cinobufagin and cinobufotalin

The secreted poisonin bufonids (Anura: Bufonidae) include proteins, biogenic amines, toxic bufadienolides and alkaloids. The chemical composition of the methanolic extract of parotoid gland secretions by the Amazonian toad Rhinella margaritifera was evaluated in a UFLC-DAD-micrOTOF system. Of the twenty three compounds found in the methanolic extract, eighteen were identified by the mass/charge ratio as: five arginine diacids, six bufagenins (telocinobufagin, marinobufagin, bufotalin, cinobufotalin, bufalin and cinobufagin), six bufotoxins, and an alkaloid (dehydrobufotenin).

Topics: Amphibian Venoms; Animals; Bufanolides; Bufonidae; Cell Line, Tumor; Chromatography, High Pressure Liquid; Parotid Gland

Chemical defences are widespread in nature, yet we know little about whether and how climatic and geographic factors affect their evolution. In this study, we investigated the natural variation in the concentration and composition of the main bufogenin toxin in adult Asian toads (Bufo gargarizans Cantor) captured in twenty-two regions. Moreover, we explored the relative importance of eight climatic factors (average temperature, maximum temperature, minimum temperature, average relative humidity, 20-20 time precipitation, maximum continuous precipitation, maximum ground temperature, and minimum ground temperature) in regulating toxin production. We found that compared to toads captured from central and southwestern China, toads from eastern China secreted higher concentrations of cinobufagin (CBG) and resibufogenin (RBG) but lower concentrations of telocinobufagin (TBG) and cinobufotalin (CFL). All 8 climatic variables had significant effects on bufogenin production (r

Topics: Animals; Bufanolides; Bufo bufo; Geography; Temperature; Toxins, Biological

A preparative, high-speed, counter-current chromatographic (HSCCC) method for the isolation and purification of bufadienolides from Chansu was successfully developed by using stepwise elution with a two-phase solvent system composed of n-hexane: chloroform: methanol: water (4:1:2.5:5 and 4:1:4:5, v/v). A total of 7.5 mg of cinobufotalin (1), 8.0 mg of bufalin (2), 14.0 mg of cinobufagin (3) and 9.5 mg of resibufogenin (4) were obtained in a one-step separation from 80 mg of the crude extract with purities of 93.2%, 98.7%, 99.2%, and 99.4%, respectively. The chemical structures were determined from 1H NMR and 13C NMR spectroscopic data.

Topics: Bufanolides; Chromatography, High Pressure Liquid; Countercurrent Distribution; Drugs, Chinese Herbal; Molecular Structure

Microbial transformation of a cytotoxic bufadienolide, cinobufagin (1), was performed by Syncephalastrum racemosum. The six metabolites obtained were identified as 7beta-hydroxycinobufagin ( 2), 12beta-hydroxycinobufagin (3), cinobufotalin (4), 5,12beta-dihydroxycinobufagin (5), 4beta,11alpha-dihydroxycinobufagin (6), and 4beta,12alpha-dihydroxycinobufagin (7), respectively, on the basis of spectroscopic studies. Metabolites 2 and 5-7 were characterized as new compounds, and 2-7 proved to be cytotoxic against Bel-7402 human hepatoma cells.

Topics: Antineoplastic Agents; Biotransformation; Bufanolides; Drug Screening Assays, Antitumor; Humans; Mucorales; Nuclear Magnetic Resonance, Biomolecular

Toxicity from toad venom poisoning is similar to digoxin toxicity and carries a high mortality rate. We report on six previously healthy men who developed vomiting and bradycardia after ingesting a purported topical aphrodisiac. Each patient had positive apparent digoxin levels and the first four patients died of cardiac dysrhythmias. The last two patients recovered following treatment with digoxin Fab fragments. We analyzed samples of the purported aphrodisiac and found that it was identical to Chan Su, a Chinese medication made from toad venom. To our knowledge, this is the first reported use of digoxin Fab fragments to treat toad venom poisoning.

Topics: Adolescent; Adult; Amphibian Venoms; Animals; Aphrodisiacs; Bradycardia; Bufanolides; Bufonidae; Bufotenin; Digoxin; Fatal Outcome; Humans; Immunoglobulin Fab Fragments; Male; Materia Medica; Ventricular Fibrillation; Vomiting

Topics: Animals; Anura; Bufanolides; Bufonidae; Digitalis; Digitalis Glycosides; Heart; Hedera; Venoms