Gentisein (BioDeep_00000007853)

 

Secondary id: BioDeep_00000862061

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


1,3,7-Trihydroxy-9H-xanthen-9-one, 9CI

化学式: C13H8O5 (244.0371718)
中文名称: 1,3,7-三羟基-9H-氧杂蒽-9-酮
谱图信息: 最多检出来源 Viridiplantae(plant) 0.95%

分子结构信息

SMILES: c1(cc(c2c(c1)oc1c(c2=O)cc(cc1)O)O)O
InChI: InChI=1S/C13H8O5/c14-6-1-2-10-8(3-6)13(17)12-9(16)4-7(15)5-11(12)18-10/h1-5,14-16H

描述信息

Gentisein is a member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3 and 7. It has a role as a plant metabolite. It is a member of xanthones and a polyphenol.
Gentisein is a natural product found in Hypericum scabrum, Cratoxylum formosum, and other organisms with data available.
A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3 and 7.
Gentisein is found in alcoholic beverages. Gentisein is isolated from Gentiana lutea (yellow gentian
Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2].
Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2].
Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2].

同义名列表

14 个代谢物同义名

1,3,7-Trihydroxy-9H-xanthen-9-one, 9CI; 9H-Xanthen-9-one, 1,3,7-trihydroxy-; 9H-Xanthen-9-one,1,3,7-trihydroxy-; 1,3,7-trihydroxy-9H-xanthen-9-one; Xanthen-9-one, 1,3,7-trihydroxy-; 1,3,7-Trihydroxy-xanthen-9-one; 1,3,7-trihydroxyxanthen-9-one; 1,3,7-trihydroxy-xanthone; 1,3,7-trihydroxyxanthone; UNII-0P3G42TQ63; XANTHONE DERIV; 0P3G42TQ63; Gentisein; NSC 329491



数据库引用编号

20 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(2)

代谢反应

4 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(4)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

16 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

  • Edwin Risky Sukandar, Sutin Kaennakam, Kitiya Rassamee, Taslim Ersam, Pongpun Siripong, Santi Tip-Pyang. Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra. Journal of natural products. 2019 05; 82(5):1312-1318. doi: 10.1021/acs.jnatprod.9b00046. [PMID: 30978023]
  • Jie Liu, Cao Zhang, Huailing Wang, Lei Zhang, Zhenlei Jiang, Jianrun Zhang, Zhijun Liu, Heru Chen. Incorporation of nitric oxide donor into 1,3-dioxyxanthones leads to synergistic anticancer activity. European journal of medicinal chemistry. 2018 May; 151(?):158-172. doi: 10.1016/j.ejmech.2018.03.072. [PMID: 29609121]
  • Jie Liu, Jianrun Zhang, Huailing Wang, Zhijun Liu, Cao Zhang, Zhenlei Jiang, Heru Chen. Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them. European journal of medicinal chemistry. 2017 Jun; 133(?):50-61. doi: 10.1016/j.ejmech.2017.03.068. [PMID: 28376372]
  • Qiwen Wang, Chenyao Ma, Yun Ma, Xiang Li, Yong Chen, Jianwei Chen. Structure-activity relationships of diverse xanthones against multidrug resistant human tumor cells. Bioorganic & medicinal chemistry letters. 2017 02; 27(3):447-449. doi: 10.1016/j.bmcl.2016.12.045. [PMID: 28065566]
  • Ruishan Wang, Ridao Chen, Jianhua Li, Xiao Liu, Kebo Xie, Dawei Chen, Ying Peng, Jungui Dai. Regiospecific Prenylation of Hydroxyxanthones by a Plant Flavonoid Prenyltransferase. Journal of natural products. 2016 08; 79(8):2143-7. doi: 10.1021/acs.jnatprod.6b00417. [PMID: 27466696]
  • Mumtaz Ali, Muhammad Arfan, Manzoor Ahmad, Kuldip Singh, Itrat Anis, Habib Ahmad, Muhammad Iqbal Choudhary, Muhammad Raza Shah. Anti-inflammatory xanthones from the twigs of Hypericum oblongifolium wall. Planta medica. 2011 Dec; 77(18):2013-8. doi: 10.1055/s-0031-1280114. [PMID: 21870324]
  • Ngoc Trang Nhu Ngo, Vy Thuy Nguyen, Hoa Van Vo, Ole Vang, Fritz Duus, Thuy-Duong Huynh Ho, Hung Dinh Pham, Lien-Hoa Dieu Nguyen. Cytotoxic Coumarins from the Bark of Mammea siamensis. Chemical & pharmaceutical bulletin. 2010 Nov; 58(11):1487-91. doi: 10.1248/cpb.58.1487. [PMID: 21048341]
  • He Zhong Jiang, Xiao Fang Quan, Wei Xi Tian, Jiang Miao Hu, Peng Cheng Wang, Sheng Zhuo Huang, Zhong Quan Cheng, Wen Juan Liang, Jun Zhou, Xiao Feng Ma, You Xing Zhao. Fatty acid synthase inhibitors of phenolic constituents isolated from Garcinia mangostana. Bioorganic & medicinal chemistry letters. 2010 Oct; 20(20):6045-7. doi: 10.1016/j.bmcl.2010.08.061. [PMID: 20817450]
  • Mohammad Arfan, Mumtaz Ali, Habib Ahmad, Itrat Anis, Ajmal Khan, M Iqbal Choudhary, Muhammad Raza Shah. Urease inhibitors from Hypericum oblongifolium WALL. Journal of enzyme inhibition and medicinal chemistry. 2010 Apr; 25(2):296-9. doi: 10.3109/14756360903179385. [PMID: 20222765]
  • Hui Wang, Guan Ye, Chun-Hui Ma, Yi-Hong Tang, Ming-Song Fan, Zhi-Xiong Li, Cheng-Gang Huang. Identification and determination of four metabolites of mangiferin in rat urine. Journal of pharmaceutical and biomedical analysis. 2007 Dec; 45(5):793-8. doi: 10.1016/j.jpba.2007.07.019. [PMID: 17723287]
  • Hai-Tao Chang, Feng Niu, Jing Wen, Yong Jiang, Peng-Fei Tu. [Studies on xanthones from herbs of Polygala telephioides]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Nov; 32(21):2259-61. doi: . [PMID: 18309668]
  • D Zheleva-Dimitrova, R Gevrenova, P Nedialkov, G Kitanov. Simultaneous determination of benzophenones and gentisein in Hypericum annulatum Moris by high-performance liquid chromatography. Phytochemical analysis : PCA. 2007 Jan; 18(1):1-6. doi: 10.1002/pca.940. [PMID: 17260692]
  • Georgi Momekov, Paraskev T Nedialkov, Gerassim M Kitanov, Dimitrina Zh Zheleva-Dimitrova, Tzvetomira Tzanova, Ulrich Girreser, Margarita Karaivanova. Cytoprotective effects of 5 benzophenones and a xanthone from Hypericum annulatum in models of epirubicin-induced cytotoxicity: SAR-analysis and mechanistic investigations. Medicinal chemistry (Shariqah (United Arab Emirates)). 2006 Jul; 2(4):377-84. doi: 10.2174/157340606777724103. [PMID: 16848749]
  • Mitka Mitcheva, Magdalena Kondeva, Vessela Vitcheva, Paraskev Nedialkov, Gerassim Kitanov. Effect of benzophenones from Hypericum annulatum on carbon tetrachloride-induced toxicity in freshly isolated rat hepatocytes. Redox report : communications in free radical research. 2006; 11(1):3-8. doi: 10.1179/135100006x100968. [PMID: 16571270]
  • Zhizhen Zhang, Hala N ElSohly, Melissa R Jacob, David S Pasco, Larry A Walker, Alice M Clark. Natural products inhibiting Candida albicans secreted aspartic proteases from Tovomita krukovii. Planta medica. 2002 Jan; 68(1):49-54. doi: 10.1055/s-2002-20049. [PMID: 11842327]
  • Cécile Morel, Denis Séraphin, Agnès Teyrouz, Gérald Larcher, Jean-Philippe Bouchara, Marc Litaudon, Pascal Richomme, Jean Bruneton. New and antifungal xanthones from Calophyllum caledonicum. Planta medica. 2002 Jan; 68(1):41-4. doi: 10.1055/s-2002-19867. [PMID: 11842325]