Title:
METHOD FOR PRODUCING NOVEL MELANOIDIN HAVING ANTIMICROBIAL ACTIVITY AND APPLICATION THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/068112
Kind Code:
A1
Abstract:
Provided are: a method for producing an antimicrobial composition, said method comprising heating a reducing sugar selected from xylose and ribose and an amino acid selected from phenylalanine and proline to produce a melanoidin and blending the melanoidin as an active ingredient; an antimicrobial composition that comprises a melanoidin produced from xylose or ribose and phenylalanine as reaction substrates and/or a melanoidin produced from xylose or ribose and proline as reaction substrates; etc.
Inventors:
KOSEKI SHIGENOBU (JP)
KITAOKA NAOKI (JP)
MATSUURA HIDEYUKI (JP)
KITAOKA NAOKI (JP)
MATSUURA HIDEYUKI (JP)
Application Number:
PCT/JP2022/037898
Publication Date:
April 27, 2023
Filing Date:
October 11, 2022
Export Citation:
Assignee:
UNIV HOKKAIDO NAT UNIV CORP (JP)
International Classes:
A01N61/00; A01N43/36; A01P1/00; A23L3/3526; A23L3/3544; A61K8/49; A61K31/40; A61P31/04; A61Q19/00; C07D207/327
Other References:
BADRAN AL‐SHIMAA, EL‐GOHARY NASSER M., IBRAHIM MAGDY A., HASHIEM SALSABEEL H.: "Reactivity of some 3‐substituted‐6,8‐dimethylchromones toward some nucleophilic reagents", JOURNAL OF HETEROCYCLIC CHEMISTRY, WILEY-BLACKWELL PUBLISHING, INC., US, vol. 57, no. 6, 1 June 2020 (2020-06-01), US , pages 2570 - 2585, XP093059327, ISSN: 0022-152X, DOI: 10.1002/jhet.3975
ALBRECHT, U. ; LALK, M. ; LANGER, P.: "Synthesis and structure-activity relationships of 2-vinylchroman-4-ones as potent antibiotic agents", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 13, no. 5, 1 March 2005 (2005-03-01), AMSTERDAM, NL, pages 1531 - 1536, XP027637720, ISSN: 0968-0896
CHANDRASEKHAR, M. V. ET AL.: " Studies on chromones.", ACTA CIENTIA INDICA., PRAGATI PRAKASHAN, MEERUT., IN, vol. 16c, no. 4, 1 January 1985 (1985-01-01), IN , pages 247 - 251, XP009545122, ISSN: 0253-7338
HÖGBERG THOMAS, VORA MEHBOOB, DRAKE STEVEN D., MITSCHER LESTER A., CHU DANIEL T. W.: "Structure--Activity Relationships among DNA-Gyrase Inhibitors. Synthesis and Antimicrobial Evaluation of Chromones and Coumarins Related to Oxolinic Acid.", ACTA CHEMICA SCANDINAVICA., MUNKSGAARD, COPENHAGEN., DK, vol. 38, no. 5, 1 February 1984 (1984-02-01), DK , pages 359 - 366, XP093059351, ISSN: 0904-213X, DOI: 10.3891/acta.chem.scand.38b-0359
SIMIZU TOSISADA, KAZUYOSHI SUZUKI, AKIRA DEGAWA: "Survival of Some Pathogenic and Food Poisoning Bacteria in Seasoning. 調味料中における数種病原および食中毒菌の生存期間について", JOURNAL OF THE JAPANESE SOCIETY FOR FOOD SCIENCE AND TECHNOLOGY, vol. 9, no. 5, 1 January 1962 (1962-01-01), pages 198 - 200, XP093059356
OHSHITA KATSUNORI: "On the Physiological Functions of Soy Sauce", JOURNAL OF THE BREWING SOCIETY OF JAPAN, vol. 85, no. 11, 1 January 1990 (1990-01-01), pages 762 - 770, XP093059359
ANONYMOUS: "Sequel: Detection method for sugars", SHIMADYU, 13 July 2016 (2016-07-13), XP093059305, Retrieved from the Internet [retrieved on 20230629]
ANONYMOUS: "Standards Tables of Food Consumption in Japan -2015- (Seventh Revised Edition) -Amino Acids-, 17 Seasonings and spices", MINISTRY OF EDUCATION, CULTURE, SPORTS, SCIENCE AND TECHNOLOGY, 1 December 2015 (2015-12-01), pages 212 - 219, XP093059278, Retrieved from the Internet [retrieved on 20230629]
NAKAJIMA, TOMOYOSHI: "Antimicrobial action of aminocarbonyl reaction products", SHOKUHIN NO HOSO - PACKAGING OF FOODSTUFF, HOSO SHOKUHIN GIJUTSU KYOKAI, NAGOYA, JP, vol. 20, no. 1, 1 January 1988 (1988-01-01), JP , pages 33 - 40, XP009545669, ISSN: 0285-4449
LINDGREN G, PERNEMALM P.A: " A high performance preparative procedure for the isolation of degradation products from D-xylose.", JOURNAL OF LIQUID CHROMATOGRAPHY, vol. 3, no. 11, 1 January 1980 (1980-01-01), pages 1737 - 1742, XP009545125
ANDEREGG, P.; NEUKOM, H. : "Formation of dehydration products from pentoses and purine ribosides by heating in buffer at pH2-7", LEBENSMITTEL-WISSENSCHAFT UND -TECHNOLOGIE, ACADEMIC PRESS, vol. 7, no. 4, 1 January 1974 (1974-01-01), pages 239 - 241, XP009545627, ISSN: 0460-1173
ALAVEZ-ROSAS DAVID; MALDONADO-DOMíNGUEZ MAURICIO; GONZáLEZ-ANTONIO OSCAR; ROMERO-ÁVILA MARGARITA; MéNDEZ-STIVA: "Synthesis of 1,3- and 1,2,3-functionalized pyrrolesviaIr(I)-catalyzed vinylation of allyl alcohols", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, SPRINGER US, NEW YORK, vol. 53, no. 5, 13 June 2017 (2017-06-13), New York , pages 526 - 531, XP036262337, ISSN: 0009-3122, DOI: 10.1007/s10593-017-2087-8
KOSEKI, SHIGENOBU: "Control foodborne bacteria with sugars and amino acids: Antibacterial activity of Maillard reactants generated during food processing", ANNUAL REPORT, THE TOJURO IIJIMA FOUNDATION FOR FOOD SCIENCE AND TECHNOLOGY, JAPAN, vol. 37, 1 August 2022 (2022-08-01), Japan, pages 120 - 128, XP009546680, ISSN: 2188-0662
ALBRECHT, U. ; LALK, M. ; LANGER, P.: "Synthesis and structure-activity relationships of 2-vinylchroman-4-ones as potent antibiotic agents", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 13, no. 5, 1 March 2005 (2005-03-01), AMSTERDAM, NL, pages 1531 - 1536, XP027637720, ISSN: 0968-0896
CHANDRASEKHAR, M. V. ET AL.: " Studies on chromones.", ACTA CIENTIA INDICA., PRAGATI PRAKASHAN, MEERUT., IN, vol. 16c, no. 4, 1 January 1985 (1985-01-01), IN , pages 247 - 251, XP009545122, ISSN: 0253-7338
HÖGBERG THOMAS, VORA MEHBOOB, DRAKE STEVEN D., MITSCHER LESTER A., CHU DANIEL T. W.: "Structure--Activity Relationships among DNA-Gyrase Inhibitors. Synthesis and Antimicrobial Evaluation of Chromones and Coumarins Related to Oxolinic Acid.", ACTA CHEMICA SCANDINAVICA., MUNKSGAARD, COPENHAGEN., DK, vol. 38, no. 5, 1 February 1984 (1984-02-01), DK , pages 359 - 366, XP093059351, ISSN: 0904-213X, DOI: 10.3891/acta.chem.scand.38b-0359
SIMIZU TOSISADA, KAZUYOSHI SUZUKI, AKIRA DEGAWA: "Survival of Some Pathogenic and Food Poisoning Bacteria in Seasoning. 調味料中における数種病原および食中毒菌の生存期間について", JOURNAL OF THE JAPANESE SOCIETY FOR FOOD SCIENCE AND TECHNOLOGY, vol. 9, no. 5, 1 January 1962 (1962-01-01), pages 198 - 200, XP093059356
OHSHITA KATSUNORI: "On the Physiological Functions of Soy Sauce", JOURNAL OF THE BREWING SOCIETY OF JAPAN, vol. 85, no. 11, 1 January 1990 (1990-01-01), pages 762 - 770, XP093059359
ANONYMOUS: "Sequel: Detection method for sugars", SHIMADYU, 13 July 2016 (2016-07-13), XP093059305, Retrieved from the Internet
ANONYMOUS: "Standards Tables of Food Consumption in Japan -2015- (Seventh Revised Edition) -Amino Acids-, 17 Seasonings and spices", MINISTRY OF EDUCATION, CULTURE, SPORTS, SCIENCE AND TECHNOLOGY, 1 December 2015 (2015-12-01), pages 212 - 219, XP093059278, Retrieved from the Internet
NAKAJIMA, TOMOYOSHI: "Antimicrobial action of aminocarbonyl reaction products", SHOKUHIN NO HOSO - PACKAGING OF FOODSTUFF, HOSO SHOKUHIN GIJUTSU KYOKAI, NAGOYA, JP, vol. 20, no. 1, 1 January 1988 (1988-01-01), JP , pages 33 - 40, XP009545669, ISSN: 0285-4449
LINDGREN G, PERNEMALM P.A: " A high performance preparative procedure for the isolation of degradation products from D-xylose.", JOURNAL OF LIQUID CHROMATOGRAPHY, vol. 3, no. 11, 1 January 1980 (1980-01-01), pages 1737 - 1742, XP009545125
ANDEREGG, P.; NEUKOM, H. : "Formation of dehydration products from pentoses and purine ribosides by heating in buffer at pH2-7", LEBENSMITTEL-WISSENSCHAFT UND -TECHNOLOGIE, ACADEMIC PRESS, vol. 7, no. 4, 1 January 1974 (1974-01-01), pages 239 - 241, XP009545627, ISSN: 0460-1173
ALAVEZ-ROSAS DAVID; MALDONADO-DOMíNGUEZ MAURICIO; GONZáLEZ-ANTONIO OSCAR; ROMERO-ÁVILA MARGARITA; MéNDEZ-STIVA: "Synthesis of 1,3- and 1,2,3-functionalized pyrrolesviaIr(I)-catalyzed vinylation of allyl alcohols", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, SPRINGER US, NEW YORK, vol. 53, no. 5, 13 June 2017 (2017-06-13), New York , pages 526 - 531, XP036262337, ISSN: 0009-3122, DOI: 10.1007/s10593-017-2087-8
KOSEKI, SHIGENOBU: "Control foodborne bacteria with sugars and amino acids: Antibacterial activity of Maillard reactants generated during food processing", ANNUAL REPORT, THE TOJURO IIJIMA FOUNDATION FOR FOOD SCIENCE AND TECHNOLOGY, JAPAN, vol. 37, 1 August 2022 (2022-08-01), Japan, pages 120 - 128, XP009546680, ISSN: 2188-0662
Attorney, Agent or Firm:
YAMAO, Norihito et al. (JP)
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