Biosynthesis of bufadienolides in toads. VI. Experiments with [1,2-3H]cholesterol, [21-14C]coprostanol, and 5 beta-[21-14 C]pregnanolone in the toad Bufo arenarum.
[1,2-3H]Cholesterol, 5 beta-[21-14C]cholestan-3 beta-ol (coprostanol), and 3 beta-hydroxy-5 beta-[21-14C]pregnan-20-one were injected into intact Bufo arenarum toads. Arenobufagin, the main bufadienolide present in the venom of the mentioned toad, was isolated and purified by means of chromatographic procedures. The first two compounds, having an intact cholesterol side chain, were incorporated, at comparable levels, into the bufadienolide while the labeled pregnane derivative yielded non-radioactive arenobufagin. The above results support the hypothesis that cholesterol and those steroids having an intact cholesterol-type side chain are able to penetrate to the site of bufadienolide biosynthesis and are converted into bufadienolides by a still-unknown mechanism. On the other hand, those steroid derivatives bearing a degraded side chain, e.g., 20-keto-pregnanes, are not converted into bufadienolides because they are not incorporated into the bufadienolide-producing cells.
D000818:Animals; D002018:Bufanolides / Q000096:biosynthesis*; D002022:Bufo arenarum; D055598:Chemical Phenomena; D002621:Chemistry; D004083:Cholestanol / Q000378:metabolism*; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000378:metabolism*; D008297:Male; D011278:Pregnanes / Q000378:metabolism*; D011280:Pregnanolone / Q000378:metabolism*
D002018:Bufanolides; D011278:Pregnanes; C055393:arenobufagin; D004083:Cholestanol; D002784:Cholesterol; D011280:Pregnanolone