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Molecules 2012, 17(2), 1744-1750;

The Incubation of 13a,17-Dihydroxystemodane with Cephalosporium aphidicola

Instituto de Productos Naturales y Agrobiología, C.S.I.C., Avda. Astrofísico F. Sánchez 3, La Laguna, Tenerife, Canary Islands, 38206, Spain
Instituto Universitario de Bioorgánica “Antonio González”, Departamento de Química Orgánica, Universidad de La Laguna, Tenerife, 38206, Spain
Departamento de Química, Universidad Andrés Bello, Viña del Mar, Chile
Departamento de Química, Universidad Técnica Federico Santa María, Casilla-110V, Valparaiso, Chile
Author to whom correspondence should be addressed.
Received: 30 November 2011 / Revised: 19 January 2012 / Accepted: 3 February 2012 / Published: 9 February 2012
(This article belongs to the Special Issue Terpenoids)
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The biotransformation of 13a,17-dihydroxystemodane (3) with the fungus Cephalosporium aphidicola afforded 13a,17,18-trihydroxystemodane (4), 3b,13a,17-tri-hydroxystemodane (5), 13a,17-dihydroxy-stemodan-18-oic acid (6), 3b,11β,13a,17-tetra-hydroxystemodane (7), 11β,13a,17,18-tetrahydroxystemodane (8) and 3b,13a,17,18-tetra-hydroxystemodane (9). The hydroxylation at C-18 of the substrate points to a biosynthetically-directed transformation, because aphidicolin (2) is hydroxylated at this carbon. However, the C-3(b) and C-11(b) hydroxylations seem to indicate a xenobiotic biotransformation. View Full-Text
Keywords: Cephalosporium aphidicola; biotransformations; diterpenes; stemodane Cephalosporium aphidicola; biotransformations; diterpenes; stemodane

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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Fraga, B.M.; Guillermo, R.; Hernández, M.G.; Chamy, M.C.; Garbarino, J.A. The Incubation of 13a,17-Dihydroxystemodane with Cephalosporium aphidicola. Molecules 2012, 17, 1744-1750.

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