Ginkgolide C (BioDeep_00000002924)

 

Secondary id: BioDeep_00000230235, BioDeep_00000409281

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


8-tert-butyl-6,9,12,17-tetrahydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione

化学式: C20H24O11 (440.1319)
中文名称: 银杏内酯 C
谱图信息: 最多检出来源 Viridiplantae(plant) 23.98%

分子结构信息

SMILES: CC1C(=O)OC2C(O)C34C5OC(=O)C3(OC3OC(=O)C(O)C34C(C(C)(C)C)C5O)C12O
InChI: InChI=1S/C20H24O11/c1-5-12(24)28-11-8(22)18-10-6(21)7(16(2,3)4)17(18)9(23)13(25)30-15(17)31-20(18,14(26)29-10)19(5,11)27/h5-11,15,21-23,27H,1-4H3

描述信息

Ginkgolide C is found in fats and oils. Ginkgolide C is a bitter principle from Ginkgo biloba (ginkgo).
Bitter principle from Ginkgo biloba (ginkgo). Ginkgolide C is found in ginkgo nuts and fats and oils.
Ginkgolide C is a flavone isolated from Ginkgo biloba leaves, possessing multiple biological functions, such as decreasing platelet aggregation and ameliorating Alzheimer disease.
Ginkgolide C is a flavone isolated from Ginkgo biloba leaves, possessing multiple biological functions, such as decreasing platelet aggregation and ameliorating Alzheimer disease.
Ginkgolide C is a flavone isolated from Ginkgo biloba leaves, possessing multiple biological functions, such as decreasing platelet aggregation and ameliorating Alzheimer disease.
Ginkgolide C is a flavone isolated from Ginkgo biloba leaves, possessing multiple biological functions, such as decreasing platelet aggregation and ameliorating Alzheimer disease.

同义名列表

9 个代谢物同义名

8-tert-butyl-6,9,12,17-tetrahydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0¹,¹¹.0³,⁷.0⁷,¹¹.0¹³,¹⁷]nonadecane-5,15,18-trione; 1,7-Dihydroxy-(1alpha,7beta)-ginkgolide a; 1alpha,7beta-Dihydroxyginkgolide A; ginkgolide-C; Ginkgokide c; Ginkgolide C; CID 441295; BN-52022; Ginkgolide C



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(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)

20 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。

亚细胞结构定位 关联基因列表
Cytoplasm 14 BIRC5, CCND1, CTNNB1, CYP2B6, CYP3A4, IKBKB, MARVELD1, MYC, NR1I3, NR3C1, PNPLA2, PTGS2, SIRT1, TJP1
Peripheral membrane protein 4 CYP2B6, GORASP1, PTGS2, TJP1
Endoplasmic reticulum membrane 4 CYP2B6, CYP3A4, PNPLA2, PTGS2
Nucleus 12 BIRC5, CCND1, CTNNB1, IKBKB, MARVELD1, MPO, MYC, NR1I2, NR1I3, NR3C1, SIRT1, TJP1
cytosol 9 BIRC5, CCND1, CTNNB1, IKBKB, NR1I3, NR3C1, PNPLA2, SIRT1, TJP1
nuclear body 1 NR1I2
centrosome 3 CCND1, CTNNB1, NR3C1
nucleoplasm 10 BIRC5, CCND1, CTNNB1, MPO, MYC, NR1I2, NR1I3, NR3C1, PNPLA2, SIRT1
Cell membrane 6 CLDN3, CTNNB1, MARVELD1, PNPLA2, TJP1, TNF
Cytoplasmic side 2 GORASP1, TJP1
lamellipodium 1 CTNNB1
Multi-pass membrane protein 3 CLDN3, MARVELD1, PNPLA2
Golgi apparatus membrane 1 GORASP1
Synapse 2 CTNNB1, NR3C1
cell cortex 1 CTNNB1
cell junction 2 CTNNB1, TJP1
cell surface 2 CD40, TNF
glutamatergic synapse 1 CTNNB1
Golgi apparatus 1 GORASP1
Golgi membrane 1 GORASP1
neuronal cell body 2 CD40, TNF
presynaptic membrane 1 CTNNB1
Lysosome 1 MPO
plasma membrane 7 CD40, CLDN3, CTNNB1, MARVELD1, PNPLA2, TJP1, TNF
Membrane 8 CD40, CLDN3, CTNNB1, CYP3A4, MARVELD1, MYC, NR3C1, PNPLA2
apical plasma membrane 1 TJP1
basolateral plasma membrane 2 CTNNB1, TJP1
caveola 1 PTGS2
extracellular exosome 3 CD40, CTNNB1, MPO
endoplasmic reticulum 1 PTGS2
extracellular space 3 CD40, MPO, TNF
perinuclear region of cytoplasm 1 CTNNB1
Schaffer collateral - CA1 synapse 1 CTNNB1
Cell junction, tight junction 2 CLDN3, TJP1
adherens junction 2 CTNNB1, TJP1
apicolateral plasma membrane 3 CLDN3, CTNNB1, TJP1
bicellular tight junction 4 CCND1, CLDN3, CTNNB1, TJP1
gap junction 1 TJP1
intercalated disc 1 TJP1
intercellular canaliculus 1 TJP1
mitochondrion 3 NR3C1, SIRT1, TJP1
protein-containing complex 7 BIRC5, CLDN3, CTNNB1, MYC, NR3C1, PTGS2, TJP1
intracellular membrane-bounded organelle 4 CD40, CYP2B6, CYP3A4, MPO
Microsome membrane 3 CYP2B6, CYP3A4, PTGS2
chromatin silencing complex 1 SIRT1
Single-pass type I membrane protein 1 CD40
extracellular region 2 MPO, TNF
cytoplasmic side of plasma membrane 1 IKBKB
mitochondrial matrix 1 NR3C1
transcription regulator complex 2 CTNNB1, NR1I2
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 NR3C1
Nucleus membrane 1 CCND1
nuclear membrane 1 CCND1
CD40 receptor complex 2 CD40, IKBKB
external side of plasma membrane 2 CD40, TNF
varicosity 1 CD40
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
microtubule cytoskeleton 1 BIRC5
nucleolus 2 MYC, SIRT1
Wnt signalosome 1 CTNNB1
midbody 1 BIRC5
apical part of cell 2 CTNNB1, TJP1
cell-cell junction 2 CLDN3, CTNNB1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 CTNNB1
heterochromatin 1 SIRT1
Membrane raft 2 IKBKB, TNF
Cytoplasm, cytoskeleton 3 CTNNB1, MARVELD1, NR1I3
Cytoplasm, cytoskeleton, spindle 2 BIRC5, NR3C1
focal adhesion 1 CTNNB1
microtubule 1 BIRC5
spindle 2 BIRC5, NR3C1
cis-Golgi network 1 GORASP1
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
Nucleus, PML body 1 SIRT1
PML body 1 SIRT1
secretory granule 1 MPO
fascia adherens 1 CTNNB1
lateral plasma membrane 2 CLDN3, CTNNB1
nuclear speck 1 NR3C1
interphase microtubule organizing center 1 BIRC5
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 2 PTGS2, SIRT1
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
chromatin 5 MYC, NR1I2, NR1I3, NR3C1, SIRT1
cell projection 1 TJP1
phagocytic cup 1 TNF
cell periphery 1 CTNNB1
Chromosome 2 BIRC5, NR3C1
cytoskeleton 2 MARVELD1, NR1I3
Cell projection, podosome 1 TJP1
podosome 1 TJP1
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
centriole 1 BIRC5
Nucleus, nucleolus 1 MYC
spindle pole 1 CTNNB1
nuclear chromosome 1 BIRC5
postsynaptic density, intracellular component 1 CTNNB1
microvillus membrane 1 CTNNB1
fibrillar center 1 SIRT1
serine/threonine protein kinase complex 1 IKBKB
nuclear envelope 2 MYC, SIRT1
Endomembrane system 1 CTNNB1
Lipid droplet 1 PNPLA2
Chromosome, centromere 1 BIRC5
Chromosome, centromere, kinetochore 1 BIRC5
Nucleus, nucleoplasm 2 MYC, NR3C1
euchromatin 2 CTNNB1, SIRT1
intermediate filament cytoskeleton 1 NR1I2
azurophil granule 1 MPO
endoplasmic reticulum lumen 2 PNPLA2, PTGS2
transcription repressor complex 1 CCND1
kinetochore 1 BIRC5
RNA polymerase II transcription repressor complex 1 MYC
tight junction 2 CLDN3, TJP1
beta-catenin-TCF complex 1 CTNNB1
azurophil granule lumen 1 MPO
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
chromosome, centromeric region 1 BIRC5
presynaptic active zone cytoplasmic component 1 CTNNB1
IkappaB kinase complex 1 IKBKB
phagocytic vesicle lumen 1 MPO
chromosome passenger complex 1 BIRC5
cytoplasmic microtubule 1 BIRC5
protein-DNA complex 1 CTNNB1
spindle microtubule 1 BIRC5
survivin complex 1 BIRC5
apical junction complex 2 CLDN3, TJP1
eNoSc complex 1 SIRT1
rDNA heterochromatin 1 SIRT1
Rough endoplasmic reticulum 1 MYC
catenin complex 1 CTNNB1
[Isoform Alpha]: Cytoplasm 1 NR3C1
cyclin-dependent protein kinase holoenzyme complex 1 CCND1
Myc-Max complex 1 MYC
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform Beta]: Nucleus 1 NR3C1
[Isoform Alpha-B]: Nucleus 1 NR3C1
cyclin D1-CDK4 complex 1 CCND1
beta-catenin-TCF7L2 complex 1 CTNNB1
cyclin D1-CDK6 complex 1 CCND1
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[SirtT1 75 kDa fragment]: Cytoplasm 1 SIRT1
nucleoplasmic reticulum 1 MYC


文献列表

  • Lina Jia, Yingchao Gong, Xinru Jiang, Xianan Fan, Zhenghua Ji, Tianwen Ma, Rui Li, Fangping Liu. Ginkgolide C inhibits ROS-mediated activation of NLRP3 inflammasome in chondrocytes to ameliorate osteoarthritis. Journal of ethnopharmacology. 2024 May; 325(?):117887. doi: 10.1016/j.jep.2024.117887. [PMID: 38346525]
  • Bin Li, Baoke Zhang, Zhenyu Li, Shasha Li, Jun Li, Aiwu Wang, Jinling Hou, Jiping Xu, Rui Zhang. Ginkgolide C attenuates cerebral ischemia/reperfusion-induced inflammatory impairments by suppressing CD40/NF-κB pathway. Journal of ethnopharmacology. 2023 Aug; 312(?):116537. doi: 10.1016/j.jep.2023.116537. [PMID: 37094696]
  • Martin Hébert, Gabriel Bellavance, Louis Barriault. Total Synthesis of Ginkgolide C and Formal Syntheses of Ginkgolides A and B. Journal of the American Chemical Society. 2022 10; 144(39):17792-17796. doi: 10.1021/jacs.2c08351. [PMID: 36150149]
  • Min Hee Yang, In Jin Ha, Seok-Geun Lee, Jae-Young Um, Kwang Seok Ahn. Abrogation of STAT3 activation cascade by Ginkgolide C mitigates tumourigenesis in lung cancer preclinical model. The Journal of pharmacy and pharmacology. 2021 Dec; 73(12):1630-1642. doi: 10.1093/jpp/rgab114. [PMID: 34559878]
  • Suchitra K Panigrahy, Awanish Kumar, Renu Bhatt. Hedychium coronarium Rhizomes: Promising Antidiabetic and Natural Inhibitor of α-Amylase and α-Glucosidase. Journal of dietary supplements. 2020; 17(1):81-87. doi: 10.1080/19390211.2018.1483462. [PMID: 30325249]
  • Wenping Wang, Qian Kang, Na Liu, Qing Zhang, Yewen Zhang, Hui Li, Bochen Zhao, Yanyan Chen, Yi Lan, Qiang Ma, Qing Wu. Enhanced dissolution rate and oral bioavailability of Ginkgo biloba extract by preparing solid dispersion via hot-melt extrusion. Fitoterapia. 2015 Apr; 102(?):189-97. doi: 10.1016/j.fitote.2014.10.004. [PMID: 25446043]
  • Ping Huang, Liang Zhang, Chuan Chai, Xiao-Cui Qian, Wen Li, Jun-Song Li, Liu-Qing Di, Bao-Chang Cai. Effects of food and gender on the pharmacokinetics of ginkgolides A, B, C and bilobalide in rats after oral dosing with ginkgo terpene lactones extract. Journal of pharmaceutical and biomedical analysis. 2014 Nov; 100(?):138-144. doi: 10.1016/j.jpba.2014.07.030. [PMID: 25165009]
  • Jiashu Xie, Cungang Ding, Qinghua Ge, Zhen Zhou, Xiaojin Zhi. Simultaneous determination of ginkgolides A, B, C and bilobalide in plasma by LC-MS/MS and its application to the pharmacokinetic study of Ginkgo biloba extract in rats. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Mar; 864(1-2):87-94. doi: 10.1016/j.jchromb.2008.01.045. [PMID: 18295555]
  • Hyun-Jeong Cho, Yun-Hee Shon, Kyung-Soo Nam. Ginkgolide C inhibits platelet aggregation in cAMP- and cGMP-dependent manner by activating MMP-9. Biological & pharmaceutical bulletin. 2007 Dec; 30(12):2340-4. doi: 10.1248/bpb.30.2340. [PMID: 18057723]
  • Jan Krzek, Janusz S Czekaj, Włodzimierz Rzeszutko, Radosław J Ekiert. Validation of capillary gas chromatographic method for determination of bilobalide and ginkgolides A, B, C in Ginkgo biloba dry and liquid extracts. Acta poloniae pharmaceutica. 2007 Jul; 64(4):303-10. doi: . [PMID: 18536155]
  • Pierluigi Mauri, Antonella De Palma, Francesca Pozzi, Fabrizio Basilico, Antonella Riva, Paolo Morazzoni, Ezio Bombardelli, Giuseppe Rossoni. LC-MS characterization of terpene lactones in plasma of experimental animals treated with Ginkgo biloba extracts Correlation with pharmacological activity. Journal of pharmaceutical and biomedical analysis. 2006 Feb; 40(3):763-8. doi: 10.1016/j.jpba.2005.10.048. [PMID: 16343838]
  • Xin Zhou, Xue-Qin Zhang, Mu Yuan, Dao-Ping Wang. [Quantitative determination of ginkgolides by liquid chromatography-electrospray mass spectrometry]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Dec; 30(24):1915-8. doi: ". [PMID: 16494022]
  • Xueguo Chen, Liang Kong, Lianghong Sheng, Xin Li, Hanfa Zou. [Applications of two-dimensional liquid chromatography coupled to mass spectrometry for the separation and identification of compounds in ginkgo biloba extracts]. Se pu = Chinese journal of chromatography. 2005 Jan; 23(1):46-51. doi: . [PMID: 15881366]
  • Stanislav Jaracz, Shahid Malik, Koji Nakanishi. Isolation of ginkgolides A, B, C, J and bilobalide from G. biloba extracts. Phytochemistry. 2004 Nov; 65(21):2897-902. doi: 10.1016/j.phytochem.2004.08.026. [PMID: 15501258]
  • Chen Ding, Erqin Chen, Weijia Zhou, Robert C Lindsay. A method for extraction and quantification of Ginkgo terpene trilactones. Analytical chemistry. 2004 Aug; 76(15):4332-6. doi: 10.1021/ac049809a. [PMID: 15283569]
  • I fan Kuo, Jie Chen, Thomas K H Chang. Effect of Ginkgo biloba extract on rat hepatic microsomal CYP1A activity: role of ginkgolides, bilobalide, and flavonols. Canadian journal of physiology and pharmacology. 2004 Jan; 82(1):57-64. doi: 10.1139/y03-133. [PMID: 15052306]
  • Qingfei Liu, Liling Zhou. [Determination of GA, GB and GC in total lactone of ginkgo (TLG) raw material]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2004 Jan; 27(1):19-20. doi: . [PMID: 15179783]
  • Hisashi Kuribara, Susan T Weintraub, Tatsumi Yoshihama, Yuji Maruyama. An anxiolytic-like effect of Ginkgo biloba extract and its constituent, ginkgolide-A, in mice. Journal of natural products. 2003 Oct; 66(10):1333-7. doi: 10.1021/np030122f. [PMID: 14575433]
  • Young Hae Choi, Hyung-Kyoon Choi, Arno Hazekamp, Paloma Bermejo, Yvonne Schilder, Cornelis Erkelens, Robert Verpoorte. Quantitative analysis of bilobalide and ginkgolides from Ginkgo biloba leaves and Ginkgo products using (1)H-NMR. Chemical & pharmaceutical bulletin. 2003 Feb; 51(2):158-61. doi: 10.1248/cpb.51.158. [PMID: 12576648]
  • Eva Gogös. Identification and the retention index of bilobalide and ginkgolides using capillary gas chromatography. Journal of chromatographic science. 2002 Oct; 40(9):519-22. doi: 10.1093/chromsci/40.9.519. [PMID: 12433115]
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  • G Dive, J J Godfroid, J Lamotte-Brasseur, J P Batt, F Heymans, L Dupont, P Braquet. PAF-receptor. 1. 'Cache-oreilles' effect of selected high-potency platelet-activating factor (PAF) antagonists. Journal of lipid mediators. 1989 Jul; 1(4):201-15. doi: ". [PMID: 2562434]
  • R Korth, D Nunez, J Bidault, J Benveniste. Comparison of three paf-acether receptor antagonist ginkgolides. European journal of pharmacology. 1988 Jul; 152(1-2):101-10. doi: 10.1016/0014-2999(88)90840-0. [PMID: 2850196]