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      An Overview of Biotransformation and Toxicity of Diterpenes

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          Abstract

          Diterpenes have been identified as active compounds in several medicinal plants showing remarkable biological activities, and some isolated diterpenes are produced at commercial scale to be used as medicines, food additives, in the synthesis of fragrances, or in agriculture. There is great interest in developing methods to obtain derivatives of these compounds, and biotransformation processes are interesting tools for the structural modification of natural products with complex chemical structures. Biotransformation processes also have a crucial role in drug development and/or optimization. The understanding of the metabolic pathways for both phase I and II biotransformation of new drug candidates is mandatory for toxicity and efficacy evaluation and part of preclinical studies. This review presents an overview of biotransformation processes of diterpenes carried out by microorganisms, plant cell cultures, animal and human liver microsomes, and rats, chickens, and swine in vivo and highlights the main enzymatic reactions involved in these processes and the role of diterpenes that may be effectively exploited by other fields.

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          Most cited references107

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          A raison d'être for two distinct pathways in the early steps of plant isoprenoid biosynthesis?

          When compared to other organisms, plants are atypical with respect to isoprenoid biosynthesis: they utilize two distinct and separately compartmentalized pathways to build up isoprene units. The co-existence of these pathways in the cytosol and in plastids might permit the synthesis of many vital compounds, being essential for a sessile organism. While substrate exchange across membranes has been shown for a variety of plant species, lack of complementation of strong phenotypes, resulting from inactivation of either the cytosolic pathway (growth and development defects) or the plastidial pathway (pigment bleaching), seems to be surprising at first sight. Hundreds of isoprenoids have been analyzed to determine their biosynthetic origins. It can be concluded that in angiosperms, under standard growth conditions, C₂₀-phytyl moieties, C₃₀-triterpenes and C₄₀-carotenoids are made nearly exclusively within compartmentalized pathways, while mixed origins are widespread for other types of isoprenoid-derived molecules. It seems likely that this coexistence is essential for the interaction of plants with their environment. A major purpose of this review is to summarize such observations, especially within an ecological and functional context and with some emphasis on regulation. This latter aspect still requires more work and present conclusions are preliminary, although some general features seem to exist. Copyright © 2011 Elsevier Ltd. All rights reserved.
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            Two rings in them all: the labdane-related diterpenoids.

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              Glossary of terms used in medicinal chemistry (IUPAC Recommendations 1998)

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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
                MDPI
                1420-3049
                08 June 2018
                June 2018
                : 23
                : 6
                : 1387
                Affiliations
                Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Av. do Café, s/n, Ribeirão Preto, São Paulo 14040903, Brazil; ingrid.sousa@ 123456usp.br (I.P.d.S.); valdeline_sousa@ 123456hotmail.com (M.V.S.T.)
                Author notes
                [* ]Correspondence: niege@ 123456fcfrp.usp.br ; Tel.: +55-16-3315-4305
                Author information
                https://orcid.org/0000-0003-4775-8153
                Article
                molecules-23-01387
                10.3390/molecules23061387
                6100218
                29890639
                ba78d846-98b9-4d4c-ba26-6193287213db
                © 2018 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 (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 27 April 2018
                : 05 June 2018
                Categories
                Review

                diterpenes,biotransformation,toxicity
                diterpenes, biotransformation, toxicity

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