Gardenoside (BioDeep_00000003849)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


Methyl (1S,4aS,7S,7aS)-7-hydroxy-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

化学式: C17H24O11 (404.13185539999995)
中文名称: 山栀子苷B, 羟异栀子苷, 栀子苷
谱图信息: 最多检出来源 Viridiplantae(plant) 0.55%

分子结构信息

SMILES: COC(=O)C1=COC(C2C1C=CC2(CO)O)OC3C(C(C(C(O3)CO)O)O)O
InChI: InChI=1S/C17H24O11/c1-25-14(23)8-5-26-15(10-7(8)2-3-17(10,24)6-19)28-16-13(22)12(21)11(20)9(4-18)27-16/h2-3,5,7,9-13,15-16,18-22,24H,4,6H2,1H3

描述信息

A cyclopentapyran that is 7-deoxyloganin with a methyl and hydrogen replaced by hydroxy and hydroxymethyl groups at position 7.
Gardenoside is a natural product found in Gardenia jasminoides, Catunaregam obovata, and other organisms with data available.
Gardenoside is a natural compound found in Gardenia fruits, with hepatoprotective properties. Gardenoside suppresses the pain of chronic constriction injury by regulating the P2X3 and P2X7 receptors. Gardenoside has an inhibitory effect on free fatty acids (FFA)-induced cellular steatosis[1][2].
Gardenoside is a natural compound found in Gardenia fruits, with hepatoprotective properties. Gardenoside suppresses the pain of chronic constriction injury by regulating the P2X3 and P2X7 receptors. Gardenoside has an inhibitory effect on free fatty acids (FFA)-induced cellular steatosis[1][2].
Gardenoside is a natural compound found in Gardenia fruits, with hepatoprotective properties. Gardenoside suppresses the pain of chronic constriction injury by regulating the P2X3 and P2X7 receptors. Gardenoside has an inhibitory effect on free fatty acids (FFA)-induced cellular steatosis[1][2].

同义名列表

12 个代谢物同义名

Gardenoside; methyl (1R,4aR,7R,7aR)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylate; NCGC00169504-02_C17H24O11_Methyl 1-(hexopyranosyloxy)-7-hydroxy-7-(hydroxymethyl)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate; Methyl (1S,4aS,7S,7aS)-7-hydroxy-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate; Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, methyl ester, (1S-(1alpha,4aalpha,7alpha,7aalpha))-; CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,7,7A-TETRAHYDRO-7-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1S,4AS,7S,7AS)-; Cyclopenta[c]pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7S,7aS)-; Cyclopenta[c]pyran-4-carboxylic acid, 1-(ss-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7S,7aS)-; gardenoside, 1S(1alpha,4alplha,7beta,7alpha); UNII-INE79XNR2C; INE79XNR2C; methyl 7-hydroxy-7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylate



数据库引用编号

40 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)

21 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

  • Tianyi Zhao, Shiyi Lun, Maoying Yan, JongPil Park, Shumin Wang, Changbao Chen. 6,7-Dimethoxycoumarin, Gardenoside and Rhein combination improves non-alcoholic fatty liver disease in rats. Journal of ethnopharmacology. 2024 Mar; 322(?):117646. doi: 10.1016/j.jep.2023.117646. [PMID: 38135236]
  • Wei-Wei Ma, Ye Tao, Yan-Ying Wang, I-Feng Peng. Effects of Gardenia jasminoides extracts on cognition and innate immune response in an adult Drosophila model of Alzheimer's disease. Chinese journal of natural medicines. 2017 Dec; 15(12):899-904. doi: 10.1016/s1875-5364(18)30005-0. [PMID: 29329646]
  • Hu Zhang, Ning Feng, Yan-Tong Xu, Tian-Xiang Li, Xiu-Mei Gao, Yan Zhu, Yun Seon Song, Ya-Nan Wang, Hong-Hua Wu. Chemical Constituents from the Flowers of Wild Gardenia jasminoides J.Ellis. Chemistry & biodiversity. 2017 May; 14(5):. doi: 10.1002/cbdv.201600437. [PMID: 28130824]
  • Shaocheng Chen, Xin Zhao, Peng Sun, Jun Qian, Yanhong Shi, Rui Wang. Preventive effect of Gardenia jasminoides on HCl/ethanol induced gastric injury in mice. Journal of pharmacological sciences. 2017 Jan; 133(1):1-8. doi: 10.1016/j.jphs.2016.05.011. [PMID: 27435384]
  • Xuan Zhou, Cen Chen, Xiaolan Ye, Fenyun Song, Guorong Fan, Fuhai Wu. Study of Separation and Identification of the Active Ingredients in Gardenia jasminoides Ellis Based on a Two-Dimensional Liquid Chromatography by Coupling Reversed Phase Liquid Chromatography and Hydrophilic Interaction Liquid Chromatography. Journal of chromatographic science. 2017 01; 55(1):75-81. doi: 10.1093/chromsci/bmw154. [PMID: 27737927]
  • Huiqing Liang, Limin Zhang, Hongguo Wang, Jinmo Tang, Jiaen Yang, Chuncheng Wu, Shaodong Chen. Inhibitory Effect of Gardenoside on Free Fatty Acid-Induced Steatosis in HepG2 Hepatocytes. International journal of molecular sciences. 2015 Nov; 16(11):27749-56. doi: 10.3390/ijms161126058. [PMID: 26610473]
  • Eun Ju Lee, Jun Kee Hong, Wan Kyunn Whang. Simultaneous determination of bioactive marker compounds from Gardeniae fructus by high performance liquid chromatography. Archives of pharmacal research. 2014 Aug; 37(8):992-1000. doi: 10.1007/s12272-013-0293-1. [PMID: 24277694]
  • Yang-Jing Luo, Yue-Ming Zuo, Zhong-Li Zhang, Miao-Ting Cai, Guang-Ming Luo. [Study on chemical constituents of Gardenia jasminoides(III)]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Jul; 37(7):1196-9. doi: ". [PMID: 25566656]
  • Ran Zuo, Hong-Jie Wang, Nan Si, Hai-Yu Zhao, Jian Yang, Bao-Lin Bian. [LC-FT-ICR-MS analysis of the prototypes and metabolites in rat plasma after administration of huang-lian-jie-du decoction]. Yao xue xue bao = Acta pharmaceutica Sinica. 2014 Feb; 49(2):237-43. doi: NULL. [PMID: 24761615]
  • Huaxu Zhu, Zhilei Qian, Feng He, Mengzhu Liu, Linmei Pan, Qichun Zhang, Yuping Tang. Novel pharmacokinetic studies of the Chinese formula Huang-Lian-Jie-Du-Tang in MCAO rats. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Jul; 20(10):767-74. doi: 10.1016/j.phymed.2012.11.012. [PMID: 23628154]
  • Zhong-Li Zhang, Yue-Ming Zuo, Guang-Ming Luo, Yang-Jing Luo, Yan-Yan Wang, Ya-Qin Yang. [Study on the chemical components of Gardenia jasminoides (II)]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2013 Mar; 36(3):401-3. doi: ". [PMID: 24010321]
  • Gang Chen, Shi-xiang Hou, Li-min Ye, Ping Hu. [Studies on purification of the extract of fructus Gardeniae for injection by macroreticular resins]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Feb; 30(3):188-90. doi: ". [PMID: 15719635]
  • Guangyi Liang, Peixue Cao, Li Chai, Furong Xian, Xia Li. Effects of different compounding of formulae on content of gardenoside in Yin Chen Hao decoction. Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan. 2002 Mar; 22(1):55-60. doi: ". [PMID: 11977525]
  • C Zhou, X Zhang, J Luo, H Yu. [Correlativity among biological characteristics of Gardenia jasminoides Eills]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1997 Apr; 22(4):208-10, 253. doi: ". [PMID: 10743211]
  • Z Gao, P Jiang, Q Wu, J Wang. [A comparative study on the chemical constituents of cultivated and wild fructus Gardeniae]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1995 Nov; 20(11):654-6, 702. doi: ". [PMID: 8737465]
  • Y Kawata, M Hattori, T Akao, K Kobashi, T Namba. Formation of nitrogen-containing metabolites from geniposide and gardenoside by human intestinal bacteria. Planta medica. 1991 Dec; 57(6):536-42. doi: 10.1055/s-2006-960201. [PMID: 1818345]
  • S Ueda, Y Iwahashi, H Tokuda. Production of anti-tumor-promoting iridoid glucosides in Genipa americana and its cell cultures. Journal of natural products. 1991 Nov; 54(6):1677-80. doi: 10.1021/np50078a032. [PMID: 1667413]