Bufotalin (BioDeep_00000000042)

 

Secondary id: BioDeep_00000637427

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-3,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate

化学式: C26H36O6 (444.2512)
中文名称: 蟾毒它灵
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 55.79%

Reviewed

Last reviewed on 2024-06-29.

Cite this Page

Bufotalin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/bufotalin (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000000042). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(C1([H])2)CC(C4C(C=5)=COC(=O)C5)(C(CC(OC(C)=O)4)(C1([H])CCC([H])(C3)C2(C)CCC3O)O)C
InChI: InChI=1S/C26H36O6/c1-15(27)32-21-13-26(30)20-6-5-17-12-18(28)8-10-24(17,2)19(20)9-11-25(26,3)23(21)16-4-7-22(29)31-14-16/h4,7,14,17-21,23,28,30H,5-6,8-13H2,1-3H3

描述信息

Bufotalin is a steroid lactone. It is functionally related to a bufanolide.
Bufotalin is a natural product found in Bufo gargarizans, Duttaphrynus melanostictus

Bufotalin is a cardiotoxic bufanolide steroid, cardiac glycoside analogue, secreted by a number of toad species.[2][3] Bufotalin can be extracted from the skin parotoid glands of several types of toad.

Rhinella marina (Cane toad), Rhaebo guttatus (Smooth-sided toad), Bufo melanostictus (Asian toad), and Bufo bufo (common European toad) are sources of bufotalin.

Traditional medicine
Bufotalin is part of Ch'an Su, a traditional Chinese medicine used for cancer. It is also known as Venenum Bufonis or senso (Japanese).[5]

Toxicity
Specifically, in cats the lethal median dose is 0.13 mg/kg.[1] and in dogs is 0.36 mg/kg (intravenous).[6]

Knowing this it is advisable to monitor those functions continuously using an EKG. As there is no antidote against bufotalin all occurring symptoms need to be treated separately or if possible in combination with others. To increase the clearance theoretically, due to the similarities with digitoxin, cholestyramine, a bile salt, might help.[6] Recent animal studies have shown that taurine restores cardiac functions.[7]

Symptomatic measures include lignocaine, atropine and phenytoin for cardiac toxicity and intravenous potassium compounds to correct hyperkalaemia from its effect on the Na+/K+ ATPase pump.[6]

Pharmacology and mechanism of action
After a single intravenous injection, bufotalin gets quickly distributed and eliminated from the blood plasma with a half-time of 28.6 minutes and a MRT of 14.7 min. After 30 minutes after an administration of bufotalin, the concentrations within the brain and lungs are significantly higher than those in blood and other tissues.[8] It also increases cancer cell's susceptibility to apoptosis via TNF-α signalling by the BH3 interacting domain death agonist and STAT proteins.[9]

Bufotalin induces apoptosis in vitro in human hepatocellular carcinoma Hep 3B cells and might involve caspases and apoptosis inducing factor (AIF).[10] The use of bufotalin as a cancer treating compound is still in the experimental phase. It also arrests cell cycle at G(2)/M, by up- and down- regulation of several enzymes.

Bufotalin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=471-95-4 (retrieved 2024-06-29) (CAS RN: 471-95-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Bufotalin is a steroid lactone isolated from Venenum Bufonis with potently antitumor activities. Bufotalin induces cancer cell apoptosis and also induces endoplasmic reticulum (ER) stress activation[1][2].
Bufotalin is a steroid lactone isolated from Venenum Bufonis with potently antitumor activities. Bufotalin induces cancer cell apoptosis and also induces endoplasmic reticulum (ER) stress activation[1][2].

同义名列表

16 个代谢物同义名

[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-3,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate; (3S,5R,8R,9S,10S,13R,14S,16S,17R)-3,14-dihydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-16-yl acetate; Bufa-20,22-dienolide, 16-(acetyloxy)-3,14-dihydroxy-, (3beta,5beta,16beta)-; 5-beta-BUFA-20,22-DIENOLIDE, 3-beta,14,16-beta-TRIHYDROXY-, 16-ACETATE; 3.BETA.,14,16.BETA.-TRIHYDROXY-5.BETA.-BUFA-20,22-DIENOLIDE 16-ACETATE; 5beta-Bufa-20,22-dienolide, 3beta,14,16beta-trihydroxy-, 16-acetate; 3beta,14,16beta-Trihydroxy-5beta-bufa-20,22-dienolide 16-acetate; 3beta,14beta-dihydroxy-16beta-acetoxy-5beta-bufa-20,22-dienolide; 3beta-14,16beta-Trihydroxy-5beta-bufa-20,22-dienolide; VOZHMAYHYHEWBW-NVOOAVKYSA-N; Closantelsodium; BUFOTALIN [MI]; ST 26:5;O6; Bufotaline; Bufotalin; Bufotalin



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

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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)

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PharmGKB(0)

50 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 13 ATM, BCL2, BCL2L1, CASP3, CASP9, CDC25C, CDK1, CHEK2, CTNNB1, CYP3A4, FOXP3, MCL1, STAT3
Endoplasmic reticulum membrane 4 BCL2, CD4, CDK1, CYP3A4
Mitochondrion membrane 1 BCL2L1
Nucleus 13 ATM, BCL2, CASP3, CASP9, CDC25C, CDK1, CHEK2, CTNNB1, FOXP3, GPX4, MCL1, PARP1, STAT3
cytosol 13 ATM, BCL2, BCL2L1, CASP3, CASP9, CDC25C, CDK1, CTNNB1, FOXP3, GPX4, MCL1, PARP1, STAT3
nuclear body 1 PARP1
centrosome 4 ATM, BCL2L1, CDK1, CTNNB1
nucleoplasm 10 ATM, CASP3, CDC25C, CDK1, CHEK2, CTNNB1, FOXP3, MCL1, PARP1, STAT3
RNA polymerase II transcription regulator complex 1 STAT3
Cell membrane 3 CD4, CTNNB1, ITGAM
Cytoplasmic side 1 BCL2L1
lamellipodium 1 CTNNB1
Synapse 1 CTNNB1
cell cortex 1 CTNNB1
cell junction 1 CTNNB1
cell surface 1 ITGAM
glutamatergic synapse 2 CASP3, CTNNB1
Golgi apparatus 1 CHEK2
mitochondrial inner membrane 1 BCL2L1
neuronal cell body 1 CASP3
presynaptic membrane 1 CTNNB1
Cytoplasm, cytosol 2 BCL2L1, PARP1
plasma membrane 5 CD4, CTNNB1, IGHE, ITGAM, STAT3
synaptic vesicle membrane 1 BCL2L1
Membrane 7 BCL2, CDK1, CTNNB1, CYP3A4, ITGAM, MCL1, PARP1
basolateral plasma membrane 1 CTNNB1
extracellular exosome 4 CDK1, CTNNB1, GPX4, ITGAM
endoplasmic reticulum 2 BCL2, BCL2L1
extracellular space 4 CSHL1, IGHE, IL10, ITGAM
perinuclear region of cytoplasm 2 CDC25C, CTNNB1
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
mitochondrion 7 BCL2, BCL2L1, CASP9, CDK1, GPX4, MCL1, PARP1
protein-containing complex 6 BCL2, CASP9, CTNNB1, FOXP3, GPX4, PARP1
intracellular membrane-bounded organelle 2 ATM, CYP3A4
Microsome membrane 1 CYP3A4
postsynaptic density 1 CASP3
Single-pass type I membrane protein 3 CD4, IGHE, ITGAM
Secreted 2 CSHL1, IL10
extracellular region 3 CSHL1, IGHE, IL10
Mitochondrion outer membrane 2 BCL2, BCL2L1
Single-pass membrane protein 3 BCL2, BCL2L1, MCL1
mitochondrial outer membrane 3 BCL2, BCL2L1, MCL1
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 2 BCL2L1, CDK1
transcription regulator complex 3 CTNNB1, PARP1, STAT3
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 3 ATM, BCL2L1, CDK1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 2 BCL2, BCL2L1
Bcl-2 family protein complex 3 BCL2, BCL2L1, MCL1
nuclear membrane 2 BCL2, BCL2L1
external side of plasma membrane 2 CD4, ITGAM
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
cytoplasmic vesicle 1 ATM
nucleolus 2 ATM, PARP1
Wnt signalosome 1 CTNNB1
midbody 1 CDK1
Early endosome 1 CD4
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
postsynaptic membrane 1 CTNNB1
Membrane raft 2 CD4, ITGAM
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 CTNNB1
focal adhesion 1 CTNNB1
spindle 1 ATM
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
Peroxisome matrix 1 ATM
peroxisomal matrix 1 ATM
PML body 1 CHEK2
mitochondrial intermembrane space 1 CDC25C
fascia adherens 1 CTNNB1
lateral plasma membrane 1 CTNNB1
chromatin 3 FOXP3, PARP1, STAT3
IgE immunoglobulin complex 1 IGHE
cell periphery 1 CTNNB1
mitotic spindle 1 CDK1
Chromosome 1 PARP1
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
Nucleus, nucleolus 1 PARP1
spindle pole 1 CTNNB1
nuclear replication fork 1 PARP1
chromosome, telomeric region 2 CDK1, PARP1
postsynaptic density, intracellular component 1 CTNNB1
microvillus membrane 1 CTNNB1
[Isoform 2]: Cell membrane 1 IGHE
site of double-strand break 2 ATM, PARP1
nuclear envelope 2 GPX4, PARP1
Endomembrane system 1 CTNNB1
myosin complex 1 MCL1
Nucleus, nucleoplasm 1 MCL1
specific granule membrane 1 ITGAM
tertiary granule membrane 1 ITGAM
euchromatin 1 CTNNB1
myelin sheath 1 BCL2
plasma membrane raft 1 ITGAM
endoplasmic reticulum lumen 1 CD4
extrinsic component of synaptic vesicle membrane 1 ATM
beta-catenin-TCF complex 1 CTNNB1
apoptosome 1 CASP9
presynaptic active zone cytoplasmic component 1 CTNNB1
clathrin-coated endocytic vesicle membrane 1 CD4
protein-DNA complex 2 CTNNB1, PARP1
spindle microtubule 1 CDK1
death-inducing signaling complex 1 CASP3
DNA repair complex 1 ATM
catenin complex 1 CTNNB1
site of DNA damage 1 PARP1
integrin complex 1 ITGAM
[Isoform 3]: Cell membrane 1 IGHE
cyclin-dependent protein kinase holoenzyme complex 1 CDK1
T cell receptor complex 1 CD4
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
integrin alphaM-beta2 complex 1 ITGAM
cyclin A1-CDK1 complex 1 CDK1
cyclin A2-CDK1 complex 1 CDK1
cyclin B1-CDK1 complex 1 CDK1
[Isoform Mitochondrial]: Mitochondrion 1 GPX4
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
BAD-BCL-2 complex 1 BCL2
beta-catenin-TCF7L2 complex 1 CTNNB1
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
[Isoform Cytoplasmic]: Cytoplasm 1 GPX4
caspase complex 1 CASP9
[Isoform Bcl-X(L)]: Mitochondrion inner membrane 1 BCL2L1


文献列表

  • Yi Wu, Jiahui Tian, Jialu Yang, Qian Peng, Zhengchun Wu, Rushi Liu, Mengjie Luo, Yilan Qiu, Ruiyun Cao. Bufotalin-loaded biomimetic Prussian blue nanoparticles for colorectal cancer chemo-photothermal ferroptosis therapy. Nanomedicine (London, England). 2024 Jan; 19(2):109-125. doi: 10.2217/nnm-2023-0293. [PMID: 38197393]
  • Wen Zhang, Baoping Jiang, Yunxin Liu, Li Xu, Meng Wan. Bufotalin induces ferroptosis in non-small cell lung cancer cells by facilitating the ubiquitination and degradation of GPX4. Free radical biology & medicine. 2022 02; 180(?):75-84. doi: 10.1016/j.freeradbiomed.2022.01.009. [PMID: 35038550]
  • Candelario Rodriguez, Roberto Ibáñez, Luis Mojica, Michelle Ng, Carmenza Spadafora, Armando A Durant-Archibold, Marcelino Gutiérrez. Bufadienolides from the Skin Secretions of the Neotropical Toad Rhinella alata (Anura: Bufonidae): Antiprotozoal Activity against Trypanosoma cruzi. Molecules (Basel, Switzerland). 2021 Jul; 26(14):. doi: 10.3390/molecules26144217. [PMID: 34299492]
  • Yang Huang, Guangxia Yang, Jing Fei, Yingyi Wu, Juzhen Yan. Bufotalin ameliorates experimental Sjögren's syndrome development by inhibiting Th17 generation. Naunyn-Schmiedeberg's archives of pharmacology. 2020 10; 393(10):1977-1985. doi: 10.1007/s00210-020-01817-1. [PMID: 31950221]
  • Zhaohai Pan, Chuanjun Qu, Ying Chen, Xiaoyu Chen, Xiaona Liu, Wenjin Hao, Wenjuan Xu, Lei Ye, Peng Lu, Defang Li, Qiusheng Zheng. Bufotalin induces cell cycle arrest and cell apoptosis in human malignant melanoma A375 cells. Oncology reports. 2019 Apr; 41(4):2409-2417. doi: 10.3892/or.2019.7032. [PMID: 30816542]
  • Hai-Yan Tian, Shi-Lin Luo, Jun-Shan Liu, Lei Wang, Ying Wang, Dong-Mei Zhang, Xiao-Qi Zhang, Ren-Wang Jiang, Wen-Cai Ye. C23 steroids from the venom of Bufo bufo gargarizans. Journal of natural products. 2013 Oct; 76(10):1842-7. doi: 10.1021/np400174f. [PMID: 24050254]
  • Dong-Mei Zhang, Jun-Shan Liu, Ming-Kuen Tang, Anita Yiu, Hui-hui Cao, Lei Jiang, Judy Yuet-Wa Chan, Hai-Yan Tian, Kwok-Pui Fung, Wen-Cai Ye. Bufotalin from Venenum Bufonis inhibits growth of multidrug resistant HepG2 cells through G2/M cell cycle arrest and apoptosis. European journal of pharmacology. 2012 Oct; 692(1-3):19-28. doi: 10.1016/j.ejphar.2012.06.045. [PMID: 22841670]
  • Pei-Hao Yin, Xuan Liu, Yan-Yan Qiu, Jian-feng Cai, Jian-min Qin, Hui-Rong Zhu, Qi Li. Anti-tumor activity and apoptosis-regulation mechanisms of bufalin in various cancers: new hope for cancer patients. Asian Pacific journal of cancer prevention : APJCP. 2012; 13(11):5339-43. doi: 10.7314/apjcp.2012.13.11.5339. [PMID: 23317181]
  • 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]
  • Yinhui Dong, Shutao Yin, Jinghua Li, Cheng Jiang, Min Ye, Hongbo Hu. Bufadienolide compounds sensitize human breast cancer cells to TRAIL-induced apoptosis via inhibition of STAT3/Mcl-1 pathway. Apoptosis : an international journal on programmed cell death. 2011 Apr; 16(4):394-403. doi: 10.1007/s10495-011-0573-5. [PMID: 21259053]
  • Chui-liang Yu, Hui-min Hou. Plasma pharmacokinetics and tissue distribution of bufotalin in mice following single-bolus injection and constant-rate infusion of bufotalin solution. European journal of drug metabolism and pharmacokinetics. 2011 Jan; 35(3-4):115-21. doi: 10.1007/s13318-010-0017-6. [PMID: 21302038]
  • 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]
  • 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]
  • Chun-Li Su, Ting-Yu Lin, Chun-Nan Lin, Shen-Jeu Won. Involvement of caspases and apoptosis-inducing factor in bufotalin-induced apoptosis of Hep 3B cells. Journal of agricultural and food chemistry. 2009 Jan; 57(1):55-61. doi: 10.1021/jf802769g. [PMID: 19055367]
  • Wen Xu, Heng Luo, Yaping Zhang, Lei Shan, Haiyun Li, Ming Yang, Runhui Liu, Weidong Zhang. Simultaneous determination of five main active bufadienolides of Chan Su in rat plasma by liquid chromatography tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Nov; 859(2):157-63. doi: 10.1016/j.jchromb.2007.09.026. [PMID: 17928276]
  • 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]
  • RAYMOND-HAMET. [Toxicity of orally administered bufotalin]. Comptes rendus des seances de la Societe de biologie et de ses filiales. 1958; 152(4):571-4. doi: ". [PMID: 13597344]