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The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations

The use of biotransformations in organic chemistry is widespread, with highlights of interesting applications in the functionalization of natural products containing unactivated carbons, like the kaurane diterpenes. A number of compounds with kaurane skeletons can be isolated in large amounts from s...

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Autores principales: Takahashi, Jacqueline A., Gomes, Dhionne C., Lyra, Fernanda H., dos Santos, Gabriel F., Martins, Leonardo R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271197/
https://www.ncbi.nlm.nih.gov/pubmed/24518806
http://dx.doi.org/10.3390/molecules19021856
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author Takahashi, Jacqueline A.
Gomes, Dhionne C.
Lyra, Fernanda H.
dos Santos, Gabriel F.
Martins, Leonardo R.
author_facet Takahashi, Jacqueline A.
Gomes, Dhionne C.
Lyra, Fernanda H.
dos Santos, Gabriel F.
Martins, Leonardo R.
author_sort Takahashi, Jacqueline A.
collection PubMed
description The use of biotransformations in organic chemistry is widespread, with highlights of interesting applications in the functionalization of natural products containing unactivated carbons, like the kaurane diterpenes. A number of compounds with kaurane skeletons can be isolated in large amounts from several plant species and a myriad of biological activities has been related to these compounds. Studies on structure versus activity have showed that, in most cases, in kaurane diterpenes, activity increases with the increase of functionalization. Since naturally occurring kaurane diterpenes usually have limited functional groups to be used as targets for semi-synthetic modifications, production of more polar derivatives from kaurane diterpenes have been achieved mostly through the use of fungal biotransformations. In this review, selected examples the wonderful chemical diversity produced by fungi in kaurane diterpenes is presented. This diversity includes mainly hydroxylation of nearly all carbon atoms of the kaurane molecule, many of them carried out stereoselectively, as well as ring rearrangements, among other chemical modifications. Sources of starting materials, general biotransformation protocols employed, fungi with most consistent regioselectivity towards kaurane skeleton, as well as biological activities associated with starting materials and products are also described.
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spelling pubmed-62711972018-12-20 The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations Takahashi, Jacqueline A. Gomes, Dhionne C. Lyra, Fernanda H. dos Santos, Gabriel F. Martins, Leonardo R. Molecules Review The use of biotransformations in organic chemistry is widespread, with highlights of interesting applications in the functionalization of natural products containing unactivated carbons, like the kaurane diterpenes. A number of compounds with kaurane skeletons can be isolated in large amounts from several plant species and a myriad of biological activities has been related to these compounds. Studies on structure versus activity have showed that, in most cases, in kaurane diterpenes, activity increases with the increase of functionalization. Since naturally occurring kaurane diterpenes usually have limited functional groups to be used as targets for semi-synthetic modifications, production of more polar derivatives from kaurane diterpenes have been achieved mostly through the use of fungal biotransformations. In this review, selected examples the wonderful chemical diversity produced by fungi in kaurane diterpenes is presented. This diversity includes mainly hydroxylation of nearly all carbon atoms of the kaurane molecule, many of them carried out stereoselectively, as well as ring rearrangements, among other chemical modifications. Sources of starting materials, general biotransformation protocols employed, fungi with most consistent regioselectivity towards kaurane skeleton, as well as biological activities associated with starting materials and products are also described. MDPI 2014-02-10 /pmc/articles/PMC6271197/ /pubmed/24518806 http://dx.doi.org/10.3390/molecules19021856 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. 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 Review
Takahashi, Jacqueline A.
Gomes, Dhionne C.
Lyra, Fernanda H.
dos Santos, Gabriel F.
Martins, Leonardo R.
The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations
title The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations
title_full The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations
title_fullStr The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations
title_full_unstemmed The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations
title_short The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations
title_sort remarkable structural diversity achieved in ent-kaurane diterpenes by fungal biotransformations
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271197/
https://www.ncbi.nlm.nih.gov/pubmed/24518806
http://dx.doi.org/10.3390/molecules19021856
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