Bufalin

Last updated
Bufalin
Bufalin.svg
Names
IUPAC name
3β,14-Dihydroxy-5β-bufa-20,22-dienolide
Systematic IUPAC name
4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2H-pyran-2-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.150.073 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1
    Key: QEEBRPGZBVVINN-BMPKRDENSA-N
  • C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@@]3(CC[C@@H]4c5ccc(=O)oc5)O)C)O
Properties
C24H34O4
Molar mass 386.532 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-skull.svg
Danger
H300
P264, P270, P301+P310, P321, P330, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bufalin is a cardiotonic steroid toxin [1] originally isolated from Chinese toad venom, which is a component of some traditional Chinese medicines. [2] [3]

Research

Bufalin has in vitro antitumor effects against various malignant cell lines, including hepatocellular [4] and lung carcinoma. [5] However, as with other bufadienolides, its potential use is hampered by its cardiotoxicity. [6]

Related Research Articles

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5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine) or O-methyl-bufotenin is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Colorado River toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, the power, bufo, and toad venom.

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<span class="mw-page-title-main">Bufotoxin</span> Class of chemical compounds

Bufotoxins are a family of toxic steroid lactones or substituted tryptamines of which some are toxic. They occur in the parotoid glands, skin, and poison of many toads and other amphibians, and in some plants and mushrooms. The exact composition varies greatly with the specific source of the toxin. It can contain 5-MeO-DMT, bufagins, bufalin, bufotalin, bufotenin, bufothionine, dehydrobufotenine, epinephrine, norepinephrine, and serotonin. Some authors have also used the term bufotoxin to describe the conjugate of a bufagin with suberylarginine.

Bufagin is a toxic steroid C24H34O5 obtained from toad's milk, the poisonous secretion of a skin gland on the back of the neck of a large toad (Rhinella marina, synonym Bufo marinus, the cane toad). The toad produces this secretion when it is injured, scared or provoked. Bufagin resembles chemical substances from digitalis in physiological activity and chemical structure.

<span class="mw-page-title-main">Bufotalin</span> Chemical compound

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

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<span class="mw-page-title-main">Sodium-coupled monocarboxylate transporter 1</span> Protein-coding gene in the species Homo sapiens

Sodium-coupled monocarboxylate transporter 1 (i.e., SMCT1) and sodium-coupled monocarboxylate transporter 2 (i.e., SMCT2) are plasma membrane transport proteins in the solute carrier family. They transport sodium cations in association with the anionic forms (see conjugated base) of certain short-chain fatty acids (i.e., SC-FAs) through the plasma membrane from the outside to the inside of cells. For example, propionic acid (i.e., CH
3
CH
2
CO
2
H
) in its anionic "propionate" form (i.e., CH
3
CH
2
CO
2
) along with sodium cations (i.e., Na+) are co-transported from the extracellular fluid into a SMCT1-epxressing cell's cytoplasm. Monocarboxylate transporters (MCTs) are also transport proteins in the solute carrier family. They co-transport the anionic forms of various compounds into cells in association with proton cations (i.e. H+). Four of the 14 MCTs, i.e. SLC16A1 (i.e., MCT1), SLC16A7 (i.e., MCT22), SLC16A8 (i.e., MCT3), and SLC16A3 (i.e., MCT4), transport some of the same SC-FAs anions that the SMCTs transport into cells. SC-FAs do diffuse into cells independently of transport proteins but at the levels normally occurring in tissues far greater amounts of the SC-FAs are brought into cells that express a SC-FA transporter.

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<span class="mw-page-title-main">Arenobufagin</span> Chemical compound

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<span class="mw-page-title-main">Cinobufagin</span> Chemical compound

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<span class="mw-page-title-main">Tetrandrine</span> Chemical compound

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<span class="mw-page-title-main">Bufothionine</span> Chemical compound

Bufothionine is a sulfur-containing compound which is present in the bufotoxins secreted by the parotoid gland of certain toads of the genera Bufo and Chaunus. This specific compound can be found in the skin of certain species of toad such as the Asiatic Toad, Chaunus arunco, Chaunus crucifer, Chaunus spinulosus, and Chaunus arenarum.

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HuaChanSu is a traditional Chinese medicine extracted from the skin of toads from the genus Bufo that is believed by some to slow the spread of cancerous cells. The parotoid gland of toads of the Bufo genus secrete a venom, which is dried and dissolved in water. This solution, HuaChanSu, is injected into a cancerous area and targets specific cancer cells. HuaChanSu is undergoing further trials, and its effect is not completely understood.

References

  1. A Dasgupta, P Datta (1998). "Rapid detection of cardioactive bufalin toxicity using fluorescence polarization immunoassay for digitoxin". Ther Drug Monit. 20 (1): 104–108. doi:10.1097/00007691-199802000-00019. PMID   9485564.
  2. "Datasheet: Bufotalin sc-sc-200136" (PDF). Santa Cruz Biotechnology, Inc.
  3. Okada, Masahiro; Suga, Toshiro; et al. (April 1960). "Pharmacology of the principles isolated from Senso (Ch'an Su) the dried venom of the Chinese toad (IV)" (PDF). Asian Medical Journal . 3 (4): 155–160.
  4. Zhang ZJ (Feb 2014). "Bufalin attenuates the stage and metastatic potential of hepatocellular carcinoma in nude mice". J Transl Med. 12: 57. doi: 10.1186/1479-5876-12-57 . PMC   4015709 . PMID   24581171.
  5. Wu SH (2014). "Bufalin induces cell death in human lung cancer cells through disruption of DNA damage response pathways". Am J Chin Med. 42 (3): 729–42. doi:10.1142/S0192415X14500475. PMID   24871662.
  6. Ma H (Jul 2012). "The novel antidote Bezoar Bovis prevents the cardiotoxicity of Toad (Bufo bufo gargarizans Canto) Venom in mice". Exp Toxicol Pathol. 64 (5): 417–23. doi:10.1016/j.etp.2010.10.007. PMID   21084181.