Gambogenic Acid (BioDeep_00000179315)

   

human metabolite blood metabolite natural product


代谢物信息卡片


4-[7-(3,7-dimethylocta-2,6-dien-1-yl)-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid

化学式: C38H46O8 (630.3192516)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 96.3%

分子结构信息

SMILES: CC(C)=CCCC(C)=CCC1=C(O)C(CC=C(C)C)=C2OC34C5CC(C=C3C(=O)C2=C1O)C(=O)C4(CC=C(C)C(O)=O)OC5(C)C
InChI: InChI=1S/C38H46O8/c1-20(2)10-9-11-22(5)13-15-25-30(39)26(14-12-21(3)4)33-29(31(25)40)32(41)27-18-24-19-28-36(7,8)46-37(34(24)42,38(27,28)45-33)17-16-23(6)35(43)44/h10,12-13,16,18,24,28,39-40H,9,11,14-15,17,19H2,1-8H3,(H,43,44)

描述信息

同义名列表

9 个代谢物同义名

4-[7-(3,7-dimethylocta-2,6-dien-1-yl)-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid; 4-[7-(3,7-Dimethylocta-2,6-dien-1-yl)-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoate; 4-[7-(3,7-Dimethylocta-2,6-dien-1-yl)-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.0,.0,.0,]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoate; Isogambogenic acid; neo-gambogic acid; neogambogic acid; gambogenic acid; Gambogenate; iso-GNA



数据库引用编号

3 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)

12 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

  • Qing Huang, Keke Guo, Yitao Ren, Jiaqi Tan, Yi Ren, Li Zhang, Changwu Zheng, Hongxi Xu. Design, synthesis, and biological evaluation of gambogenic acid derivatives: Unraveling their anti-cancer effects by inducing pyroptosis. Bioorganic chemistry. 2024 Apr; 145(?):107182. doi: 10.1016/j.bioorg.2024.107182. [PMID: 38359707]
  • Zilin Liu, Xuezhong Wang, Jianping Li, Xiaoming Yang, Jun Huang, Chuang Ji, Xuyang Li, Lan Li, Jianlin Zhou, Yong Hu. Gambogenic acid induces cell death in human osteosarcoma through altering iron metabolism, disturbing the redox balance, and activating the P53 signaling pathway. Chemico-biological interactions. 2023 Jun; 382(?):110602. doi: 10.1016/j.cbi.2023.110602. [PMID: 37302459]
  • Jing Sun, Mengdi Pang, Xiaozhu Tang, Qianqian Xu, Daiyin Peng, Weidong Chen. Anti-tumor effect of gambogenic acid and its effect on CYP2C and CYP3A after oral administration. Chemical & pharmaceutical bulletin. 2023 Mar; ?(?):. doi: 10.1248/cpb.c22-00656. [PMID: 36858593]
  • Meng Wang, Fan Zhan, Hui Cheng, Qinglin Li. Gambogenic Acid Inhibits Basal Autophagy of Drug-Resistant Hepatoma Cells and Improves Its Sensitivity to Adriamycin. Biological & pharmaceutical bulletin. 2022; 45(1):63-70. doi: 10.1248/bpb.b21-00511. [PMID: 34980780]
  • Beilei Wang, Tengteng Yuan, Liqiong Zha, Yuanxu Liu, Weidong Chen, Caiyun Zhang, Youmei Bao, Qiannian Dong. Oral Delivery of Gambogenic Acid by Functional Polydopamine Nanoparticles for Targeted Tumor Therapy. Molecular pharmaceutics. 2021 03; 18(3):1470-1479. doi: 10.1021/acs.molpharmaceut.1c00030. [PMID: 33586444]
  • Zhongyang Ding, Ying Li, Zhangfeng Tang, Xiaoyi Song, Fa Jing, Haotian Wu, Bei Lu. Role of gambogenic acid in regulating PI3K/Akt/NF-kβ signaling pathways in rat model of acute hepatotoxicity. Bioscience, biotechnology, and biochemistry. 2021 Feb; 85(3):520-527. doi: 10.1093/bbb/zbaa039. [PMID: 33624779]
  • Daofu Shen, Yu Wang, Hongmei Niu, Chunying Liu. Gambogenic acid exerts anticancer effects in cisplatin‑resistant non‑small cell lung cancer cells. Molecular medicine reports. 2020 03; 21(3):1267-1275. doi: 10.3892/mmr.2020.10909. [PMID: 31922223]
  • Tong-Yuan Lin, Ting-Ting Zhu, Yan Xun, Yun-Song Tao, Yu-Qin Yang, Jia-Li Xie, Xiao-Ming Zhang, Shi-Xiong Chen, Bai-Jing Ding, Wei-Dong Chen. A novel drug delivery system of mixed micelles based on poly(ethylene glycol)-poly(lactide) and poly(ethylene glycol)-poly(ɛ-caprolactone) for gambogenic acid. The Kaohsiung journal of medical sciences. 2019 Dec; 35(12):757-764. doi: 10.1002/kjm2.12110. [PMID: 31433556]
  • Weiye Cheng, Beilei Wang, Caiyun Zhang, Qiannian Dong, Jiajia Qian, Liqiong Zha, Weidong Chen, Lufeng Hong. Preparation and preliminary pharmacokinetics study of GNA-loaded zein nanoparticles. The Journal of pharmacy and pharmacology. 2019 Nov; 71(11):1626-1634. doi: 10.1111/jphp.13151. [PMID: 31468524]
  • Jingjing Su, Ting Xu, Genling Jiang, Mei Hou, Mengru Liang, Hui Cheng, Qinglin Li. Gambogenic acid triggers apoptosis in human nasopharyngeal carcinoma CNE-2Z cells by activating volume-sensitive outwardly rectifying chloride channel. Fitoterapia. 2019 Mar; 133(?):150-158. doi: 10.1016/j.fitote.2019.01.002. [PMID: 30654125]
  • Shi-Juan Liu, Jia-Wei Liu, Jun-Zi Cong, Lei Tong, Ying Zhang, Xue-Mei Li, Jia-Fu Hou. Preparation of Neogambogic Acid Nanoliposomes and its Pharmacokinetics in Rats. Journal of the College of Physicians and Surgeons--Pakistan : JCPSP. 2018 Dec; 28(12):937-940. doi: 10.29271/jcpsp.2018.12.937. [PMID: 30501831]
  • Rui Sun, Hong-Ming Zhang, Bao-An Chen. Anticancer activity and underlying mechanism of neogambogic acid. Chinese journal of natural medicines. 2018 Sep; 16(9):641-643. doi: 10.1016/s1875-5364(18)30103-1. [PMID: 30269840]
  • Gu Jin, Fang-Fang Wang, Tao Li, Dong-Dong Jia, Yong Shen, Hai-Chao Xu. Neogambogic Acid Suppresses Receptor Activator of Nuclear Factor κB Ligand (RANKL)-Induced Osteoclastogenesis by Inhibiting the JNK and NF-κB Pathways in Mouse Bone Marrow-Derived Monocyte/Macrophages. Medical science monitor : international medical journal of experimental and clinical research. 2018 Apr; 24(?):2569-2577. doi: 10.12659/msm.909651. [PMID: 29698379]
  • Linfeng Xu, Xiaoxiao Meng, Naihan Xu, Wenwei Fu, Hongsheng Tan, Li Zhang, Qianjun Zhou, Jianan Qian, Shiwei Tu, Xueting Li, Yuanzhi Lao, Hongxi Xu. Gambogenic acid inhibits fibroblast growth factor receptor signaling pathway in erlotinib-resistant non-small-cell lung cancer and suppresses patient-derived xenograft growth. Cell death & disease. 2018 02; 9(3):262. doi: 10.1038/s41419-018-0314-6. [PMID: 29449529]
  • Tongyuan Lin, Xia Huang, Yanyan Wang, Tingting Zhu, Qing Luo, Xiaoxiao Wang, Kai Zhou, Hao Cheng, Daiyin Peng, Weidong Chen. Long circulation nanostructured lipid carriers for gambogenic acid: formulation design, characterization, and pharmacokinetic. Xenobiotica; the fate of foreign compounds in biological systems. 2017 Sep; 47(9):793-799. doi: 10.1080/00498254.2016.1229084. [PMID: 27618478]
  • Xiangdong Hua, Chuang Liang, Lei Dong, Xiaotong Qu, Tong Zhao. Simultaneous determination and pharmacokinetic study of gambogic acid and gambogenic acid in rat plasma after oral administration of Garcinia hanburyi extracts by LC-MS/MS. Biomedical chromatography : BMC. 2015 Apr; 29(4):545-51. doi: 10.1002/bmc.3311. [PMID: 25159917]
  • Jin Pei Chen, Dian Lei Wang, Li Li Yang, Chen Yin Wang, Shan Shan Wang. Ultra-high-performance liquid chromatography tandem mass spectrometry method for the determination of gambogenic acid in dog plasma and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2014 Dec; 28(12):1854-9. doi: 10.1002/bmc.3231. [PMID: 24802389]
  • Wang Mei, Chen Dong, Cheng Hui, Li Bin, Yan Fenggen, Su Jingjing, Peng Cheng, Sun Meiling, Hu Yawen, Wang Xiaoshan, Wang Guanghui, Chen Zhiwu, Li Qinglin. Gambogenic acid kills lung cancer cells through aberrant autophagy. PloS one. 2014; 9(1):e83604. doi: 10.1371/journal.pone.0083604. [PMID: 24427275]
  • Yi Fan, Aihua Peng, Shichao He, Ximing Shao, Chunlai Nie, Lijuan Chen. Isogambogenic acid inhibits tumour angiogenesis by suppressing Rho GTPases and vascular endothelial growth factor receptor 2 signalling pathway. Journal of chemotherapy (Florence, Italy). 2013 Oct; 25(5):298-308. doi: 10.1179/1973947813y.0000000079. [PMID: 24070138]
  • Tongyuan Lin, Qingying Fang, Daiyin Peng, Xia Huang, Tingting Zhu, Qing Luo, Kai Zhou, Weidong Chen. PEGylated non-ionic surfactant vesicles as drug delivery systems for Gambogenic acid. Drug delivery. 2013 Sep; 20(7):277-84. doi: 10.3109/10717544.2013.836618. [PMID: 24044645]
  • Xia Huang, Yan-Jie Chen, Dai-Yin Peng, Qing-Lin Li, Xiao-Shan Wang, Dian-Lei Wang, Wei-Dong Chen. Solid lipid nanoparticles as delivery systems for Gambogenic acid. Colloids and surfaces. B, Biointerfaces. 2013 Feb; 102(?):391-7. doi: 10.1016/j.colsurfb.2012.08.058. [PMID: 23010123]
  • Fenggen Yan, Mei Wang, Jiaming Li, Hui Cheng, Jingjing Su, Xiaoshan Wang, Haiyun Wu, Lunzhu Xia, Xiaoxiang Li, Hebron C Chang, Qinglin Li. Gambogenic acid induced mitochondrial-dependent apoptosis and referred to phospho-Erk1/2 and phospho-p38 MAPK in human hepatoma HepG2 cells. Environmental toxicology and pharmacology. 2012 Mar; 33(2):181-90. doi: 10.1016/j.etap.2011.12.006. [PMID: 22222560]
  • Si-Jia Tao, Yang Wang, Xing Zhang, Shu-Hong Guan, De-An Guo. Biotransformation of gambogenic acid by Chaetomium globosum CICC 2445. Natural product communications. 2012 Feb; 7(2):197-8. doi: ". [PMID: 22474955]
  • Hui Cheng, Jing-Jing Su, Jian-Ya Peng, Mei Wang, Xun-Cui Wang, Feng-Gen Yan, Xiao-Shan Wang, Qing-Lin Li. Gambogenic acid inhibits proliferation of A549 cells through apoptosis inducing through up-regulation of the p38 MAPK cascade. Journal of Asian natural products research. 2011 Oct; 13(11):993-1002. doi: 10.1080/10286020.2011.605062. [PMID: 22007630]
  • Li Yang, Mei Wang, Hui Cheng, Qinglin Li. [Gambogenic acid inhibits proliferation of A549 cells through apoptosis-inducing]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 May; 36(9):1217-21. doi: 10.4268/cjcmm20110923. [PMID: 21842653]
  • Fenggen Yan, Mei Wang, Hui Chen, Jingjing Su, Xiaoshan Wang, Fei Wang, Lunzhu Xia, Qinglin Li. Gambogenic acid mediated apoptosis through the mitochondrial oxidative stress and inactivation of Akt signaling pathway in human nasopharyngeal carcinoma CNE-1 cells. European journal of pharmacology. 2011 Feb; 652(1-3):23-32. doi: 10.1016/j.ejphar.2010.11.018. [PMID: 21118682]
  • Qinglin Li, Hui Cheng, Guoqi Zhu, Li Yang, An Zhou, Xiaoshan Wang, Nianbai Fang, Lunzhu Xia, Jingjing Su, Mei Wang, Daiying Peng, Qi Xu. Gambogenic acid inhibits proliferation of A549 cells through apoptosis-inducing and cell cycle arresting. Biological & pharmaceutical bulletin. 2010; 33(3):415-20. doi: 10.1248/bpb.33.415. [PMID: 20190402]