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Abstract:

[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.

Registro:

Documento: Artículo
Título: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
Autor:Garraffo, H.M.; Gros, E.G.
Filiación:Departamento de Química Orgánica, UMYMFOR, Facultad de Ciencias Exactas y Naturales, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave: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
Año:1986
Volumen:48
Número:3-4
Página de inicio:251
Página de fin:257
DOI: http://dx.doi.org/10.1016/0039-128X(86)90008-5
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:cholestanol, 29466-38-4, 80-97-7; cholesterol, 57-88-5; eltanolone, 128-20-1; arenobufagin, 464-74-4; Bufanolides; Cholestanol, 80-97-7; Cholesterol, 57-88-5; Pregnanes; Pregnanolone, 128-20-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v48_n3-4_p251_Garraffo

Referencias:

  • Siperstein, Murray, Titus, Biosynthesis of cardiotonic sterols from cholesterol in the toad Bufo marinus (1957) Arch Biochem Biophys, 67, pp. 154-160
  • Porto, Gros, Biosynthesis of the bufadienolide marinobufagin in toads Bufo paracnemis from cholesterol-20-14C (1971) Experientia, 27, p. 506
  • Porto, Gros, Biosynthesis of animal and plant bufadienolides (1970) Parallel experiments with pregn-5-en-3β-o1-20-one-20-14C in Scilla maritima and Bufo paracnemis, 26, p. 11. , Experientia
  • Porto, Baralle, Gros, Biosynthesis of bufadienolides in toads (1972) III. Experiments with [2-14C]mevalonic acid, [20-14C]3β-hydroxy-5-pregnen-20-one and [20-14C]cholesterol, 3, pp. 11-17. , J Steroid Biochem
  • Garraffo, Burton, Porto, Gros, Biosínte sis de bufadienólidos en sapos (1982) IV. Ensayos con [24-14C]colesterol, ácido [24-14C]3β-hidroxi-5-colénico y [20-14]3β-hidroxi-5β-pregnan-20-ona, 70, pp. 743-747. , An Asoc Quim Argent
  • Tschesche, Biosynthesis of cardenolides, bufadienolides and steroids sapogenins (1972) Proc R Soc Lond, 180 B, pp. 187-202
  • Galagovsky, Porto, Burton, Gros, Biosynthesis of the bufadienolide ring of scillirosid in Scilla maritima (1984) Z Naturforsch, 39 c, pp. 38-44
  • Santa Coloma, Garraffo, Pignataro, Charreau, Gros, Biosynthesis of bufadienolides in toads (1984) V. The origin of the cholesterol used by toad parotoid glands for the biosynthesis of bufadienolides, 44, pp. 11-22. , Steroids
  • Deluca, Seldes, Garraffo, Gros, Preparation of 3β-acetoxy-5β-pregnan-20-one from 3α-acetoxy-5β-cholan-24-oic acid aimed at the isotopic labelling of the pregnane side chain (1984) Z Naturforsch, 39 b, pp. 1617-1621
  • Garraffo, Deluca, Seldes, Gros, Synthesis of [21-14C]3β-hydroxy-5β-pregnan-20-one and [21-14C]5β-cholestan-3β-o1 (1985) J Lab Compds Radiopharm, 22, pp. 673-676
  • Linde, Ergenc, Meyer, Zur Frage der Existenz von γ-sitosterol (1966) Nachweis von Cholesterol als Bestandeil des γ-sitosterols einer Digitalis-Art, 49, pp. 1246-1249. , Helv Chim Acta
  • Iseli, Kotake, Weiss, Reichstein, Die Sterine und Bufadienolide der Haut von Bufo formosus (1965) Helvetica Chimica Acta, 48, pp. 1093-1112
  • Gros, Porto, Estudios acerca de la biosíntesis de bufadienólidos en sapos (1967) I. an Asoc Quim Argent, 55, pp. 177-184
  • Maier, Seldes, Gros, Biosynthesis of the butenolide ring of cardenolides in Digitalis purpurea (1986) Phytochemistry, 25, pp. 1327-1329. , and references cited therein

Citas:

---------- APA ----------
Garraffo, H.M. & Gros, E.G. (1986) . 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. Steroids, 48(3-4), 251-257.
http://dx.doi.org/10.1016/0039-128X(86)90008-5
---------- CHICAGO ----------
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" . Steroids 48, no. 3-4 (1986) : 251-257.
http://dx.doi.org/10.1016/0039-128X(86)90008-5
---------- MLA ----------
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" . Steroids, vol. 48, no. 3-4, 1986, pp. 251-257.
http://dx.doi.org/10.1016/0039-128X(86)90008-5
---------- VANCOUVER ----------
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. Steroids. 1986;48(3-4):251-257.
http://dx.doi.org/10.1016/0039-128X(86)90008-5