-
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 -
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 -
International Journal of Molecular... Apr 2021Terpenes-a diverse group of secondary metabolites-constitute the largest class of natural products abundant in almost every plant species. The properties of concrete... (Review)
Review
Terpenes-a diverse group of secondary metabolites-constitute the largest class of natural products abundant in almost every plant species. The properties of concrete terpenes and essential oils have been intensively studied due to their widespread use in the pharmaceutical, food and cosmetics industries. Despite the popularity of these aromatic compounds, their derivatives, terpenoids, are still not comprehensively characterized despite exhibiting potent bioactive properties. This review aims to assess the anticancer properties of selected monoterpenes including carvone, carvacrol, perillyl alcohol, perillaldehyde, limonene, menthol and their derivatives while also evaluating potential applications as novel anticancer treatments. Special attention is paid to functional groups that improve the bioactivity of monoterpene molecules. This review also covers the therapeutic potential of deep eutectic solvents that contain monoterpene substances. Taken together, the literature supports the use of monoterpene derivatives in the development of new alternatives for disease treatment and prevention.
Topics: Animals; Antineoplastic Agents, Phytogenic; Drug Discovery; Humans; Monoterpenes; Neoplasms; Plants
PubMed: 33946245
DOI: 10.3390/ijms22094763 -
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 -
Journal of Food Biochemistry Dec 2021Globally, cancer is one of the deadliest diseases, estimated to cause 9.9 million deaths in 2020. Conventional cancer treatments commonly involve mono-chemotherapy or a... (Review)
Review
Globally, cancer is one of the deadliest diseases, estimated to cause 9.9 million deaths in 2020. Conventional cancer treatments commonly involve mono-chemotherapy or a combination of radiotherapy and mono-chemotherapy. However, the negative side effects of these approaches have been extensively reported and have prompted the search for new therapeutic drugs. Over the past few years, numerous dietary agents, medicinal plants, and their phytochemicals gained considerable therapeutic importance because of their anticancer, antiviral, anti-inflammatory, and antioxidant activities. Recent years have shown that essential oils possess therapeutic effects against numerous cancers. They are primarily used due to their lesser side effects than standard chemotherapeutic drugs. Carvacrol (CRV) is a phenolic monoterpenoid found in essential oils of oregano, thyme, pepperwort, wild bergamot, and other plants. Numerous anticancer reports of CRV substantiated that the main mechanistic action of CRV involves reduction in the viability of cancer cells and induction of apoptosis via both intrinsic and extrinsic pathways. CRV also obstructs the migration and invasion of cells leading to the suppressed proliferation rate. Furthermore, CRV mediates augmented ROS generation resulting in DNA damage and also halts the progression of cell cycle. Treatment of CRV modulates the expression of apoptotic proteins (Bax, Bad) and molecular targets of various signaling pathways (PI3K/AKT/mTOR, MAPKs, and Notch) in multiple solid carcinomas. Hence, this review aimed to acquire and disseminate the knowledge of chemopreventive and anticancer effects of CRV and the mechanisms of action already described for the compound against numerous cancers, including solid carcinomas, to guide future research. PRACTICAL APPLICATIONS: Development and formulation of phytocompound based anticancer drug agents to counteract the aftereffects of chemotherapeutic drugs is a propitious approach. CRV is a monoterpenoid consisting of a phenolic group obtained from the essential oils of oregano and thyme. These plants are being used as food flavoring spice and as fragrance ingredient in various cosmetic formulations. For the use of CRV as an efficient chemopreventive agent, different therapeutic interactions of CRV along with its targeted pathways and molecules, involved in the regulation of onset and progression of various types of solid carcinomas, need to be studied and explored thoroughly.
Topics: Carcinoma; Cymenes; Humans; Monoterpenes; Phosphatidylinositol 3-Kinases
PubMed: 34796513
DOI: 10.1111/jfbc.14010 -
Biotechnology Letters Mar 2018To investigate the biocatalytic potential of Colletotrichum acutatum and Colletotrichum nymphaeae for monoterpene biotransformation.
OBJECTIVE
To investigate the biocatalytic potential of Colletotrichum acutatum and Colletotrichum nymphaeae for monoterpene biotransformation.
RESULTS
C. acutatum and C. nymphaeae used limonene, α-pinene, β-pinene, farnesene, citronellol, linalool, geraniol, perillyl alcohol, and carveol as sole carbon and energy sources. Both species biotransformed limonene and linalool, accumulating limonene-1,2-diol and linalool oxides, respectively. α-Pinene was only biotransformed by C. nymphaeae producing campholenic aldehyde, pinanone and verbenone. The biotransformation of limonene by C. nymphaeae yielded 3.34-4.01 g limonene-1,2-diol l, depending on the substrate (R-(+)-limonene, S-(-)-limonene or citrus terpene (an agro-industrial by-product). This is among the highest concentrations already reported for this product.
CONCLUSIONS
This is the first report on the biotransformation of these terpenes by Colletotrichum spp. and the biotransformation of limonene to limonene-1,2-diol possibly involves enzymes similar to those found in Grosmannia clavigera.
Topics: Acyclic Monoterpenes; Biotransformation; Carbon; Colletotrichum; Computational Biology; Cyclohexenes; Limonene; Monoterpenes; Plant Oils; Terpenes
PubMed: 29288353
DOI: 10.1007/s10529-017-2503-2 -
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 -
Phytochemistry Nov 2022Three undescribed dimeric pyridine-containing alkaloids, caryopterisines C - E, and four unreported cyclopenta[c]pyridine-derived alkaloids, caryopterisines F - I, were...
Three undescribed dimeric pyridine-containing alkaloids, caryopterisines C - E, and four unreported cyclopenta[c]pyridine-derived alkaloids, caryopterisines F - I, were identified from Caryopteris glutinosa Rehder (Lamiaceae), together with two known monoterpene alkaloids. Caryopterisine C, featuring with an unprecedented 6/5/6/6/5 pentacyclic rings scaffold, may biosynthetically stem from a Diels-Alder reaction of two cyclopenta[c]pyridine-containing monomers and a following aromatization rearrangement reaction. Caryopterisines D and E, possessing an unprecedented 6/6/6/6/5 fused rings framework, may originate from a same Diels-Alder reaction of two monomers and subsequent aromatization arrangement, Baeyer-Villiger oxidation, and a set of tailoring reactions. Caryopterisine C showed strong inhibition on collagen accumulation in NIH3T3 cells (IC = 14.26 ± 1.46 μM). Caryopterisines G and I reduce collagen accumulation with IC values 88.91 ± 0.95 μM and 33.09 ± 1.38 μM, respectively. The Western blotting of the transforming growth factor-β-activated signaling pathways revealed that caryopterisine C inhibits collagen expression and accumulation via suppression of the phosphorylation of ERK1/2, P38, and SMAD2/3. The present works indicate caryopterisine C is a potential lead compound for the development of antifibrotic drugs.
Topics: Alkaloids; Animals; Collagen; Lamiaceae; Mice; Monoterpenes; NIH 3T3 Cells; Pyridines; Transforming Growth Factors
PubMed: 36007661
DOI: 10.1016/j.phytochem.2022.113378 -
Food Research International (Ottawa,... May 2021Citrus peel (CP), a by-product of the citrus fruit processing, comprises nearly forty to fifty percent of the fruit portion. Interestingly, the essential oil (EO) is... (Review)
Review
Citrus peel (CP), a by-product of the citrus fruit processing, comprises nearly forty to fifty percent of the fruit portion. Interestingly, the essential oil (EO) is primarily concentrated in the peel portion of the citrus fruit. Extraction of CP essential oil (CPEO) is an effective way of utilizing the citrus fruit processing waste. The CPEO can be more efficiently recovered from CP waste by improving the efficiency of conventional extraction processes. The main components of CPEO include monoterpenes, sesquiterpenes and their oxygenated derivatives. Specifically, limonene is the major oil component identified in the peel of different citrus species. The health promoting biological activities of CPEO are functioning as antioxidant, anti-inflammatory, analgesic, antimicrobial and anticancer agents, thereby can be used as a source of functional components and preservatives for the development of nutritionally safe newer food products. This paper provides an in-depth knowledge about the chemical constituents and bioactivities of EOs extracted from peels of different citrus species.
Topics: Citrus; Fruit; Limonene; Monoterpenes; Oils, Volatile
PubMed: 33992345
DOI: 10.1016/j.foodres.2021.110231 -
Colloids and Surfaces. B, Biointerfaces Nov 2018The medicinal properties of essential oils from aromatic plants are known since antiquity. Currently, the technological innovation enabled the reinvention of the ancient... (Review)
Review
The medicinal properties of essential oils from aromatic plants are known since antiquity. Currently, the technological innovation enabled the reinvention of the ancient plant knowledge leading to the identification and extraction of organic compounds present in essential oils. These organic compounds belong mainly to the terpene group and are accountable for the wide range of bioactive properties attributed to essential oils. Linalool (CHO), so-called 3,7-dimethyl-1,6-octadien-3-ol, is a monoterpene alcohol broadly present as a major constituent of plant essential oils, particularly lavender and coriander. Linalool per se is non-toxic and, according to recent in vitro and in vivo scientific studies, it has demonstrated to have a comprehensive range of bioactive properties, which can be exploited for pharmaceutic and cosmetic applications. The present review focuses on the anti-inflammatory, anticancer, anti-hyperlipidemic, antimicrobial, antinoceptive, analgesic, anxiolytic, antidepressive and neuroprotective properties of linalool. The advantages of the loading in nanotechnology-based drug delivery systems, with the purpose of enhancing its bioactive properties are also discussed.
Topics: Acyclic Monoterpenes; Animals; Drug Carriers; Drug Delivery Systems; Humans; Monoterpenes; Nanotechnology; Particle Size; Surface Properties
PubMed: 30098535
DOI: 10.1016/j.colsurfb.2018.08.001