Biosynthesis of bufadienolides in toads. VI. experiments with [1,2-3H]cholesterol, [21-14C]coprostanol, and 5β-[21-14C]pregnanolone in the toad Bufo arenarum
[1,2-3H]Cholesterol, 5β-[21-14C]cholestan-3β-ol (coprostanol), and 3β-hydroxy-5β-[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. Th...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_0039128X_v48_n3-4_p251_Garraffo |
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todo:paper_0039128X_v48_n3-4_p251_Garraffo2023-10-03T14:49:21Z Biosynthesis of bufadienolides in toads. VI. experiments with [1,2-3H]cholesterol, [21-14C]coprostanol, and 5β-[21-14C]pregnanolone in the toad Bufo arenarum Garraffo, H.M. Gros, E.G. arenobufagin bufadienolide derivative cholestanol cholesterol drug derivative eltanolone pregnane derivative animal article biosynthesis chemistry male metabolism toad Animal Bufanolides Bufo arenarum Chemistry Cholestanol Cholesterol Male Pregnanes Pregnanolone Support, Non-U.S. Gov't [1,2-3H]Cholesterol, 5β-[21-14C]cholestan-3β-ol (coprostanol), and 3β-hydroxy-5β-[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 stillunknown 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. © 1986. Fil:Garraffo, H.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gros, E.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0039128X_v48_n3-4_p251_Garraffo |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
arenobufagin bufadienolide derivative cholestanol cholesterol drug derivative eltanolone pregnane derivative animal article biosynthesis chemistry male metabolism toad Animal Bufanolides Bufo arenarum Chemistry Cholestanol Cholesterol Male Pregnanes Pregnanolone Support, Non-U.S. Gov't |
| spellingShingle |
arenobufagin bufadienolide derivative cholestanol cholesterol drug derivative eltanolone pregnane derivative animal article biosynthesis chemistry male metabolism toad Animal Bufanolides Bufo arenarum Chemistry Cholestanol Cholesterol Male Pregnanes Pregnanolone Support, Non-U.S. Gov't Garraffo, H.M. Gros, E.G. Biosynthesis of bufadienolides in toads. VI. experiments with [1,2-3H]cholesterol, [21-14C]coprostanol, and 5β-[21-14C]pregnanolone in the toad Bufo arenarum |
| topic_facet |
arenobufagin bufadienolide derivative cholestanol cholesterol drug derivative eltanolone pregnane derivative animal article biosynthesis chemistry male metabolism toad Animal Bufanolides Bufo arenarum Chemistry Cholestanol Cholesterol Male Pregnanes Pregnanolone Support, Non-U.S. Gov't |
| description |
[1,2-3H]Cholesterol, 5β-[21-14C]cholestan-3β-ol (coprostanol), and 3β-hydroxy-5β-[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 stillunknown 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. © 1986. |
| format |
JOUR |
| author |
Garraffo, H.M. Gros, E.G. |
| author_facet |
Garraffo, H.M. Gros, E.G. |
| author_sort |
Garraffo, H.M. |
| title |
Biosynthesis of bufadienolides in toads. VI. experiments with [1,2-3H]cholesterol, [21-14C]coprostanol, and 5β-[21-14C]pregnanolone in the toad Bufo arenarum |
| title_short |
Biosynthesis of bufadienolides in toads. VI. experiments with [1,2-3H]cholesterol, [21-14C]coprostanol, and 5β-[21-14C]pregnanolone in the toad Bufo arenarum |
| title_full |
Biosynthesis of bufadienolides in toads. VI. experiments with [1,2-3H]cholesterol, [21-14C]coprostanol, and 5β-[21-14C]pregnanolone in the toad Bufo arenarum |
| title_fullStr |
Biosynthesis of bufadienolides in toads. VI. experiments with [1,2-3H]cholesterol, [21-14C]coprostanol, and 5β-[21-14C]pregnanolone in the toad Bufo arenarum |
| title_full_unstemmed |
Biosynthesis of bufadienolides in toads. VI. experiments with [1,2-3H]cholesterol, [21-14C]coprostanol, and 5β-[21-14C]pregnanolone in the toad Bufo arenarum |
| title_sort |
biosynthesis of bufadienolides in toads. vi. experiments with [1,2-3h]cholesterol, [21-14c]coprostanol, and 5β-[21-14c]pregnanolone in the toad bufo arenarum |
| url |
http://hdl.handle.net/20.500.12110/paper_0039128X_v48_n3-4_p251_Garraffo |
| work_keys_str_mv |
AT garraffohm biosynthesisofbufadienolidesintoadsviexperimentswith123hcholesterol2114ccoprostanoland5b2114cpregnanoloneinthetoadbufoarenarum AT groseg biosynthesisofbufadienolidesintoadsviexperimentswith123hcholesterol2114ccoprostanoland5b2114cpregnanoloneinthetoadbufoarenarum |
| _version_ |
1782030033584390144 |