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Journal of Food Biochemistry Jan 2021D-limonene or 4-isopropenyl-1-methylcyclohexene (C H ) is a monocyclic monoterpene abundant in citrus plants like lemon, orange, and grape. The application of D-limonene... (Review)
Review
D-limonene or 4-isopropenyl-1-methylcyclohexene (C H ) is a monocyclic monoterpene abundant in citrus plants like lemon, orange, and grape. The application of D-limonene in the form of flavor and fragrance additive in perfumes, soaps, foods, and beverages is consistently increased due to its high-quality fragrance property. This review is intended to analyze and delineate every possible available evidence and details about D-limonene with the special focus on its therapeutic efficacy. Many studies have reported that D-limonene effectively plays a valuable role in the prevention of several chronic and degenerative diseases. This review provides worthy information about the beneficial effects of D-limonene such as antioxidant, antidiabetic, anticancer, anti-inflammatory, cardioprotective, gastroprotective, hepatoprotective, immune modulatory, anti-fibrotic, anti-genotoxic etc. This could in turn help in the application of D-limonene for clinical studies. PRACTICAL IMPLICATIONS: Various plant families contain Terpenes as their secondary metabolites. Monoterpenes constitute an important part of these secondary metabolites. D-limonene is a well-identified monoterpene that is commonly applied as a fragrance ingredient in essential oils. D-limonene is known to possess remarkable biological activities. It can be effectively used for treating various ailments and diseases. Due to its diverse functions, it can be efficiently utilized for human health.
Topics: Cyclohexenes; Humans; Limonene; Monoterpenes; Oils, Volatile; Terpenes
PubMed: 33289132
DOI: 10.1111/jfbc.13566 -
Current Opinion in Chemical Biology Oct 2016Synthetic biology is opening up new opportunities for the sustainable and efficient production of valuable chemicals in engineered microbial factories. Here we review... (Review)
Review
Synthetic biology is opening up new opportunities for the sustainable and efficient production of valuable chemicals in engineered microbial factories. Here we review the application of synthetic biology approaches to the engineering of monoterpene/monoterpenoid production, highlighting the discovery of novel catalytic building blocks, their accelerated assembly into functional pathways, general strategies for product diversification, and new methods for the optimization of productivity to economically viable levels. Together, these emerging tools allow the rapid creation of microbial production systems for a wide range of monoterpenes and their derivatives for a diversity of industrial applications.
Topics: Monoterpenes; Synthetic Biology
PubMed: 27315341
DOI: 10.1016/j.cbpa.2016.06.002 -
Molecules (Basel, Switzerland) Feb 2022Two undescribed ether derivatives of sesquiterpenes, 1-ethoxycaryolane-1, 9-diol () and 2-ethoxyclovane-2, 9-diol (), and one new monoterpene glycoside,...
Two undescribed ether derivatives of sesquiterpenes, 1-ethoxycaryolane-1, 9-diol () and 2-ethoxyclovane-2, 9-diol (), and one new monoterpene glycoside, p-menthane-1,2,8-triol-4-O--D-glucoside (), were obtained, together with eight known compounds from the stems and leaves of . Their structures were elucidated by spectroscopic methods. Compounds - were evaluated for their potency against and clinical methicillin-resistant (MRSA). Among them, compound was weakly active against (MIC = 128 μg/mL), and compounds and exhibited good antibacterial activity against and MRSA (MICs = 2-8 µg/mL). A primary mechanism study revealed that compounds and could kill bacteria by destroying bacterial cell membranes. Moreover, compounds and were not susceptible to drug resistance development.
Topics: Anti-Bacterial Agents; Humans; Illicium; Methicillin-Resistant Staphylococcus aureus; Monoterpenes; Plant Leaves; Plant Stems; Sesquiterpenes; Staphylococcal Infections
PubMed: 35164380
DOI: 10.3390/molecules27031115 -
Natural Product Research Feb 2017As a result of our efforts to identify bioactive agents from marine algae, we have isolated and identified one new halogenated monoterpene 1...
As a result of our efforts to identify bioactive agents from marine algae, we have isolated and identified one new halogenated monoterpene 1 [(-)-(5E,7Z)-348-trichloro-7-dichloromethyl-3-methyl-157-octatriene] in addition to three known compounds (2, 3 and 4) from the red alga Plocamium cartilagineum collected by hand from the eastern coast of South Africa. Compound 1 was found to be active as a cytotoxic agent in human lung cancer (NCI-H460) and mouse neuro-2a cell lines (IC 4 μg/mL). Two of these compounds (3 and 4) were found to have cytotoxic activity in other cell line assays, especially against human leukaemia and human colon cancers (IC 1.3 μg/mL). None of these metabolites were active as sodium channel blockers or activators. All structures were determined by spectroscopic methods (UV, IR, LRMS, HRMS, 1D NMR and 2D NMR). 1D and 2D NOE experiments were carried out on these compounds to confirm the geometry of the double bonds.
Topics: Animals; Antineoplastic Agents; Cell Line, Tumor; Colonic Neoplasms; Halogenation; Humans; Leukemia; Lung Neoplasms; Magnetic Resonance Spectroscopy; Mice; Molecular Structure; Monoterpenes; Plocamium; Spectrum Analysis
PubMed: 27627578
DOI: 10.1080/14786419.2016.1230115 -
Zeitschrift Fur Naturforschung. C,... May 2022Monoterpenes, a class of isoprenoid compounds, are extensively used in flavor, fragrance, perfumery, and cosmetics. They display many astonishing bioactive properties of...
Monoterpenes, a class of isoprenoid compounds, are extensively used in flavor, fragrance, perfumery, and cosmetics. They display many astonishing bioactive properties of biological and pharmacological significance. All monoterpenes are derived from universal precursor geranyl diphosphate. The demand for new monoterpenoids has been increasing in flavor, fragrances, perfumery, and pharmaceuticals. Chemical methods, which are harmful for human and the environment, synthesize most of these products. Over the years, researchers have developed alternative methods for the production of newer monoterpenoids. Microbial biotransformation is one of them, which relied on microbes and their enzymes. It has produced many new desirable commercially important monoterpenoids. A growing number of reports reflect an ever-expanding scope of microbial biotransformation in food and aroma industries. Simultaneously, our knowledge of the enzymology of monoterpene biosynthetic pathways has been increasing, which facilitated the biotransformation of monoterpenes. In this article, we have covered the progress made on microbial biotransformation of commercial monoterpenes with a brief introduction to their biosynthesis. We have collected several reports from authentic web sources, including Google Scholar, Pubmed, Web of Science, and Scopus published in the past few years to extract information on the topic.
Topics: Biosynthetic Pathways; Biotransformation; Humans; Monoterpenes; Terpenes
PubMed: 34881551
DOI: 10.1515/znc-2021-0192 -
Chemistry & Biodiversity Aug 2022Secondary plant metabolites are chemical compounds produced by plants through a variety of metabolic pathways. It is known that these compounds, among others,...
Secondary plant metabolites are chemical compounds produced by plants through a variety of metabolic pathways. It is known that these compounds, among others, monoterpenes, are characterized by holding valuable pro-health activities when consumed or applied. Taking into account the development of civilizational diseases, eating foods enriched with compounds such as the monoterpenes is highly recommended. Good sources of such health-promoting food items include common fruits and vegetables, seed sources and plant parts used to enhance flavour such as spices. It is known that monoterpene compounds instigate or contribute to a variety of biological activities. It is known that the compounds can scavenge free radicals, reduce Fe(III) and inhibit AChE which are considered as possible anti-neurodegenerative activities. The aim of the presented study was to determinate another activity of selected monoterpenes, namely towards reducing and chelating Cu(II) and Fe(II), respectively. The assays were based on colorimetric CUPRAC and ferrozine-based methods. Study results explicitly indicated chelation and reduction activities of the selected monoterpenes. These properties considerably support the benefits of consuming plants rich in these compounds.
Topics: Copper; Ferrozine; Ions; Iron; Monoterpenes
PubMed: 35773202
DOI: 10.1002/cbdv.202200461 -
Nature Chemical Biology Apr 2023
Topics: Monoterpenes; Intramolecular Lyases; Biochemical Phenomena
PubMed: 36991161
DOI: 10.1038/s41589-023-01307-4 -
Phytochemistry Apr 2017Protium heptaphyllum (Burseraceae) oleoresins are rich in volatile monoterpenes, exhibiting a chemical composition that can be strongly altered with time. The present...
Protium heptaphyllum (Burseraceae) oleoresins are rich in volatile monoterpenes, exhibiting a chemical composition that can be strongly altered with time. The present work aimed to discuss the temporal change of the volatile composition of these oleoresins, and search for related supporting evidence. Samples of P. heptaphyllum oleoresin were collected separately for fresh (n = 10) and aged (n = 8) oleoresins, with the essential oils obtained by hydrodistillation analyzed by GC-FID and GC-MS. Fresh oleoresins were characterized by a high content of terpinolene (28.2-69.7%), whereas aged ones contained large amounts of p-cymene (18.7-43.0%) and p-cymen-8-ol (8.2-31.8%). Multivariate analyses were performed based on the yield and major essential oil components to clearly demonstrate the existence of two subsets (fresh and aged oleoresins). In addition, an analysis of the partial genome sequencing of the species was carried out, producing the largest amount of data for the genus Protium. Subsequently, were searched for nucleotide sequences responsible for the enzymes involved in the biosynthesis of monoterpenes. Two hypotheses were formulated to understand the oxidation process during aging of the oleoresins: (i) a natural chemical oxidation of terpenes and (ii) an oxidation catalyzed by enzymes produced by microorganisms associated with the plant. The results suggested that terpinolene was most likely oxidized to p-cymene, which, in turn, was oxidized into p-cymen-8-ol during natural aging of the exudate due to abiotic factors.
Topics: Burseraceae; Cyclohexane Monoterpenes; Cymenes; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Oxidation-Reduction; Plant Extracts; Terpenes
PubMed: 28143669
DOI: 10.1016/j.phytochem.2017.01.013 -
Yakugaku Zasshi : Journal of the... 2022Olive weevils, Pimelocerus (Dyscerus) perforatus Roelofs, utilize olive trees as a host plant. The adult female uses an elongated snout to puncture the trunk and lay one...
Olive weevils, Pimelocerus (Dyscerus) perforatus Roelofs, utilize olive trees as a host plant. The adult female uses an elongated snout to puncture the trunk and lay one egg a day, resulting in dozens of eggs over its lifetime. The hatched larvae grow by eating the olive trunk. When olive trees die due to feeding damage, olive productivity is seriously impaired. Since there is no effective pesticide for olive weevils so far, the authors aimed to develop a repellent for adult olive weevils from the viewpoint of integrated pest management. We prepared a measurable apparatus for the repellent action against olive weevils and screened chemical substances by using the apparatus. When the repellent activity was measured using vanillin and its derivatives, a clear repellent effect could be confirmed for two types of vanillin derivatives, such as o-vanillin, and 2-hydroxy-4-methoxybenzaldehyde. In addition, when the repellent activity against olive weevils was measured using monoterpenes, four types of acyclic monoterpenes, geraniol, β-citronellol, citral, and linalool, and three types of monocyclic monoterpenes, (-)-limonene, (+)-limonene, and (-)-menthol, and a bicyclic monoterpene, (1R)-(+)-α-pinene, were found to have dose-dependent repellent activity with statistical significance. In the future, it is expected that the formulation for applying the repellent substances to olive trees and the study of their practicality in olive fields will progress.
Topics: Animals; Benzaldehydes; Monoterpenes; Olea; Weevils
PubMed: 36047212
DOI: 10.1248/yakushi.22-00086 -
Biochemical and Biophysical Research... Mar 2022In a previous study, we identified CYP5035S7 of the white-rot fungus Polyporus arcularius with a broad activity towards monoterpenes such as p-cymene. Therefore, in this...
In a previous study, we identified CYP5035S7 of the white-rot fungus Polyporus arcularius with a broad activity towards monoterpenes such as p-cymene. Therefore, in this study we aimed at further exploring the substrate scope of detoxifying CYP5035S7 towards terpenes and semi-preparatively isolating some of the products via whole-cell biotransformation, in order to obtain information about the enzyme's reactivity. We noticed a clear preference for the monoterpene skeleton and elucidated a distinct regioselectivity pattern based on key structural and electronic features of its substrates. This study illustrates how minimal characterisation effort may already suffice to provide vital information on enzymatic reactivity by the comparison of structural derivatives.
Topics: Biotransformation; Carbon; Cytochrome P-450 Enzyme System; Fungal Proteins; Hydroxylation; Molecular Structure; Monoterpenes; Polyporus; Stereoisomerism; Substrate Specificity
PubMed: 35093638
DOI: 10.1016/j.bbrc.2022.01.072