Arenobufagin (BioDeep_00000000039)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


5-[(3S,5R,8R,9S,10S,11S,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-12-oxo-2,3,4,5,6,7,8,9,11,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one

化学式: C24H32O6 (416.2198772)
中文名称: 沙蟾蜍精, 沙蟾毒精
谱图信息: 最多检出来源 Viridiplantae(otcml) 0.44%

分子结构信息

SMILES: CC12CCC(CC1CCC3C2C(C(=O)C4(C3(CCC4C5=COC(=O)C=C5)O)C)O)O
InChI: InChI=1S/C24H32O6/c1-22-9-7-15(25)11-14(22)4-5-17-19(22)20(27)21(28)23(2)16(8-10-24(17,23)29)13-3-6-18(26)30-12-13/h3,6,12,14-17,19-20,25,27,29H,4-5,7-11H2,1-2H3

描述信息

Arenobufagin is a natural product found in Bufo gargarizans, Bufotes viridis, and other organisms with data available.
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002018 - Bufanolides
Arenobufagin is a natural bufadienolide from toad venom; has potent antineoplastic activity against HCC HepG2 cells as well as corresponding multidrug-resistant HepG2/ADM cells. IC50 value: Target: in vitro: arenobufagin induced mitochondria-mediated apoptosis in HCC cells, with decreasing mitochondrial potential, as well as increasing Bax/Bcl-2 expression ratio, Bax translocation from cytosol to mitochondria. Arenobufagin also induced autophagy in HepG2/ADM cells. Autophagy-specific inhibitors (3-methyladenine, chloroquine and bafilomycin A1) or Beclin1 and Atg 5 small interfering RNAs (siRNAs) enhanced arenobufagin-induced apoptosis, indicating that arenobufagin-mediated autophagy may protect HepG2/ADM cells from undergoing apoptotic cell death [1]. arenobufagin inhibited vascular endothelial growth factor (VEGF)-induced viability, migration, invasion and tube formation in human umbilical vein endothelial cells (HUVECs) in vitro [2]. Arenobufagin blocked the Na+/K+ pump current in a dose-dependent manner with a half-maximal concentration of 0.29 microM and a Hill coefficient of 1.1 [3]. in vivo: arenobufagin inhibited the growth of HepG2/ADM xenograft tumors, which were associated with poly (ADP-ribose) polymerase cleavage, light chain 3-II activation and mTOR inhibition [1]. Arenobufagin also suppressed sprouting formation from VEGF-treated aortic rings in an ex vivo model [2].
Arenobufagin is a natural bufadienolide from toad venom; has potent antineoplastic activity against HCC HepG2 cells as well as corresponding multidrug-resistant HepG2/ADM cells. IC50 value: Target: in vitro: arenobufagin induced mitochondria-mediated apoptosis in HCC cells, with decreasing mitochondrial potential, as well as increasing Bax/Bcl-2 expression ratio, Bax translocation from cytosol to mitochondria. Arenobufagin also induced autophagy in HepG2/ADM cells. Autophagy-specific inhibitors (3-methyladenine, chloroquine and bafilomycin A1) or Beclin1 and Atg 5 small interfering RNAs (siRNAs) enhanced arenobufagin-induced apoptosis, indicating that arenobufagin-mediated autophagy may protect HepG2/ADM cells from undergoing apoptotic cell death [1]. arenobufagin inhibited vascular endothelial growth factor (VEGF)-induced viability, migration, invasion and tube formation in human umbilical vein endothelial cells (HUVECs) in vitro [2]. Arenobufagin blocked the Na+/K+ pump current in a dose-dependent manner with a half-maximal concentration of 0.29 microM and a Hill coefficient of 1.1 [3]. in vivo: arenobufagin inhibited the growth of HepG2/ADM xenograft tumors, which were associated with poly (ADP-ribose) polymerase cleavage, light chain 3-II activation and mTOR inhibition [1]. Arenobufagin also suppressed sprouting formation from VEGF-treated aortic rings in an ex vivo model [2].

同义名列表

14 个代谢物同义名

5-[(3S,5R,8R,9S,10S,11S,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-12-oxo-2,3,4,5,6,7,8,9,11,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one; 5-((3S,5R,8R,9S,10S,11S,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-one; Bufa-20,22-dienolide, 3,11,14-trihydroxy-12-oxo-, (3.beta.,5.beta.,11.alpha.)-; Bufa-20,22-dienolide, 3,11,14-trihydroxy-12-oxo- (3-beta,5-beta,11-alpha)-; (3.BETA.,5.BETA.,11.ALPHA.)-3,11,14-TRIHYDROXY-12-OXOBUFA-20,22-DIENOLIDE; 5.beta.-Bufa-20,22-dienolide, 3.beta.,11.alpha.,14-trihydroxy-12-oxo-; 5-beta-BUFA-20,22-DIENOLIDE, 12-OXO-3-beta,11-alpha,14-TRIHYDROXY-; 12-Oxo-3-beta,11-alpha,14-trihydroxy-5-beta-bufa-20,22-dienolide; 3,11,14-trihydroxy-12-oxo-bufa-20,22-dienolide; UNII-27R42QLM25; Arenobufogenin; Arenobufagin; 27R42QLM25; 3,11,14-Trihydroxy-12-oxobufa-20,22-dienolide #



数据库引用编号

16 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)

41 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

  • Yueyue Li, Yang Chen, Cheng Zhao, Yuting Yang, Mei Zhang, Hui Cheng, Qinglin Li, Meng Wang. Arenobufagin modulation of PCSK9-mediated cholesterol metabolism induces tumor-associated macrophages polarisation to inhibit hepatocellular carcinoma progression. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Jun; 128(?):155532. doi: 10.1016/j.phymed.2024.155532. [PMID: 38493722]
  • Zhihao Shang, Yiping Fan, Songyang Xi, Shang Zhang, Weixing Shen, Lihuiping Tao, Changliang Xu, Jiani Tan, Minmin Fan, Hongyue Ma, Yueyang Lai, Dongdong Sun, Haibo Cheng. Arenobufagin enhances T-cell anti-tumor immunity in colorectal cancer by modulating HSP90β accessibility. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Jun; 128(?):155497. doi: 10.1016/j.phymed.2024.155497. [PMID: 38640855]
  • Qiang Dong, Gulmira Turdu, Haji Akber Aisa, Abulimiti Yili. Arenobufagin, isolated from Bufo viridis toad venom, inhibits A549 cells proliferation by inducing apoptosis and G2/M cell cycle arrest. Toxicon : official journal of the International Society on Toxinology. 2024 Mar; 240(?):107641. doi: 10.1016/j.toxicon.2024.107641. [PMID: 38331108]
  • Jiao Long, Wenjun Wang, Jing Chu, Yueyue Li, Meng Wang, Jingjing Su, Yuting Yang, GuoKai Wang, Qinglin Li, Hui Cheng. Overexpression of Nrf2 reverses ferroptosis induced by Arenobufagin in gastric cancer. Toxicology and applied pharmacology. 2024 Jan; ?(?):116842. doi: 10.1016/j.taap.2024.116842. [PMID: 38307257]
  • Yang Jiaying, Sun Bo, Wei Xiaolu, Zhou Yanyan, Wang Hongjie, Si Nan, Gao Bo, Wang Linna, Zhang Yan, Gao Wenya, Luo Keke, Jiang Shan, Luo Chuan, Zhao Yu, Zhao Qinghe, Zhao Haiyu. Arenobufagin-loaded PEG-PLA nanoparticles for reducing toxicity and enhancing cancer therapy. Drug delivery. 2023 Dec; 30(1):2177362. doi: 10.1080/10717544.2023.2177362. [PMID: 36772846]
  • Wenmin Tang, Yanming Zhang, Keli Yang, Jianjiang Ma, Lian Dong, Chen Wu, Rongxue Lv, Chuanhao Wang, Chuan Luo, Huojun Zhang, Zhenyuan Miao, Yuelin Wu. Discovery of Novel 3,11-Bispeptide Ester Arenobufagin Derivatives with Potential in Vivo Antitumor Activity and Reduced Cardiotoxicity. Chemistry & biodiversity. 2023 Feb; 20(2):e202200911. doi: 10.1002/cbdv.202200911. [PMID: 36627123]
  • Li-Juan Deng, Yu-He Lei, Jing-Yu Quan, Bao-Jing Li, Dong-Mei Zhang, Hai-Yan Tian, Ye Chen, En-Xin Zhang, Lei Chen, Wen-Cai Ye, Wei-Min Ning, Lin-Zhong Yu, Jun-Shan Liu. 1β-OH-arenobufagin induces mitochondrial apoptosis in hepatocellular carcinoma through the suppression of mTOR signaling pathway. Journal of ethnopharmacology. 2021 Feb; 266(?):113443. doi: 10.1016/j.jep.2020.113443. [PMID: 33022344]
  • Li-Juan Zhao, Hai-Yu Zhao, Xiao-Lu Wei, Fei-Fei Guo, Jun-Ying Wei, Hong-Jie Wang, Jian Yang, Zhi-Gang Yang, Nan Si, Bao-Lin Bian. The lipid homeostasis regulation study of arenobufagin in zebrafish HepG2 xenograft model and HepG2 cells using integrated lipidomics-proteomics approach. Journal of ethnopharmacology. 2020 Oct; 260(?):112943. doi: 10.1016/j.jep.2020.112943. [PMID: 32422359]
  • Liang Ma, Yindi Zhu, Sheng Fang, Hongyan Long, Xiang Liu, Zi Liu. Arenobufagin Induces Apoptotic Cell Death in Human Non-Small-Cell Lung Cancer Cells via the Noxa-Related Pathway. Molecules (Basel, Switzerland). 2017 Sep; 22(9):. doi: 10.3390/molecules22091525. [PMID: 28892004]
  • Liping Chen, Weiqian Mai, Minfeng Chen, Jianyang Hu, Zhenjian Zhuo, Xueping Lei, Lijuan Deng, Junshan Liu, Nan Yao, Maohua Huang, Yinghui Peng, Wencai Ye, Dongmei Zhang. Arenobufagin inhibits prostate cancer epithelial-mesenchymal transition and metastasis by down-regulating β-catenin. Pharmacological research. 2017 Sep; 123(?):130-142. doi: 10.1016/j.phrs.2017.07.009. [PMID: 28712972]
  • Yujie Feng, Chao Wang, Xiangge Tian, Xiaokui Huo, Lei Feng, Chengpeng Sun, Guangbo Ge, Ling Yang, Jing Ning, Xiaochi Ma. In vitro phase I metabolism of gamabufotalin and arenobufagin: Reveal the effect of substituent group on metabolic stability. Fitoterapia. 2017 Sep; 121(?):38-45. doi: 10.1016/j.fitote.2017.06.022. [PMID: 28666968]
  • Li-Juan Deng, Long-Hai Wang, Cheng-Kang Peng, Yi-Bin Li, Mao-Hua Huang, Min-Feng Chen, Xue-Ping Lei, Ming Qi, Yun Cen, Wen-Cai Ye, Dong-Mei Zhang, Wei-Min Chen. Fibroblast Activation Protein α Activated Tripeptide Bufadienolide Antitumor Prodrug with Reduced Cardiotoxicity. Journal of medicinal chemistry. 2017 07; 60(13):5320-5333. doi: 10.1021/acs.jmedchem.6b01755. [PMID: 28595013]
  • Xue Yuan, Qian Xie, Keyu Su, Zhijie Li, Dong Dong, Baojian Wu. Systemic delivery of the anticancer agent arenobufagin using polymeric nanomicelles. International journal of nanomedicine. 2017; 12(?):4981-4989. doi: 10.2147/ijn.s139128. [PMID: 28761339]
  • Qingxi Yue, Hong Zhen, Ming Huang, Xi Zheng, Lixing Feng, Baohong Jiang, Min Yang, Wanying Wu, Xuan Liu, Dean Guo. Proteasome Inhibition Contributed to the Cytotoxicity of Arenobufagin after Its Binding with Na, K-ATPase in Human Cervical Carcinoma HeLa Cells. PloS one. 2016; 11(7):e0159034. doi: 10.1371/journal.pone.0159034. [PMID: 27428326]
  • Li-Juan Deng, Qun-Long Peng, Long-Hai Wang, Jun Xu, Jun-Shan Liu, Ying-Jie Li, Zhen-Jian Zhuo, Liang-Liang Bai, Li-Ping Hu, Wei-Min Chen, Wen-Cai Ye, Dong-Mei Zhang. Arenobufagin intercalates with DNA leading to G2 cell cycle arrest via ATM/ATR pathway. Oncotarget. 2015 Oct; 6(33):34258-75. doi: 10.18632/oncotarget.5545. [PMID: 26485758]
  • Wenjuan Xu, Linlin Jing, Quanshi Wang, Chung-Chih Lin, Xiaoting Chen, Jianxin Diao, Yuanliang Liu, Xuegang Sun. Bax-PGAM5L-Drp1 complex is required for intrinsic apoptosis execution. Oncotarget. 2015 Oct; 6(30):30017-34. doi: 10.18632/oncotarget.5013. [PMID: 26356820]
  • Guoliang Li, Weili Han, Wei Jiang, Dongmei Zhang, Wencai Ye, Xiaojia Chen, Ande Ma. Quantitative determination of arenobufagin in rat plasma by ultra fast liquid chromatography-tandem mass spectrometry and its application in a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Nov; 939(?):86-91. doi: 10.1016/j.jchromb.2013.09.019. [PMID: 24113236]
  • Dong-Mei Zhang, Jun-Shan Liu, Li-Juan Deng, Min-Feng Chen, Anita Yiu, Hui-Hui Cao, Hai-Yan Tian, Kwok-Pui Fung, Hiroshi Kurihara, Jing-Xuan Pan, Wen-Cai Ye. Arenobufagin, a natural bufadienolide from toad venom, induces apoptosis and autophagy in human hepatocellular carcinoma cells through inhibition of PI3K/Akt/mTOR pathway. Carcinogenesis. 2013 Jun; 34(6):1331-42. doi: 10.1093/carcin/bgt060. [PMID: 23393227]
  • Manmei Li, Shuai Wu, Zhong Liu, Wei Zhang, Jing Xu, Ying Wang, Junshan Liu, Dongmei Zhang, Haiyan Tian, Yaolan Li, Wencai Ye. Arenobufagin, a bufadienolide compound from toad venom, inhibits VEGF-mediated angiogenesis through suppression of VEGFR-2 signaling pathway. Biochemical pharmacology. 2012 May; 83(9):1251-60. doi: 10.1016/j.bcp.2012.01.023. [PMID: 22305746]
  • Guo-di Lu, Jing Zhou, Hong-Yue Ma, De-Kang Wu, Da-Wei Qian, Yu-Ping Tang, Ming Hong, Yong-Qing Hua, Jing-Ao Duan. [Analysis on competitive interaction between arenobufagin and verapamil hydrochloride with serum albumin]. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2011 Jul; 9(7):768-74. doi: 10.3736/jcim20110711. [PMID: 21749828]
  • Jun-shan Liu, Dong-mei Zhang, Min-feng Chen, Man-mei Li, Qing-dao Luo, Hiroshi Kurihara, Wen-cai Ye. [Anti-angiogenetic effect of arenobufagin in vitro and in vivo]. Yao xue xue bao = Acta pharmaceutica Sinica. 2011 May; 46(5):527-33. doi: . [PMID: 21800539]