Title:
AQUEOUS SOLUTION CONTAINING STILBENE COMPOUND, AND SUPEROXIDE GENERATION INHIBITOR COMPRISING STILBENE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2021/261062
Kind Code:
A1
Abstract:
Provided is an aqueous solution having, dissolved therein, 0.3 to 200 mM of a stilbene compound (A) that is a compound represented by formula (1) or a glycoside thereof and 0.3 to 200 mM of a flavin derivative (B) selected from riboflavin, FMN and FAD. It is possible to provide an aqueous solution containing a stilbene compound at a high concentration. Also provided is a superoxide generation inhibitor which is catalyzed by a xanthine oxidase. In formula (1), R1, R2 and R3 independently represent a hydrogen atom or a methyl group, and X represents a hydrogen atom, a hydroxy group or a methoxy group.
Inventors:
MASUOKA NORIYOSHI (JP)
Application Number:
PCT/JP2021/015889
Publication Date:
December 30, 2021
Filing Date:
April 19, 2021
Export Citation:
Assignee:
MASUOKA NORIYOSHI (JP)
International Classes:
C07C39/21; C07C37/72; C07C43/23; C07D475/14; C07F9/6561; C07H19/207
Domestic Patent References:
| WO2019202508A1 | 2019-10-24 |
Foreign References:
| CN102652760A | 2012-09-05 | |||
| CN101669938A | 2010-03-17 | |||
| CN107212423A | 2017-09-29 | |||
| US9561175B1 | 2017-02-07 |
Other References:
SONG JUHEE, NAM GYU SEOL, MI-JA KIM, JAEHWAN LEE : "Riboflavin Phototransformation on the Changes of Antioxidant Capacities in Phenolic Compounds", JOURNAL OF FOOD SCIENCE, vol. 81, no. 8, 31 August 2016 (2016-08-31), pages C1914 - C1920, XP055883415, DOI: 10.1111/1750-3841.13392
ANONYMOUS: "Water-soluble wine yeast extract", TOWAKO MEDICAL COSMETIC, 6 May 2016 (2016-05-06), XP055883414, Retrieved from the Internet
DEHGHANI ALI; BAHLAKEH GHASEM; RAMEZANZADEH BAHRAM; RAMEZANZADEH MOHAMMAD: "A combined experimental and theoretical study of green corrosion inhibition of mild steel in HCl solution by aqueousCitrullus lanatusfruit (CLF) extract", JOURNAL OF MOLECULAR LIQUIDS, ELSEVIER, AMSTERDAM, NL, vol. 279, 1 January 1900 (1900-01-01), NL , pages 603 - 624, XP085616239, ISSN: 0167-7322, DOI: 10.1016/j.molliq.2019.02.010
WANG GUANG, MENGMENG ZHANG, QING ZHONG, ZHUOGUI LEI, HUI WU, FURAO LAI: "Protective effects of resveratrol against hypoxanthine-xanthine oxidase-induced toxicity on humanerythrocytes", JOURNAL OF FUNCTIONAL FOODS, vol. 23, 31 March 2016 (2016-03-31), pages 144 - 153, XP055883411, DOI: 10.1016/j.jff.2016.02.031
TANG XIAOSHENG, TANG PING, MA LEI, LIU LIANGLIANG: "Screening and Evaluation of Xanthine Oxidase Inhibitors from Gnetum parvifolium in China", MOLECULES, vol. 24, no. 14, 23 July 2019 (2019-07-23), XP055883408, DOI: 10.3390/molecules24142671
SCHMEDA-HIRSCHMANN G., M. I. GUTIKRREZ, J. I. LOYOLA, J. ZIRFIIGA: "Biological Activity and Xanthine Oxidase Inhibitors from Scirpus californicus (C.A. Mey.) Steud.", PHYSIOTHERAPY RESEARCH, JOHN WILEY & SONS LTD. CHICHESTER., GB, vol. 10, 31 December 1996 (1996-12-31), GB , pages 683 - 685, XP055883406, ISSN: 0951-418X, DOI: 10.1002/(SICI)1099-1573(199612)10:8<683::AID-PTR916>3.0.CO;2-T
QIN YAN HUA, ZHANG JIE, CUI JIANG TAO, GUO ZHI KAI, JIANG NAN, TAN REN XIANG, GE HUI MING: "Oligostilbenes from Vatica mangachapoi with xanthine oxidase and acetylcholinesterase inhibitory activities", RSC ADVANCES, vol. 1, no. 1, 1 January 2011 (2011-01-01), pages 135, XP055883402, DOI: 10.1039/c1ra00007a
ZHOU, C.X.; KONG, L.D.; YE, W.C.; CHENG, C.H.K.; TAN, R.X.: "Inhibition of xanthine and monoamine oxidases by stilbenoids from Veratrum taliense", MEDICINAL & AROMATIC PLANTS ABSTRACTS, SCIENTIFIC PUBLISHERS, SCIENTIFIC PUBLISHERS, NEW DELHI - INDIA, vol. 23, no. 6, 1 December 2001 (2001-12-01), Scientific Publishers, New Delhi - India , XP018012181, ISSN: 0250-4367
WU NAN, KONG YU, FU YUJIE, ZU YUANGANG, YANG ZHIWEI, YANG MEI, PENG XIAO, EFFERTH THOMAS: "In Vitro Antioxidant Properties, DNA Damage Protective Activity, and Xanthine Oxidase Inhibitory Effect of Cajaninstilbene Acid, a Stilbene Compound Derived from Pigeon Pea [ Cajanus cajan (L.) Millsp.] Leaves", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 59, no. 1, 12 January 2011 (2011-01-12), US , pages 437 - 443, XP055883394, ISSN: 0021-8561, ISBN: 978-4-86233-281-3, DOI: 10.1021/jf103970b
MALIK NEELAM, DHIMAN PRIYANKA, KHATKAR ANURAG: "In silico design and synthesis of targeted rutin derivatives as xanthine oxidase inhibitors", BMC CHEMISTRY, vol. 13, no. 1, 1 December 2019 (2019-12-01), XP055883393, DOI: 10.1186/s13065-019-0585-8
FUJITA TADASHI: "Formation and Removal of Reactive Oxygen Species, Lipid Peroxides and Free Radicals, and Their Biological EĊ ects", THE PHARMACEUTICAL SOCIETY OF JAPAN, vol. 122, no. 3, 31 March 2002 (2002-03-31), pages 203 - 218, XP055883390, DOI: 10.1248/yakushi.122.203
ANONYMOUS: "Water-soluble wine yeast extract", TOWAKO MEDICAL COSMETIC, 6 May 2016 (2016-05-06), XP055883414, Retrieved from the Internet
DEHGHANI ALI; BAHLAKEH GHASEM; RAMEZANZADEH BAHRAM; RAMEZANZADEH MOHAMMAD: "A combined experimental and theoretical study of green corrosion inhibition of mild steel in HCl solution by aqueousCitrullus lanatusfruit (CLF) extract", JOURNAL OF MOLECULAR LIQUIDS, ELSEVIER, AMSTERDAM, NL, vol. 279, 1 January 1900 (1900-01-01), NL , pages 603 - 624, XP085616239, ISSN: 0167-7322, DOI: 10.1016/j.molliq.2019.02.010
WANG GUANG, MENGMENG ZHANG, QING ZHONG, ZHUOGUI LEI, HUI WU, FURAO LAI: "Protective effects of resveratrol against hypoxanthine-xanthine oxidase-induced toxicity on humanerythrocytes", JOURNAL OF FUNCTIONAL FOODS, vol. 23, 31 March 2016 (2016-03-31), pages 144 - 153, XP055883411, DOI: 10.1016/j.jff.2016.02.031
TANG XIAOSHENG, TANG PING, MA LEI, LIU LIANGLIANG: "Screening and Evaluation of Xanthine Oxidase Inhibitors from Gnetum parvifolium in China", MOLECULES, vol. 24, no. 14, 23 July 2019 (2019-07-23), XP055883408, DOI: 10.3390/molecules24142671
SCHMEDA-HIRSCHMANN G., M. I. GUTIKRREZ, J. I. LOYOLA, J. ZIRFIIGA: "Biological Activity and Xanthine Oxidase Inhibitors from Scirpus californicus (C.A. Mey.) Steud.", PHYSIOTHERAPY RESEARCH, JOHN WILEY & SONS LTD. CHICHESTER., GB, vol. 10, 31 December 1996 (1996-12-31), GB , pages 683 - 685, XP055883406, ISSN: 0951-418X, DOI: 10.1002/(SICI)1099-1573(199612)10:8<683::AID-PTR916>3.0.CO;2-T
QIN YAN HUA, ZHANG JIE, CUI JIANG TAO, GUO ZHI KAI, JIANG NAN, TAN REN XIANG, GE HUI MING: "Oligostilbenes from Vatica mangachapoi with xanthine oxidase and acetylcholinesterase inhibitory activities", RSC ADVANCES, vol. 1, no. 1, 1 January 2011 (2011-01-01), pages 135, XP055883402, DOI: 10.1039/c1ra00007a
ZHOU, C.X.; KONG, L.D.; YE, W.C.; CHENG, C.H.K.; TAN, R.X.: "Inhibition of xanthine and monoamine oxidases by stilbenoids from Veratrum taliense", MEDICINAL & AROMATIC PLANTS ABSTRACTS, SCIENTIFIC PUBLISHERS, SCIENTIFIC PUBLISHERS, NEW DELHI - INDIA, vol. 23, no. 6, 1 December 2001 (2001-12-01), Scientific Publishers, New Delhi - India , XP018012181, ISSN: 0250-4367
WU NAN, KONG YU, FU YUJIE, ZU YUANGANG, YANG ZHIWEI, YANG MEI, PENG XIAO, EFFERTH THOMAS: "In Vitro Antioxidant Properties, DNA Damage Protective Activity, and Xanthine Oxidase Inhibitory Effect of Cajaninstilbene Acid, a Stilbene Compound Derived from Pigeon Pea [ Cajanus cajan (L.) Millsp.] Leaves", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 59, no. 1, 12 January 2011 (2011-01-12), US , pages 437 - 443, XP055883394, ISSN: 0021-8561, ISBN: 978-4-86233-281-3, DOI: 10.1021/jf103970b
MALIK NEELAM, DHIMAN PRIYANKA, KHATKAR ANURAG: "In silico design and synthesis of targeted rutin derivatives as xanthine oxidase inhibitors", BMC CHEMISTRY, vol. 13, no. 1, 1 December 2019 (2019-12-01), XP055883393, DOI: 10.1186/s13065-019-0585-8
FUJITA TADASHI: "Formation and Removal of Reactive Oxygen Species, Lipid Peroxides and Free Radicals, and Their Biological EĊ ects", THE PHARMACEUTICAL SOCIETY OF JAPAN, vol. 122, no. 3, 31 March 2002 (2002-03-31), pages 203 - 218, XP055883390, DOI: 10.1248/yakushi.122.203
Attorney, Agent or Firm:
SETOUCHI INTERNATIONAL PATENT FIRM (JP)
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