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Molecules 2012, 17(2), 1744-1750; doi:10.3390/molecules17021744
Article

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

1,* , 2, 1, 3 and 4
1 Instituto de Productos Naturales y Agrobiología, C.S.I.C., Avda. Astrofísico F. Sánchez 3, La Laguna, Tenerife, Canary Islands, 38206, Spain 2 Instituto Universitario de Bioorgánica “Antonio González”, Departamento de Química Orgánica, Universidad de La Laguna, Tenerife, 38206, Spain 3 Departamento de Química, Universidad Andrés Bello, Viña del Mar, Chile 4 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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Abstract

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.
Keywords: Cephalosporium aphidicola; biotransformations; diterpenes; stemodane Cephalosporium aphidicola; biotransformations; diterpenes; stemodane
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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