Title:
XANTHOHUMOL GLYCOSIDE, METHOD FOR PRODUCING XANTHOHUMOL GLYCOSIDE, AND METHOD FOR IMPROVING WATER SOLUBILITY OF XANTHOHUMOL
Document Type and Number:
WIPO Patent Application WO/2022/131129
Kind Code:
A1
Abstract:
A purpose of the present invention is to provide a xanthohumol glycoside in which a sugar chain constructed from two or more hexoses is bonded to xanthohumol and a method for producing the same, a xanthohumol glycoside in which one hexose is bonded to xanthohumol and a method for producing the same, a method for improving the water solubility of xanthohumol, a method for reducing the bitter taste of xanthohumol, and a method for improving the stability of xanthohumol, etc. The present invention relates to a xanthohumol glycoside in which a sugar chain constructed from 2-10 hexoses is bonded to the 4'-position or 4-position of xanthohumol.
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Inventors:
OCHIAI MISA (JP)
ONO EIICHIRO (JP)
ONO EIICHIRO (JP)
Application Number:
PCT/JP2021/045359
Publication Date:
June 23, 2022
Filing Date:
December 09, 2021
Export Citation:
Assignee:
SUNTORY HOLDINGS LTD (JP)
International Classes:
C12P19/18; A23L2/00; C07H15/203; C12N15/29; C12N15/54; C12P19/44
Domestic Patent References:
| WO2021131900A1 | 2021-07-01 |
Other References:
YILMAZER, M. ET AL.: "In vitro glucuronidation of xanthohumol, a flavonoid in hop and beer, by rat and human liver microsomes", FEBS LETT, vol. 491, 2001, pages 252 - 256, XP071241982, DOI: 10.1016/S0014-5793(01)02210-4
C HO, YOUNG-CHANG ET AL.: "Xanthohumol inhibits IL -12 production and reduces chronic allergic contact dermatitis", INT. IMMUNOPHARMACOL, vol. 10, 2010, pages 556 - 561, XP026996003
TRONINA, TOMASZ ET AL.: "The Influence of Glycosylation of Natural and Synthetic Prenylated Flavonoids on Binding to Human Serum Albumin and Inhibition of Cyclooxygenases COX-1 and COX-2", MOLECULES, vol. 22, no. 1230, 2017, pages 1 - 20, XP055945636
TRONINA, TOMASZ ET AL.: "Antioxidant and antiproliferative activity of glycosides obtained by biotransformation of xanthohumol", BIOORG. MED. CHEM. LETT, vol. 23, 2013, pages 1957 - 1960, XP028997325, DOI: 10.1016/j.bmcl.2013.02.031
YOSHIKAWA, SHINICHI ET AL.: "Transglycosylation of Mogroside V, a Triterpene Glycoside in Siraitia grosvenori, by Cyclodextrin Glucanotransferase and Improvement of the Qualities of Sweetness", J. APPL. GLYCOSCI, vol. 52, 2005, pages 247 - 252, XP055502085
TORRES, PAMELA ET AL.: "Enzymatic Synthesis of alpha-Glucosides of Resveratrol with Surfactant Activity", ADV. SYNTH. CATAL, vol. 353, 2011, pages 1077 - 1086, XP055230125, DOI: 10.1002/adsc.201000968
LI, SH A ET AL.: "Transglycosylation of stevioside to improve the edulcorant quality by lower substitution using cornstarch hydrolyzate and CGTase", FOOD CHEM, vol. 138, 2013, pages 2064 - 2069, XP055762566, DOI: 10.1016/j.foodchem.2012.10.124
NOGUCHI, AKIO ET AL.: "A UDP-Glucose:Isoflavone 7-O-Glucosyltransferase from the Roots of Soybean (Glycine max) Seedlings", J. BIOL. CHEM., vol. 282, no. 32, 2007, pages 23581 - 23590, XP055945637
OTA, AMI ET AL.: "3A34p05 Improving the solubility by glycosylation of xanthohumol using filamentous fungi", ANNUAL MEETING OF THE JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY AND AGROCHEMISTRY (JSBBA 2015), vol. 2015, 30 November 2014 (2014-11-30), pages 1065, XP009537783
C HO, YOUNG-CHANG ET AL.: "Xanthohumol inhibits IL -12 production and reduces chronic allergic contact dermatitis", INT. IMMUNOPHARMACOL, vol. 10, 2010, pages 556 - 561, XP026996003
TRONINA, TOMASZ ET AL.: "The Influence of Glycosylation of Natural and Synthetic Prenylated Flavonoids on Binding to Human Serum Albumin and Inhibition of Cyclooxygenases COX-1 and COX-2", MOLECULES, vol. 22, no. 1230, 2017, pages 1 - 20, XP055945636
TRONINA, TOMASZ ET AL.: "Antioxidant and antiproliferative activity of glycosides obtained by biotransformation of xanthohumol", BIOORG. MED. CHEM. LETT, vol. 23, 2013, pages 1957 - 1960, XP028997325, DOI: 10.1016/j.bmcl.2013.02.031
YOSHIKAWA, SHINICHI ET AL.: "Transglycosylation of Mogroside V, a Triterpene Glycoside in Siraitia grosvenori, by Cyclodextrin Glucanotransferase and Improvement of the Qualities of Sweetness", J. APPL. GLYCOSCI, vol. 52, 2005, pages 247 - 252, XP055502085
TORRES, PAMELA ET AL.: "Enzymatic Synthesis of alpha-Glucosides of Resveratrol with Surfactant Activity", ADV. SYNTH. CATAL, vol. 353, 2011, pages 1077 - 1086, XP055230125, DOI: 10.1002/adsc.201000968
LI, SH A ET AL.: "Transglycosylation of stevioside to improve the edulcorant quality by lower substitution using cornstarch hydrolyzate and CGTase", FOOD CHEM, vol. 138, 2013, pages 2064 - 2069, XP055762566, DOI: 10.1016/j.foodchem.2012.10.124
NOGUCHI, AKIO ET AL.: "A UDP-Glucose:Isoflavone 7-O-Glucosyltransferase from the Roots of Soybean (Glycine max) Seedlings", J. BIOL. CHEM., vol. 282, no. 32, 2007, pages 23581 - 23590, XP055945637
OTA, AMI ET AL.: "3A34p05 Improving the solubility by glycosylation of xanthohumol using filamentous fungi", ANNUAL MEETING OF THE JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY AND AGROCHEMISTRY (JSBBA 2015), vol. 2015, 30 November 2014 (2014-11-30), pages 1065, XP009537783
Attorney, Agent or Firm:
YASUTOMI & ASSOCIATES (JP)
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