LIPID MAPS

Structure Database (LMSD)

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Common Name

Bufotalin

Systematic Name

3β,14β-dihydroxy-16β-acetoxy-5β-bufa-20,22-dienolide

Synonyms

Bufotaline

LM ID

LMST01130023

Formula

C₂₆H₃₆O₆

Exact Mass

Calculate m/z

444.251191

Sum Composition

ST 26:5;O6

Status

Curated

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View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Bufotalin is a bufadienolide that has been found in toad (B. asiaticus) venom and has cytotoxic and immunomodulatory activities.^1,2 It induces cell cycle arrest at the G1 phase and apoptosis in Hep3B cells when used at concentrations ranging from 0.13 to 1.13 µM.¹ Bufotalin (100 µg/kg) reduces autoantibody production, serum levels of TNF-α, IL-1β, IFN-γ, IL-22, and IL-17, and the number of splenic and lymph node Th17 cells, as well as increases saliva flow rates in a mouse model of experimental Sjörgren’s syndrome, an autoimmune disease characterized by the reduced secretion of exocrine glands.² It also induces lethality in anesthetized dogs (LD50 = 0.36 mg/kg).³

This information has been provided by Cayman Chemical

References

1. Su, C.-L., Lin, T.-Y., Lin, C.-N., et al. Involvement of caspases and apoptosis-inducing factor in bufotalin-induced apoptosis of Hep 3B cells. J. Agric. Food Chem. 57(1), 55-61 (2009).

2. Huang, Y., Yang, G., Fei, J., et al. Bufotalin ameliorates experimental Sjögren's syndrome development by inhibiting Th17 generation. Naunyn-Schmiedeberg's Arch. Pharmacol. 393(10), 1977-1985 (2020).

3. Hamet, R. Toxicity of bufotalin administered by oral route. Compt. Rend. Soc. Biol. 152, 571-574 (1958).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Duttaphrynus melanostictus (#30335)

Amphibia (#8292)

Isolation and structure of five new cancer cell growth inhibitory bufadienolides from the Chinese traditional drug Ch'an Su.,
J Nat Prod, 2001

Pubmed ID: 11575946

DOI: 10.1021/np0101088

String Representations

InChiKey (Click to copy)

VOZHMAYHYHEWBW-NVOOAVKYSA-N

InChi (Click to copy)

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/t17-,18+,19+,20-,21+,23+,24+,25-,26+/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])(C5=COC(=O)C=C5)[C@@H](OC(=O)C)C[C@]4(O)[C@]3([H])CC[C@]2([H])C[C@@H](O)C1