Diterpenes

Diterpenes are a structurally diverse class of C 20 natural compounds, widely distributed in nature diterpenes originating by condensation of four isoprene units derived from mevalonate or deoxyxylulose phosphate pathways, 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 ].

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. A total of diterpenoids from various sources like plants, marine species, and fungi are summarized in this systematic review, including their chemical structures, classification, and significant antimicrobial activities together with their reported mechanism of action and structure—activity relationships. The outcomes herein would provide researchers with new insights to find new credible leads and to work on their synthetic and semisynthetic derivatives to develop new antimicrobial agents. Over the past few decades, the world population has witnessed an alarming surge of antimicrobial resistance AMR —the tip of the iceberg being witnessed during the ongoing coronavirus pandemic. Continued emergence of antibiotic resistance has posed a big risk for health, which increases the mortality and economic burden worldwide Ciorba et al. Innovative targeted therapeutic strategies involving newer technology are being considered to deal with these multi-drug-resistant pathogenic bacteria Yang et al. New strategies are being developed for sustainable discovery of antibiotics in order to keep up with the ever-increasing demand of novel antimicrobials and reduce the lack of investment in their development Miethke et al. Particularly, antimicrobial agents derived from natural sources could be a great tool to deal with these multi-drug-resistant pathogens.

Terpenes are colorless, although impure samples are often yellow.

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.

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Diterpenes

Terpenes are major biosynthetic building blocks. Comprising more than 30, compounds, these unsaturated hydrocarbons are produced predominantly by plants , particularly conifers. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control. Terpenes are classified by the number of carbons: monoterpenes C 10 , sesquiterpenes C 15 , diterpenes C 20 , as examples. The terpene alpha-pinene is a major component of the common solvent , turpentine. The one terpene that has major applications is natural rubber i.

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Others are prepared from those terpenes and terpenoids that are readily isolated in quantity, say from the paper and tall oil industries. Murillo, J. Structures of abietane, cembrane, diterpenoid alkaloids, epi-neoverrucosane, indole, isopimarane, kaurene, labdane, phenolic, pimarane, tetraquinane, and miscellaneous diterpenoids with significant antifungal activity. In ancient times, conifer exudates were used for caulking boats and waterproofing ropes. The biotransformation facilitates metabolite excretion through the urine or the bile and avoid toxic effects from the accumulation of non-polar xenobiotics in the body. Only exhibited antifungal activity against four fungal species— P. The diterpenoids were tested for antimicrobial activity against 11 human and aqua-pathogenic bacterial strains and also for antifungal activity against seven plant pathogenic fungi. The possibility that other terpenes could be used as precursors to produce synthetic polymers has been investigated. Pinene , a monoterpene which exists as two isomers, is a major consistituent of turpentine. Retrieved 22 July Compounds 52 — 55 along with drechmerin B showed significant accessibility to the ligand-binding domain of the PDF protein binding energy ranging from —3. Ogawa, K. According to Liu et al.

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.

Reduction of carboxyl groups at non-active sites are important enzymatic reactions catalyzed by microorganisms, for example. Major classes include acyclic diterpenes phytane , monocyclic diterpenes retinol—vitamin A , bicyclic diterpenes clerodane, halimane, and labdane , tricyclic diterpenes abietane, rosane, pimarane, podocarpane, cassane, vouacapane, and chinane , tetracyclic diterpenes kaurene, gibberellane, trachylobane, scopadulane, aphidicolane, atisane, stemodane, beyerene, stemarane , macrocyclic diterpenes polycyclic—cembrane, jatrophane, taxane, ingenane, daphnane, and tigliane , and miscellaneous structures Eksi et al. Grayanane diterpenoids with diverse bioactivities from the roots of Pieris formosa. Langat, M. The diterpenes arise from geranylgeranyl diphosphate GGPP , which is formed by addition of isopentenyl diphosphate to farnesyl diphosphate [ 7 ]. Peters R. Du et al. Don [Cupressaceae] sugi were tested against two fungal strains, namely, T. Lambrechts, I. Among the isolated diterpenoids, compounds 97 — 99 showed moderate antibacterial activity against the selected strains with MIC values ranging from Class of oily organic compounds found in plants. Therefore, the role of diterpenoids as synergists and adjuvant therapies should be explored extensively to potentiate the available antibiotics. Several diterpenes are produced by plants and cyanobacteria. The authors proposed 16 phase I metabolites compounds 2. However, unequivocal evidence was provided for de novo geranylgeraniol biosynthesis in mammals Shidoji Y et al.