-
Chemistry & Biodiversity Dec 2019Terpenes are a widespread group of secondary metabolites that can be found in various family plants such as the Lamiaceae. In view of their numerous valuable biological... (Review)
Review
Terpenes are a widespread group of secondary metabolites that can be found in various family plants such as the Lamiaceae. In view of their numerous valuable biological activities, the industrial production of concrete terpenes and essential oils rich in the substances is intensively studied. Monoterpenes constitute a significant part of the whole group of the aforementioned secondary metabolites. This is due to their numerous biological activities and their ability to permeate the skin. Despite the fact that these substances have gain popularity, they are not comprehensively characterized. The presented review is based on studies of the biological activities of the most important monoterpenes and the essential oils rich in these compounds. The authors focused attention on antioxidant activity, inhibition towards acetyl- and butyrylcholinesterase, and α-amylase and α-glucosidase, antifungal, hepatoprotective, sedative properties, and their skin permeation enhancement.
Topics: Alzheimer Disease; Animals; Antioxidants; Cholinesterases; Lamiaceae; Monoterpenes; NF-E2-Related Factor 2; Oils, Volatile; Oxidative Stress
PubMed: 31587473
DOI: 10.1002/cbdv.201900434 -
Mini Reviews in Medicinal Chemistry 2020Medicinal plants have a wide range of secondary metabolites including monoterpene. These volatile compounds are the main components of essential oils, belonging to the... (Review)
Review
Medicinal plants have a wide range of secondary metabolites including monoterpene. These volatile compounds are the main components of essential oils, belonging to the isoprenoid group and possessing valuable features for plants and humans. This review provides comprehensive information on chemical structures and classification of monoterpenes. It describes their biosynthesis pathways and introduces plant families and species rich in noteworthy monoterpenes. Bio-activities, pharmacological and pesticide effects as well as their mechanism of action are reported. Applications of these compounds in various industries are also included.
Topics: Anti-Infective Agents; Antineoplastic Agents, Phytogenic; Antioxidants; Humans; Molecular Structure; Monoterpenes; Oils, Volatile; Pesticides
PubMed: 31969098
DOI: 10.2174/1389557520666200122144703 -
Critical Reviews in Food Science and... 2023Monoterpenes, volatile metabolites produced by plants, are involved in the taste and aroma perception of fruits and vegetables and have been used for centuries in... (Review)
Review
Monoterpenes, volatile metabolites produced by plants, are involved in the taste and aroma perception of fruits and vegetables and have been used for centuries in gastronomy, as food preservatives and for therapeutic purposes. Biological activities such as antimicrobial, analgesic and anti-inflammatory are well-established for some of these molecules. More recently, the ability of monoterpenes to regulate energy metabolism, and exert antidiabetic, anti-obesity and gut microbiota modulation activities have been described. Despite their promising health effects, the lack of reliable quantification of monoterpenes in food, hindered the investigation of their role as dietary bioactive compounds in epidemiological studies. Moreover, only few studies have documented the biotransformation of these compounds and identified the monoterpene metabolites with biological activity. This review presents up-to-date knowledge about the occurrence of monoterpenes in food, their bioavailability and potential role in the modulation of intermediate metabolism and inflammation, focusing on novel findings of molecular mechanisms, underlining research gaps and new avenues to be explored.
Topics: Monoterpenes; Plants; Fruit; Anti-Inflammatory Agents
PubMed: 34387521
DOI: 10.1080/10408398.2021.1963945 -
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 -
Journal of Agricultural and Food... Apr 2022Synthetic pesticides are often associated with issues such as pest resistance, persistent residue, nontarget toxicity, and environmental issues. Therefore, the research... (Review)
Review
Synthetic pesticides are often associated with issues such as pest resistance, persistent residue, nontarget toxicity, and environmental issues. Therefore, the research and development of novel, safe, and effective pesticides has become a focus in pesticide discovery. Monoterpenes are secondary plant metabolites that commonly have multiple action targets and have been used in aromatherapy, alternative medicine, and food industries. Some are highly potent and stereoselective. They can potentially be botanical pesticides and serve as lead candidates for the design and synthesis of new monoterpenoid pesticides for agricultural applications. This article reviews publications and patents found in SciFinder Scholar between 2000 and May 2021 on monoterpenes and mainly focuses on pesticidal activities of frequently studied monoterpenes and their modes of action. The presented information and our views are hopefully useful for the development of monoterpenes as biopesticides and monoterpenoid pesticides.
Topics: Agriculture; Biological Control Agents; Monoterpenes; Pesticides; Plants
PubMed: 35380824
DOI: 10.1021/acs.jafc.2c00635 -
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 -
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) 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 -
Phytochemistry Nov 2022Plant monoterpenes are challenging compounds, since they often act as solvents, and thus have both phytotoxic and antimicrobial properties. In this study an approach is...
Plant monoterpenes are challenging compounds, since they often act as solvents, and thus have both phytotoxic and antimicrobial properties. In this study an approach is developed to identify and characterize enzymes that can detoxify monoterpenoids, and thus would protect both plants and microbial production systems from these compounds. Plants respond to the presence of monoterpenes by expressing glycosyltransferases (UGTs), which conjugate the monoterpenoids into glycosides. By identifying these enzymes in a transcriptomics approach using Mentha × piperita, a family of UGTs was identified which is active on cyclic monoterpenoids such as menthol, and on acyclic monoterpenoids such as geranic acid. Other members of this family, from tomato, were also shown to be active on these monoterpenoids. In vitro and in vivo activity of different UGTs were tested with different substrates. We found that some glycosyltransferases significantly affect the toxicity of selected monoterpenoids in Escherichia coli, suggesting that glycosyltransferases can protect cells from monoterpenoid toxicity.
Topics: Glycosides; Glycosyltransferases; Mentha piperita; Menthol; Monoterpenes; Solvents
PubMed: 36037906
DOI: 10.1016/j.phytochem.2022.113371 -
ACS Synthetic Biology Jan 2022Prokaryotic transcription factors can be repurposed as analytical and synthetic tools for precise chemical measurement and regulation. Monoterpenes encompass a broad...
Prokaryotic transcription factors can be repurposed as analytical and synthetic tools for precise chemical measurement and regulation. Monoterpenes encompass a broad chemical family that are commercially valuable as flavors, cosmetics, and fragrances, but have proven difficult to measure, especially in cells. Herein, we develop genetically encoded, generalist monoterpene biosensors by using directed evolution to expand the effector specificity of the camphor-responsive TetR-family regulator CamR from . Using a novel negative selection coupled with a high-throughput positive screen (Seamless Enrichment of Ligand-Inducible Sensors, SELIS), we evolve CamR biosensors that can recognize four distinct monoterpenes: borneol, fenchol, eucalyptol, and camphene. Different evolutionary trajectories surprisingly yielded common mutations, emphasizing the utility of CamR as a platform for creating generalist biosensors. Systematic promoter optimization driving the reporter increased the system's signal-to-noise ratio to 150-fold. These sensors can serve as a starting point for the high-throughput screening and dynamic regulation of bicyclic monoterpene production strains.
Topics: Bicyclic Monoterpenes; Biosensing Techniques; Camphor; Monoterpenes; Pseudomonas putida; Transcription Factors
PubMed: 34985281
DOI: 10.1021/acssynbio.1c00402