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

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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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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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