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Biodegradation 1990Monoterpenes are important renewable resources for the perfume and flavour industry but the pathways and enzymology of their degradation by microorganisms are not well...
Monoterpenes are important renewable resources for the perfume and flavour industry but the pathways and enzymology of their degradation by microorganisms are not well documented. Until recently the acyclic monoterpene alcohols, (+)-camphor and the isomers of limonene were the only compounds for which significant sections of catabolic pathways and associated enzymology had been reported. In this paper recent developments in our understanding of the enzymology of ring cleavage by microorganisms capable of growth with 1,8-cineole and alpha-pinene are described. 1,8-Cineole has the carbocyclic skeleton of a monocyclic monoterpene with the added complication of an internal ether linkage. Ring hydroxylation strategy and biological Baeyer-Villiger oxygenation lead to an efficient method for cleaving the ether linkage. alpha-Pinene is an unsaturated bicyclic monoterpene hydrocarbon. At least two catabolic pathways exist. Information concerning one of them, in which alpha-pinene may be initially converted into limonene, is rudimentary. The other involves attack at the double bond resulting in formation of alpha-pinene epoxide. Ring cleavage is then catalysed by a novel lyase that requires no additional components and breaks both carbocyclic rings in a concerted manner.
Topics: Bicyclic Monoterpenes; Biodegradation, Environmental; Cyclohexanols; Eucalyptol; Menthol; Monoterpenes; Nocardia; Pseudomonas; Rhodococcus; Terpenes
PubMed: 1368150
DOI: 10.1007/BF00058829 -
Applied Microbiology and Biotechnology Jul 1996Batch experiments were conducted to assess the biotransformation potential of four hydrocarbon monoterpenes (d-limonene, alpha-pinene, gamma-terpinene, and terpinolene)...
Batch experiments were conducted to assess the biotransformation potential of four hydrocarbon monoterpenes (d-limonene, alpha-pinene, gamma-terpinene, and terpinolene) and four alcohols (arbanol, linalool, plinol, and alpha-terpineol) under aerobic conditions at 23 degrees C. Both forest-soil extract and enriched cultures were used as inocula for the biodegradation experiments conducted first without, then with prior microbial acclimation to the monoterpenes tested. All four hydrocarbons and two alcohols were readily degraded. The increase in biomass and headspace CO2 concentrations paralleled the depletion of monoterpenes, thus confirming that terpene disappearance was the result of biodegradation accompanied by microbial growth and mineralization. Plinol resisted degradation in assays using inocula from diverse sources, while arbanol degraded very slowly. A significant fraction of d-limonene-derived carbon was accounted for as non-extractable, dissolved organic carbon, whereas terpineol exhibited a much higher degree of utilization. The rate and extent of monoterpene biodegradation were not significantly affected by the presence of dissolved natural organic matter.
Topics: Acetates; Acyclic Monoterpenes; Aerobiosis; Bicyclic Monoterpenes; Biodegradation, Environmental; Cyclohexane Monoterpenes; Cyclohexenes; Glucose; Limonene; Molecular Structure; Monoterpenes; Soil Microbiology; Terpenes; Water Microbiology
PubMed: 8987470
DOI: 10.1007/s002530050770 -
Journal of Chemical Ecology Aug 2016A cell culture of Cupressus lusitanica was used to investigate the reaction of a plant to certain airborne chemicals. Compared with laboratory and field methods using...
A cell culture of Cupressus lusitanica was used to investigate the reaction of a plant to certain airborne chemicals. Compared with laboratory and field methods using intact plants or tissues, a cell culture is advantageous because it is not affected by environmental factors, and the experiments are easier to reproduce. When exposed to an elicitor, our cell line produces 10 monoterpenes and β-thujaplicin, which is a strong phytoalexin. These monoterpenes are emitted into the vapor phase and are expected to play a role in airborne signaling. In the present study, the cells were exposed to monoterpene vapors, and the volatiles present in the culture flasks were monitored. When the culture cells were exposed to low doses of sabinene, we detected γ-terpinene and p-cymene. After exposure to γ-terpinene, we found p-cymene and terpinolene, whereas p-cymene exposure resulted in terpinolene emission. By contrast, the other seven monoterpenes we investigated did not induce any emissions of other monoterpenes. These results strongly suggest that in C. lusitanica a signaling cascade exists that starts with the emission of sabinene and moves to γ-terpinene, p-cymene, and finally to terpinolene, which accelerates the production of the phytoalexin β-thujaplicin.
Topics: Air; Cells, Cultured; Cupressus; Cyclohexane Monoterpenes; Dose-Response Relationship, Drug; Monoterpenes; Signal Transduction; Terpenes; Tropolone
PubMed: 27596215
DOI: 10.1007/s10886-016-0739-2 -
Molecules (Basel, Switzerland) Sep 2010Monoterpenes, the main constituents of essential oils, are known for their many biological activities. The present work studied the potential biological activity of...
Monoterpenes, the main constituents of essential oils, are known for their many biological activities. The present work studied the potential biological activity of twenty-seven monoterpenes, including monoterpene hydrocarbons and oxygenated ones, against seed germination and subsequent primary radicle growth of Raphanus sativus L. (radish) and Lepidium sativum L. (garden cress), under laboratory conditions. The compounds, belonging to different chemical classes, showed different potency in affecting both parameters evaluated. The assayed compounds demonstrated a good inhibitory activity in a dose-dependent way. In general, radish seed is more sensitive than garden cress and its germination appeares more inhibited by alcohols; at the highest concentration tested, the more active substances were geraniol, borneol, (±)-β-citronellol and α-terpineol. Geraniol and carvone inhibited, in a significant way, the germination of garden cress, at the highest concentration tested. Radicle elongation of two test species was inhibited mainly by alcohols and ketones. Carvone inhibited the radicle elongation of both seeds, at almost all concentrations assayed, while 1,8-cineole inhibited their radicle elongation at the lowest concentrations (10(-5) M, 10(-6) M).
Topics: Alcohols; Dose-Response Relationship, Drug; Germination; Lepidium sativum; Monoterpenes; Raphanus; Seeds; Structure-Activity Relationship
PubMed: 20877249
DOI: 10.3390/molecules15096630 -
Critical Reviews in Food Science and... 2015Carvacrol is a monoterpenic phenol produced by an abundant number of aromatic plants, including thyme and oregano. Presently, carvacrol is used in low concentrations as... (Review)
Review
Carvacrol is a monoterpenic phenol produced by an abundant number of aromatic plants, including thyme and oregano. Presently, carvacrol is used in low concentrations as a food flavoring ingredient and preservative, as well as a fragrance ingredient in cosmetic formulations. In recent years, considerable research has been undertaken in an effort to establish the biological actions of carvacrol for its potential use in clinical applications. Results from in vitro and in vivo studies show that carvacrol possess a variety of biological and pharmacological properties including antioxidant, antibacterial, antifungal, anticancer, anti-inflammatory, hepatoprotective, spasmolytic, and vasorelaxant. The focus of this review is to evaluate the existing knowledge regarding the biological, pharmacological, and toxicological effects of carvacrol.
Topics: Animals; Anti-Bacterial Agents; Anti-Inflammatory Agents; Antifungal Agents; Antioxidants; Cymenes; Humans; Monoterpenes; Oils, Volatile; Plant Oils
PubMed: 24915411
DOI: 10.1080/10408398.2011.653458 -
Natural Product Research Jun 2004During our systematic study on the species of genus Linaria (Scrophulariaceae) present in Italy, we examined the glycosidic fraction of Linaria capraria Moris et De...
During our systematic study on the species of genus Linaria (Scrophulariaceae) present in Italy, we examined the glycosidic fraction of Linaria capraria Moris et De Not., a species endemic of Tuscany archipelago. This fraction is particularly complex and we considered in this article only the medium polarity components. In accordance with previous studies, L. capraria shows acyl derivatives of antirrhinoside 1 as specific chemotaxonomic iridoidic markers. L. capraria exhibits a complex composition, with regard to iridoidic constituents, with several chromatographic problems to be resolved. We then isolated, besides the known antirrhinoside 1, two acyl derivatives of antirrhinoside, the 6'-O-senecioyl derivative, 2, and the 6'-O-angeloyl derivative, 3. In addition a glucoside of an acyclic monoterpene, 4, was also isolated, which may be correlated to the other monoterpenic glycosides isolated from other species of Scrophulariaceae.
Topics: Glycosides; Italy; Linaria; Monoterpenes
PubMed: 15143834
DOI: 10.1080/1478641031000111589 -
Pharmaceutical Development and... Sep 2020Glycerol monostearate solid lipid nanoparticles (SLN) were produced by hot high-pressure homogenization technique to load alpha-pinene, citral, geraniol or limonene. SLN...
Glycerol monostearate solid lipid nanoparticles (SLN) were produced by hot high-pressure homogenization technique to load alpha-pinene, citral, geraniol or limonene. SLN were composed of 1 wt.% monoterpene, 4 wt.% of Imwitor 900K as a solid lipid and 2.5 wt.% of Poloxamer188 as a surfactant. Empty SLN consisted of 5 wt.% of Imwitor 900K and 2.5 wt.% of Poloxamer188. The mean particles size (Z-Ave) and polydispersity index (PDI) of SLN were analyzed by dynamic light scattering (DLS), while the zeta potential (ZP) of each formulation were measured by electrophoretic light scattering. LUMiSizer was applied to calculate the velocity distribution in the centrifugal field and instability index. Drug release profile from SLN was analyzed using Franz cell diffusion cells assayed by UV-Vis spectrophotometry, whereas the gas chromatography technique was applied to determine the encapsulation parameters of volatile monoterpenes. The matrix state, polymorphism and phase behavior of SLN were studied by X-ray diffraction (XRD, low and wide angles) and differential scanning calorimetry (DSC). Selected monoterpenes were successfully loaded in glycerol monostearate SLN. A burst release profile within the first 15 min was observed for all formulations, being the modified release profile dependent on the type of monoterpene and on the encapsulation efficiency.
Topics: Chemistry, Pharmaceutical; Drug Carriers; Drug Liberation; Drug Stability; Lipids; Monoterpenes; Nanoparticles; Particle Size
PubMed: 32204628
DOI: 10.1080/10837450.2020.1744008 -
Phytochemistry Apr 2022Natural products from plants have gained prominence in the search for therapeutic alternatives. Monoterpenes, such as carvone, are suggested as candidates for the... (Review)
Review
Natural products from plants have gained prominence in the search for therapeutic alternatives. Monoterpenes, such as carvone, are suggested as candidates for the treatment of several diseases. Therefore, the objective of this study is to review the pharmacological activities of carvone in experimental models in vitro and in vivo. For this, the searches were carried out in May 2020 (upgraded in July 2021) in the databases of PubMed, Web of Science and Scopus and gathered studies on the pharmacological activities of carvone. Two independent reviewers performed the selection of articles using the Rayyan application, extracted the relevant data and assessed the methodological quality of the selected studies using Syrcle's risk of bias tool. Ninety-one articles were selected that described 10 pharmacological activities of carvone, such as antimicrobial, antispasmodic, anti-inflammatory, antioxidant, antinociceptive, anticonvulsant, among others. The evaluation of the methodological quality presented an uncertain risk of bias for most studies. In light of that, carvone stands out as a viable and promising alternative in the treatment of several pathological conditions. However, carrying out studies to evaluate possible mechanisms of action and the safety of this monoterpene is recommended.
Topics: Anti-Infective Agents; Anti-Inflammatory Agents; Cyclohexane Monoterpenes; Monoterpenes
PubMed: 34999510
DOI: 10.1016/j.phytochem.2021.113080 -
Journal of Plant Physiology May 2009Elicitor treatment initiates defense responses in cultured Cupressus lusitanica cells. In order to investigate the defense mechanism with a yeast extract elicitor, we...
Elicitor treatment initiates defense responses in cultured Cupressus lusitanica cells. In order to investigate the defense mechanism with a yeast extract elicitor, we carried out solid-phase microextraction coupled with gas chromatography for monoterpene analysis. Ten hydrocarbon monoterpenes, including high amounts of sabinene and limonene, were detected in the gas phase of the elicitor-treated cell cultures. Six oxidized monoterpenes including beta-thujaplicin were also detected in the ether extract of the cells and the medium. Time-course profiles of volatile monoterpenes showed that one group of hydrocarbon monoterpenes was maximized on the second day after elicitation, while the other group was maximized on the third day. There were no oxidized monoterpenes that are structurally related to sabinene and limonene in the gas phase or cell extracts, suggesting that these compounds are produced exclusively for emission. Other monoterpenes, which are produced during later stages of elicitation, are metabolized into more complex compounds such as oxidized monoterpenes, including beta-thujaplicin. Although terpinolene synthase was the principal monoterpene synthase in these cell cultures, terpinolene was detected only as a minor compound in the gas phase. The time course for terpinolene synthase activity coincided with beta-thujaplicin biosynthesis. Thus, most of the terpinolene is metabolized rapidly to oxidized terpenes such as beta-thujaplicin rather than emitted.
Topics: Cell Extracts; Cells, Cultured; Cupressus; Gas Chromatography-Mass Spectrometry; Monoterpenes; Solid Phase Microextraction; Time Factors; Tropolone; Volatilization; Yeasts
PubMed: 19027192
DOI: 10.1016/j.jplph.2008.09.009 -
Mechanisms of Ageing and Development Mar 2020Senescent cells have been suspected, because of their secretory phenotype (SASP or Senescence Associated Secretory Profile), to contribute to the extension of the... (Review)
Review
Senescent cells have been suspected, because of their secretory phenotype (SASP or Senescence Associated Secretory Profile), to contribute to the extension of the chronic inflammatory condition leading to unhealthy aging processes. AISA (Anti-Inflammatory Senescence Actives) monoterpens have been characterized as possessing anti-inflammatory capacities in young cells submitted to pro-inflammatory cytokine stimulation. They have also been demonstrated to have the ability to act on senescent cells, reversing their characteristic pro-inflammatory phenotype. This is due to the fact that AISA act on the cytoskeleton scaffold of cells where actin polymerization induces the expression of adhesion molecules, fueling the infernal inflammatory loop. In comparison to other isoprenoid actives in degenerative diseases, the AISA monoterpene adds a mood-modulating capacity inducing the vagus nerve tone and its potent anti-inflammatory role.
Topics: Aging; Cellular Senescence; Humans; Inflammation; Monoterpenes
PubMed: 31904411
DOI: 10.1016/j.mad.2019.111206