Cinobufotalin (BioDeep_00000011487)

 

Secondary id: BioDeep_00000177516, BioDeep_00001870893

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


(1R,2R,2aR,3aS,3bR,5aS,7S,9aR,9bS,11aR)-5a,7-dihydroxy-9a,11a-dimethyl-1-(2-oxo-2H-pyran-5-yl)hexadecahydronaphtho[1,2:6,7]indeno[1,7a-b]oxiren-2-yl acetate

化学式: C26H34O7 (458.2304414)
中文名称: 华蟾毒它灵, 华蟾素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 3.17%

分子结构信息

SMILES: C(OC(C5C(C=6)=COC(=O)C6)C(C(C52C)1C(C4)(C(C(C)(C(O)3C4)CCC(C3)O)(CC2)[H])[H])O1)(C)=O
InChI: InChI=1S/C26H34O7/c1-14(27)32-21-20(15-4-5-19(29)31-13-15)24(3)10-7-17-18(26(24)22(21)33-26)8-11-25(30)12-16(28)6-9-23(17,25)2/h4-5,13,16-18,20-22,28,30H,6-12H2,1-3H3/t16-,17-,18+,20-,21+,22+,23+,24+,25-,26+/m0/s1

描述信息

Cinobufotalin is a natural product found in Bufo and Bufo bufo with data available.
Cinobufotalin is a bufadienolide isolated from toad venom and utilized in traditional Chinese medicine (TCM) for its cardiotonic, diuretic and hemostatic effects, with potential cytotoxic and antineoplastic activities. Upon administration and although the exact mechanism of action(s) (MoAs) through which this agent exerts its effects have yet to be fully discovered, cinobufotalin causes DNA fragmentation, decreases mitochondrial membrane potential (MMP), increases intracellular calcium (Ca2+) ion concentrations and reactive oxygen species (ROS) production, upregulates Fas protein and activates cytochrome C, various caspases, Bid and Bax. This causes cell cycle arrest, induces apoptosis and inhibits tumor cell growth and survival. In addition, cinobufotalin inhibits the activity of sphingosine kinase 1 (SphK1) and induces pro-apoptotic ceramide production, which further promotes tumor cell apoptosis. Cinobufotalin also induces mitochondrial protein cyclophilin D (Cyp-D)-dependent opening of the mitochondrial permeability transition pore (mPTP), which may contribute to cinobufotalin-induced non-apoptotic death of certain tumor cells.
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002018 - Bufanolides
Cinobufotalin is a cardiotonic steroids or bufadienolides, is extracted from the skin secretions of the giant toads. Cinobufotalin has been used as a cardiotonic, diuretic and a hemostatic agent, Cinobufotalin is also a potential anti-lung cancer agent[1].

同义名列表

20 个代谢物同义名

Cinobufotalin; (1R,2R,2aR,3aS,3bR,5aS,7S,9aR,9bS,11aR)-5a,7-dihydroxy-9a,11a-dimethyl-1-(2-oxo-2H-pyran-5-yl)hexadecahydronaphtho[1,2:6,7]indeno[1,7a-b]oxiren-2-yl acetate; [(1R,2S,4R,5R,6R,7R,10S,11R,14S,16S)-14,16-dihydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl] acetate; Bufa-20,22-dienolide, 16-(acetyloxy)-14,15-epoxy-3,5-dihydroxy-, (3.beta.,5.beta.,15.beta.,16.beta.)-; (3.BETA.,5.BETA.,15.BETA.,16.BETA.)-16-(ACETYLOXY)-14,15-EPOXY-3,5-DIHYDROXYBUFA-20,22-DIENOLIDE; Bufa-20,22-dienolide, 16-(acetyloxy)-14,15-epoxy-3,5-dihydroxy-, (3beta,5beta,15beta,16beta)-; Bufa-20, 16-(acetyloxy)-14,15-epoxy-3,5-dihydroxy-, (3.beta.,5.beta.,15.beta.,16.beta.)-; 14,15.BETA.-EPOXY-3.BETA.,5,16.BETA.-TRIHYDROXY-5.BETA.-BUFA-20,22-DIENOLIDE 16-ACETATE; 5-beta-Bufa-20,22-dienolide, 14,15-beta-epoxy-3-beta,5,16-beta-trihydroxy-, 16-acetate; 3beta,5beta-dihydroxy-16beta-acetoxy-14beta,15beta-epoxy-bufa-20,22-dienolide; 5.beta.-Bufa-20, 14,15.beta.-epoxy-3.beta.,5,16.beta.-trihydroxy-, 16-acetate; Cinobufagin metabolite m-2; CINOBUFOTALIN [WHO-DD]; CINOBUFOTALIN [MI]; UNII-L0QBZ37386; CINOBUFOTLIN; L0QBZ37386; ST 26:6;O7; CID 14203; Cinobufotalin



数据库引用编号

22 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

  • Lei Yang, Bihui Bai, Hongyu Chen, Tielian Li, Mingting Wang, Xuedong Zhu. Cinobufotalin effect and mechanism on serum MMP-2, MMP-9, Beclin1, LC3-II in advanced NSCLC patients. Cellular and molecular biology (Noisy-le-Grand, France). 2023 Dec; 69(15):58-62. doi: 10.14715/cmb/2023.69.15.9. [PMID: 38279494]
  • Jia-Hao Liu, Hui-Ling Yang, Shu-Ting Deng, Zhe Hu, Wei-Feng Chen, Wei-Wei Yan, Ren-Tao Hou, Yong-Hao Li, Rui-Ting Xian, Ying-Ying Xie, Yun Su, Li-Yang Wu, Ping Xu, Zhi-Bo Zhu, Xiong Liu, Yu-Ling Deng, Yu-Bing Wang, Zhen Liu, Wei-Yi Fang. The small molecule chemical compound cinobufotalin attenuates resistance to DDP by inducing ENKUR expression to suppress MYH9-mediated c-Myc deubiquitination in lung adenocarcinoma. Acta pharmacologica Sinica. 2022 Oct; 43(10):2687-2695. doi: 10.1038/s41401-022-00890-x. [PMID: 35296779]
  • Riyu Chen, Zeyi Guan, Xianxing Zhong, Wenzheng Zhang, Ya Zhang. Network Pharmacology Prediction: The Possible Mechanisms of Cinobufotalin against Osteosarcoma. Computational and mathematical methods in medicine. 2022; 2022(?):3197402. doi: 10.1155/2022/3197402. [PMID: 35069780]
  • Rentao Hou, Yonghao Li, Xiaojun Luo, Wan Zhang, Huiling Yang, Yewei Zhang, Jiahao Liu, Shaohua Liu, Siyuan Han, Chen Liu, Yun Huang, Zhen Liu, Aimin Li, Weiyi Fang. ENKUR expression induced by chemically synthesized cinobufotalin suppresses malignant activities of hepatocellular carcinoma by modulating β-catenin/c-Jun/MYH9/USP7/c-Myc axis. International journal of biological sciences. 2022; 18(6):2553-2567. doi: 10.7150/ijbs.67476. [PMID: 35414777]
  • Huannan Meng, Mengqin Shen, Jiajin Li, Ruixue Zhang, Xi Li, Li Zhao, Gang Huang, Jianjun Liu. Novel SREBP1 inhibitor cinobufotalin suppresses proliferation of hepatocellular carcinoma by targeting lipogenesis. European journal of pharmacology. 2021 Sep; 906(?):174280. doi: 10.1016/j.ejphar.2021.174280. [PMID: 34174265]
  • Cong Li, Hanyu Guo, Chao Wang, Wengang Zhan, Qijia Tan, Caijun Xie, Aruna Sharma, Hari Shanker Sharma, Lin Chen, Zhiqiang Zhang. Network pharmacological mechanism of Cinobufotalin against glioma. Progress in brain research. 2021; 265(?):119-137. doi: 10.1016/bs.pbr.2021.06.001. [PMID: 34560920]
  • Yiyi Liu, Qingping Jiang, Xiong Liu, Xian Lin, ZiBo Tang, Chen Liu, Jin Zhou, Mengyang Zhao, Xin Li, Zhao Cheng, Libo Li, Yingying Xie, Zhen Liu, Weiyi Fang. Cinobufotalin powerfully reversed EBV-miR-BART22-induced cisplatin resistance via stimulating MAP2K4 to antagonize non-muscle myosin heavy chain IIA/glycogen synthase 3β/β-catenin signaling pathway. EBioMedicine. 2019 Oct; 48(?):386-404. doi: 10.1016/j.ebiom.2019.08.040. [PMID: 31594754]
  • Jie Li, Min-Hua Rong, Yi-Wu Dang, Rong-Quan He, Peng Lin, Hong Yang, Xiao-Jiao Li, Dan-Dan Xiong, Li-Jie Zhang, Hui Qin, Cai-Xia Feng, Xiao-Yi Chen, Jin-Cai Zhong, Jie Ma, Gang Chen. Differentially expressed gene profile and relevant pathways of the traditional Chinese medicine cinobufotalin on MCF‑7 breast cancer cells. Molecular medicine reports. 2019 May; 19(5):4256-4270. doi: 10.3892/mmr.2019.10062. [PMID: 30896874]
  • Heba Emam, Qing-Li Zhao, Yukihiro Furusawa, Alaa Refaat, Kanwal Ahmed, Makoto Kadowaki, Takashi Kondo. Apoptotic cell death by the novel natural compound, cinobufotalin. Chemico-biological interactions. 2012 Sep; 199(3):154-60. doi: 10.1016/j.cbi.2012.07.005. [PMID: 22898211]
  • Zongyun Li, Huimin Gao, Jinhua Wang, Ting Qu, Liangmian Chen, Zhimin Wang, Qiwei Zhang. [Inhibitory effect of total bufadienolides from toad venom against H22 tumor in mice and their metabolites]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Nov; 36(21):2987-93. doi: . [PMID: 22308689]
  • Xiao-Chi Ma, Jing Ning, Guang-Bo Ge, Si-Cheng Liang, Xiu-Li Wang, Bao-Jing Zhang, Shan-Shan Huang, Jing-Kui Li, Ling Yang. Comparative metabolism of cinobufagin in liver microsomes from mouse, rat, dog, minipig, monkey, and human. Drug metabolism and disposition: the biological fate of chemicals. 2011 Apr; 39(4):675-82. doi: 10.1124/dmd.110.036830. [PMID: 21205911]
  • Kun Feng, Huai-Jun Zhou, Ya-Li Hu. [Effect of cinobufotalin on growth of xenograft of endometrial carcinoma cell line ishikawa in nude mouse and its impact on RRM2 expression]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 2010 Nov; 30(11):1183-5. doi: . [PMID: 21275172]
  • Xiu Lan Xin, Junying Liu, Xiao Chi Ma, Qing Wei, Li Lv, Chang Yuan Wang, Ji Hong Yao, Jian Cui. Preparative separation of four major bufadienolides from the Chinese traditional medicine, Chansu, using high-speed counter-current chromatography. Natural product communications. 2010 Jul; 5(7):1031-4. doi: . [PMID: 20734934]
  • Jingkui Li, Xiaochi Ma, Fengyun Li, Jingkui Wang, Huirong Chen, Gang Wang, Xia Lv, Changkai Sun, Jingming Jia. Preparative separation and purification of bufadienolides from Chinese traditional medicine of ChanSu using high-speed counter-current chromatography. Journal of separation science. 2010 May; 33(9):1325-30. doi: 10.1002/jssc.200900782. [PMID: 20201046]
  • Ting-Ting Wang, Guo-Xing Xu. [Effect of cinobufagin on the expressions of bcl-2 mRNA and bax mRNA and the proliferation of lens epithelial cells]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 2009 Oct; 29(10):915-7. doi: ". [PMID: 20073224]
  • Xiao Chi Ma, Bao Jing Zhang, Xin Lan Xin, Shan Shan Huang, Sha Deng, Hou Li Zhang, Xiao Hong Shu, Yun Peng Diao, Jian Cui. Simultaneous quantification of seven major bufadienolides in three traditional Chinese medicinal preparations of chansu by HPLC-DAD. Natural product communications. 2009 Feb; 4(2):179-84. doi: . [PMID: 19370919]
  • Yan Liang, Ai-hua Liu, Song Qin, Jiang-hao Sun, Min Yang, Ping Li, De-an Guo. Simultaneous determination and pharmacokinetics of five bufadienolides in rat plasma after oral administration of Chansu extract by SPE-HPLC method. Journal of pharmaceutical and biomedical analysis. 2008 Feb; 46(3):442-8. doi: 10.1016/j.jpba.2007.11.001. [PMID: 18093784]
  • Xin Liu, Bao-jin Hua. [Effect of traditional Chinese medicine on quality of life and survival period in patients with progressive gastric cancer]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 2008 Feb; 28(2):105-7. doi: . [PMID: 18386568]
  • Kai Xu, Hai-Ying Luo, Liu-Ning Li. [Clinical study on comprehensive treatment of primary liver cancer mainly with chinese medicinal perfusion/embolization]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 2005 Apr; 25(4):299-302. doi: . [PMID: 15892270]
  • Olga A Akimova, Alexei Y Bagrov, Olga D Lopina, Alexey V Kamernitsky, Johanne Tremblay, Pavel Hamet, Sergei N Orlov. Cardiotonic steroids differentially affect intracellular Na+ and [Na+]i/[K+]i-independent signaling in C7-MDCK cells. The Journal of biological chemistry. 2005 Jan; 280(1):832-9. doi: 10.1074/jbc.m411011200. [PMID: 15494417]
  • T Nogawa, Y Kamano, A Yamashita, G R Pettit. Isolation and structure of five new cancer cell growth inhibitory bufadienolides from the Chinese traditional drug Ch'an Su. Journal of natural products. 2001 Sep; 64(9):1148-52. doi: 10.1021/np0101088. [PMID: 11575946]
  • A Dasgupta, L Emerson. Neutralization of cardiac toxins oleandrin, oleandrigenin, bufalin, and cinobufotalin by digibind: monitoring the effect by measuring free digitoxin concentrations. Life sciences. 1998; 63(9):781-8. doi: 10.1016/s0024-3205(98)00333-6. [PMID: 9740315]
  • Z Liu, X X Fu, N L Zhang. [Inhibitory effects of co-cinobufotalin oral liquor on hepatitis B in vitro]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 1996 Dec; 16(12):738-40. doi: . [PMID: 9772592]
  • X T Xu. [Clinical study on cinobufotalin in treating chronic hepatitis B virus carriers]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 1993 Aug; 13(8):473-5, 453. doi: ". [PMID: 8111200]
  • A A Brownlee, P Johnson, I H Mills. Actions of bufalin and cinobufotalin, two bufadienolides respectively more active and less active than ouabain, on ouabain binding and 86Rb uptake by human erythrocytes. Clinical science (London, England : 1979). 1990 Feb; 78(2):169-74. doi: 10.1042/cs0780169. [PMID: 2155744]