferably 8% to 11% of the reaction mixture. The hydrolysis of the glyceride containing material may be only partial or it may be carried out such that complete hydrolysis occurs. The hydrolysis is typically carried out such that the glyceride is at least 40% hydrolysed, even more preferably at least 60% hydrolysed, even more preferably at least 60% hydrolysed, more preferably 80% hydrolysed, even more preferably at least 90% hydrolysed. As would be clear to a skilled addressee a higher level of hydrolysis is preferred as this leads to a greater atom efficiency and thus higher yields of polysaccharide ester for the same amount of glyceride used. As such this is more commercially attractive. The level of hydrolysis may be followed using standard analytical techniques (such as HPLC, GLC etc.) or the process may be carried out for a sufficient time to ensure adequate hydrolysis. The process is preferably conducted in the presence of a base. The base may be an organic or an inorganic base. Examples of suitable inorganic bases include sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, calcium carbonate, and magnesium carbonate. Examples of suitable organic bases are sodium acetate and potassium acetate. The base is preferably sodium acetate. The amount of base is typically of the order of 10% to 30 wt.% based on the total reaction mixture, more preferably 8% to 20 wt.%, most preferably 10% to 13 wt.%. The process can be carried out at any suitable temperature. The temperature chosen will depend on a number of factors including the rate of reaction required, the amount of lipase, the type of lipase, the concentration of the reaction mixture and the like. It is found, however, that the temperature should be chosen to minimise side reactions occurring. For example it is found that many glyceride containing materials are sensitive to elevated temperature. Whilst not wishing to be bound by theory, it is felt that those glycerides that contain fatty acid chains with either conjugated double bonds or a large number of double bonds are susceptible to side reactions (such as oxidation). As such it is preferred that the temperature is from 200C to 600C, more preferably from 30°C to 50°C, even more preferably from 350C to 44°C, most preferably about 38°C. The process is typically carried out for a period of from 3 to 24 hours, more preferably from 6 to 15 hours, more preferably from 8 to 11 hours, most preferably for about 8 hours. Any suitable saccharide or saccharide containing material can be used although it is preferred that it is a polysaccharide or polysaccharide containing material. The polysaccharide can be a disaccharide (such as sucrose or maltose, a tri-saccharide, a tetra-saccharide or a polysaccharide derived from sago). Examples of polysaccharides that may be used in the surface active agent of the invention include starches and their derivatives, cellulose including derivatives, amino sugars and the like. Of course a mixture of difficult polysaccharides may also be employed. When this is done it ensures that the material includes a plurality of acylated polysaccharides as the polysaccharide components are different. The amount of the saccharide or saccharide containing material utilised is from 0.5% to 15 wt.%, more preferably from 1.5% to 10 wt.%, even more preferably from 2% to 8 wt.%, most preferably from 4% to 6 wt.%. It is preferred that the saccharide contains one or more amine groups. In one preferred embodiment the polysaccharide is chitosan. Chitosan is a polysaccharide material product that is derived from chitin and is available commercially. Any grade of chitosan may be used but it is found that the purer the chitosan the greater the purity of the final product. The polysaccharide is found in the exoskeleton of shellfish such as shrimp and crabs. The structure of chitosan is as follows:

In another preferred embodiment the polysaccharide containing material is rice husk. It is found that if the saccharide containing material is rice husk then the final product will have properties of the rice husk. Whilst the composition of rice husks typically vary it has the following general composition.

Chemical and Physical Composition rice husk Crude protein, % N x 6.25 1.9 - 3.0 Crude fat, % 0.3 - 0.8 Crude fiber, % 34.5 - 45.9 Available carbohydrates, % 26.5 - 29.8 Crude ash, % 13.2 - 21.0 Silica, % 18.8 - 22.3 Calcium, mg/g 0.6 - 1.3 Phosphorus, mg/g 0.3 - 0.7 Neutral detergent fiber, % 66 - 74 Acid detergent fiber, % 58-62 Lignin, % 9 - 20 Cellulose, % 28 - 36 Pentosans, % 21 - 22 Hemicelluloses, % 12 Total digestible nutrients, % 9.3 - 9.5 Table 2 Amino Acid Analysis in Rice Husk Amino Acid (%) Amino Acid (%) Aspartic acid 0.09 Tyrosine 0.86 Glutamic acid 0.42 Valine 0.35 Serine 0.23 Methionine (MET) 0.23 Glycine 0.60 Cystine (CYS. CYS) 0.03 Histidine 0.00 lsoleucine 0.07 Arginine 0.15 Leucine 0.33 Threonine 0.59 Phenylalanine 0.39 lanine 0.78 Tryptophan 0.06 Lysine 0.15

It is preferred that the saccharide is not sucrose. The step of hydrolysing the glyceride containing material to form free fatty acids and reacting the free fatty acids with the saccharide or saccharide containing material can occur sequentially or simultaneously. Thus, for example, if desired one could partially hydrolyse glyceride containing material to form a fatty acid containing solution. The fatty acids could in theory be isolated from the solution or the solution then reacted further. For example following the completion of hydrolysis the solution could then be contacted with a saccharide or saccharide containing material in order to allow the free fatty acids or derivatives thereof to react with free hydroxy groups (or amine groups if present) on the polysaccharide. It is found, however, that it is not desirable to carry out the process sequentially or to isolate the free fatty acids. The step of isolation of the free fatty acids is undesirable as this is difficult and quite expensive to achieve in a cost-effective manner. The difficulty with carrying out the steps sequentially is that as the concentration of free fatty acids and glycerol increases there is the tendency for the fatty acids to react with the free hydroxy groups on the glycerol thus leading to re-esterification of the glycerol and formation of the starting glyceride. This is clearly undesirable and should be avoided. As such whilst sequential steps are possible they are not preferred. Accordingly it is preferred that the steps are carried out simultaneously wherein the saccharide or saccharide containing material is present when the glyceridθ containing material is hydrolysed and the free fatty acids liberated. This ensures that as the free fatty acids are liberated they will have the tendency to esterify hydroxy groups from the polysaccharide rather than re- esterifying the glycerol. Accordingly in a further aspect there is provided a method of producing a material including one or more acylated saccharides, the method including partially hydrolysing a glyceride containing material to form free fatty acids and derivatives thereof in the presence of a saccharide or saccharide containing material. This ensures that as the free fatty acids are liberated in the hydrolysis reaction they are available for reaction with free hydroxy groups on the saccharide. The best way of achieving this is to admix all ingredients and add the lipase last once the other ingredients had been mixed. During the process of the invention it is preferred that the components are agitated rapidly to ensure adequate mixing of the components during reaction. If mixing is not sufficient the rate of reaction slows considerably. Upon completion of reaction the product can be isolated in a number of ways. It is typically found, however, that the product precipitates as it is produced and it can thus be isolated by filtration. In order to facilitate precipitation a solvent in which the product is not soluble such as t-butanol typically is added to produce a crude precipitate. This can then be isolated using techniques well known in the art. Following removal of the crude material by filtration the filtrate can be recycled. It is found that the filtrate will typically contain unreacted starting materials, lipase and solvent. This can be resubjected to the process of the invention, typically with addition of further substrate. It is found that it is preferable to dry the filtrate to remove any water before resubjecting it to the process. The crude precipitate typically has surface active properties and may be used as a surfactant. It may be partially purified by washing with a solvent in which the surface active agent is not soluble. For example it is found that washing of the crude with tertiary butanol will serve to remove any excess glyceride containing material from the product. If a higher level of purity is required the crude material may be further washed with TBA or any solvent. Increased purity can be achieved by adding the crude material to water followed by filtration to remove water insoluble impurities. It is found that the material is soluble in water whereas the other ingredients in the mixture are not. As such addition of the crude precipitate to water allows for the removal of these insoluble ingredients. A typical process would involve addition of approximately 10Og of crude to 5 litres of water, filtration of the solution leading to removal of the solids leading to a solution with a concentration of 4 g/L of the surface active agent.

Biological uses of the material of the invention As stated above the surface active materials of the invention typically have anti-microbial activity. Accordingly in yet a further aspect the invention provides a method of controlling a population of micro-organisms, the method including contacting the population with an effective amount of a material including one or more acylated saccharides of the invention as described above. In one preferred embodiment the population is on a surface such as a bench top or the like and the method includes washing the surface with a composition including the material. In another preferred embodiment the micro¬ organism population has infected a host and the step of contacting includes administration of an effective amount of a composition including the material to the host. The materials of the invention may also be used in the prevention or treatment of a number of biological conditions in subjects. In yet a further aspect the invention provides a method of treatment or prevention of a biological condition of a subject the method including administration of an effective amount of a surface active material according to the invention. It is found that the materials are particularly applicable to those conditions caused by living organisms and so in a preferred embodiment the biological condition is caused by a living organism. In one preferred embodiment the biological condition is selected from the group consisting of a fungal infection, a scale infection, a bacterial infection, a viral infection and an insect infestation. The materials may be used in the treatment of a wide range of biological conditions in a wide range of subjects. In one preferred embodiment the subject is a human. In another preferred embodiment the subject is an animal selected from the group consisting of fish, pigs, cattle, sheep, horses, goats, cats, dogs, chickens and ducks. In yet a further preferred embodiment the subject is a plant. The materials of the invention have also been found to be useful in the treatment of skin conditions. In one embodiment the biological condition is a skin condition. It is preferred that the skin condition is selected from the group consisting of acne, eczema, psoriasis and skin wrinkling. In the treatment of skin condition of this type it is preferred that the surface active material is applied topically to the skin. A particularly preferred mode of administration is one in which the surface active material is applied as a composition having a concentration of 2% by weight of surface active agent. In another embodiment the condition is a bacterial or viral infection, preferably a viral infection. The material may be used against a number of viral infections but it is preferred that the viral infection is HIV-AIDS. In using the materials of the invention they can be administered in any form or mode which makes the compound bioavailable. One skilled in the art of preparing formulations can readily select the proper form and mode of administration depending upon the particular characteristics of the compound selected, the condition to be treated, the stage of the condition to be treated and other relevant circumstances. We refer the reader to Remingtons Pharmaceutical Sciences, 18th edition, Mach Publishing Co. (1990) for further information. For example administration of materials of the invention to animal subjects such as to humans can be by any of the accepted modes for enteral administration such as oral or rectal, or by parenteral administration such as subcutaneous, intramuscular, intravenous and intradermal routes. Injection can be bolus or via constant or intermittent infusion or by topical application. The material is typically included in a pharmaceutically acceptable carrier or diluent and in an amount sufficient to deliver to the subject an effective dose. The materials of the present invention can be administered alone or in the form of a pharmaceutical composition in combination with a pharmaceutically acceptable carrier, diluent or excipient. The materials are, however, typically used in the form of pharmaceutical compositions which are formulated depending on the desired mode of administration. As such in a further embodiment the present invention provides a pharmaceutical composition including a material of the invention and a pharmaceutically acceptable carrier, diluent or excipient. The compositions are prepared in manners well known in the art. Pharmaceutical compositions of this invention for parenteral injection comprise pharmaceutically acceptable sterile aqueous or nonaqueous solutions, dispersions, suspensions or emulsions as well as sterile powders for reconstitution into sterile injectable solutions or dispersions just prior to use. Examples of suitable aqueous and nonaqueous carriers, diluents, solvents or vehicles include water, ethanol, polyols (such as glycerol, propylene glycol, polyethylene glycol, and the like), and suitable mixtures thereof, vegetable oils (such as olive oil), and injectable organic esters such as ethyl oleate. Proper fluidity can be maintained, for example, by the use of coating materials such as lecithin, by the maintenance of the required particle size in the case of dispersions, and by the use of surfactants. These compositions may also contain adjuvants such as preservative, wetting agents, emulsifying agents, and dispersing agents. Prevention of the action of microorganisms may be ensured by the inclusion of various antibacterial and antifungal agents, for example, paraben, chlorobutanol, phenol sorbic acid, and the like. It may also be desirable to include isotonic agents such as sugars, sodium chloride, and the like. Prolonged absorption of the injectable pharmaceutical form may be brought about by the inclusion of agents that delay absorption such as aluminium monostearate and gelatin. If desired, and for more effective distribution, the materials can be incorporated into slow release or targeted delivery systems such as polymer matrices, liposomes, and microspheres. The injectable formulations can be sterilized, for example, by filtration through a bacterial-retaining filter, or by incorporating sterilizing agents in the form of sterile solid compositions that can be dissolved or dispersed in sterile water or other sterile injectable medium just prior to use. Solid dosage forms for oral administration include capsules, tablets, pills, powders, and granules. In such solid dosage forms, the material is mixed with at least one inert, pharmaceutically acceptable excipient or carrier such as sodium citrate or dicalcium phosphate and/or a) fillers or extenders such as starches, lactose, sucrose, glucose, mannitol, and silicic acid, b) binders such as, for example, carboxymethylcellulose, alginates, gelatin, polyvinylpyrrolidone, sucrose, and acacia, c) humectants such as glycerol, d) disintegrating agents such as agar-agar, calcium carbonate, potato or tapioca starch, alginic acid, certain silicates, and sodium carbonate, e) solution retarding agents such as paraffin, f) absorption accelerators such as quaternary ammonium compounds, g) wetting agents such as, for example, cetyl alcohol and glycerol monostearate, h) absorbents such as kaolin and bentonite clay, and i) lubricants such as talc, calcium stearate, magnesium stearate, solid polyethylene glycols, sodium lauryl sulfate, and mixtures thereof. In the case of capsules, tablets and pills, the dosage form may also comprise buffering agents. Solid compositions of a similar type may also be employed as fillers in soft and hard-filled gelatin capsules using such excipients as lactose or milk sugar as well as high molecular weight polyethylene glycols and the like. The solid dosage forms of tablets, dragees, capsules, pills, and granules can be prepared with coatings and shells such as enteric coatings and other coatings well known in the pharmaceutical formulating art. They may optionally contain opacifying agents and can also be of a composition that they release the active ingredient(s) only, or preferentially, in a certain part of the intestinal tract, optionally, in a delayed manner. Examples of embedding compositions which can be used include polymeric substances and waxes. If desired, and for more effective distribution, the materials can be incorporated into slow release or targeted delivery systems such as polymer matrices, liposomes, and microspheres. The active materials can also be in microencapsulated form, if appropriate, with one or more of the above- mentioned excipients. Liquid dosage forms for oral administration include pharmaceutically acceptable emulsions, solutions, suspensions, syrups and elixirs. In addition to the active materials, the liquid dosage forms may contain inert diluents commonly used in the art such as, for example, water or other solvents, solubilizing agents and emulsifiers such as ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 ,3-butylene glycol, dimethyl formamide, oils (in particular, cottonseed, groundnut, corn, germ, olive, castor, and sesame oils), glycerol, 92

36 tetrahydrofurfuryl alcohol, polyethylene glycols and fatty acid esters of sorbitan, and mixtures thereof. Besides inert diluents, the oral compositions can also include adjuvants such as wetting agents, emulsifying and suspending agents, sweetening, flavoring, and perfuming agents. Suspensions, in addition to the active materials, may contain suspending agents as, for example, ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminium metahydroxide, bentonite, agar-agar, and tragacanth, and mixtures thereof. Compositions for rectal or vaginal administration are preferably suppositories which can be prepared by mixing the materials of this invention with suitable non-irritating excipients or carriers such as cocoa butter, polyethylene glycol or a suppository wax which are solid at room temperature but liquid at body temperature and therefore melt in the rectum or vaginal cavity and release the active compound. Dosage forms for topical administration of a material of this invention include powders, patches, sprays, ointments and inhalants. The active material is mixed under sterile conditions with a pharmaceutically acceptable carrier and any needed preservatives, buffers, or propellants which may be required. The amount of material administered will preferably treat and reduce or alleviate the condition. A therapeutically effective amount can be readily determined by an attending diagnostician by the use of conventional techniques and by observing results obtained under analogous circumstances. In determining the therapeutically effective amount a number of factors are to be considered including but not limited to, the species of animal, its size, age and general health, the specific condition involved, the severity of the condition, the response of the patient to treatment, the particular compound administered, the mode of administration, the bioavailability of the preparation administered, the dose regime selected, the use of other medications and other relevant circumstances. A preferred dosage will be a range from about 0.01 to 300 mg per kilogram of body weight per day. A more preferred dosage will be in the range from 0.1 to 100 mg per kilogram of body weight per day, more preferably from 0.2 to 80 mg per kilogram of body weight per day, even more preferably 0.2 to 50 mg per kilogram of body weight per day. A suitable dose can be administered in multiple sub-doses per day. In a further embodiment the invention provides the use of an acylated saccharide in the preparation of a medicament for the treatment of a skin condition in a patient. The skin condition is preferably a dermatological condition such as acne, eczema, psoriasis or skin wrinkling. In one preferred embodiment the subject is a fish. The material has been found to be applicable to the treatment of a number of conditions of fish but is particularly applicable to bacterial or parasitic infection of fish. In one embodiment the condition is a protozoa infection. A particularly preferred protozoa infection is one where the protozoa is Trichodina sp. The material may be administered in a number of ways well known in the art but it is preferred that the surface active material is administered by contacting the fish with a composition containing the surface active material. It is preferred that the concentration of the surface active material in the composition is greater than 2000 ppm, more preferably greater than 4000 ppm. In a particularly preferred embodiment the fish is contacted with the composition for more than 30 seconds. In use in these applications the material of the invention is formulated into a suitable form for administration to the fish either by preparing a composition which can be used in the form of a dip or as a concentrate that may be added to the water containing the fish such as an additive to a fish tank. Agricultural applications The materials of the invention may be used to treat a number of conditions of plants including bacterial infections, viral infections, fungal infections, scale infections and insect infestations. It may be used in the treatment of a wide variety of fungal infections but is found to be particularly suitable in the treatment of fungal infections selected from the group consisting of Powdery Mildew, Anthracnose, Plumier Rust, Fig Rust, Rice Blast Fungus and Black Spot. The materials of the invention may also be used in the treatment of scale infections such as Florida red Scale, False Oleander Scale, Soft Green Scale, Snot Scale, San Jose Scale and Torpedo Scale. Examples of bacterial infections that may be treated by the material include Asiatic citrus Psyllid. In another preferred embodiment the biological condition is a viral infection. A preferred viral infection is Aphid Citrus Tristeza virus. In another embodiment the biological condition is an insect infestation. In this form of the invention it is preferred that the insect is selected from the group consisting of Mealy bugs, Aphids, Leaf Hoppers, White Flies and Thrips. The material may be administered to the plant in any way well known in the art but it is preferably achieved by applying a composition containing the surface active material to the plant. It is preferred that the concentration of surface active agent in the less than 0.5 %, more preferably in the range 0.001 % to 0.1%, most preferably in the range 0.005% to 0.04%. In order to achieve these low concentrations the material may be diluted at such low level at first instance or it may be provided as a dilute solution which is further diluted. For example it is preferred that it is provided as a 2% solution which is then diluted by factors of 1 :50 or 1 :400 to provide the desired end point dilutions. In general the concentration will depend upon the type of infestation and whether the treatment is to treat an infected plant or whether it is a preventative treatment. In general higher concentrations are required to treat infected plants. The following table provides indicative dilutions (and the resultant concentrations for a variety of plant conditions. The table lists preferred concentrations for the treatment of infected species as well as maintenance treatments.

The composition may be applied at any suitable rate to achieve the desired effect however it is preferred that the composition is applied at a rate of between 40 and 200 mL per square metre. The composition may be formulated using techniques well known in the art and may contain other additives well known to be suitable in agricultural formulations of this type such as surfactants, stabilizers, preservatives, adjuvants, and trace elements merely by way of example. EXAMPLES The invention will now be described with reference to the following examples. EXAMPLE 1 - Procedure for Formation of Acylated Saccharide In a 1000 ml reaction vessel 202 ml of tert. Butyl alcohol was added to a mixture of palm oil (380 ml), sodium acetate tri-hydrate (85g), a polysaccharide containing material (24g) and a lipase (72g). The material was then heated at between 35-44°C and agitated for a period of 11 hours followed by filtration to produce the crude product. EXAMPLE 2 - Further Materials Produced Following the general procedure outlined in Example 1 but using different saccharides as starting materials a number of materials were produced and the results obtained shown in Table 3. TABLE 3

EXAMPLE 3 - Characterisation of Acylated Saccharides Two of the acylated saccharides produced using the procedures described above were subjected to analysis by gas chromatography to determine the free fatty acid profile of the materials. The two materials chosen were one produced using (1 ) Chitosan as the saccharide and Palm Kernel Oil as the acyl source, and a second produced using (2) Chitosan as the saccharide and a 1 :1 mixture of Palm Kernel oil (PKO) and Rice Bran Oil (RBO) as the acyl source. The free fatty acid analysis is as shown in Table 4.

TABLE 4

PKO - Palm kernel oil RBO - Rice Bran Oil EXAMPLE 4 Control of micro-organisms A 2 % solution of the surface active materials produced in example 1 were tested using standard procedures to determine their ability to kill the following organisms:

Escherichia CoIi (ATCC4157) Staphylococcus Aureus (ATCC 6538) Salmonella typhimurium (ATCC 14028) Aspergillus Niger (ATCC 16404)

It was found that in each instance a 2% solution of the surface active material of example 1 was sufficient to kill the organism.

EXAMPLE 5 ANTI-WRINKLE Four volunteers were taken to conduct the trial. Two Asians (Indian original), two English, all ladies ranging from 48 years to 68 years. All were told to massage a composition containing 2% of the material onto the skin once a day at night and wash the face next morning. The trial was conducted for forty days and results demonstrated a reduction in skin wrinkling. This trial therefore established that the material of the invention could be used to achieve a reduction in wrinkling of the skin in subjects prone to this condition.

EXAMPLE 6 - ACNE Four volunteers were taken into the trial, all of Indian origin, two males and two females, between 18 to 26 years. A concentration of 2% of the material of Example 1 is formulated with flower acids, nano-vitamins A, D- panthenol and E. All were told to use a cotton bud to apply the material. Each acne spot was damped with the solution. All application was done during night and washed the following morning. In each instance the acne cleared 14 days from the commencement of the trial.

EXAMPLE 7 - SKIN DISEASE - PSORIASIS Three adults all males, two Indian origin and one Malay, ages between 44 to 56 years. All were suffering this disorder for at least four to six years. A composition containing the material of example 1 at e concentration of 2% is formulated with flower acids, nano-vitamins A, D-panthenol and E. Every night the lesions were swabbed with the composition, then after the skin had dried the volunteers wore their clothes. After 7 days all patients registered that the itchiness had stopped, the adherent scales that were present had also reduced. During the course of treatment no other medication was used.

EXAMPLE 8 - SKIN DISEASE - PSORIASIS Following the general procedure outlined in example 7 a trial was conducted on 240 patients with psoriasis. The trial group was comprised of 192 males and 48 females ranging in age from 8 - 78 years. The trial group contained the following nationalities 99 - Indians, 75 - Chinese, 52 - Malays, 2 - Australians, 8 - Americans, 2 - Norwegians, 2 - Saudi Arabia. Following treatment recovery was observed with the recovery period being from 2 to 8 months depending upon the severity of the condition.

EXAMPLE 9 - anti-viral activity A sample of 15 patients all diagnosed with HIV Aids (Table 5) with ages ranging from 22 to 38 years, 5 males and 10 females were selected for trial. None of the patients had previously ever received anti-HIV treatment. The males averaged 58 k in weight (49 to 68 k) and the females, 54 k (39 to 65 k). Seven showed elevated liver enzymes (ALT and AST) and 12 had unexplained eosinophilia. Two patients had high serum cholesterol and one had elevated triglyceride. No one had renal dysfunction. Their viral load ranged from 1 ,960 to 1 ,190,000 except for one patient (#1244) whose load was too low to count (below 400). This fact unfortunately was not determined before the random assignment of the patients to the treatment group. Table 5 Results of all patients before treatment

The product used was fortified with Vitamins A, D and E and packed into 450 ml spray containers. The patients sprayed their body from the neck to the pubic region (Back and in-front of the body). The patients sprayed their body from the neck to the pubic region (Back and in-front of the body). The patients spayed the body once during the night. Each time of spray approximately 35-40 ml of the product is used. All patients were observed daily for any side effects. Baseline, 3-month and 6-month laboratory examinations included: viral load (by PCR method), CD4 and CD8 counts (by-flow-cytometric method), complete blood count, and tests for liver function (ALT, AST), renal function (urea N and creatinine), blood lipids (cholesterol, triglycerides, HDL) and body weight (k). Treatment benefit was defined as reduction in viral load and increase in CD4 count. Tables 6 summarizes the effects of the treatment group on the viral load, CD4 and CD8 counts. Table 6 Viral Count On the 3rd month, 7 showed decreased viral count. The other patients all had increased viral load. Patient #1244 continued to have undeterminable viral load and was excluded from the computation. On the 6th month, and end of the study. 8 of the 14 patients had decreased viral count, The CD4 and CD8 counts (Table z) increased only in 5 patients and did not quite correlate with the fall in viral load, decreasing even when the viral load fell and increasing when the viral load rose. Patient #1238 had a steady viral load during the first 3 months but suffered a severe secondary infection in the 5th and 6th month, which caused the HIV infection to worsen despite fairly good CD4/CD8 response. AIDS (CD4 less than 200) developed in 3 patients on the 3rd month. Eleven (11) patients gained weight - from I k to 23 k - including the 2 who developed AIDS and were recovering. The other 3 who failed to gain weight had decreasing viral and rising CD4 counts. About one-half of the patients in this study complained of feeling of warmth and a greenish hue to their urine, both occurred at the beginning of the study and did not interfere with its continuation. Another 3 patients had flaring up of their acne. There were 11 patients with eosinophilia at the start and 7 subjects with some liver dysfunction. The treatment caused a rise of the eosinophilia in 7 of the 11 , and a rise in ALT/AST in 3 of the 7. The patients with normal liver and kidney functions showed no effect from the treatments. At the beginning, 2 patients had elevated cholesterol and another one had high serum triglyceride. After 6 months, 4 patients had abnormal cholesterol and triglyceride, 3 had high cholesterol only and 2 had high triglyceride only. This trial confirmed that the material has an anti-viral effect and can beneficially reduce the viral load of HIV patients. Without wishing to be bound by theory it is felt that as this was applied as a topical spray the material in the form of a micelle was able to penetrate through the skin pores and get into the blood and lymphatic system to reach the target site. The patients were also studied to determine whether there was an effect on the cholesterol triglyceride levels of the patients. In general it was found that the levels did not show any significant appreciable changes as shown in table 7. Normal Values (Cholesterol) Choi ≤ 5.2 (Triglyceride) Tri < 2.0 (High Density Lipid) HDL < 1.4

Plant Treatments For the purposes of the plant treatment the concentration of material use in each example was determined upon the basis of a dilution of a 2% solution as shown in the following table unless otherwise specified. The final concentrations are also shown. As can readily be seen the concentration required for a treatment dose is typically twice the concentration used for a maintenance or preventative dose. In addition slightly different preferred dosages are used based upon the condition to be treated. All references in the examples to dilutions relate to dilutions of a 2% solution. Concentrations for application

EXAMPLE 10 - treatment of Aphid infection An aphid field test was conducted in which the material of the invention was compared with two comparable products, a carbonate and a pyrethroid. In each instance a plant was treated with one of the 3 products at the indicated dosage Actual counts of the number of live aphids were made at 1 , 4 and 7 days after treatment. With each treatment no live aphids were observed after 24 hours.

EXAMPLE 11 - Aphid treatment Tests were conducted on a number of plant species including ornamental plants, potted plants, green pepper, and cherry trees. The dilution of the material tested was 1 :500 (0.2%) and 1 :600 (0.16%). The material was applied to the plant infested with aphids. After the application of the material the number of aphids on each plant in the study was counted and after three days, the mortality observed was 98%.

EXAMPLE 12 - Scale Infection A test was conducted in which a plant infected with scale was treated with spraying with a composition containing 0.16% of the material of the invention. The treated plants were assessed on a daily basis and a 100% mortality rate was observed fro the scale after three days.

EXAMPLE 13 - Powdery Mildew A trial was conducted on melon, tomato and ornamental plants infected with powdery mildew. In each case the plant was sprayed with a composition containing the material of the invention at a dilution of 1 :400 (0.25%), 1 :500 (0.2%) or 1 :600 (0.16%). After application of the material the plants were observed for death of the powdery mildew. 98% of the infected areas were cleaned at 1 :400 and 1 :500 dilutions with 90% of the infected were cleaned at1 :600dilutions. After 15 days, no new infestations were occurred.

EXAMPLE 14 - Asiatic Citrus Psyllid A plant infected with Asiatic Citrus Psyllid (ACP) was treated with a composition containing the material of the invention. The plant was observed following the treatment and it was observed that the spread of ACP was stopped.

EXAMPLE 15 Rice Blast Fungus A trial was conducted which involved spraying a composition containing a 10 % concentration of the material of the invention on rice seedlings pre-and post-inoculation with rice Blast Fungus. It was observed that those plants that had been treated with the material of the invention showed sharply reduced incidence of the blast disease symptoms under growth chamber conditions, with no negative impact on healthy plants observed.

EXAMPLE 16 Rice Blast Fungus - in vitro A number of in-vitro tests on Rice Blast fungi were carried out in which an inocculum of Rice Blast fungus Petri dish were contacted with varying concentrations of compositions containing the material of the invention. It was observed that a 100% kill of the fungus was detected at a dilution of 300:1.

EXAMPLE 17 - Whitefly A trial was conducted in which the material of the invention was applied by spraying as a 1 :200 composition to tomatoes, peppers, potatoes and in order to control whitefly infestation. The observed results indicate a significant lowering of the whitefly infestation in the treated plants when compared to the control plants. EXAMPLE 18 - Tomato Leaf curl Virus A trial was conducted on field tomatoes susceptible to tomato leaf curl virus, the test was conducted using a composition containing the material of the invention and six different chemical based Admire products (produced by Bayer). Following application of the material the plants were assessed for the presence of symptoms of TYLCV. Six percent (6%) of the plants treated with the material of the invention showed symptoms of TYLCV (tomato yellow leaf curl virus), compared with 6.0%, 6.8%, 6.8%, 8.8%, 10.7% and 12.4% for the Admire products.

EXAMPLE 19 - fish diseases A trial was conducted in which Sea bass fingerlings (5-6 cm) infected with protozoa (Trichodina sp) were treated with a composition containing the material of the invention using either a dipping technique or a bath technique.

The trial groups were: (a). 5 fish/control group (b). 5 fish dip in 4000ppm /1 min (c). 5 fish dip in 4000ppm/5mins (d). 5 fish short bath in 4000ppm/1 hr (e). 5 fish long bath in 4000ppm/96 hrs

Following addition of the fingerlings were studied to determine survival rates. The survival rates were Group Survival rate (a). 5 fish/control group 40% (b). 5 fish dip in 4000ppm /1 min 80% (c). 5 fish dip in 4000ppm/5mins 60% (d). 5 fish short bath in 4000ppm/1 hr 60% (e). 5 fish long bath in 4000ppm/96 hrs 80%.

Diseased fish exposed to dip and long bath showed a better survival rate (60 - 80%) compare to diseased fish which were not exposed to Bio- surfactant(40%). Under Bio-surfactant group, the highest survival rate was 80% for the dip bath (1 min) and long bath (96hrs) followed by 60% in dip bath (5 mins) and short bath (1 hr) respectively.

Finally, it is to be understood that various alterations, modifications and/or additions may be introduced into the constructions and arrangements of parts previously described without departing from the spirit or ambit of the invention.