Bigelovin (BioDeep_00000395517)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(3ar,4s,4ar,7ar,8r,9as)-4a,8-Dimethyl-3-Methylidene-2,5-Dioxo-2,3,3a,4,4a,5,7a,8,9,9a-Decahydroazuleno[6,5-B]furan-4-Yl Acetate

化学式: C17H20O5 (304.1311)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=C1C(=O)O[C@H]2C[C@@H](C)[C@@H]3C=CC(=O)[C@@]3(C)[C@@H](OC(C)=O)[C@H]12
InChI: InChI=1S/C17H20O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8,11-12,14-15H,2,7H2,1,3-4H3/t8-,11+,12+,14-,15+,17+/m1/s1

描述信息

Bigelovin is a sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetoxy group at position 4. Isolated from Inula hupehensis, it exhibits antineoplastic activity. It has a role as an apoptosis inducer, an immunomodulator, an antineoplastic agent and a plant metabolite. It is an acetate ester, an organic heterotricyclic compound, a sesquiterpene lactone, a cyclic ketone and a gamma-lactone.
Bigelovin is a natural product found in Dittrichia graveolens, Inula hupehensis, and other organisms with data available.
A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetoxy group at position 4. Isolated from Inula hupehensis, it exhibits antineoplastic activity.
Bigelovin, a sesquiterpene lactone isolated from Inula hupehensis, is a selective retinoid X receptor α agonist. Bigelovin suppresses tumor growth through inducing apoptosis and autophagy via the inhibition of mTOR pathway regulated by ROS generation[1].

同义名列表

7 个代谢物同义名

(3ar,4s,4ar,7ar,8r,9as)-4a,8-Dimethyl-3-Methylidene-2,5-Dioxo-2,3,3a,4,4a,5,7a,8,9,9a-Decahydroazuleno[6,5-B]furan-4-Yl Acetate; [(3aS,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate; Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8alpha-dihydroxy-4-oxo-, 12,8-lactone, acetate; 6alpha,8alpha-dihydroxy-4-oxo-ambrosa-2,11(13)-dien-12-oic acid-12,8-lactone acetate; 6-O-acetylmexicanin; Bigelovin; 3ozj



数据库引用编号

9 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

17 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


文献列表

  • Bei Wang, Chun-Hui Nie, Jun Xu, Da-Long Wan, Xiao Xu, Jiang-Juan He. Bigelovin inhibits hepatocellular carcinoma cell growth and metastasis by regulating the MAPT-mediated Fas/FasL pathway. Neoplasma. 2023 Feb; ?(?):. doi: 10.4149/neo_2023_221125n1132. [PMID: 36812233]
  • Yuan Feng, Jun Xia, Xin Xu, Tong Zhao, Zhengzhi Tan, Qun Wang, Jun Wang, Jia Meng, Christopher Sanderson, Zhiliang Lu, Yili Yang. Sesquiterpene lactone Bigelovin induces apoptosis of colon cancer cells through inducing IKK-β degradation and suppressing nuclear factor kappa B activation. Anti-cancer drugs. 2021 06; 32(6):664-673. doi: 10.1097/cad.0000000000001073. [PMID: 33929997]
  • Mingyue Li, Grace Gar-Lee Yue, Li-Hua Song, Mao-Bo Huang, Julia Kin-Ming Lee, Stephen Kwok-Wing Tsui, Kwok-Pui Fung, Ning-Hua Tan, Clara Bik-San Lau. Natural small molecule bigelovin suppresses orthotopic colorectal tumor growth and inhibits colorectal cancer metastasis via IL6/STAT3 pathway. Biochemical pharmacology. 2018 04; 150(?):191-201. doi: 10.1016/j.bcp.2018.02.017. [PMID: 29454618]
  • Mingyue Li, Li-Hua Song, Grace Gar-Lee Yue, Julia Kin-Ming Lee, Li-Mei Zhao, Lin Li, Xunian Zhou, Stephen Kwok-Wing Tsui, Simon Siu-Man Ng, Kwok-Pui Fung, Ning-Hua Tan, Clara Bik-San Lau. Bigelovin triggered apoptosis in colorectal cancer in vitro and in vivo via upregulating death receptor 5 and reactive oxidative species. Scientific reports. 2017 02; 7(?):42176. doi: 10.1038/srep42176. [PMID: 28181527]
  • Makoto Inoue, Hiroki Tanabe, Ken-ichi Nakashima, Yukihiro Ishida, Hitoshi Kotani. Rexinoids isolated from Sophora tonkinensis with a gene expression profile distinct from the synthetic rexinoid bexarotene. Journal of natural products. 2014 Jul; 77(7):1670-7. doi: 10.1021/np5002016. [PMID: 24959987]
  • Jiang-Jiang Qin, Hui-Zi Jin, Ying Huang, Shou-De Zhang, Lei Shan, Sukesh Voruganti, Subhasree Nag, Wei Wang, Wei-Dong Zhang, Ruiwen Zhang. Selective cytotoxicity, inhibition of cell cycle progression, and induction of apoptosis in human breast cancer cells by sesquiterpenoids from Inula lineariifolia Turcz. European journal of medicinal chemistry. 2013 Oct; 68(?):473-481. doi: 10.1016/j.ejmech.2013.07.018. [PMID: 24044895]
  • Grace G L Yue, Ben C L Chan, Hin-Fai Kwok, Yuk-Lau Wong, Hoi-Wing Leung, Chang-Jiu Ji, Kwok-Pui Fung, Ping-Chung Leung, Ning-Hua Tan, Clara B S Lau. Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica. European journal of medicinal chemistry. 2013 Jan; 59(?):243-52. doi: 10.1016/j.ejmech.2012.11.029. [PMID: 23231968]
  • Haitao Zhang, Li Li, Lili Chen, Lihong Hu, Hualiang Jiang, Xu Shen. Structure basis of bigelovin as a selective RXR agonist with a distinct binding mode. Journal of molecular biology. 2011 Mar; 407(1):13-20. doi: 10.1016/j.jmb.2011.01.032. [PMID: 21262235]
  • Guang-Zhi Zeng, Ning-Hua Tan, Chang-Jiu Ji, Jun-Ting Fan, Huo-Qiang Huang, Hong-Jin Han, Guang-Biao Zhou. Apoptosis inducement of bigelovin from Inula helianthus-aquatica on human Leukemia U937 cells. Phytotherapy research : PTR. 2009 Jun; 23(6):885-91. doi: 10.1002/ptr.2671. [PMID: 19107858]