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Journal of Medicine and Life 2014The study was designed to determine the chemical composition and antimicrobial properties of the essential oil of Thymus vulgaris cultivated in Romania. The essential...
The study was designed to determine the chemical composition and antimicrobial properties of the essential oil of Thymus vulgaris cultivated in Romania. The essential oil was isolated in a yield of 1.25% by steam distillation from the aerial part of the plant and subsequently analyzed by GC-MS. The major components were p-cymene (8.41%), γ-terpinene (30.90%) and thymol (47.59%). Its antimicrobial activity was evaluated on 7 common food-related bacteria and fungus by using the disk diffusion method. The results demonstrate that the Thymus vulgaris essential oil tested possesses strong antimicrobial properties, and may in the future represent a new source of natural antiseptics with applications in the pharmaceutical and food industry.
Topics: Anti-Infective Agents; Cyclohexane Monoterpenes; Cymenes; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Thymol; Thymus Plant
PubMed: 25870697
DOI: No ID Found -
Phytochemistry Oct 2021α-Pinene represents a member of the monoterpene class and is highly distributed in higher plants like conifers, Juniper ssp. and Cannabis ssp. α-Pinene has been used... (Review)
Review
α-Pinene represents a member of the monoterpene class and is highly distributed in higher plants like conifers, Juniper ssp. and Cannabis ssp. α-Pinene has been used to treat respiratory tract infections for centuries. Furthermore, it plays a crucial role in the fragrance and flavor industry. In vitro assays have shown an enantioselective profile of (+)- and (-)-α-pinene for antibacterial and insecticidal activity, respectively. Recent research has used pre-validated biological structures to synthesize new chemical entities with pharmacological and herbicidal activities. In summary, this review focuses on recent literature covering synthetic pathways of flavor compounds and scaffold hopping based on the α-pinene core domaine, as well as the (enantioselective) activities of α-pinene. Recent approaches for authenticity control of essential oils based on their enantiomeric profile are also presented.
Topics: Bicyclic Monoterpenes; Juniperus; Monoterpenes; Oils, Volatile
PubMed: 34365295
DOI: 10.1016/j.phytochem.2021.112857 -
Nature Communications Jan 2020The bicyclo[3.3.1]nonane architecture is a privileged structural motif found in over 1000 natural products with relevance to neurodegenerative disease, bacterial and...
The bicyclo[3.3.1]nonane architecture is a privileged structural motif found in over 1000 natural products with relevance to neurodegenerative disease, bacterial and parasitic infection, and cancer among others. Despite disparate biosynthetic machinery, alkaloid, terpene, and polyketide-producing organisms have all evolved pathways to incorporate this carbocyclic ring system. Natural products of mixed polyketide/terpenoid origins (meroterpenes) are a particularly rich and important source of biologically active bicyclo[3.3.1]nonane-containing molecules. Herein we detail a fully synthetic strategy toward this broad family of targets based on an abiotic annulation/rearrangement strategy resulting in a 10-step total synthesis of garsubellin A, an enhancer of choline acetyltransferase and member of the large family of polycyclic polyprenylated acylphloroglucinols. This work solidifies a strategy for making multiple, diverse meroterpene chemotypes in a programmable assembly process involving a minimal number of chemical transformations.
Topics: Biosynthetic Pathways; Monoterpenes; Oxidation-Reduction; Stereoisomerism; Terpenes
PubMed: 31980637
DOI: 10.1038/s41467-020-14354-5 -
Molecules (Basel, Switzerland) Jul 2020Geraniol is a monoterpenic alcohol with a pleasant rose-like aroma, known as an important ingredient in many essential oils, and is used commercially as a fragrance... (Review)
Review
Geraniol is a monoterpenic alcohol with a pleasant rose-like aroma, known as an important ingredient in many essential oils, and is used commercially as a fragrance compound in cosmetic and household products. However, geraniol has a number of biological activities, such as antioxidant and anti-inflammatory properties. In addition, numerous in vitro and in vivo studies have shown the activity of geraniol against prostate, bowel, liver, kidney and skin cancer. It can induce apoptosis and increase the expression of proapoptotic proteins. The synergy of this with other drugs may further increase the range of chemotherapeutic agents. The antibacterial activity of this compound was also observed on respiratory pathogens, skin and food-derived strains. This review discusses some of the most important uses of geraniol.
Topics: Acyclic Monoterpenes; Animals; Anti-Infective Agents; Anti-Inflammatory Agents; Antineoplastic Agents; Antioxidants; Humans; Odorants; Oils, Volatile; Perfume
PubMed: 32708169
DOI: 10.3390/molecules25143303 -
Molecules (Basel, Switzerland) Mar 2022Monoterpenes make up the largest group of plant secondary metabolites. They can be found in numerous plants, among others, the family. The compounds demonstrate... (Review)
Review
Monoterpenes make up the largest group of plant secondary metabolites. They can be found in numerous plants, among others, the family. The compounds demonstrate antioxidative, antibacterial, sedative and anti-inflammatory activity, hence, they are often employed in medicine and pharmaceuticals. Additionally, their fragrant character is often made use of, notably in the food and cosmetic industries. Nevertheless, long-lasting studies have revealed their toxic properties. This fact has led to a detailed analysis of the compounds towards their side effects on the human organism. Although most are safe for human food and medical applications, there are monoterpene compounds that, in certain amounts or under particular circumstances (e.g., pregnancy), can cause serious disorders. The presented review characterises in vitro and in vivo, the toxic character of selected monoterpenes (α-terpinene, camphor, citral, limonene, pulegone, thujone), as well as that of their original plant sources and their essential oils. The selected monoterpenes reveal various toxic properties among which are embryotoxic, neurotoxic, allergenic and genotoxic. It is also known that the essential oils of popular plants can also reveal toxic characteristics that many people are unaware of.
Topics: Camphor; Female; Humans; Lamiaceae; Limonene; Monoterpenes; Oils, Volatile; Plant Oils; Pregnancy
PubMed: 35268817
DOI: 10.3390/molecules27051716 -
Molecules (Basel, Switzerland) Oct 2023Plant products have been employed in medicine for centuries. As the world becomes more health-conscious, there is a growing interest in natural and minimally processed... (Review)
Review
Plant products have been employed in medicine for centuries. As the world becomes more health-conscious, there is a growing interest in natural and minimally processed products for oral health care. This has led to an increase in research into the bioactive compounds found in plant products, particularly monoterpenes. Monoterpenes are known to have beneficial biological properties, but the specific mechanisms by which they exert their effects are not yet fully understood. Despite this, some monoterpenes are already being used in oral health care. For example, thymol, which has antibacterial properties, is an ingredient in varnish used for caries prevention. In addition to this, monoterpenes have also demonstrated antifungal, antiviral, and anti-inflammatory properties, making them versatile for various applications. As research continues, there is potential for even more discoveries regarding the benefits of monoterpenes in oral health care. This narrative literature review gives an overview of the biological properties and current and potential applications of selected monoterpenes and their derivatives in oral health care. These compounds demonstrate promising potential for future medical development, and their applications in future research are expected to expand.
Topics: Monoterpenes; Oils, Volatile; Thymol; Antifungal Agents; Delivery of Health Care
PubMed: 37894657
DOI: 10.3390/molecules28207178 -
Marine Drugs Sep 2019Macroalgae produce a wide range of monoterpenes as secondary metabolites of mevalonate (MVA) and/or methylerythritol phosphate (MEP) pathway (often including... (Review)
Review
Macroalgae produce a wide range of monoterpenes as secondary metabolites of mevalonate (MVA) and/or methylerythritol phosphate (MEP) pathway (often including haloperoxidase action). Great biodiversity of macroalgal monoterpenes was reported including acyclic, monocyclic, and bicyclic structures. Halogenated monoterpenes exhibited significant biological activity (e.g., anticancer, antiplasmodial, and insecticidal) that is influenced by the number of present halogens (higher halogen content is preferable, especially bromine) and their position within the monoterpene skeleton. In distinction from the existing reviews, the present review provides novelty with respect to: (a) exclusively monoterpenes from red macroalgae are targeted; (b) biosynthesis, isolation, and analysis, as well as bioactivity of monoterpenes are represented; (c) the methods of their isolation, analysis, and structure elucidation are summarized; (d) the bioactivity of macroalgal monoterpenes is systematically presented with emphasis on anticancer activity; (e) the literature references were updated.
Topics: Animals; Antineoplastic Agents; Cell Line, Tumor; Erythritol; Humans; Mevalonic Acid; Molecular Structure; Monoterpenes; Rhodophyta; Seaweed; Sugar Phosphates
PubMed: 31527497
DOI: 10.3390/md17090537 -
Molecules (Basel, Switzerland) Jan 2018Iridoids are a class of monoterpenoid compounds constructed from 10-carbon skeleton of isoprene building units. These compounds in their aglycones and glycosylated forms... (Review)
Review
Iridoids are a class of monoterpenoid compounds constructed from 10-carbon skeleton of isoprene building units. These compounds in their aglycones and glycosylated forms exist in nature to contribute to mechanisms related to plant defenses and diverse plant-animal interactions. Recent studies have also shown that iridoids and other structurally related monoterpenes display a vast array of pharmacological effects that make them potential modulators of the Alzheimer's disease (AD). This review critically evaluates the therapeutic potential of these natural products by assessing key in vitro and in vivo data published in the scientific literature. Mechanistic approach of scrutiny addressing their effects in the Alzheimer's brain including the τ-protein phosphorylation signaling, amyloid beta (Aβ) formation, aggregation, toxicity and clearance along with various effects from antioxidant to antiinflammatory mechanisms are discussed. The drug likeness of these compounds and future prospects to consider in their development as potential leads are addressed.
Topics: Alzheimer Disease; Amyloid beta-Peptides; Animals; Brain; Humans; Iridoids; Monoterpenes; Neuroprotective Agents
PubMed: 29316661
DOI: 10.3390/molecules23010117 -
Molecules (Basel, Switzerland) Jan 2014The search for more effective and lower cost therapeutic approaches for wound healing remains a challenge for modern medicine. In the search for new therapeutic options,... (Review)
Review
The search for more effective and lower cost therapeutic approaches for wound healing remains a challenge for modern medicine. In the search for new therapeutic options, plants and their metabolites are a great source of novel biomolecules. Among their constituents, the monoterpenes represent 90% of essential oils, and have a variety of structures with several activities such as antimicrobial, anti-inflammatory, antioxidant and wound healing. Based on that, and also due to the lack of reviews concerning the wound-healing activity of monoterpenes, we performed this systematic review-which provides an overview of their characteristics and mechanisms of action. In this search, the terms "terpenes", "monoterpenes", "wound healing" and "wound closure techniques" were used to retrieve articles published in LILACS, PUBMED and EMBASE until May 2013. Seven papers were found concerning the potential wound healing effect of five compouds (three monoterpenes and two iridoid derivatives) in preclinical studies. Among the products used for wound care, the films were the most studied pharmaceutical form. Monoterpenes are a class of compounds of great diversity of biological activities and therapeutic potential. The data reviewed here suggest that monoterpenes, although poorly studied in this context, are promising compounds for the treatment of chronic wound conditions.
Topics: Animals; Drug Evaluation, Preclinical; Humans; Iridoids; Monoterpenes; Plant Extracts; Plants, Medicinal; Wound Healing
PubMed: 24419138
DOI: 10.3390/molecules19010846 -
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