Gossypetin (BioDeep_00000000648)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxy-

化学式: C15H10O8 (318.037566)
中文名称: 棉花素
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.37%

分子结构信息

SMILES: C1(O)=C(O)C2OC(C3C=C(O)C(O)=CC=3)=C(O)C(=O)C=2C(O)=C1
InChI: InChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)14-13(22)12(21)10-8(18)4-9(19)11(20)15(10)23-14/h1-4,16-20,22H

描述信息

Gossypetin is a hexahydroxyflavone having the hydroxy groups placed at the 3-, 3-, 4-, 5- 7- and 8-positions. It has a role as a plant metabolite. It is a 7-hydroxyflavonol and a hexahydroxyflavone. It is a conjugate acid of a gossypetin-3-olate and a gossypetin(1-).
Gossypetin is a natural product found in Sedum brevifolium, Rhododendron stenophyllum, and other organisms with data available.
See also: Primula veris flower (part of); Larrea tridentata whole (part of).
A hexahydroxyflavone having the hydroxy groups placed at the 3-, 3-, 4-, 5- 7- and 8-positions.

同义名列表

25 个代谢物同义名

4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxy-; 2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxy-4H-chromen-4-one #; 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxy-4H-chromen-4-one; 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxy-chromen-4-one; 2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxychromen-4-one; FLAVONE, 3,3,4,5,7,8-HEXAHYDROXY-; 3,5,7,8,3,4-Hexahydroxyflavone; 3,3,4,5,7,8-Hexahydroxyflavone; YRRAGUMVDQQZIY-UHFFFAOYSA-N; 8-hydroxy-quercetin; 8-hydroxyquercetin; UNII-SET4M23ZTM; articulatidin; Gossypetin; SET4M23ZTM; equisporol; 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxy-4-chromenone; 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxy-chromone; SPECTRUM1505143; NCGC00096031-01; BSPBio_002552; CHEBI:16400; ST059622; 489-35-0; C04109



数据库引用编号

37 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)

127 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

  • Daisuke Takahashi, Eri Matsunaga, Tomohiro Yamashita, Jose M M Caaveiro, Yoshito Abe, Tadashi Ueda. Compound screening identified gossypetin and isoquercitrin as novel inhibitors for amyloid fibril formations of Vλ6 proteins associated with AL amyloidosis. Biochemical and biophysical research communications. 2022 03; 596(?):22-28. doi: 10.1016/j.bbrc.2022.01.066. [PMID: 35108650]
  • Yasuhide Hiraga, Norimoto Shimada, Yoshiki Nagashima, Kunihiro Suda, Tina Kanamori, Kanako Ishiguro, Yuka Sato, Hideki Hirakawa, Shusei Sato, Tomoyoshi Akashi, Yoshikazu Tanaka, Daisaku Ohta, Koh Aoki, Daisuke Shibata, Hideyuki Suzuki, Kota Kera. Identification of a Flavin Monooxygenase-Like Flavonoid 8-Hydroxylase with Gossypetin Synthase Activity from Lotus japonicus. Plant & cell physiology. 2021 Jul; 62(3):411-423. doi: 10.1093/pcp/pcaa171. [PMID: 33416873]
  • Mansour Sobeh, Ganna Petruk, Samir Osman, Mohamed A El Raey, Paola Imbimbo, Daria Maria Monti, Michael Wink. Isolation of Myricitrin and 3,5-di-O-Methyl Gossypetin from Syzygium samarangense and Evaluation of their Involvement in Protecting Keratinocytes against Oxidative Stress via Activation of the Nrf-2 Pathway. Molecules (Basel, Switzerland). 2019 May; 24(9):. doi: 10.3390/molecules24091839. [PMID: 31086086]
  • Hong-die Cai, Wei-wei Tao, Shu-lan Su, Sheng Guo, Yue Zhu, Jian-ming Guo, Da-wei Qian, Xu-dong Cong, Ren-mao Tang, Jin-ao Duan. [Antidepressant activity of flavonoid ethanol extract of Abelmoschus manihot corolla with BDNF up-regulation in the hippocampus]. Yao xue xue bao = Acta pharmaceutica Sinica. 2017 Feb; 52(2):222-8. doi: . [PMID: 29979503]
  • Le-Yue Du, Jin-Hua Tao, Shu Jiang, Da-Wei Qian, Jian-Ming Guo, Jin-Ao Duan. Metabolic profiles of the Flos Abelmoschus manihot extract by intestinal bacteria from the normal and CKD model rats based on UPLC-Q-TOF/MS. Biomedical chromatography : BMC. 2017 Feb; 31(2):. doi: 10.1002/bmc.3795. [PMID: 27451133]
  • Yelin Kang, Bong-Gyu Kim, Sunghoon Kim, Youngshim Lee, Youngdae Yoon. Inhibitory potential of flavonoids on PtdIns(3,4,5)P3 binding with the phosphoinositide-dependent kinase 1 pleckstrin homology domain. Bioorganic & medicinal chemistry letters. 2017 02; 27(3):420-426. doi: 10.1016/j.bmcl.2016.12.051. [PMID: 28049590]
  • Amitava Khan, Krishnendu Manna, Dipesh Kr Das, Swaraj Bandhu Kesh, Mahuya Sinha, Ujjal Das, Sushobhan Biswas, Aaveri Sengupta, Kunal Sikder, Sanjukta Datta, Mahua Ghosh, Anindita Chakrabarty, Asoke Banerji, Sanjit Dey. Gossypetin ameliorates ionizing radiation-induced oxidative stress in mice liver--a molecular approach. Free radical research. 2015 Oct; 49(10):1173-86. doi: 10.3109/10715762.2015.1053878. [PMID: 25994373]
  • Yearam Jung, Soon Young Shin, Yeonjoong Yong, Hyeryoung Jung, Seunghyun Ahn, Young Han Lee, Yoongho Lim. Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships. Chemical biology & drug design. 2015 May; 85(5):574-85. doi: 10.1111/cbdd.12445. [PMID: 25298094]
  • Haiying Zhang, Ning Li, Kun Li, Peng Li. Protective effect of Urtica dioica methanol extract against experimentally induced urinary calculi in rats. Molecular medicine reports. 2014 Dec; 10(6):3157-62. doi: 10.3892/mmr.2014.2610. [PMID: 25310585]
  • Jun-Yu Liang, Xin-Yu Du, Yan Chen, Xiao-Mei Ma, Rui Xie, Ji Zhang. [Chemical constituents from leaf of Rhododendron przewalskii]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Aug; 37(8):1381-2. doi: . [PMID: 25726644]
  • Jing-Hsien Chen, Chia-Wen Tsai, Chi-Ping Wang, Hui-Hsuan Lin. Anti-atherosclerotic potential of gossypetin via inhibiting LDL oxidation and foam cell formation. Toxicology and applied pharmacology. 2013 Oct; 272(2):313-24. doi: 10.1016/j.taap.2013.06.027. [PMID: 23845592]
  • Mengyue Wang, Ke Li, Yuxiao Nie, Yingfang Wei, Xiaobo Li. Antirheumatoid Arthritis Activities and Chemical Compositions of Phenolic Compounds-Rich Fraction from Urtica atrichocaulis, an Endemic Plant to China. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):818230. doi: 10.1155/2012/818230. [PMID: 21904564]
  • Wafa Marouane, Ahlem Soussi, Jean-Claude Murat, Sofiane Bezzine, Abdelfattah El Feki. The protective effect of Malva sylvestris on rat kidney damaged by vanadium. Lipids in health and disease. 2011 Apr; 10(?):65. doi: 10.1186/1476-511x-10-65. [PMID: 21513564]
  • Elizabeth A Mazzio, Fran Close, Karam F A Soliman. The biochemical and cellular basis for nutraceutical strategies to attenuate neurodegeneration in Parkinson's disease. International journal of molecular sciences. 2011 Jan; 12(1):506-69. doi: 10.3390/ijms12010506. [PMID: 21340000]
  • Tongtong Xu, Hui Guo, Bin Wang, Yuying Zhao, Qingying Zhang. [Metabolites in rat urine after orally administrating gossypetin-8-O-beta-D-glucuronide]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Oct; 35(19):2585-9. doi: . [PMID: 21174770]
  • Hyung Jae Jeong, Young Bae Ryu, Su-Jin Park, Jang Hoon Kim, Hyung-Jun Kwon, Jin Hyo Kim, Ki Hun Park, Mun-Chual Rho, Woo Song Lee. Neuraminidase inhibitory activities of flavonols isolated from Rhodiola rosea roots and their in vitro anti-influenza viral activities. Bioorganic & medicinal chemistry. 2009 Oct; 17(19):6816-23. doi: 10.1016/j.bmc.2009.08.036. [PMID: 19729316]
  • Fumio Matsuda, Keiko Yonekura-Sakakibara, Rie Niida, Takashi Kuromori, Kazuo Shinozaki, Kazuki Saito. MS/MS spectral tag-based annotation of non-targeted profile of plant secondary metabolites. The Plant journal : for cell and molecular biology. 2009 Feb; 57(3):555-77. doi: 10.1111/j.1365-313x.2008.03705.x. [PMID: 18939963]
  • S Paoletta, G B Steventon, D Wildeboer, T M Ehrman, P J Hylands, D J Barlow. Screening of herbal constituents for aromatase inhibitory activity. Bioorganic & medicinal chemistry. 2008 Sep; 16(18):8466-70. doi: 10.1016/j.bmc.2008.08.034. [PMID: 18778944]
  • Ghada A Fawzy, Hossam M Abdallah, Mohamed S A Marzouk, Fathy M Soliman, Amany A Sleem. Antidiabetic and antioxidant activities of major flavonoids of Cynanchum acutum L. (Asclepiadaceae) growing in Egypt. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Sep; 63(9-10):658-62. doi: 10.1515/znc-2008-9-1008. [PMID: 19040103]
  • Eckhard Wollenweber, Ralf Fischer, Marion Dörr, Kathryn Irvine, Cliff Pereira, Jan F Stevens. Chemodiversity of exudate flavonoids in Cassinia and Ozothamnus (Asteraceae, Gnaphalieae). Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Sep; 63(9-10):731-9. doi: 10.1515/znc-2008-9-1019. [PMID: 19040114]
  • Hideyuki Suzuki, Ryosuke Sasaki, Yoshiyuki Ogata, Yukiko Nakamura, Nozomu Sakurai, Mariko Kitajima, Hiromitsu Takayama, Shigehiko Kanaya, Koh Aoki, Daisuke Shibata, Kazuki Saito. Metabolic profiling of flavonoids in Lotus japonicus using liquid chromatography Fourier transform ion cyclotron resonance mass spectrometry. Phytochemistry. 2008 Jan; 69(1):99-111. doi: 10.1016/j.phytochem.2007.06.017. [PMID: 17669449]
  • James D Adams, Cecilia Garcia. Women's health among the Chumash. Evidence-based complementary and alternative medicine : eCAM. 2006 Mar; 3(1):125-31. doi: 10.1093/ecam/nek021. [PMID: 16550233]
  • Sahar R Gedara, Osama B Abdel-Halim, Saleh H el-Sharkawy, Osama M Salama, Thomas W Shier, Ahmed F Halim. New erythroxane-type diterpenoids from Fagonia boveana (Hadidi) Hadidi & Graf. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2003 Jan; 58(1-2):23-32. doi: 10.1515/znc-2003-1-204. [PMID: 12622221]
  • S M Rankin, C V de Whalley, J R Hoult, W Jessup, G M Wilkins, J Collard, D S Leake. The modification of low density lipoprotein by the flavonoids myricetin and gossypetin. Biochemical pharmacology. 1993 Jan; 45(1):67-75. doi: 10.1016/0006-2952(93)90378-a. [PMID: 8424824]
  • C V de Whalley, S M Rankin, J R Hoult, W Jessup, D S Leake. Flavonoids inhibit the oxidative modification of low density lipoproteins by macrophages. Biochemical pharmacology. 1990 Jun; 39(11):1743-50. doi: 10.1016/0006-2952(90)90120-a. [PMID: 2344371]