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International Journal of Biological... Dec 2023Despite the high economic value of the monoterpene-rich essential oils from different genotypes of Cymbopogon, the knowledge about the genes and metabolic route(s)...
Development and analysis of de novo transcriptome assemblies of multiple genotypes of Cymbopogon spp. reveal candidate genes involved in the biosynthesis of aromatic monoterpenes.
Despite the high economic value of the monoterpene-rich essential oils from different genotypes of Cymbopogon, the knowledge about the genes and metabolic route(s) involved in the biosynthesis of aromatic monoterpenes in this genus is limited. In the present study, a comprehensive transcriptome analysis of four genotypes of Cymbopogon, displaying diverse quantitative and qualitative profiles of volatile monoterpenes in their essential oils has been carried out. The comparative analysis of the deduced protein sequences corresponding to the transcriptomes of the four genotypes revealed 4609 genotype-specific orthogroups, which might contribute in defining genotype-specific phenotypes. The transcriptome data mining led to the identification of unigenes involved in the isoprenogenesis. The homology searches, combined with the phylogenetic and expression analyses provided information about candidate genes concerning the biosynthesis of monoterpene aldehyde, monoterpene alcohol, and monoterpene esters. In addition, the present study suggests a potential role of geranial reductase like enzyme in the biosynthesis of monoterpene aldehyde in Cymbopogon spp. The detailed analysis of the candidate pathway genes suggested that multiple enzymatic routes might be involved in the biosynthesis of aromatic monoterpenes in the genus Cymbopogon. The present study provides deeper insights into the biosynthesis of monoterpenes, which will be useful for the genetic improvement of these aromatic grasses.
Topics: Monoterpenes; Transcriptome; Cymbopogon; Phylogeny; Monoterpene Aldehydes and Ketones; Oils, Volatile; Genotype
PubMed: 37865377
DOI: 10.1016/j.ijbiomac.2023.127508 -
Journal of Natural Medicines Jan 2010Two novel monoterpenes, sibiscolacton (1) and sibiraic acid (2), were isolated from the aerial part of Sibiraea angustata RCHD: . along with seven known compounds,...
Two novel monoterpenes, sibiscolacton (1) and sibiraic acid (2), were isolated from the aerial part of Sibiraea angustata RCHD: . along with seven known compounds, namely three phenylpropanoids (3-5), two flavonoids (6,7), one glucityl ferulate (8, sibirate), and a monoterpene glucoside (9, sibiskoside). The structures of 1 and 2 were established on the basis of spectroscopic and chemical data.
Topics: Medicine, Tibetan Traditional; Monoterpenes; Plant Components, Aerial; Plant Extracts; Rosaceae; Spectrum Analysis
PubMed: 19787420
DOI: 10.1007/s11418-009-0362-4 -
Talanta Jun 2016Three methods, i.e., the cylindrical wet effluent diffusion denuder (CWEDD)-GCMS, Tenax tubes-GCMS and Proton-Transfer-Reaction Time-of-Flight Mass Spectrometry...
Three methods, i.e., the cylindrical wet effluent diffusion denuder (CWEDD)-GCMS, Tenax tubes-GCMS and Proton-Transfer-Reaction Time-of-Flight Mass Spectrometry (PTR-TOF-MS) were compared for the determination of monoterpenes in forest. While the on-line technique (PTR-TOF-MS) allows only for the measurement of sum of monoterpenes, both the off-line preconcentration techniques (CWEDD and Tenax tubes) are suitable for the determination of concentrations of individual monoterpenes due to subsequent analysis of samples by GCMS. The CWEDD-GCMS is the only method that allows sampling of individual monoterpenes with short time intervals of 2-5min. Monoterpenes are absorbed into a liquid (n-heptane), flowing down on the inner wall of the CWEDD, and then the collected liquid with monoterpenes is immediately taken away for the GCMS analysis, which minimizes time when collected monoterpenes are exposed to oxidants presented in the air during sampling. The limits of detection of CWEDD-GCMS are in the range 1-7pptv for individual monoterpenes.
Topics: Forests; Heptanes; Mass Spectrometry; Monoterpenes
PubMed: 27130117
DOI: 10.1016/j.talanta.2016.03.032 -
PloS One 2024Monoterpenes are a large class of naturally occurring fragrant molecules. These chemicals are commonly used in olfactory studies to survey neural activity and probe the...
Monoterpenes are a large class of naturally occurring fragrant molecules. These chemicals are commonly used in olfactory studies to survey neural activity and probe the behavioral limits of odor discrimination. Monoterpenes (typically in the form of essential oils) have been used for centuries for therapeutic purposes and have pivotal roles in various biological and medical applications. Despite their importance for multiple lines of research using rodent models and the role of the olfactory system in detecting these volatile chemicals, the murine sensitivity to monoterpenes remains mostly unexplored. We assayed the ability of C57BL/6J mice to detect nine different monoterpenes (the acyclic monoterpenes: geraniol, citral, and linalool; the monocyclic monoterpenes: r-limonene, s-limonene, and γ-terpinene; and the bicyclic monoterpenes: eucalyptol, α-pinene, and β-pinene) using a head-fixed Go / No-Go operant conditioning assay. We found that mice can reliably detect monoterpene concentrations in the low parts per billion (ppb) range. Specifically, mice were most sensitive to geraniol (threshold: 0.7 ppb) and least sensitive to γ-terpinene (threshold: 18.1 ppb). These estimations of sensitivity serve to set the lower limit of relevant monoterpene concentrations for functional experiments in mice. To define an upper limit, we estimated the maximum concentrations that a mouse may experience in nature by collating published headspace analyses of monoterpene concentrations emitted from natural sources. We found that natural monoterpenes concentrations typically ranged from ~1 to 1000 ppb. It is our hope that this dataset will help researchers use appropriate monoterpene concentrations for functional studies and provide context for the vapor-phase delivery of these chemicals in studies investigating their biological activity in mice.
Topics: Mice; Animals; Limonene; Mice, Inbred C57BL; Monoterpenes; Bicyclic Monoterpenes; Acyclic Monoterpenes; Cyclohexane Monoterpenes
PubMed: 38394306
DOI: 10.1371/journal.pone.0298448 -
Natural Product Research 2009The effects of the monoterpenes of 3-carene, 1,8-cineole, beta-pinene, terpinene and terpinolene on the repellent, contact toxicity of Tribolium castaneum adults and...
The effects of the monoterpenes of 3-carene, 1,8-cineole, beta-pinene, terpinene and terpinolene on the repellent, contact toxicity of Tribolium castaneum adults and sustaining fumigant toxicity of Sitophilus zeamaise adults were examined. Monoterpene of 1,8-cineole in 20 microL mL(-1) and beta-pinene in 20 microL mL(-1) exhibited the highest percentage repellency, whereas 3-carene in concentration of 4 microL mL(-1) exhibited the significantly lower percentage repellency. Topical application and fumigant assays were used across a range of concentrations to develop dosage-mortality regressions. Among the monoterpenes tested, the most contact toxic compound was beta-pinene (with LC(50) values ranging between 31.44 and 62.07 microg mg(-1)), whereas 3-carene was the least (with LC(50) values ranging between 66.58 and 93.68 microg mg(-1)). All five monoterpenes were fumigant toxic to S. zeamaise adults, and the fumigant effect varied, along with the exposure time and the dosage. Terpinene and terpinolene were consistently the most fumigant toxic compounds on S. zeamaise, and the trend of high-to-low toxicity based on LC(50) values was not changed when treated for 24, 48, 72 and 96 h; the lethal concentration causing 50% mortality (LC(50)) with terpinolene was reduced by 71.5% after a 96 h treatment time, compared to beta-pinene and 3-carene, where only 35.0 and 31.4% reduction were observed, respectively. The data presented here indicated that the monoterpenes had repellent or toxic effects and could be screened for the control of storage pests.
Topics: Animals; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Coleoptera; Cyclohexane Monoterpenes; Cyclohexanols; Eucalyptol; Insect Repellents; Monoterpenes; Terpenes; Tribolium
PubMed: 19662572
DOI: 10.1080/14786410802267759 -
International Journal of Molecular... Nov 2023Monoterpene thiols are one of the classes of natural flavors that impart the smell of citrus fruits, grape must and wine, black currants, and guava and are used as... (Review)
Review
Monoterpene thiols are one of the classes of natural flavors that impart the smell of citrus fruits, grape must and wine, black currants, and guava and are used as flavoring agents in the food and perfume industries. Synthetic monoterpene thiols have found an application in asymmetric synthesis as chiral auxiliaries, derivatizing agents, and ligands for metal complex catalysis and organocatalysts. Since monoterpenes and monoterpenoids are a renewable source, there are emerging trends to use monoterpene thiols as monomers for producing new types of green polymers. Monoterpene thioderivatives are also known to possess antioxidant, anticoagulant, antifungal, and antibacterial activity. The current review covers methods for the synthesis of acyclic, mono-, and bicyclic monoterpene thiols, as well as some investigations related to their usage for the preparation of the compounds with antimicrobial properties.
Topics: Monoterpenes; Sulfhydryl Compounds; Wine; Vitis
PubMed: 37958865
DOI: 10.3390/ijms242115884 -
Archives of Biochemistry and Biophysics Nov 2022Rhodococcus globerulus (R. globerulus) isolated from soil beneath Eucalyptus sp. was found to live on the monoterpenes 1,8-cineole, p-cymene and (R)- and (S)-limonene as...
Rhodococcus globerulus (R. globerulus) isolated from soil beneath Eucalyptus sp. was found to live on the monoterpenes 1,8-cineole, p-cymene and (R)- and (S)-limonene as sole sources of carbon and energy. Previous metabolic studies revealed that R. globerulus is capable of living on 1,8-cineole, the main monoterpene component of eucalyptus essential oil through the activity of cytochrome P450 (CYP176A1) [1]. Genomic sequencing of R. globerulus revealed a novel putative cytochrome P450 (CYP108N12) that shares 48% sequence identity with CYP108A1 (P450) from Pseudomonas sp., an α-terpineol hydroxylase. Given the sequence similarity between CYP108N12 and P450, it was hypothesised that CYP108N12 may be responsible for initiating the biodegradation of a monoterpene structurally similar to α-terpineol such as (R)-limonene, (S)-limonene or p-cymene. Encoded within the operon containing CYP108N12 were two putative bacterial P450 redox partners and putative alcohol and aldehyde dehydrogenases, suggesting a complete catalytic system for activating these monoterpenes. Binding studies revealed that p-cymene and (R)- and (S)-limonene all bound tightly to CYP108N12 but α-terpineol did not. A catalytically active system was reconstituted using the non-native redox partner putidaredoxin and putidaredoxin reductase that act with CYP101A1 (P450) from Pseudomonas. This reconstituted system catalysed the hydroxylation of p-cymene to 4-isopropylbenzyl alcohol, and (R)- and (S)-limonene to (R)- and (S)-perillyl alcohol, respectively. R. globerulus was successfully grown on solely p-cymene, (R)-limonene or (S)-limonene. CYP108N12 was detected when R. globerulus was grown on p-cymene, but not either limonene enantiomer. The native function of CYP108N12 is therefore proposed to be initiation of p-cymene biodegradation by methyl oxidation and is a potentially attractive biocatalyst capable of specific benzylic and allylic hydroxylation.
Topics: Limonene; Eucalyptol; Monoterpenes; Cytochrome P-450 Enzyme System; Pseudomonas; Carbon; Soil; Oils, Volatile; Aldehydes; Terpenes
PubMed: 36155781
DOI: 10.1016/j.abb.2022.109410 -
Biomedicine & Pharmacotherapy =... Oct 2020Increasing pharmacological evidence supports that paeoniflorin, a water-soluble monoterpene glycoside isolated from Paeonia lactiflora Pall. (Shaoyao in Chinese), has a... (Review)
Review
Increasing pharmacological evidence supports that paeoniflorin, a water-soluble monoterpene glycoside isolated from Paeonia lactiflora Pall. (Shaoyao in Chinese), has a wide range of medicinal properties including anti-inflammatory, antioxidant, antithrombotic, anticonvulsive, analgesic, cardioprotective, neuroprotective, hepatoprotective, antidepressant-like, antitumoral, and immune-regulatory activities; as well as enhancing cognition and attenuating learning impairment. In addition to pharmacodynamic studies, information on pharmacokinetics is also significant for the further development and utilization of paeoniflorin. The present review focuses on the absorption, distribution, metabolism, and excretion of paeoniflorin, especially main pharmacological activities of paeoniflorin on inflammation and immune function. According to the findings obtained both in vitro and in vivo, a broad application prospect has been opened for paeoniflorin. However, further studies are needed to clarity the direct molecular mechanisms and key targets underlying the beneficial effects of paeoniflorin on inflammation and immunity.
Topics: Animals; Anti-Inflammatory Agents; Glucosides; Humans; Immunologic Factors; Inflammation; Monoterpenes; Paeonia; Signal Transduction
PubMed: 32682112
DOI: 10.1016/j.biopha.2020.110505 -
Current Pharmaceutical Design Dec 2018Carvacrol has a high therapeutic potential, with in vitro studies showing promising results in different cellular models using a variety of methodological designs.... (Review)
Review
Carvacrol has a high therapeutic potential, with in vitro studies showing promising results in different cellular models using a variety of methodological designs. Therefore, the objective of this study was to conduct a systematic review to analyze the pharmacological effects of carvacrol in in vitro studies. A comprehensive search of the literature was made using four databases: Science Direct, Scopus, MEDLINE-PubMed, and Web of Science using different combinations of the following keywords: carvacrol, drug therapy, therapeutic uses, in vitro study. The search of the databases was for studies conducted in the period up to and including September 2016. A total of 3,269 studies were initially identified, with only 31 meeting the inclusion criteria. The included studies contained a variety of in vitro models able to determine the properties of Carvacrol. The following properties of Carvacrol were identified: antimicrobial (7 studies), bactericidal (4), bactericidal and antifungal (1), antiinflammatory (4), anticancer (4), mutagenic (4), antioxidant (3), antifungal (3), antidepressant (1), as a modulator of nerve impulses (1) and an immunological modulator (1). The In vitro studies with Carvacrol included in this review showed a diversity of models and confirmed the therapeutic potential of this product in relation to several diseases.
Topics: Animals; Anti-Infective Agents; Anti-Inflammatory Agents; Antineoplastic Agents; Antioxidants; Cymenes; Drug Design; Humans; Monoterpenes
PubMed: 30280662
DOI: 10.2174/1381612824666181003123400 -
International Journal of Molecular... Feb 2024Monoterpenes are secondary plant metabolites, and such volatile compounds have antioxidant, antibacterial, antiviral, and enzyme inhibitory properties. These compounds...
Monoterpenes are secondary plant metabolites, and such volatile compounds have antioxidant, antibacterial, antiviral, and enzyme inhibitory properties. These compounds are also able to reduce the potentially pro-neurodegenerative trace metal ions that can be sources of free radicals. One basic method used to evaluate the ability of chemical compounds to reduce Fe(III) is FRAP. To date, most studies based on a FRAP assay were performed within several dozen minutes. However, taking into account the diversity of compounds, it is justified to observe their activity over a much longer period of time. The present study aimed to observe the activity of isopulegol, γ-terpinene, α-terpinene, linalool, carvone, citral, and α-phellandrene over a 48 h period. Our study indicates that the lengthened reaction period enhanced activity from several dozen to several hundred percent. The obtained results also revealed an explicit high correlation of the increase in the activity of compounds with the increase in monoterpene concentration. Due to the hydrophobic character of monoterpenes, the FRAP method was modified by the addition of Tween 20. The highest activity was obtained for α-terpinene and γ-terpinene.
Topics: Monoterpenes; Ferric Compounds; Antioxidants; Anti-Bacterial Agents; Cyclohexane Monoterpenes
PubMed: 38396868
DOI: 10.3390/ijms25042191