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Phytochemistry
Article . 2007 . Peer-reviewed
License: Elsevier TDM
Data sources: Crossref
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Phytochemistry
Article . 2007
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The microbiological transformation of 7α-hydroxy-ent-kaur-16-ene derivatives by Gibberella fujikuroi

Authors: Fraga, Braulio M.; Bressa, Carlo; González, Pedro; Guillermo, Ricardo; Hernández, Melchor G.; Suárez, Sergio;

The microbiological transformation of 7α-hydroxy-ent-kaur-16-ene derivatives by Gibberella fujikuroi

Abstract

The biotransformation of 7alpha-hydroxy-ent-kaur-16-ene (epi-candol A) by the fungus Gibberella fujikuroi gave 7alpha,16alpha,17-trihydroxy-ent-kaur-16-ene and a seco-ring B derivative, fujenoic acid, whilst the incubation of candicandiol (7alpha,18-dihydroxy-ent-kaur-16-ene) and canditriol (7alpha,15alpha,18-trihydroxy-ent-kaur-16-ene) afforded 7alpha,18,19-trihydroxy-ent-kaur-16-ene and 7alpha,11beta,15alpha,18-tetrahydroxy-ent-kaur-16-ene, respectively. The presence of a 7alpha-hydroxyl group in epi-candol A avoids its biotransformation along the biosynthetic pathway of gibberellins, and directs it to the seco-ring B acids route. The 15alpha-hydroxyl group in canditriol inhibits oxidation at C-19 and direct hydroxylation at C-11(beta). The formation of fujenoic acid, from 7alpha-hydroxy-ent-kaur-16-ene, probably occurs via 7alpha-hydroxykaurenoic acid and 7-oxokaurenoic acid, with subsequent hydroxylation at the C-6(beta) position.

Keywords

ent-Kaur-16-ene derivatives, Gibberella, Gibberella fujikuroi MP-C, epi-Candol A, Canditriol, Diterpenes, Candicandiol, Biotransformation, Substrate Specificity

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popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
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influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
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impulse
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