Rhapontigenin (BioDeep_00000230945)

 

Secondary id: BioDeep_00000020174

PANOMIX_OTCML-2023 Antitumor activity natural product


代谢物信息卡片


trans-1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene

化学式: C15H14O4 (258.0892044)
中文名称: 丹叶大黄素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 2.44%

分子结构信息

SMILES: COC1=C(C=C(C=C1)C=CC2=CC(=CC(=C2)O)O)O
InChI: InChI=1S/C15H14O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+

描述信息

Rhapontigenin is a stilbenoid.
Rhapontigenin is a natural product found in Rheum undulatum, Gnetum hainanense, and other organisms with data available.
Rhapontigenin is a natural analog of resveratrol with anticancer, antioxidant, antifungal and antibacterial activities. Rhapontigenin is amechanism-based, potent and selective cytochrome P450 1A1?inactivator (IC50 ?= 400 nM). Rhapontigenin exhibits 400-fold and 23-fold selectivity for P450 1A1 over P450 1A2 and P450 1B1, respectively[1].
Rhapontigenin is a natural analog of resveratrol with anticancer, antioxidant, antifungal and antibacterial activities. Rhapontigenin is amechanism-based, potent and selective cytochrome P450 1A1?inactivator (IC50 ?= 400 nM). Rhapontigenin exhibits 400-fold and 23-fold selectivity for P450 1A1 over P450 1A2 and P450 1B1, respectively[1].

同义名列表

24 个代谢物同义名

trans-1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene; 1,3-BENZENEDIOL, 5-(2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)-, (E)-; 1,3-BENZENEDIOL, 5-((1E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)-; 5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol; 5-((1E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)-1,3-BENZENEDIOL; 5-[(1E)-2-(3-Hydroxy-4-methoxyphenyl)ethenyl]-1,3-benzenediol; 5-((E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)BENZENE-1,3-DIOL; (E)-5-[2-(3-Hydroxy-4-methoxyphenyl)ethenyl]-1,3-benzenediol; 5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol; Rhapontigenin is known as a natural analog of resveratrol.; 5-[2-(3-hydroxy-4-methoxy-phenyl)vinyl]benzene-1,3-diol; (E)-5-(3-Hydroxy-4-methoxystyryl)benzene-1,3-diol; 3,3,5-Trihydroxy-4-methoxy-trans-stilbene; 3,3,5-STILBENETRIOL, 4-METHOXY-, (E)-; PHMHDRYYFAYWEG-NSCUHMNNSA-N; RHAPONTIN AGLYCONE; Rhapontin genin; UNII-22BG4NNH6W; ?rhapontigenin; Rhapontigenin; PRONTIGENIN; Protigenin; Pontigenin; 22BG4NNH6W



数据库引用编号

11 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)

63 个相关的物种来源信息

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

  • Jingzhi An, Jie Yang, Yuan Wei, Yunsi Liu, Yan Song, Zuzhuo Zhang, Ying Pan. Identification of the metabolites of rhapontigenin in rat and human by ultra-high-performance liquid chromatography-high-resolution mass spectrometry. Rapid communications in mass spectrometry : RCM. 2021 Oct; 35(20):e9180. doi: 10.1002/rcm.9180. [PMID: 34363627]
  • Manh Tuan Ha, Minji Kim, Chung Sub Kim, Se-Eun Park, Jeong Ah Kim, Mi Hee Woo, Jae Sue Choi, Byung Sun Min. Tetra-aryl cyclobutane and stilbenes from the rhizomes of Rheum undulatum and their α-glucosidase inhibitory activity: Biological evaluation, kinetic analysis, and molecular docking simulation. Bioorganic & medicinal chemistry letters. 2020 04; 30(8):127049. doi: 10.1016/j.bmcl.2020.127049. [PMID: 32111435]
  • Dan Chen, Jing-Ru Liu, Yanjin Cheng, Hua Cheng, Ping He, Yang Sun. Metabolism of Rhaponticin and Activities of its Metabolite, Rhapontigenin: A Review. Current medicinal chemistry. 2020; 27(19):3168-3186. doi: 10.2174/0929867326666190121143252. [PMID: 30666906]
  • Dahae Lee, SeonJu Park, Sungyoul Choi, Seung Hyun Kim, Ki Sung Kang. In Vitro Estrogenic and Breast Cancer Inhibitory Activities of Chemical Constituents Isolated from Rheum undulatum L. Molecules (Basel, Switzerland). 2018 May; 23(5):. doi: 10.3390/molecules23051215. [PMID: 29783719]
  • SeonJu Park, Yun Na Kim, Hee Jae Kwak, Eun Ju Jeong, Seung Hyun Kim. Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné. Bioorganic & medicinal chemistry letters. 2018 02; 28(4):552-557. doi: 10.1016/j.bmcl.2018.01.063. [PMID: 29402747]
  • Yanfeng He, Xiaoyan Wang, Yourui Suo, Chenxu Ding, Honglun Wang. Efficient Protocol for Isolation of Rhaponticin and Rhapontigenin with Consecutive Sample Injection from Fenugreek (Trigonella foenum-graecum L.) by HSCCC. Journal of chromatographic science. 2016 Mar; 54(3):479-85. doi: 10.1093/chromsci/bmv169. [PMID: 26598549]
  • Sung-Pil Jo, Jeong-Keun Kim, Young-Hee Lim. Antihyperlipidemic effects of rhapontin and rhapontigenin from rheum undulatum in rats fed a high-cholesterol diet. Planta medica. 2014 Aug; 80(13):1067-71. doi: 10.1055/s-0034-1382999. [PMID: 25127020]
  • Carolina Cieniak, Rui Liu, Alexandra Fottinger, Sheila A M Smiley, Jose A Guerrero-Analco, Steffany A L Bennett, Pierre S Haddad, Alain Cuerrier, Ammar Saleem, John T Arnason, Brian C Foster. In vitro inhibition of metabolism but not transport of gliclazide and repaglinide by Cree medicinal plant extracts. Journal of ethnopharmacology. 2013 Dec; 150(3):1087-95. doi: 10.1016/j.jep.2013.10.029. [PMID: 24184081]
  • Fang-Fang Chen, Xiao-Yu Xie, Yan-Ping Shi. Preparation of magnetic molecularly imprinted polymer for selective recognition of resveratrol in wine. Journal of chromatography. A. 2013 Jul; 1300(?):112-8. doi: 10.1016/j.chroma.2013.02.018. [PMID: 23481473]
  • Ying-Yong Zhao, Qi Su, Xian-Long Cheng, Xiao-Jie Tan, Xu Bai, Rui-Chao Lin. Pharmacokinetics, bioavailability and metabolism of rhaponticin in rat plasma by UHPLC-Q-TOF/MS and UHPLC-DAD-MSn. Bioanalysis. 2012 Mar; 4(6):713-23. doi: 10.4155/bio.12.24. [PMID: 22452262]
  • Jeong-Keun Kim, Narae Kim, Young-Hee Lim. Evaluation of the antibacterial activity of rhapontigenin produced from rhapontin by biotransformation against Propionibacterium acnes. Journal of microbiology and biotechnology. 2010 Jan; 20(1):82-7. doi: 10.4014/jmb.0907.07022. [PMID: 20134237]
  • Jannette Wober, Frank Möller, Tobias Richter, Catharina Unger, Carmen Weigt, Anett Jandausch, Oliver Zierau, Reinhard Rettenberger, Marietta Kaszkin-Bettag, Günter Vollmer. Activation of estrogen receptor-beta by a special extract of Rheum rhaponticum (ERr 731), its aglycones and structurally related compounds. The Journal of steroid biochemistry and molecular biology. 2007 Nov; 107(3-5):191-201. doi: 10.1016/j.jsbmb.2007.04.002. [PMID: 17692514]
  • Frank Möller, Oliver Zierau, Anett Jandausch, Reinhard Rettenberger, Marietta Kaszkin-Bettag, Günter Vollmer. Subtype-specific activation of estrogen receptors by a special extract of Rheum rhaponticum (ERr 731), its aglycones and structurally related compounds in U2OS human osteosarcoma cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2007 Nov; 14(11):716-26. doi: 10.1016/j.phymed.2007.09.001. [PMID: 17935960]
  • Rui Zhang, Kyoung Ah Kang, Mei Jing Piao, Kyoung Hwa Lee, Hye Suk Jang, Min Jeong Park, Bum Joon Kim, Jin Sook Kim, Young Sup Kim, Shi Yong Ryu, Jin Won Hyun. Rhapontigenin from Rheum undulatum protects against oxidative-stress-induced cell damage through antioxidant activity. Journal of toxicology and environmental health. Part A. 2007 Jul; 70(13):1155-66. doi: 10.1080/15287390701252766. [PMID: 17558811]
  • F Misiti, B Sampaolese, D Mezzogori, F Orsini, M Pezzotti, B Giardina, M E Clementi. Protective effect of rhubarb derivatives on amyloid beta (1-42) peptide-induced apoptosis in IMR-32 cells: a case of nutrigenomic. Brain research bulletin. 2006 Dec; 71(1-3):29-36. doi: 10.1016/j.brainresbull.2006.07.012. [PMID: 17113925]
  • Kathryn A Roupe, Jaime A Yáñez, Xiao Wei Teng, Neal M Davies. Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats. The Journal of pharmacy and pharmacology. 2006 Nov; 58(11):1443-50. doi: 10.1211/jpp.58.11.0004. [PMID: 17132206]
  • Kathryn A Roupe, Connie M Remsberg, Jaime A Yáñez, Neal M Davies. Pharmacometrics of stilbenes: seguing towards the clinic. Current clinical pharmacology. 2006 Jan; 1(1):81-101. doi: 10.2174/157488406775268246. [PMID: 18666380]
  • Kathryn A Roupe, Greg L Helms, Steven C Halls, Jaime A Yáñez, Neal M Davies. Preparative enzymatic synthesis and HPLC analysis of rhapontigenin: applications to metabolism, pharmacokinetics and anti-cancer studies. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2005 Aug; 8(3):374-86. doi: NULL. [PMID: 16401387]
  • K Suresh Babu, Ashok K Tiwari, Pullela V Srinivas, Amtul Z Ali, B China Raju, J Madhusudana Rao. Yeast and mammalian alpha-glucosidase inhibitory constituents from Himalayan rhubarb Rheum emodi Wall.ex Meisson. Bioorganic & medicinal chemistry letters. 2004 Jul; 14(14):3841-5. doi: 10.1016/j.bmcl.2004.04.062. [PMID: 15203173]
  • H Matsuda, T Kageura, T Morikawa, I Toguchida, S Harima, M Yoshikawa. Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages. Bioorganic & medicinal chemistry letters. 2000 Feb; 10(4):323-7. doi: 10.1016/s0960-894x(99)00702-7. [PMID: 10714491]