Title:
CURCUMINOID GLYCOSIDE AND PROCESS FOR PRODUCING THE SAME
Document Type and Number:
WIPO Patent Application WO/2005/007667
Kind Code:
A1
Abstract:
[PROBLEMS] A novel curcuminoid glycoside; a pigment composition containing the glycoside; a medicinal composition for allergy treatments which contains the curcuminoid glycoside or the like; and an efficient process for producing various curcuminoid glycosides. [MEANS FOR SOLVING PROBLEMS] A curcuminoid glycoside represented by the formula (I) and a salt thereof (I) (wherein when R1 is methoxy, then R3 is methoxy or hydrogen, and when R1 is hydrogen, then R3 is hydrogen; R2 is hydrogen, a residue of a sugar, or a residue of an acetylated sugar; R4 is a residue of a sugar or a residue of an acetylated sugar; and R5 and R6 each is an oxygenic functional group or hydrogen); and a process for producing a curcuminoid glycoside which comprises reacting a benzaldehyde compound having a phenolic hydroxy group with an acetylacetone -B2O3 complex and subjecting the reaction product to deboronizing in the presence of an alcohol solvent.
Inventors:
ISOBE KIMIAKI (JP)
MOHRI KUNIHIKO (JP)
MOHRI KUNIHIKO (JP)
Application Number:
PCT/JP2004/010753
Publication Date:
January 27, 2005
Filing Date:
July 22, 2004
Export Citation:
Assignee:
ISOBE KIMIAKI (JP)
MOHRI KUNIHIKO (JP)
MOHRI KUNIHIKO (JP)
International Classes:
A23L1/275; A61K8/60; A61K31/7034; A61P37/08; A61P43/00; C07H15/203; (IPC1-7): C07H15/203; A61K31/7034; A61P37/08; A61P43/00
Domestic Patent References:
| WO2002002582A1 | 2002-01-10 |
Foreign References:
| EP1348418A1 | 2003-10-01 | |||
| EP1348424A1 | 2003-10-01 | |||
| JPH07206669A | 1995-08-08 | |||
| JP2000109496A | 2000-04-18 |
Other References:
PAN M-H ET AL: "Biotransformation of curcumin through reduction and glucuronidation in mice", DRUG METABOLISM AND DISPOSITION, vol. 27, no. 4, 1999, pages 486 - 494, XP001041393
KAMINAGA Y. ET AL: "Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus", FEBS LETTERS, vol. 55, no. 2, 2003, pages 311 - 316, XP004477117
MOHRI K. ET AL: "Synthesis of glycosylcurcuminoids", CHEM. AND PHARM. BULL., vol. 51, no. 11, 2003, pages 1268 - 1272, XP002977750
ROUGHLEY P.J. ET AL: "Experiments in the biosynthesis of curcumin", J OF THE CHEMICAL SOCIETY ERKIN TRANSACTIONS I, no. 20, 1973, pages 2379 - 2388, XP002977751
KAMINAGA Y. ET AL: "Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus", FEBS LETTERS, vol. 55, no. 2, 2003, pages 311 - 316, XP004477117
MOHRI K. ET AL: "Synthesis of glycosylcurcuminoids", CHEM. AND PHARM. BULL., vol. 51, no. 11, 2003, pages 1268 - 1272, XP002977750
ROUGHLEY P.J. ET AL: "Experiments in the biosynthesis of curcumin", J OF THE CHEMICAL SOCIETY ERKIN TRANSACTIONS I, no. 20, 1973, pages 2379 - 2388, XP002977751
Attorney, Agent or Firm:
Ishikawa, Toru (2nd Floor Fuji Bldg., 24-12, Kanumadai 2-chom, Sagamihara-shi Kanagawa 33, JP)
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