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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 -
Zeitschrift Fur Naturforschung. C,... Jul 2020Isothiocyanates, monoterpenes, and leaf volatiles that are components of essential oils induce the expression of heat shock protein genes in plant systems. Here, the... (Review)
Review
Isothiocyanates, monoterpenes, and leaf volatiles that are components of essential oils induce the expression of heat shock protein genes in plant systems. Here, the modes of heat shock responses induced by the essential oil compounds and their heat-tolerance-enhancing activities are described. Traditionally, green manure produced from essential-oil-containing plants has been used because such manure is thought to have beneficial effects in fertilizing, allelopathic, antibacterial, and animal-repellent activities. In addition to these effects, stress (especially heat stress)-tolerance-enhancing activities can be expected. Biostimulants containing such essential oils may be able to maintain the yield and quality of crops under increasing ambient temperatures. In this review, chemicals that enhance the heat tolerance of plants are designated as heat tolerance enhancers (HTLEs). Some essential oil compounds can be categorized as HTLEs available for biostimulants.
Topics: Gene Expression Regulation, Plant; Heat-Shock Response; Isothiocyanates; Monoterpenes; Oils, Volatile; Plant Physiological Phenomena; Thermotolerance
PubMed: 32755102
DOI: 10.1515/znc-2019-0233 -
Molecules (Basel, Switzerland) Jun 2022Mosquitoes represent one of the most important vectors and are responsible for the transmission of many arboviruses that affect human and animal health. The chemical...
Mosquitoes represent one of the most important vectors and are responsible for the transmission of many arboviruses that affect human and animal health. The chemical method using synthetic insecticides disturbs the environmental system and promotes the appearance of resistant insect species. Therefore, this study investigated the insecticidal effect of some binary monoterpene combinations (1,8 cineole + α-pinene and carvone + R (+)-pulegone) using a mixture design approach. The fumigant toxicity was evaluated against female adults using glass jars. The results show that the toxicity varies according to the proportions of each compound. Indeed, Mixture 1 (1,8-cineole + α-pinene) displayed a strong toxic effect (51.00 ± 0.86% after 24 h and 100.00 ± 0.70% after 48 h) when the pure compounds were tested at 0.25/0.75 proportions of 1,8-cineole and α-pinene, respectively. Nevertheless, the equal proportion (0.5/0.5) of carvone and R (+)-pulegone in Mixture 2 exhibited a toxic effect of 54.35 ± 0.75% after 24 h and 89.96 ± 0.14% after 48 h, respectively. For Mixture 1, the maximum area of mortality that the proposed model indicated was obtained between 0/1 and 0.25/0.75, while the maximum area of mortality in the case of Mixture 2 was obtained between 0.25/0.75 and 0.75/0.25. Moreover, the maximum possible values of mortality that could be achieved by the validated model were found to be 51.44% (after 24 h) and 100.24% (after 48 h) for Mixture 1 and 54.67% (after 24 h) and 89.99% (after 48 h) for Mixture 2. It can be said that all purev molecules tested through the binary mixtures acted together, which enhanced the insecticide's effectiveness. These findings are very promising, as the chemical insecticide (deltamethrin) killed only 19.29 ± 0.01% and 34.05 ± 1.01% of the female adults after 24 h and 48 h, respectively. Thus, the findings of our research could help with the development of botanical insecticides that might contribute to management programs for controlling vectors of important diseases.
Topics: Animals; Culex; Culicidae; Eucalyptol; Female; Insecticides; Larva; Monoterpenes; Mosquito Vectors
PubMed: 35807427
DOI: 10.3390/molecules27134182 -
Frontiers in Immunology 2022Epidemiological studies have shown that the incidence, prevalence and mortality of atherosclerotic cardiovascular disease (ASCVD) are increasing globally.... (Review)
Review
Epidemiological studies have shown that the incidence, prevalence and mortality of atherosclerotic cardiovascular disease (ASCVD) are increasing globally. Atherosclerosis is characterized as a chronic inflammatory disease which involves inflammation and immune dysfunction. Pall. is a plant origin traditional medicine that has been widely used for the treatment of various diseases for more than a millennium in China, Japan and Korean. Paeoniflorin is a bioactive monomer extracted from Pall. with anti-atherosclerosis effects. In this article, we comprehensively reviewed the potential therapeutic effects and molecular mechanism whereby paeoniflorin protects against atherosclerosis from the unique angle of inflammation and immune-related pathway dysfunction in vascular endothelial cells, smooth muscle cells, monocytes, macrophages, platelets and mast cells. Paeoniflorin, with multiple protective effects in atherosclerosis, has the potential to be used as a promising therapeutic agent for the treatment of atherosclerosis and its complications. We conclude with a detailed discussion of the challenges and future perspective of paeoniflorin in translational cardiovascular medicine.
Topics: Humans; Endothelial Cells; Glucosides; Inflammation; Monoterpenes
PubMed: 36618414
DOI: 10.3389/fimmu.2022.1072007 -
Molecules (Basel, Switzerland) Oct 2022Monoterpene pyridine alkaloids (MTPAs) are alkaloids derived from iridoid glycosides (IGs). The common molecular structure of MTPAs is the pyridine ring, while some of... (Review)
Review
Monoterpene pyridine alkaloids (MTPAs) are alkaloids derived from iridoid glycosides (IGs). The common molecular structure of MTPAs is the pyridine ring, while some of them have a cyclopenta[c]pyridine skeleton. Some compounds containing this structure are potentially bioactive medicinal agents. In this paper, seven drug candidates (-), ninety natural source products (-), thirty-seven synthesized compounds (-), as well as twenty-six key intermediates (-) were summarized. We categorized five types of MTPAs and one type of cyclopenta[c]pyridine alkaloids in all. Additionally, their possible genetic pathways were proposed. Then, the chemical transformation, biotransformation, chemical synthesis, as well as the bioactivity of MTPAs and cyclopenta[c]pyridine derivatives were analyzed and summarized. Cyclopenta[c]pyridine derivatives can be concisely and chirally synthesized, and they have shown potentials with antibacterial, insecticidal, antiviral, anti-inflammatory, and neuropharmacological activities.
Topics: Monoterpenes; Alkaloids; Molecular Structure; Pyridines; Biological Products
PubMed: 36364013
DOI: 10.3390/molecules27217187 -
PloS One 2023It is critical to gather biological information about rare and endangered plants to incorporate into conservation efforts. The secondary metabolism of Pityopsis ruthii,...
It is critical to gather biological information about rare and endangered plants to incorporate into conservation efforts. The secondary metabolism of Pityopsis ruthii, an endangered flowering plant that only occurs along limited sections of two rivers (Ocoee and Hiwassee) in Tennessee, USA was studied. Our long-term goal is to understand the mechanisms behind P. ruthii's adaptation to restricted areas in Tennessee. Here, we profiled the secondary metabolites, specifically in flowers, with a focus on terpenes, aiming to uncover the genomic and molecular basis of terpene biosynthesis in P. ruthii flowers using transcriptomic and biochemical approaches. By comparative profiling of the nonpolar portion of metabolites from various tissues, P. ruthii flowers were rich in terpenes, which included 4 monoterpenes and 10 sesquiterpenes. These terpenes were emitted from flowers as volatiles with monoterpenes and sesquiterpenes accounting for almost 68% and 32% of total emission of terpenes, respectively. These findings suggested that floral terpenes play important roles for the biology and adaptation of P. ruthii to its limited range. To investigate the biosynthesis of floral terpenes, transcriptome data for flowers were produced and analyzed. Genes involved in the terpene biosynthetic pathway were identified and their relative expressions determined. Using this approach, 67 putative terpene synthase (TPS) contigs were detected. TPSs in general are critical for terpene biosynthesis. Seven full-length TPS genes encoding putative monoterpene and sesquiterpene synthases were cloned and functionally characterized. Three catalyzed the biosynthesis of sesquiterpenes and four catalyzed the biosynthesis of monoterpenes. In conclusion, P. ruthii plants employ multiple TPS genes for the biosynthesis of a mixture of floral monoterpenes and sesquiterpenes, which probably play roles in chemical defense and attracting insect pollinators alike.
Topics: Terpenes; Biosynthetic Pathways; Magnoliopsida; Monoterpenes; Sesquiterpenes; Alkyl and Aryl Transferases; Gene Expression Regulation, Plant; Plant Proteins
PubMed: 37352235
DOI: 10.1371/journal.pone.0287524 -
Molecules (Basel, Switzerland) Oct 2022Differences between therapeutic effects of medical cannabis inflorescences and those of their extracts are generally attributed to the differences in administration form...
Optimal Treatment with Cannabis Extracts Formulations Is Gained via Knowledge of Their Terpene Content and via Enrichment with Specifically Selected Monoterpenes and Monoterpenoids.
Differences between therapeutic effects of medical cannabis inflorescences and those of their extracts are generally attributed to the differences in administration form and in the resultant pharmacokinetics. We hypothesized that difference may further extend to the composition of the actually consumed drug. Cannabinoid and terpene contents were compared between commercial cannabis inflorescences ( = 19) and decarboxylated extracts ( = 12), and between inflorescences and decarboxylated extracts produced from them ( = 10). While cannabinoid content was preserved in the extracts, a significant loss of terpenes was evident, mainly in the more volatile monoterpenes and monoterpenoids (representing a loss of about 90%). This loss changes the total terpene content, the proportion of monoterpenes out of the total terpenes, and the monoterpene/cannabinoid ratio. Terpene deficiency might impair extracts' pharmacological efficacy and might contribute to the patients' preference to inflorescences-smoking. This argues against the validity of terms such as "whole plant" and "full spectrum" extracts and creates a misleading assumption that extracts represent the pharmacological profile of the sourced inflorescences. Furthermore, it reduces the diversity in extracts, such as loss of differences between sativa-type and indica-type. Enriching cannabis extracts with selected terpenes may provide a suitable solution, generating a safe, precise, and reproducible drug with tailored cannabinoid and terpene contents. Careful selection of terpenes to be added enables tailor-made extracts, adjusted for various medicinal aims and for different populations.
Topics: Humans; Cannabis; Terpenes; Monoterpenes; Medical Marijuana; Cannabinoids; Hallucinogens; Cannabinoid Receptor Agonists; Plant Extracts
PubMed: 36296511
DOI: 10.3390/molecules27206920 -
Molecules (Basel, Switzerland) Apr 2022Carvone is a monoterpene compound that has been widely used as a pesticide for more than 10 years. However, little is known regarding the fate of carvone, or its...
Carvone is a monoterpene compound that has been widely used as a pesticide for more than 10 years. However, little is known regarding the fate of carvone, or its degradation products, in the environment. We used GC-MS (gas chromatography-mass spectrometry) to study the fate of carvone and its degradation and photolysis products under different soil and light conditions. We identified and quantified three degradation products of carvone in soil and water samples: dihydrocarvone, dihydrocarveol, and carvone camphor. In soil, dihydrocarveol was produced at very low levels (≤0.067 mg/kg), while dihydrocarvone was produced at much higher levels (≤2.07 mg/kg). In water exposed to differing light conditions, carvone was degraded to carvone camphor. The photolysis rate of carvone camphor under a mercury lamp was faster, but its persistence was lower than under a xenon lamp. The results of this study provide fundamental data to better understand the fate and degradation of carvone and its metabolites in the environment.
Topics: Camphor; Cyclohexane Monoterpenes; Photolysis; Soil; Water; Water Pollutants, Chemical
PubMed: 35458614
DOI: 10.3390/molecules27082415 -
Proceedings of the National Academy of... Oct 2022Iridoid monoterpenes, widely distributed in plants and insects, have many ecological functions. While the biosynthesis of iridoids has been extensively studied in...
Iridoid monoterpenes, widely distributed in plants and insects, have many ecological functions. While the biosynthesis of iridoids has been extensively studied in plants, little is known about how insects synthesize these natural products. Here, we elucidated the biosynthesis of the iridoids -nepetalactol and -nepetalactone in the pea aphid (Harris), where they act as sex pheromones. The exclusive production of iridoids in hind legs of sexual female aphids allowed us to identify iridoid genes by searching for genes specifically expressed in this tissue. Biochemical characterization of candidate enzymes revealed that the iridoid pathway in aphids proceeds through the same sequence of intermediates as described for plants. The six identified aphid enzymes are unrelated to their counterparts in plants, conclusively demonstrating an independent evolution of the entire iridoid pathway in plants and insects. In contrast to the plant pathway, at least three of the aphid iridoid enzymes are likely membrane bound. We demonstrated that a lipid environment facilitates the cyclization of a reactive enol intermediate to the iridoid cyclopentanoid-pyran scaffold in vitro, suggesting that membranes are an essential component of the aphid iridoid pathway. Altogether, our discovery of this complex insect metabolic pathway establishes the genetic and biochemical basis for the formation of iridoid sex pheromones in aphids, and this discovery also serves as a foundation for understanding the convergent evolution of complex metabolic pathways between kingdoms.
Topics: Animals; Aphids; Biological Products; Iridoids; Lipids; Monoterpenes; Pheromones; Plants; Sex Attractants
PubMed: 36227916
DOI: 10.1073/pnas.2211254119 -
The Journal of Physical Chemistry. A Aug 2022Highly oxygenated organic molecules (HOMs) are important sources of atmospheric aerosols. Resolving the molecular-level formation mechanisms of these HOMs from freshly...
Highly oxygenated organic molecules (HOMs) are important sources of atmospheric aerosols. Resolving the molecular-level formation mechanisms of these HOMs from freshly emitted hydrocarbons improves the understanding of aerosol properties and their influence on the climate. In this study, we measure the electrical mobility and mass-to-charge ratio of α-pinene oxidation products using a secondary electrospray-differential mobility analyzer-mass spectrometer (SESI-DMA-MS). The mass-mobility spectrum of the oxidation products is measured with seven different reagent ions generated by the electrospray. We analyzed the mobility-mass spectra of the oxidation products CHO. Our results show that acetate and chloride yield the highest charging efficiencies. Analysis of the mobility spectra suggests that the clusters have 1-5 isomeric structures (i.e., ion-molecule cluster structures with distinct mobilities), and the number is affected by the reagent ion. Most of the isomers are likely cluster isomers originating from binding of the reagent ion to different sites of the molecule. By comparing the number of observed isomers and measured mobilities and collision cross sections between standard pinanediol and pinonic acid to the values observed for CHO and CHO produced from oxidation of α-pinene, we confirm that pinanediol and pinonic acid are the only isomers for these elemental compositions in our experimental conditions. Our study shows that the SESI-DMA-MS produces new information from the first steps of oxidation of α-pinene.
Topics: Aerosols; Air Pollutants; Bicyclic Monoterpenes; Ions; Monoterpenes; Ozone
PubMed: 35862553
DOI: 10.1021/acs.jpca.2c03366