Glycycoumarin (BioDeep_00000017591)

 

Secondary id: BioDeep_00000270265

human metabolite PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


3-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9CI

化学式: C21H20O6 (368.125982)
中文名称: 甘草香豆素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 2.65%

分子结构信息

SMILES: C1(O)=CC2OC(=O)C(C3C(O)=CC(O)=CC=3)=CC=2C(OC)=C1C/C=C(\C)/C
InChI: InChI=1S/C21H20O6/c1-11(2)4-6-14-18(24)10-19-16(20(14)26-3)9-15(21(25)27-19)13-7-5-12(22)8-17(13)23/h4-5,7-10,22-24H,6H2,1-3H3

描述信息

Glycycoumarin is a member of the class of coumarins that is coumarin substituted by a hydroxy group at position 7, a methoxy group at position 5, a prenyl group at position 6 and a 2,4-dihydroxyphenyl group at position 3. Isolated from Glycyrrhiza uralensis, it exhibits antispasmodic activity. It has a role as an antispasmodic drug and a plant metabolite. It is a member of coumarins, an aromatic ether and a member of resorcinols.
Glycycoumarin is a natural product found in Glycyrrhiza glabra, Glycyrrhiza uralensis, and other organisms with data available.
See also: Glycyrrhiza uralensis Root (part of).
A member of the class of coumarins that is coumarin substituted by a hydroxy group at position 7, a methoxy group at position 5, a prenyl group at position 6 and a 2,4-dihydroxyphenyl group at position 3. Isolated from Glycyrrhiza uralensis, it exhibits antispasmodic activity.
Glycycoumarin is found in root vegetables. Glycycoumarin is from licorice (Glycyrrhiza glabra
From licorice (Glycyrrhiza glabra). Glycycoumarin is found in root vegetables.
Glycycoumarin is a potent antispasmodic agent. Glycycoumarin is a major bioactive coumarin of licorice and exhibits antispasmodic activity. Glycycoumarin also has hepatoprotective effect. Glycycoumarin can be used for the research of abdominal pain and liver diseases[1][2].
Glycycoumarin is a potent antispasmodic agent. Glycycoumarin is a major bioactive coumarin of licorice and exhibits antispasmodic activity. Glycycoumarin also has hepatoprotective effect. Glycycoumarin can be used for the research of abdominal pain and liver diseases[1][2].
Glycycoumarin is a potent antispasmodic agent. Glycycoumarin is a major bioactive coumarin of licorice and exhibits antispasmodic activity. Glycycoumarin also has hepatoprotective effect. Glycycoumarin can be used for the research of abdominal pain and liver diseases[1][2].

同义名列表

12 个代谢物同义名

3-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9CI; 2H-1-BENZOPYRAN-2-ONE, 3-(2,4-DIHYDROXYPHENYL)-7-HYDROXY-5-METHOXY-6-(3-METHYL-2-BUTEN-1-YL)-; 3-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-2-one; 2H-1-Benzopyran-2-one,3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)-; 3-(2,4-Dihydroxy-phenyl)-7-hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-2-one; 3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one; 3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)chromen-2-one; Glycocoumarin - Glycyrrhiza uralensis (liquorice); Flavone base + 3O, 1MeO, 1Prenyl; UNII-CWQ2B8G346; Glycycoumarin; CWQ2B8G346



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Yi Kuang, Yue Chai, Lulu Xu, Zilong Wang, Lei Liang, Xue Qiao, Min Ye. Glabrone as a specific UGT1A9 probe substrate and its application in discovering the inhibitor glycycoumarin. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2021 Jun; 161(?):105786. doi: 10.1016/j.ejps.2021.105786. [PMID: 33684484]
  • Enxiang Zhang, Shutao Yin, Chong Zhao, Lihong Fan, Hongbo Hu. Involvement of activation of PLIN5-Sirt1 axis in protective effect of glycycoumarin on hepatic lipotoxicity. Biochemical and biophysical research communications. 2020 07; 528(1):7-13. doi: 10.1016/j.bbrc.2020.05.072. [PMID: 32448510]
  • Enxiang Zhang, Shutao Yin, Shuang Zhao, Chong Zhao, Mingzhu Yan, Lihong Fan, Hongbo Hu. Protective effects of glycycoumarin on liver diseases. Phytotherapy research : PTR. 2020 Jun; 34(6):1191-1197. doi: 10.1002/ptr.6598. [PMID: 31840883]
  • Jing-Ran Fan, Yi Kuang, Ze-Yuan Dong, Yang Yi, Yan-Xia Zhou, Bin Li, Xue Qiao, Min Ye. Prenylated Phenolic Compounds from the Aerial Parts of Glycyrrhiza uralensis as PTP1B and α-Glucosidase Inhibitors. Journal of natural products. 2020 04; 83(4):814-824. doi: 10.1021/acs.jnatprod.9b00262. [PMID: 32196343]
  • Enxiang Zhang, Shutao Yin, Xiaotong Lu, Linhu Ye, Lihong Fan, Hongbo Hu. Glycycoumarin Sensitizes Liver Cancer Cells to ABT-737 by Targeting De Novo Lipogenesis and TOPK-Survivin Axis. Nutrients. 2018 Mar; 10(3):. doi: 10.3390/nu10030353. [PMID: 29543705]
  • Yi Kuang, Bin Li, Jingran Fan, Xue Qiao, Min Ye. Antitussive and expectorant activities of licorice and its major compounds. Bioorganic & medicinal chemistry. 2018 01; 26(1):278-284. doi: 10.1016/j.bmc.2017.11.046. [PMID: 29224994]
  • Takashi Matsui, Subehan Lallo, Khoirun Nisa, Hiroyuki Morita. Filamenting temperature-sensitive mutant Z inhibitors from Glycyrrhiza glabra and their inhibitory mode of action. Bioorganic & medicinal chemistry letters. 2017 03; 27(6):1420-1424. doi: 10.1016/j.bmcl.2017.01.095. [PMID: 28196701]
  • Enxiang Zhang, Shutao Yin, Xinhua Song, Lihong Fan, Hongbo Hu. Glycycoumarin inhibits hepatocyte lipoapoptosis through activation of autophagy and inhibition of ER stress/GSK-3-mediated mitochondrial pathway. Scientific reports. 2016 11; 6(?):38138. doi: 10.1038/srep38138. [PMID: 27901086]
  • Shuai Ji, Ziwei Li, Wei Song, Yongrui Wang, Wenfei Liang, Kai Li, Shunan Tang, Qi Wang, Xue Qiao, Demin Zhou, Siwang Yu, Min Ye. Bioactive Constituents of Glycyrrhiza uralensis (Licorice): Discovery of the Effective Components of a Traditional Herbal Medicine. Journal of natural products. 2016 Feb; 79(2):281-92. doi: 10.1021/acs.jnatprod.5b00877. [PMID: 26841168]
  • Xinhua Song, Shutao Yin, Yazhen Huo, Min Liang, Lihong Fan, Min Ye, Hongbo Hu. Glycycoumarin ameliorates alcohol-induced hepatotoxicity via activation of Nrf2 and autophagy. Free radical biology & medicine. 2015 Dec; 89(?):135-46. doi: 10.1016/j.freeradbiomed.2015.07.006. [PMID: 26169726]
  • Hitomi Kanno, Zenji Kawakami, Masahiro Tabuchi, Kazushige Mizoguchi, Yasushi Ikarashi, Yoshio Kase. Protective effects of glycycoumarin and procyanidin B1, active components of traditional Japanese medicine yokukansan, on amyloid β oligomer-induced neuronal death. Journal of ethnopharmacology. 2015 Jan; 159(?):122-8. doi: 10.1016/j.jep.2014.10.058. [PMID: 25446602]
  • Qi Wang, Xue Qiao, Chun-fang Liu, Shuai Ji, Lin-Min Feng, Yi Qian, De-An Guo, Min Ye. Metabolites identification of glycycoumarin, a major bioactive coumarin from licorice in rats. Journal of pharmaceutical and biomedical analysis. 2014 Sep; 98(?):287-95. doi: 10.1016/j.jpba.2014.06.001. [PMID: 24960236]
  • Myrna Adianti, Chie Aoki, Mari Komoto, Lin Deng, Ikuo Shoji, Tutik Sri Wahyuni, Maria Inge Lusida, Soetjipto, Hiroyuki Fuchino, Nobuo Kawahara, Hak Hotta. Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species. Microbiology and immunology. 2014 Mar; 58(3):180-7. doi: 10.1111/1348-0421.12127. [PMID: 24397541]
  • Keiko K Lee, Yuji Omiya, Mitsutoshi Yuzurihara, Yoshio Kase, Hiroyuki Kobayashi. Antispasmodic effect of shakuyakukanzoto extract on experimental muscle cramps in vivo: role of the active constituents of Glycyrrhizae radix. Journal of ethnopharmacology. 2013 Jan; 145(1):286-93. doi: 10.1016/j.jep.2012.11.005. [PMID: 23164761]
  • Zenji Kawakami, Yasushi Ikarashi, Yoshio Kase. Isoliquiritigenin is a novel NMDA receptor antagonist in kampo medicine yokukansan. Cellular and molecular neurobiology. 2011 Nov; 31(8):1203-12. doi: 10.1007/s10571-011-9722-1. [PMID: 21691759]
  • Songpei Li, Wei Li, Yinghua Wang, Yoshihisa Asada, Kazuo Koike. Prenylflavonoids from Glycyrrhiza uralensis and their protein tyrosine phosphatase-1B inhibitory activities. Bioorganic & medicinal chemistry letters. 2010 Sep; 20(18):5398-401. doi: 10.1016/j.bmcl.2010.07.110. [PMID: 20724155]
  • Kamal A Amin, Mohamed A Nagy. Effect of Carnitine and herbal mixture extract on obesity induced by high fat diet in rats. Diabetology & metabolic syndrome. 2009 Oct; 1(1):17. doi: 10.1186/1758-5996-1-17. [PMID: 19835614]
  • Ling Zhou, Yu-Ping Tang, Lu Gao, Xin-Sheng Fan, Chun-Mei Liu, De-Kang Wu. Separation, characterization and dose-effect relationship of the PPARgamma-activating bio-active constituents in the Chinese herb formulation 'San-Ao decoction'. Molecules (Basel, Switzerland). 2009 Oct; 14(10):3942-51. doi: 10.3390/molecules14103942. [PMID: 19924040]
  • Shu Zhu, Reiko Sugiyama, Javzan Batkhuu, Chinbat Sanchir, Kun Zou, Katsuko Komatsu. Survey of Glycyrrhizae Radix resources in Mongolia: chemical assessment of the underground part of Glycyrrhiza uralensis and comparison with Chinese Glycyrrhizea Radix. Journal of natural medicines. 2009 Apr; 63(2):137-46. doi: 10.1007/s11418-008-0303-7. [PMID: 19067115]
  • Xiu-wei Yang, Bo Xu, Fu-xiang Ran, Rui-qing Wang, Jun Wu, Jing-rong Cui. [Inhibitory effects of 11 coumarin compounds against growth of human bladder carcinoma cell line E-J in vitro]. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2007 Jan; 5(1):56-60. doi: 10.3736/jcim20070111. [PMID: 17214937]
  • Yuji Sato, Ju-Xiu He, Hidemasa Nagai, Tadato Tani, Teruaki Akao. Isoliquiritigenin, one of the antispasmodic principles of Glycyrrhiza ularensis roots, acts in the lower part of intestine. Biological & pharmaceutical bulletin. 2007 Jan; 30(1):145-9. doi: 10.1248/bpb.30.145. [PMID: 17202675]
  • Yoshiji Ohta, Mutsumi Kongo-Nishimura, Takahiro Hayashi, Akira Kitagawa, Tatsuya Matsura, Kazuo Yamada. Saikokeishito Extract Exerts a Therapeutic Effect on alpha-Naphthylisothiocyanate-Induced Liver Injury in Rats through Attenuation of Enhanced Neutrophil Infiltration and Oxidative Stress in the Liver Tissue. Journal of clinical biochemistry and nutrition. 2007 Jan; 40(1):31-41. doi: 10.3164/jcbn.40.31. [PMID: 18437211]
  • Hidemasa Nagai, Yutaka Yamamoto, Yuji Sato, Teruaki Akao, Tadato Tani. Pharmaceutical evaluation of cultivated Glycyrrhiza uralensis roots in comparison of their antispasmodic activity and glycycoumarin contents with those of licorice. Biological & pharmaceutical bulletin. 2006 Dec; 29(12):2442-5. doi: 10.1248/bpb.29.2442. [PMID: 17142979]
  • Yuji Sato, Teruaki Akao, Ju-Xiu He, Hiroshi Nojima, Yasushi Kuraishi, Takashi Morota, Takayuki Asano, Tadato Tani. Glycycoumarin from Glycyrrhizae Radix acts as a potent antispasmodic through inhibition of phosphodiesterase 3. Journal of ethnopharmacology. 2006 May; 105(3):409-14. doi: 10.1016/j.jep.2005.11.017. [PMID: 16387459]
  • Hiroaki Hayashi, Kenichiro Inoue, Kazuo Ozaki, Hitoshi Watanabe. Comparative analysis of ten strains of Glycyrrhiza uralensis cultivated in Japan. Biological & pharmaceutical bulletin. 2005 Jun; 28(6):1113-6. doi: 10.1248/bpb.28.1113. [PMID: 15930758]
  • Tatsumasa Mae, Hideyuki Kishida, Tozo Nishiyama, Misuzu Tsukagawa, Eisaku Konishi, Minpei Kuroda, Yoshihiro Mimaki, Yutaka Sashida, Kazuma Takahashi, Teruo Kawada, Kaku Nakagawa, Mikio Kitahara. A licorice ethanolic extract with peroxisome proliferator-activated receptor-gamma ligand-binding activity affects diabetes in KK-Ay mice, abdominal obesity in diet-induced obese C57BL mice and hypertension in spontaneously hypertensive rats. The Journal of nutrition. 2003 Nov; 133(11):3369-77. doi: 10.1093/jn/133.11.3369. [PMID: 14608046]
  • Hiroaki Hayashi, Sayaka Hattori, Kenichiro Inoue, Kanat Sarsenbaev, Michiho Ito, Gisho Honda. Field survey of Glycyrrhiza plants in Central Asia (1). Characterization of G. uralensis, G. glabra and the putative intermediate collected in Kazakhstan. Biological & pharmaceutical bulletin. 2003 Jun; 26(6):867-71. doi: 10.1248/bpb.26.867. [PMID: 12808302]
  • Y Tanaka, H Kikuzaki, S Fukuda, N Nakatani. Antibacterial compounds of licorice against upper airway respiratory tract pathogens. Journal of nutritional science and vitaminology. 2001 Jun; 47(3):270-3. doi: 10.3177/jnsv.47.270. [PMID: 11575586]