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Molecules (Basel, Switzerland) Apr 2023plants are rich in natural essential oils, which are widely used as materials in the fragrance, insecticidal, antibacterial agent, pharmaceutical, and food industries;...
plants are rich in natural essential oils, which are widely used as materials in the fragrance, insecticidal, antibacterial agent, pharmaceutical, and food industries; however, few studies have investigated the essential oil components of . Therefore, this study investigated the diversity of essential oils from the leaves of 885 individual plants across 32 populations in five provinces. Essential oils were extracted by hydrodistillation, and then qualitative and quantitative analyses of the compounds were performed by GC-MS and GC-FID. A total of 87 chemical constituents were identified in the essential oils, including 33 monoterpenes, 48 sesquiterpenes, and six other compounds. The average oil yield was 0.75%, and individual oil yields ranged from 0.01% to 4.28%. A total of 16 chemotypes were classified according to variations in the essential oil chemical constituents of , among which the camphor-type, citral-type, and eucalyptol-type were dominant. Moreover, the borneol-type, cymol-type, elemol-type, methylisoeugenol-type, and selina-6-en-4-ol-type were reported in for the first time. The yield and principal components of the essential oils were mainly affected by altitude, temperature, and sunshine duration, among which altitude had the most significant effect; thus, low-altitude areas are more suitable for the synthesis and accumulation of essential oils. Based on the different characteristics of the essential oils in the leaves of , several excellent populations and individuals were identified in this study. Moreover, the findings provide a foundation for breeding superior varieties and studying essential oil biosynthesis mechanisms in the future.
Topics: Humans; Oils, Volatile; Cinnamomum; Plant Breeding; Monoterpenes; Plant Leaves
PubMed: 37175069
DOI: 10.3390/molecules28093659 -
Journal of the American Chemical Society Nov 2022Chemical synthesis of natural products is typically inspired by the structure and function of a target molecule. When both factors are of interest, such as in the case...
Chemical synthesis of natural products is typically inspired by the structure and function of a target molecule. When both factors are of interest, such as in the case of taxane diterpenoids, a synthesis can both serve as a platform for synthetic strategy development and enable new biological exploration. Guided by this paradigm, we present here a unified enantiospecific approach to diverse taxane cores from the feedstock monoterpenoid ()-carvone. Key to the success of our approach was the use of a skeletal remodeling strategy which began with the divergent reorganization and convergent coupling of two carvone-derived fragments, facilitated by Pd-catalyzed C-C bond cleavage tactics. This coupling was followed by additional restructuring using a Sm(II)-mediated rearrangement and a bioinspired, visible-light induced, transannular [2 + 2] photocycloaddition. Overall, this divergent monoterpenoid remodeling/convergent fragment coupling approach to complex diterpenoid synthesis provides access to structurally disparate taxane cores which have set the stage for the preparation of a wide range of taxanes.
Topics: Stereoisomerism; Taxoids; Monoterpenes
PubMed: 36346461
DOI: 10.1021/jacs.2c10272 -
Nature Sep 2022Monoterpenes (CH) are emitted in large quantities by vegetation to the atmosphere (>100 TgC year), where they readily react with hydroxyl radicals and ozone to form...
Monoterpenes (CH) are emitted in large quantities by vegetation to the atmosphere (>100 TgC year), where they readily react with hydroxyl radicals and ozone to form new particles and, hence, clouds, affecting the Earth's radiative budget and, thereby, climate change. Although most monoterpenes exist in two chiral mirror-image forms termed enantiomers, these (+) and (-) forms are rarely distinguished in measurement or modelling studies. Therefore, the individual formation pathways of monoterpene enantiomers in plants and their ecological functions are poorly understood. Here we present enantiomerically separated atmospheric monoterpene and isoprene data from an enclosed tropical rainforest ecosystem in the absence of ultraviolet light and atmospheric oxidation chemistry, during a four-month controlled drought and rewetting experiment. Surprisingly, the emitted enantiomers showed distinct diel emission peaks, which responded differently to progressive drying. Isotopic labelling established that vegetation emitted mainly de novo-synthesized (-)-α-pinene, whereas (+)-α-pinene was emitted from storage pools. As drought progressed, the source of (-)-α-pinene emissions shifted to storage pools, favouring cloud formation. Pre-drought mixing ratios of both α-pinene enantiomers correlated better with other monoterpenes than with each other, indicating different enzymatic controls. These results show that enantiomeric distribution is key to understanding the underlying processes driving monoterpene emissions from forest ecosystems and predicting atmospheric feedbacks in response to climate change.
Topics: Atmosphere; Climate Change; Droughts; Forests; Monoterpenes; Trees
PubMed: 36071188
DOI: 10.1038/s41586-022-05020-5 -
Molecules (Basel, Switzerland) Apr 2021is used in Mexican folk medicine to treat wounds on the skin. Recently, it was shown that the essential oil (EO) of has wound healing activity, accelerating cutaneous...
is used in Mexican folk medicine to treat wounds on the skin. Recently, it was shown that the essential oil (EO) of has wound healing activity, accelerating cutaneous wound closure and generating scars with good tensile strength. α-pinene (PIN) and α-phellandrene (FEL) are terpenes that have been found in this EO, and it has been shown in different studies that both have anti-inflammatory activity. The aim of this study was to determine the wound healing activity of these two terpenes. The results of in vitro tests demonstrate that PIN and FEL are not cytotoxic at low concentrations and that they do not stimulate fibroblast cell proliferation. In vivo tests showed that the terpenes produce stress-resistant scars and accelerate wound contraction, due to collagen deposition from the early stages, in wounds treated with both terpenes. Therefore, we conclude that both α-pinene and α-phellandrene promote the healing process; this confirms the healing activity of the EO of , since having these terpenes as part of its chemical composition explains part of its demonstrated activity.
Topics: Bicyclic Monoterpenes; Bursera; Cyclohexane Monoterpenes; Humans; Mexico; Oils, Volatile; Plant Extracts; Skin; Terpenes; Wound Healing
PubMed: 33923276
DOI: 10.3390/molecules26092488 -
Molecules (Basel, Switzerland) Aug 2022Briq. is a famous Chinese traditional medicine with antipyretic, anti-inflammatory, analgesic and hemostatic effects. Many chemical components can be isolated and... (Review)
Review
Briq. is a famous Chinese traditional medicine with antipyretic, anti-inflammatory, analgesic and hemostatic effects. Many chemical components can be isolated and detected by using various analysis methods, including monoterpenes, sesquiterpenes, aldehydes, ketones, quinones, alcohols, phenols, carboxylic acids and esters, etc., in which volatile oil was considered to be the main chemical component. In this paper, the chemical constituents and their pharmacological effects were reviewed by summarizing the recent literature, revealing the relationship between them.
Topics: Drugs, Chinese Herbal; Lamiaceae; Monoterpenes; Oils, Volatile; Sesquiterpenes
PubMed: 36014489
DOI: 10.3390/molecules27165249 -
Oncotarget May 2023
Topics: Humans; Blood-Brain Barrier; Groin; Brain; Glioma; Brain Neoplasms; Monoterpenes
PubMed: 37141417
DOI: 10.18632/oncotarget.28414 -
Molecules (Basel, Switzerland) Nov 2020The objective of the present study is to obtain linalool- cyclodextrin (CDs) solid complexes for possible applications in the food industry. For this purpose, a detailed...
The objective of the present study is to obtain linalool- cyclodextrin (CDs) solid complexes for possible applications in the food industry. For this purpose, a detailed study of linalool complexation was carried out at different pH values, to optimize the type of CDs and reaction medium that support the highest quantity of encapsulated linalool. Once demonstrated the ability of hydroxypropyl-β-cyclodextrin (HP-β-CDs), to form inclusion complexes with linalool (K = 921 ± 21 L mol) and given their greater complexation efficacy (6.788) at neutral pH, HP-β-CDs were selected to produce solid inclusion complexes by using two different energy sources, ultrasounds and microwave irradiation, subsequently spraying the solutions obtained in the Spray Dryer. To provide scientific solidity to the experimental results, the complexes obtained were characterized by using different instrumental techniques in order to confirm the inclusion of linalool in the HP-β-CDs hydrophobic cavity. The linalool solid complexes obtained were characterized by using H nuclear magnetic resonance (H-NMR) and 2D nuclear magnetic resonance (ROSEY), differential scanning calorimetry, thermogravimetry and Fourier transform infrared spectrometry. Moreover, the structure of the complex obtained were also characterized by molecular modeling.
Topics: 2-Hydroxypropyl-beta-cyclodextrin; Acyclic Monoterpenes; Calorimetry, Differential Scanning; Hydrogen-Ion Concentration; Molecular Docking Simulation
PubMed: 33139617
DOI: 10.3390/molecules25215069 -
Journal of Animal Science Jan 2023A sodium pentobarbital-induced sleep time study was conducted on 15 adult intact male Boer × Spanish goats selected for high (J+, n = 7) or low (J-, n = 8) juniper...
A sodium pentobarbital-induced sleep time study was conducted on 15 adult intact male Boer × Spanish goats selected for high (J+, n = 7) or low (J-, n = 8) juniper consumption (estimated breeding values of 13.1 ± 1.0 and -14.3 ± 0.8, respectively; mean ± standard deviation). Pentobarbital sleep time is an in vivo assay of Phase I hepatic metabolism that can be induced by exposure to barbiturates and monoterpenes. Monoterpenes and pentobarbital are initially oxidized by this pathway; thus, we hypothesized that J+ goats would have shorter sleep times than J- goats. Time to the righting reflex after pentobarbital-induced sleep was measured in all goats following a minimum period of 21 d on three different diets: 1) grazing juniper-infested rangeland (JIR), 2) forage diet with no monoterpenes (M0), and 3) forage diet with 8 g/kg added monoterpenes from camphor, sabinene, and α-pinene in a w/w ratio of 5:4:1 (M+). Fecal samples from the JIR diet were analyzed with near-infrared spectroscopy for the percentage of juniper in the diet. Fecal samples from the JIR and M+ diets were analyzed for camphor and sabinene concentrations. The percentage of juniper in the diet of J+ goats grazing rangelands was greater (P = 0.001) than J- goats (31.1% and 18.6%, respectively). Sleep time did not differ between selection lines (P = 0.36). However, the sleep time of the goats fed M+ diet was 26 min shorter (P < 0.001) than JIR or M0 diets, which were equal. The concentration of camphor and sabinene in the feces was higher (P < 0.001) for goats on the M+ diet than on the JIR diet. There were no differences between selection lines in the serum enzymes indicative of liver disease (aspartate aminotransferase, bilirubin, gamma-glutamyl transferase, and glutamate dehydrogenase; P > 0.12), and all treatment means were within the reference interval. Selecting goats for juniper consumption did not affect the Phase I detoxification system, and several alternative hypotheses for differences in juniper consumption between J+ and J- goats are discussed.
Topics: Animals; Male; Juniperus; Goats; Camphor; Metabolic Detoxication, Phase I; Pentobarbital; Plant Breeding; Diet; Monoterpenes; Liver
PubMed: 37328163
DOI: 10.1093/jas/skad180 -
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 -
Molecules (Basel, Switzerland) Oct 2022Interest in plant-based diets has been on the rise in recent years owing to the potential health benefits of their individual components and the notion that plant-based...
Interest in plant-based diets has been on the rise in recent years owing to the potential health benefits of their individual components and the notion that plant-based diets might reduce the incidence of several diseases. Egyptian dukkah and Syrian za'atar are two of the most historic and famous Middle Eastern herbal blends used for their anti-inflammatory, hypolipidemic, and antidiabetic effects. Headspace SPME-GCMS and HPLC-DAD were adopted for characterizing the aroma profile and phenolic compounds of both herbal blends, respectively. Further, vapor-phase minimum inhibitory concentration was employed for assessing each blend's antibacterial potential, while their antioxidant potential was estimated via in vitro antioxidant assays. SPME headspace analysis indicated the abundance of ethers and monoterpene hydrocarbons, while HPLC revealed the presence of several phenolics including rosmarinic acid, ferulic acid, and rutin. Biological investigations affirmed that vapor-phase of the tested blends exhibited antibacterial activities against Gram-positive and Gram-negative pathogens, while the antioxidant potential of the blends was investigated and expressed as Trolox (125.15 ± 5.92 to 337.26 ± 13.84 μM T eq/mg) and EDTA (18.08 ± 1.62 to 51.69 41 ± 5.33 μM EDTA eq/mg) equivalent. The presented study offers the first insight into the chemical profile and biological activities of both dukkah and za'atar.
Topics: Anti-Bacterial Agents; Anti-Infective Agents; Antioxidants; Chromatography, High Pressure Liquid; Edetic Acid; Ethers; Gas Chromatography-Mass Spectrometry; Hypoglycemic Agents; Monoterpenes; Phenols; Plant Extracts; Rutin; Solid Phase Microextraction
PubMed: 36235006
DOI: 10.3390/molecules27196471