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Journal of Food Biochemistry Jan 2021D-limonene or 4-isopropenyl-1-methylcyclohexene (C H ) is a monocyclic monoterpene abundant in citrus plants like lemon, orange, and grape. The application of D-limonene... (Review)
Review
D-limonene or 4-isopropenyl-1-methylcyclohexene (C H ) is a monocyclic monoterpene abundant in citrus plants like lemon, orange, and grape. The application of D-limonene in the form of flavor and fragrance additive in perfumes, soaps, foods, and beverages is consistently increased due to its high-quality fragrance property. This review is intended to analyze and delineate every possible available evidence and details about D-limonene with the special focus on its therapeutic efficacy. Many studies have reported that D-limonene effectively plays a valuable role in the prevention of several chronic and degenerative diseases. This review provides worthy information about the beneficial effects of D-limonene such as antioxidant, antidiabetic, anticancer, anti-inflammatory, cardioprotective, gastroprotective, hepatoprotective, immune modulatory, anti-fibrotic, anti-genotoxic etc. This could in turn help in the application of D-limonene for clinical studies. PRACTICAL IMPLICATIONS: Various plant families contain Terpenes as their secondary metabolites. Monoterpenes constitute an important part of these secondary metabolites. D-limonene is a well-identified monoterpene that is commonly applied as a fragrance ingredient in essential oils. D-limonene is known to possess remarkable biological activities. It can be effectively used for treating various ailments and diseases. Due to its diverse functions, it can be efficiently utilized for human health.
Topics: Cyclohexenes; Humans; Limonene; Monoterpenes; Oils, Volatile; Terpenes
PubMed: 33289132
DOI: 10.1111/jfbc.13566 -
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 -
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 -
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) 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 -
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 -
Nature Chemical Biology Apr 2023
Topics: Monoterpenes; Intramolecular Lyases; Biochemical Phenomena
PubMed: 36991161
DOI: 10.1038/s41589-023-01307-4 -
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 -
International Journal of Molecular... Jan 2023Traditional herbal medicines based on natural products play a pivotal role in preventing and managing atherosclerotic diseases, which are among the leading causes of... (Review)
Review
Traditional herbal medicines based on natural products play a pivotal role in preventing and managing atherosclerotic diseases, which are among the leading causes of death globally. Monoterpenes are a large class of naturally occurring compounds commonly found in many aromatic and medicinal plants. Emerging evidence has shown that monoterpenes have many biological properties, including cardioprotective effects. Remarkably, an increasing number of studies have demonstrated the therapeutic potential of natural monoterpenes to protect against the pathogenesis of atherosclerosis. These findings shed light on developing novel effective antiatherogenic drugs from these compounds. Herein, we provide an overview of natural monoterpenes' effects on atherogenesis and the underlying mechanisms. Monoterpenes have pleiotropic and multitargeted pharmacological properties by interacting with various cell types and intracellular molecular pathways involved in atherogenesis. These properties confer remarkable advantages in managing atherosclerosis, which has been recognized as a multifaceted vascular disease. We also discuss limitations in the potential clinical application of monoterpenes as therapeutic agents against atherosclerosis. We propose perspectives to give new insights into future preclinical research and clinical practice regarding natural monoterpenes.
Topics: Monoterpenes; Plants, Medicinal; Biological Products; Atherosclerosis
PubMed: 36768748
DOI: 10.3390/ijms24032429