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Journal of Occupational Health 2012Monoterpenes can positively or negatively affect human health depending on their concentrations. To assess the atmospheric risk for greenhouse workers, monoterpene...
OBJECTIVES
Monoterpenes can positively or negatively affect human health depending on their concentrations. To assess the atmospheric risk for greenhouse workers, monoterpene concentrations and personal exposure in herb-growing greenhouses were measured.
METHODS
Monoterpene concentrations in a commercial greenhouse, where rosemary (Rosmarinus officinalis L.) and lavender (Lavandula angustifolia L.) were grown in pots, were measured every 4 hours on 11 days spread across a year. In a small experimental greenhouse, typical horticultural tasks were conducted to determine the factors increasing monoterpene concentrations.
RESULTS
Concentrations of α-pinene, camphene, β-pinene, limonene and cineole in the farmer's greenhouse were higher in winter than in summer because of longer ventilation periods of the greenhouse in summer. Further, the concentrations of these compounds were high (but <2 parts per billion in volume [ppbv]) when horticultural tasks were conducted inside the greenhouse. In a small experimental greenhouse, moving pots and cutting shoots increased ambient monoterpene concentrations to 10 ppbv. Spraying water also increased monoterpene concentrations but to a lesser extent. When performing tasks, greenhouse workers were exposed to monoterpene concentrations 2-3 times higher than the concentration in the ambient greenhouse air.
CONCLUSIONS
Our measurement results reveal that monoterpene emissions are stimulated by horticultural tasks, even by spraying water. Our calculation result suggests that if ventilation is limited, the concentrations can reach levels high enough to cause sensory irritation in greenhouse workers. Greenhouse workers should be cautious when performing tasks for hours in tightly closed herb-growing greenhouses.
Topics: Air Pollutants, Occupational; Environment, Controlled; Gardening; Humans; Industry; Japan; Lavandula; Monoterpenes; Occupational Exposure; Rosmarinus
PubMed: 23060029
DOI: 10.1539/joh.12-0138-fs -
Natural Product Research Dec 2003A novel monoterpene,(1R, 2S, 6S)-(+)-1,6-epoxy-4(8)-p-menthen-2-ol [corrected], was isolated from an elicitor-treated cell culture of Cupressus lusitanica (Mexican...
A novel monoterpene,(1R, 2S, 6S)-(+)-1,6-epoxy-4(8)-p-menthen-2-ol [corrected], was isolated from an elicitor-treated cell culture of Cupressus lusitanica (Mexican cypress). Ten known monoterpenes--limonene, myrcene, beta-ocimene, sabinene, terpinolene, 4-terpineol, alpha-terpineol, 4(8)-p-menthen-1,2-diol, 4-hydroxyphellandric acid methylester and beta-thujaplicin methylether--were also identified. Regioselective metabolisms of monoterpenes were observed in this culture.
Topics: Cell Culture Techniques; Cupressus; Monoterpenes
PubMed: 14577696
DOI: 10.1080/1478641031000111525 -
Chemistry & Biodiversity Jul 2018Callistrilones F - K (1 - 6), six new triketone-phloroglucinol-monoterpene hybrids were isolated from the twigs and leaves of Callistemon rigidus. Their structures with...
Callistrilones F - K (1 - 6), six new triketone-phloroglucinol-monoterpene hybrids were isolated from the twigs and leaves of Callistemon rigidus. Their structures with absolute configurations were established by a combination analysis of NMR spectra, X-ray diffraction, and electronic circular dichroism (ECD) calculations. Compounds 3 and 4 exhibited moderate inhibitory activities against herpes simplex virus (HSV-1) with IC values of 10.00 ± 2.50 and 12.50 ± 1.30 μm, respectively.
Topics: Antiviral Agents; Dose-Response Relationship, Drug; Ketones; Microbial Sensitivity Tests; Molecular Conformation; Monoterpenes; Myrtaceae; Phloroglucinol; Simplexvirus; Stereoisomerism; Structure-Activity Relationship
PubMed: 29806969
DOI: 10.1002/cbdv.201800172 -
Zhongguo Zhong Yao Za Zhi = Zhongguo... May 2014To investigate monoterpenes and sesquiterpenes of the stems and leaves of Clausena excavata, an AcOEt fraction of the methanol extract was subjected on column...
To investigate monoterpenes and sesquiterpenes of the stems and leaves of Clausena excavata, an AcOEt fraction of the methanol extract was subjected on column chromatographies including silica gel and RP-18, as well as preparative HPLC. The structures of compounds isolated were identified on the basis of spectroscopic data as excamonoterpene (1), (6R, 9S)-9, 10-dihydroxy-4-megastigmen-3-one (2), (3R, 6R, 7E) -3-hydroxy-4, 7-megastigmadien-9-one (3), (3S) -3-hydroxy-7, 8-dihydro-beta-ionone (4), (3S, 5R, 6S) -3-hydroxy-5,6-epoxy-beta-ionone (5), (6R, 9R) -9-hydroxy-4-megastigmen-3-one (6), (3S, SR) -dihydroxy-6, 7-megstigmadien-9-one(7), (-)-loliolide(8), caryolane-1, 9alpha-diol(9) and 2, 6-dihydroxyhumula-3 (12), 7 (13), 9(E)-triene (10), were isolated from the stems and leaves of C. excavata. Compound 1 is a new monoterpene, named as excamonoterpene. Compounds 2-10 were isolated from this plant for the first time.
Topics: Chromatography, High Pressure Liquid; Clausena; Magnetic Resonance Spectroscopy; Methanol; Molecular Structure; Monoterpenes; Plant Leaves; Plant Stems; Sesquiterpenes; Spectrometry, Mass, Electrospray Ionization
PubMed: 25095372
DOI: No ID Found -
Amino Acids Aug 2011Natural monoterpenes have proved to be good starting materials for the synthesis of β-amino acid derivatives. In the past decade, a number of well-known synthetic... (Review)
Review
Natural monoterpenes have proved to be good starting materials for the synthesis of β-amino acid derivatives. In the past decade, a number of well-known synthetic procedures have been applied for the preparation of monoterpene-based β-amino acid derivatives, e.g. from β-lactams via the 1,2-dipolar cycloaddition of chlorosulfonyl isocyanate to commercial or readily available monoterpenes [e.g. (+)- and (-)-α- or δ-pinene, (+)-3- and 2-carene, (+)- and (-)-apopinene], the conjugate addition of amides to monoterpene-based α,β-unsaturated esters or the transformations of (-)-cis-pinonoic acid prepared by the oxidative cleavage of (+)- and (-)-verbenone. β-Amino acid derivatives are excellent building blocks for versatile transformations, e.g. multicomponent reactions resulting in β-lactams, syntheses of 1,3-heterocycles and diaminopyrimidine derivatives or the formation of peptides containing an H12 helix. 1,3-Amino alcohol derivatives prepared from β-amino esters have been applied as chiral catalysts in enantioselective transformations. Several of these compounds are of noteworthy pharmacological importance, such as tyrosine kinase Axl inhibitor diaminopyrimidine-coupled β-aminocarboxamides, MDR inhibitor thiourea derivatives of β-amino esters or 2-imino-1,3-oxazines, which exhibit marked growth inhibitory activity on multiple cancer cell lines. The present review summarizes recent developments relating to the syntheses, applications and pharmaceutical importance of monoterpene-based β-amino acids and their derivatives.
Topics: Amino Acids; Bicyclic Monoterpenes; Catalysis; Esters; Monoterpenes; Peptides; Stereoisomerism; Terpenes; Thiourea; beta-Lactams
PubMed: 21448657
DOI: 10.1007/s00726-011-0891-5 -
Journal of the American Chemical Society May 2010The simplest form of terpenoid chemistry is found for the monoterpenes, which give plants fragrance, flavor, and medicinal properties. Monoterpene synthases employ...
The simplest form of terpenoid chemistry is found for the monoterpenes, which give plants fragrance, flavor, and medicinal properties. Monoterpene synthases employ geranyl diphosphate as a substrate to generate an assortment of cyclic products. In the current study we present a detailed analysis of the multiple gas-phase reaction pathways in the synthesis of bornyl cation from geranyl diphosphate. Additionally, the fate of the proposed bornyl cation intermediate in the bornyl diphosphate synthase reaction is investigated by molecular dynamics simulations. We employ accurate density functional theory (DFT) methods after careful validation against high-level ab initio data for a set of model carbocations. The gas-phase results for the monoterpene reactions indicate a diverging reaction mechanism with multiple products in the absence of enzymatic control. This complex potential energy surface includes several possible bifurcation points due to the presence of secondary cations. Additionally, the suggested bornyl cation intermediate in the bornyl diphosphate synthase reaction is studied by molecular dynamics simulations employing a hybrid quantum mechanics (DFT)-molecular mechanics potential energy function. The simulations suggest that the bornyl cation is a transient species as in the gas phase and that electrostatic steering directs the formation of the final product, bornyl diphosphate.
Topics: Alkyl and Aryl Transferases; Gases; Molecular Conformation; Molecular Dynamics Simulation; Monoterpenes; Quantum Theory; Salvia officinalis; Thermodynamics
PubMed: 20394387
DOI: 10.1021/ja910134x -
Journal of Chemical Ecology Jun 2019Bark beetles kill apparently vigorous conifers during epidemics by means of pheromone-mediated aggregation. During non-endemic conditions the beetles are limited to use...
Styrene, (+)-trans-(1R,4S,5S)-4-Thujanol and Oxygenated Monoterpenes Related to Host Stress Elicit Strong Electrophysiological Responses in the Bark Beetle Ips typographus.
Bark beetles kill apparently vigorous conifers during epidemics by means of pheromone-mediated aggregation. During non-endemic conditions the beetles are limited to use trees with poor defense, like wind-thrown. To find olfactory cues that help beetles to distinguish between trees with strong or weak defense, we collected volatiles from the bark surface of healthy felled or standing Picea abies trees. Furthermore, living trees were treated with methyl jasmonate in order to induce defense responses. Volatiles were analyzed by combined gas chromatography and electroantennographic detection (GC-EAD) on Ips typographus antennae. Compounds eliciting antennal responses were characterized by single sensillum recording for identification of specific olfactory sensory neurons (OSN). Release of monoterpene hydrocarbons decreased, while oxygenated compounds increased, from spring to early summer in felled trees. In both beetle sexes particular strong EAD activity was elicited by trace amounts of terpene alcohols and ketones. 4-Thujanol gave a very strong response and the absolute configuration of the tested natural product was assigned to be (+)-trans-(1R,4S,5S)-thujanol by stereoselective synthesis and enantioselective gas chromatography. One type of OSN responded to all ketones and five other OSN were characterized by the type of compounds that elicited responses. Three new OSN classes were found. Of the eight EAD-active compounds found in methyl jasmonate-treated bark, the known anti-attractant 1,8-cineole was the one most strongly induced. Our data support the hypothesis that highly active oxygenated host volatiles could serve as positive or negative cues for host selection in I. typographus and in other bark beetles.
Topics: Acetates; Animals; Bicyclic Monoterpenes; Coleoptera; Cyclopentanes; Electrophysiological Phenomena; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oxylipins; Picea; Plant Bark; Stereoisomerism; Styrene
PubMed: 31053976
DOI: 10.1007/s10886-019-01070-8 -
Phytochemistry Dec 2013Menthol is a cyclic monoterpene alcohol which possesses well-known cooling characteristics and a residual minty smell of the oil remnants from which it was obtained.... (Review)
Review
Menthol is a cyclic monoterpene alcohol which possesses well-known cooling characteristics and a residual minty smell of the oil remnants from which it was obtained. Because of these attributes it is one of the most important flavouring additives besides vanilla and citrus. Due to this reason it is used in a variety of consumer products ranging from confections such as chocolate and chewing gum to oral-care products such as toothpaste as well as in over-the-counter medicinal products for its cooling and biological effects. Its cooling effects are not exclusive to medicinal use. Approximately one quarter of the cigarettes on the market contain menthol and small amounts of menthol are even included in non-mentholated cigarettes. Natural menthol is isolated exclusively from Mentha canadensis, but can also be synthesised on industrial scale through various processes. Although menthol exists in eight stereoisomeric forms, (-)-menthol from the natural source and synthesised menthol with the same structure is the most preferred isomer. The demand for menthol is high and it was previously estimated that the worldwide use of menthol was 30-32,000 metric tonnes per annum. Menthol is not a predominant compound of the essential oils as it can only be found as a constituent of a limited number of aromatic plants. These plants are known to exhibit biological activity in vitro and in vivo such as antibacterial, antifungal, antipruritic, anticancer and analgesic effects, and are also an effective fumigant. In addition, menthol is one of the most effective terpenes used to enhance the dermal penetration of pharmaceuticals. This review summarises the chemical and biological properties of menthol and highlights its cooling effects and toxicity.
Topics: Body Temperature; Humans; Mentha; Menthol; Molecular Structure; Monoterpenes; Oils, Volatile
PubMed: 24054028
DOI: 10.1016/j.phytochem.2013.08.005 -
Phytomedicine : International Journal... May 2024Genus Paeonia, which is the main source of Traditional Chinese Medicine (TCM) Paeoniae Radix Rubra (Chishao in Chinese), Paeoniae Radix Alba (Baishao in Chinese) and... (Review)
Review
BACKGROUND
Genus Paeonia, which is the main source of Traditional Chinese Medicine (TCM) Paeoniae Radix Rubra (Chishao in Chinese), Paeoniae Radix Alba (Baishao in Chinese) and Moutan Cortex (Mudanpi in Chinese), is rich in active pharmaceutical ingredient such as monoterpenoid glycosides (MPGs). MPGs from Paeonia have extensive pharmacological effects, but the pharmacological effects and molecular mechanisms of MPGs has not been comprehensively reviewed.
PURPOSE
MPGs compounds are one of the main chemical components of the genus Paeonia, with a wide variety of compounds and strong pharmacological activities, and the structure of the mother nucleus-pinane skeleton is similar to that of a cage. The purpose of this review is to summarize the pharmacological activity and mechanism of action of MPGs from 2012 to 2023, providing reference direction for the development and utilization of Paeonia resources and preclinical research.
METHODS
Keywords and phrases are widely used in database searches, such as PubMed, Web of Science, Google Scholar and X-Mol to search for citations related to the new compounds, extensive pharmacological research and molecular mechanisms of MPGs compounds of genus Paeonia.
RESULTS
Modern research confirms that MPGs are the main compounds in Paeonia that exert pharmacological effects. MPGs with extensive pharmacological characteristics are mainly concentrated in two categories: paeoniflorin derivatives and albiflflorin derivatives among MPGs, which contains 32 compounds. Among them, 5 components including paeoniflorin, albiflorin, oxypaeoniflorin, 6'-O-galloylpaeoniflorin and paeoniflorigenone have been extensively studied, while the other 28 components have only been confirmed to have a certain degree of anti-inflammatory and anticomplementary effects. Studies of pharmacological effects are widely involved in nervous system, endocrine system, digestive system, immune system, etc., and some studies have identified clear mechanisms. MPGs exert pharmacological activity through multilateral mechanisms, including anti-inflammatory, antioxidant, inhibition of cell apoptosis, regulation of brain gut axis, regulation of gut microbiota and downregulation of mitochondrial apoptosis, etc. CONCLUSION: This systematic review delved into the pharmacological effects and related molecular mechanisms of MPGs. However, there are still some compounds in MPGs whose pharmacological effects and pharmacological mechanisms have not been clarified. In addition, extensive clinical randomized trials are needed to verify the efficacy and dosage of MPGs.
Topics: Glycosides; Paeonia; Drugs, Chinese Herbal; Monoterpenes; Anti-Inflammatory Agents; Glucosides
PubMed: 38432036
DOI: 10.1016/j.phymed.2024.155483 -
Recent Advances in Anti-infective Drug... 2023Pulegone ((R)-5-Methyl-2-(1-methylethylidine) cyclohexanone) is a pharmacologically active, natural monoterpene ketone obtained from leaves and flowering tops of the... (Review)
Review
Pulegone ((R)-5-Methyl-2-(1-methylethylidine) cyclohexanone) is a pharmacologically active, natural monoterpene ketone obtained from leaves and flowering tops of the mint family (Lamiaceae). The aim is to comprise the physicochemical and biological aspects of pulegone. All significant databases were collected via electronic search using Pubmed, Scopus, Web of Science, and Science Direct and were compiled. This review presents the occurrence, chemistry, and modifications of pulegone structure and its effect on the biological system. Pulegone represents various pharmacological properties, i.e., antioxidant, antimicrobial, anti-feeding, antifungal, antiviral, and pesticide activities, and has a significant role as an abortifacient and emmenagogue. Thus, this present review concludes the knowledgeable erudition on pulegone that paves the way for further work.
Topics: Monoterpenes; Monoterpene Aldehydes and Ketones; Ketones; Cyclohexane Monoterpenes; Lamiaceae
PubMed: 36263486
DOI: 10.2174/2772434418666221018090507