Diterpenes

They have 20 carbon atoms and are derived from geranylgeraniol pyrophosphate. They are of fungal or plant origin and are found in resins, gummy exudates, diterpenes, and in the resinous high-boiling fractions remaining after distillation of essential diterpenes. However, diterpenes, unequivocal evidence was provided for de novo geranylgeraniol biosynthesis in mammals Shidoji Y et al.

Diterpenes are a structurally diverse class of C 20 natural compounds, widely distributed in nature and originating by condensation of four isoprene units derived from mevalonate or deoxyxylulose phosphate pathways. The latter, recently discovered, originates the diterpene compounds in plants. Diterpenes can be classified as linear, bicyclic, tricyclic or tetracyclic, pentacyclic, and macrocyclic diterpenes depending on their skeletal core. In nature, they are commonly found in a polyoxygenated form with keto and hydroxyl groups, these last often esterified by small-sized aliphatic or aromatic acids. Diterpenes have attracted growing attention because of their interesting biological and pharmacological activities. Although thousands of diterpene compounds have been described in nature from terrestrial and marine organisms, only few of them became clinically effective. Overall, the anticancer drug taxol, used in therapy against ovarian, breast, and lung cancer, with its synthetic water-soluble analogue taxotere, is an example of unusual structure discovered from nature and used as medicine.

Diterpenes

Diterpenes are a class of terpenes composed of four isoprene units, often with the molecular formula C 20 H They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway , with geranylgeranyl pyrophosphate being a primary intermediate. Diterpenes form the basis for biologically important compounds such as retinol , retinal , and phytol. They are known to be antimicrobial and anti-inflammatory. As with most terpenes a huge number of potential structures exists, which may be broadly divided according to the number of rings present. From GGPP, structural diversity is achieved mainly by two classes of enzymes; the diterpene synthases and cytochromes P Several diterpenes are produced by plants and cyanobacteria. GGPP is also the precursor for the synthesis of the phytane by the action of the enzyme geranylgeranyl reductase. This compound is used for the biosynthesis of tocopherols and the phytyl functional group is used in the formation of chlorophyll a , ubiquinones , plastoquinone and phylloquinone. Diterpenes are formally defined as being hydrocarbons and thus contain no heteroatoms. Functionalized structures should instead be called diterpenoids [ citation needed ] , although in scientific literature the two terms are often used interchangeably. Although a wide range of terpene structures exist, few of them are biologically significant; by contrast, diterpenoids possess a rich pharmacology and include important compounds such as retinol , phytol or taxadiene. Taxanes are class of diterpenoids featuring a taxadiene core. They are produced by plants of the genus Taxus yew trees and are widely used as chemotherapy agents. Contents move to sidebar hide.

Others are prepared from those terpenes and terpenoids that diterpenes readily isolated in quantity, say from the paper and tall oil industries, diterpenes.

Federal government websites often end in. The site is secure. 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. 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. Diterpenes are, by definition, C 20 compounds based on four isoprene C 5 H 8 units and can be found in plants, fungi, bacteria, and animals in both terrestrial and marine environments [ 1 , 2 , 3 , 4 , 5 ].

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Diterpenes

Antimicrobial resistance has been posing an alarming threat to the treatment of infectious diseases over the years. Ineffectiveness of the currently available synthetic and semisynthetic antibiotics has led the researchers to discover new molecules with potent antimicrobial activities. To overcome the emerging antimicrobial resistance, new antimicrobial compounds from natural sources might be appropriate. Secondary metabolites from natural sources could be prospective candidates in the development of new antimicrobial agents with high efficacy and less side effects. Among the natural secondary metabolites, diterpenoids are of crucial importance because of their broad spectrum of antimicrobial activity, which has put it in the center of research interest in recent years. The present work is aimed at reviewing recent literature regarding different classes of natural diterpenes and diterpenoids with significant antibacterial, antifungal, antiviral, and antiprotozoal activities along with their reported structure—activity relationships.

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Twelve new and three known furanocassane-type diterpenoids were isolated from the seeds of Bowdichia virgilioides Kunth [Fabaceae] and investigated for their antiplasmodic activity against P. Han et al. XL isolated from P. Sections Sections. Gao J. Several important drugs such as morphine, tubocurarine, reserpine, cocaine, vincristine, vinblastine, lovastatin, and paclitaxel originated from natural sources. Ogawa, K. A more modern approach of fungal metabolic engineering, which combines the use of these microorganisms with molecular genetic tools and computer science, can expand the role of fungi not only in the bioproduction [ 40 ] but also in the biotransformation studies. Microbial metabolism of atovaquone and cytotoxicity of the produced phase I metabolite. Kumar R. Chemical structures used in this manuscript have been drawn using ChemDraw Trans-communic acid.

Diterpenes are a structurally diverse class of C 20 natural compounds, widely distributed in nature and originating by condensation of four isoprene units derived from mevalonate or deoxyxylulose phosphate pathways. The latter, recently discovered, originates the diterpene compounds in plants.

Steviol Retene is present in tars obtained by distillation of resinous wood, it is an important pollutant eliminated by the paper factories. The mevalonate MVA pathway is distributed in all three domains of life; archaea, bacteria and eukaryotes. Sichaem, J. Antiplasmodial Diterpenoids from Psiadia Arguta. Four new and five known labdane diterpenoids were isolated from Psiadia arguta Pers. These compounds could be targets in a new route to anti-infective therapy. The diterpenoids salvic acid 60 , Figure 26 , acetylsalvic acid 61 , propanoylsalvic acid 62 , butanoylsalvic acid 63 , and isopentanoylsalvic acid 64 were evaluated against Botrytis cinerea. These outcomes suggest that acts as a transcription inhibitor of cccDNA and is a promising lead for new anti-HBV agent development Wu et al. Another challenge in the path of new drug development from natural diterpenoids is toxicity and lack of selectivity. Among all the compounds, and exhibited significant antifungal activity against L. Mafu S. Expert Opin. Literature has shown that phase II enzymes such as sulfotransferases, UDP-glucuronosyltransferases, glycine N -acyltransferases and methyl-transferases can react with different diterpenes, increasing their molecular weight and polarity [ 44 , 45 , 46 ]. Molecules 22, The time-of-addition TOA assay and long terminal repeat LTR luciferase reporter assay results suggested that compound might inhibit the wild-type HIV-1 transcription, leading to the blocking of HIV-1 replication at the submicromolar level Zhang et al.