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

The biotransformation of 13α,17-dihydroxystemodane (3) with the fungus Cephalosporium aphidicola afforded 13α,17,18-trihydroxystemodane (4), 3β,13α,17-tri-hydroxystemodane (5), 13α,17-dihydroxy-stemodan-18-oic acid (6), 3β,11β,13α,17-tetra-hydroxystemodane (7), 11β,13α,17,18-tetrahydroxystemodane (8...

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Autores principales: Fraga, Braulio M., Guillermo, Ricardo, Hernández, Melchor G., Chamy, María C., Garbarino, Juan A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268689/
https://www.ncbi.nlm.nih.gov/pubmed/22322449
http://dx.doi.org/10.3390/molecules17021744
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author Fraga, Braulio M.
Guillermo, Ricardo
Hernández, Melchor G.
Chamy, María C.
Garbarino, Juan A.
author_facet Fraga, Braulio M.
Guillermo, Ricardo
Hernández, Melchor G.
Chamy, María C.
Garbarino, Juan A.
author_sort Fraga, Braulio M.
collection PubMed
description The biotransformation of 13α,17-dihydroxystemodane (3) with the fungus Cephalosporium aphidicola afforded 13α,17,18-trihydroxystemodane (4), 3β,13α,17-tri-hydroxystemodane (5), 13α,17-dihydroxy-stemodan-18-oic acid (6), 3β,11β,13α,17-tetra-hydroxystemodane (7), 11β,13α,17,18-tetrahydroxystemodane (8) and 3β,13α,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(β) and C-11(β) hydroxylations seem to indicate a xenobiotic biotransformation.
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spelling pubmed-62686892018-12-10 The Incubation of 13α,17-Dihydroxystemodane with Cephalosporium aphidicola Fraga, Braulio M. Guillermo, Ricardo Hernández, Melchor G. Chamy, María C. Garbarino, Juan A. Molecules Article The biotransformation of 13α,17-dihydroxystemodane (3) with the fungus Cephalosporium aphidicola afforded 13α,17,18-trihydroxystemodane (4), 3β,13α,17-tri-hydroxystemodane (5), 13α,17-dihydroxy-stemodan-18-oic acid (6), 3β,11β,13α,17-tetra-hydroxystemodane (7), 11β,13α,17,18-tetrahydroxystemodane (8) and 3β,13α,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(β) and C-11(β) hydroxylations seem to indicate a xenobiotic biotransformation. MDPI 2012-02-09 /pmc/articles/PMC6268689/ /pubmed/22322449 http://dx.doi.org/10.3390/molecules17021744 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Fraga, Braulio M.
Guillermo, Ricardo
Hernández, Melchor G.
Chamy, María C.
Garbarino, Juan A.
The Incubation of 13α,17-Dihydroxystemodane with Cephalosporium aphidicola
title The Incubation of 13α,17-Dihydroxystemodane with Cephalosporium aphidicola
title_full The Incubation of 13α,17-Dihydroxystemodane with Cephalosporium aphidicola
title_fullStr The Incubation of 13α,17-Dihydroxystemodane with Cephalosporium aphidicola
title_full_unstemmed The Incubation of 13α,17-Dihydroxystemodane with Cephalosporium aphidicola
title_short The Incubation of 13α,17-Dihydroxystemodane with Cephalosporium aphidicola
title_sort incubation of 13α,17-dihydroxystemodane with cephalosporium aphidicola
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268689/
https://www.ncbi.nlm.nih.gov/pubmed/22322449
http://dx.doi.org/10.3390/molecules17021744
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