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Aim: Environmental exposure constitutes a significant determinant in the pathogenesis of metabolic syndrome (MetS). Nevertheless, the contribution of environmental factors to MetS remains ambiguous. The present study was aimed at investigating the correlation between serum terpenes and the risk of MetS in the general population. Methods: A cross‐sectional study was conducted among 1266 individuals from the 2013–2014 National Health and Nutrition Examination Survey (NHANES). Serum terpenes and MetS risk were analyzed using a weighted logistic regression model. Weighted quantile sum (WQS) regression was utilized to explore the relationship between the mixture of serum terpenes and MetS. The restricted cubic spline (RCS) method was employed to assess the dose–response relationship between them. All data and analyses were conducted using the "Survey" package in R software (Version 4.3.2). Results: The study population, with an average age of 46.82 ± 0.46 years and a body mass index (BMI) of 28.97 kg/m2, consisted of 48.15% males and 67.99% Whites. Among the participants, 35.78% were diagnosed with MetS. The weighted logistic regression showed that tertiles of serum levels of α‐pinene, β‐pinene, and limonene were positively correlated with MetS risk with a OR value of 1.90 (1.14, 3.16), 2.02 (1.23, 3.31), and 2.35 (1.33, 4.13) and elevated triglycerides (TGs) with a OR of 2.36 (1.63, 3.43), 3.51 (2.30, 5.38), and 3.96 (2.55, 6.15) (all ptrend < 0.05). The WQS regression indicated a positive association between serum terpene mixture and MetS risk (OR = 1.65, 95% CI: 1.18–2.3), increased TG (OR = 2.69, 95% CI: 1.94–3.71), and reduced high‐density lipoprotein cholesterol (HDL‐C) (OR = 1.46, 95% CI: 1.03–2.07) (all ptrend < 0.01). The RCS analysis further supported the dose–response relationship. Conclusion: This study suggested potential adverse effects of terpene exposure on human health, emphasizing the importance of environmental interventions in maintaining health. [ABSTRACT FROM AUTHOR]

Metathesis homo- and copolymerization of bifunctional monomers bearing two norbornene moieties was studied. The monomers were synthesized from cis-5-norbornene-exo-2,3-dicarboxylic anhydride and various diamines (hexamethylenediamine, decamethylenediamine, 1R,3S-isophoronediamine). The metathesis homopolymerization of these bis(nadimides) in the presence of the second-generation Grubbs catalyst afforded glassy cross-linked polymers in more than 90% yields. The metathesis copolymerization of the bis(nadimides) and a monofunctional norbornene derivative containing the β-pinene fragment also resulted in insoluble cross-linked polymers in nearly quantitative yields. The structures and purity of the synthesized polymers were confirmed via IR spectroscopy and CP/MAS NMR spectroscopy. Conditions for the fabrication of mechanically strong solution-cast thin films based on copolymers synthesized from the comonomers mentioned above were determined by varying the content of the cross-linking agent. It was shown that the films made in this way are stable in a range of organic solvents and could be useful as semipermeable or membrane materials for use in liquid organic media. The permeability of the polymer films in question to 1-phenylethanol and mandelic acid was studied. The results obtained are discussed along with the data from the DSC, TGA, and powder X-ray diffraction studies of the properties of the synthesized metathesis homo- and copolymers. [ABSTRACT FROM AUTHOR]

Angelica is a large genus of plants belonging to the Apiaceae family that includes about 100 species of biennial or perennial herbs. Several species of this genus are extensively used in various traditional medicines and, despite their content in toxic furanocoumarins, also as food. In this study, the chemical composition of the essential oil (EO) from aerial flowering parts of Angelica sylvestris L., a plant distributed in Europe, North and Central Asia, collected in the Isle of Skey (Scotland), was analyzed by GC and GC-MS. No one report has been previously published on this accession. The result showed the presence of a large quantity of monoterpene hydrocarbons with limonene (51.89%), by far, as the most abundant component. Other metabolites present in lesser quantity were β-pinene (4.61%), α-pinene (3.54%), and thymol (3.33%). Considerations with respect to all the other EOs of A. sylvestris taxa, studied so far, were carried out. [ABSTRACT FROM AUTHOR]

A simple and effective synthetic method for (–)-nopinone via oxidation of (+)-myrtenal by oxone in DMF to form 6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl formate was proposed. Subsequent hydrolysis of the formate under basic conditions formed nopinone in preparative yields of 61–67%. [ABSTRACT FROM AUTHOR]

Pistacia palaestina Boiss. is a common tree in the Mediterranean maquis. The leaves of this plant accumulate defensive monoterpenes, whose levels greatly increase in galls induced by the aphid Baizongia pistaciae. We previously found a significant chemopolymorphism in monoterpene content among individual trees, but the chirality of these monoterpenes was unknown. Although most plant species specifically accumulate one enantiomeric form of a given compound, P. palaestina individuals display chemopolymorphism in the chirality of the key monoterpenes accumulated. We report here a marked enantiomeric variation for the limonene, α‐ and β‐pinene, camphene, sabinene, δ‐3‐carene, and terpene‐4‐ol content in leaves and galls of nine different naturally growing P. palaestina trees. Interestingly, insect‐induced gall monoterpene composition is an augmentation of the specific enantiopolymorphism originally displayed by each individual tree. [ABSTRACT FROM AUTHOR]

Ferulago nodosa (L.) Boiss. (Apiaceae) is a species occurring in the Balkan-Tyrrhenian area being present in Crete, Greece, Albania, and probably in Macedonia. Although the western disjointed population of Sicily has been classified as an endemic sub-species, F. nodosa subsp. geniculata (Guss.) Troia & Raimondo, its official acceptance is quite controversial. In order to verify the existence of two different sub-species, we investigated the chemical composition of the essential oil of F. nodosa, collected in Crete (Greece), not previously reported, and we compared it with the previously oil compositions reported in literature. Main constituents of the Cretan accessions of F. nodosa were trimethyl benzaldehyde derivatives (29.5%) and monoterpene hydrocarbons (56.14%). [ABSTRACT FROM AUTHOR]

Simultaneously detected of pressurized oxidation products of p-pinene, including pinene, nopineone and perillyl alcohol were performed by gas chromatography on a Rtx @ -Wax polar column (30 m X 0. 25 mm X 〇. 25 |jim). Standard curves of p-pinene, nopineone and perillyl alcohol were obtained as follows：y1 = 541 638街-54 935, y2 =431 452牝 - 127 193 and y3 二434 504牝 - 149 514. The correlation coefficient E2 > 0. 999, and the linear relationship was stable in the range of 2.001 ~ 2〇. 014 mg/mL, 1.014 〜10. 142 mg/mL and 〇. 983 ~ 9. 834 mg/mL. The recovery rate were 99. 03% ~ 103. 18% JOO. 43% 〜101. 84% and 99. 89% 〜101. 72%, and the RSD were 〇. 61% 〜2. 13%, 〇. 75% ~ 3. 94% and 〇. 93% ~ 3. 06% ゝ respectively. The RSD of the samples were 〇. 97% ~ 2. 06%, 1. 45% ~2. 81% and 1. 18% ~ 2. 93%. This method was fast and simple, accurate and stable, and could simultaneously detect |3-pinene, nopineone, and perillyl alcohol. [ABSTRACT FROM AUTHOR]

The genus Phagnalon Cass., included in the Asteraceae family, has a wide distribution, expanding from Macaronesia in the West to the Himalayas in the East, from South France and Nord Italy to Ethiopia and Arabian Peninsula. Various species of Phagnalon have been used in the popular medicine of several countries as medicinal herbs and food. The extracts and the secondary metabolites, have a varied application spectrum at several biological levels, with antimicrobial, antioxidant, antidiabetic, antitumor, etc. properties having been reported. The essential oils of four taxa, Phagnalon rupestre, Phagnalon saxatile var. viride, and Phagnalon rupestre subsp. illyricum var. metlesicsii collected in Sicily (Italy), never previously investigated, and of Phagnalon graecum collected in Greece, were analysed by gas chromatography–mass spectrometry (GC–MS). All the oils were very rich in monoterpene hydrocarbons, with β-pinene as main constituent. Chemotaxonomic considerations with respect to all the other oils of Phagnalon taxa were carried out. [ABSTRACT FROM AUTHOR]

IntroductionMonoterpenes, a subset of the terpene family composed of two isoprene units, have garnered significant attention in research circles owing to their potential medicinal benefits. Recent experimental studies indicate that they might exert positive effects on bone health. Nevertheless, the impact of monoterpenes exposure on bone health remains unexplored in humans.MethodsWe examined 748 adults (age ≥ 40 years) from the National Health and Nutrition Examination Survey (NHANES) 2013–2014 to explore the correlation between three monoterpenes (α-pinene, β-pinene, and limonene), bone mineral density (BMD) in the total lumbar spine and proximal femur, FRAX® scores, and prior bone fracture history.Results and discussionOur analysis unveiled a significant inverse association between a one-unit increase in the natural logarithm (ln) of α-pinene and limonene and total proximal femur BMD (ß = −0.027, S.E. = 0.008, P = 0.004 and ß = −0.019, S.E. = 0.007, P = 0.016, respectively). As serum α-pinene levels ascended across quintiles, there was a notable decrease in total proximal femur BMD (P for trend = 0.025). The inverse relationship between ln α-pinene levels and total proximal femur BMD was more pronounced in women, especially pre-menopausal women. Compared to subjects with α-pinene and limonene levels at or below the 50th percentiles, those exceeding this threshold exhibited the lowest mean value of total proximal femur BMD (0.8628 g/cm2, S.E. = 0.026, P = 0.009). However, the trend was not statistically significant (P = 0.070). Additionally, all three monoterpenes were linked to a higher prevalence of previous spine fractures, whereas β-pinene showed a reduced incidence of other types of fractures. In this comprehensive survey of American adults aged 40 and above, higher serum levels of α-pinene and limonene correlated with decreased total proximal femur BMD. Furthermore, our findings suggest a potential combined effect of α-pinene and limonene on total proximal femur BMD. Further investigation is essential to elucidate the clinical relevance and causative nature of our findings.

Atmospheric new particle formation (NPF) is an important source of aerosol particles and cloud condensation nuclei, which affect both climate and human health. In pristine environments, oxidation of biogenic volatile organic compounds (VOCs) is a major contributor to NPF. However, the impact of relative humidity (RH) on NPF from these precursors remains poorly understood. Herein, we report on NPF, as inferred from measurements of total particle number density with a particle diameter (dp) > 7 nm, from three VOCs (sabinene, α-terpineol, and myrtenol) subjected to dark ozonolysis. From a series of comparative experiments under humid (60% RH) and dry (~0% RH) conditions and a variety of VOC mixing ratios (ξVOC, parts per billion by volume, ppbv), we show varied behavior in NPF at elevated RH depending on the VOC and ξVOC. In general, RH-dependent enhancement of NPF at an ξVOC between <1 ppbv and 20 ppbv was observed for select VOCs. Our results suggest that gaseous water at particle genesis enhances NPF by promoting the formation of low-volatility organic compound gas-phase products (LVOCs). This is supported by measurements of the rate of NPF for α-pinene-derived SOA, where RH had a greater influence on the initial rate of NPF than did ξVOC and ξO3. [ABSTRACT FROM AUTHOR]

Keteleeria davidiana (C.E.Bertrand) Beissn. is a species of conifer native to southern China, Laos and Vietnam. The species has been listed as vulnerable in Vietnam. Essential oil samples have been isolated from leaves, twigs and wood, and their compositions investigated for the first time by combination of chromatographic and spectroscopic techniques [GC-FID, GC-MS and13C NMR]. The composition of leaf essential oil was dominated by α-pinene (28.1%), β-pinene (15.8%) and (E)-β-caryophyllene (13.8%). Twig essential oil contained mainly α-pinene (37.9%) and β-pinene (24.7%) accompanied by (E)-β-caryophyllene (8.3%) and β-phellandrene (7.5%). Lastly, α-pinene (27.9%), α-terpineol (20.3%) and (E)-β-caryophyllene (20.8%) were predominant in wood essential oil. [ABSTRACT FROM AUTHOR]

Metathesis homo- and copolymerization of bifunctional monomers bearing two norbornene moieties was studied. The monomers were synthesized from cis-5-norbornene-exo-2,3-dicarboxylic anhydride and various diamines (hexamethylenediamine, decamethylenediamine, 1R,3S-isophoronediamine). The metathesis homopolymerization of these bis(nadimides) in the presence of the second-generation Grubbs catalyst afforded glassy cross-linked polymers in more than 90% yields. The metathesis copolymerization of the bis(nadimides) and a monofunctional norbornene derivative containing the β-pinene fragment also resulted in insoluble cross-linked polymers in nearly quantitative yields. The structures and purity of the synthesized polymers were confirmed via IR spectroscopy and CP/MAS NMR spectroscopy. Conditions for the fabrication of mechanically strong solution-cast thin films based on copolymers synthesized from the comonomers mentioned above were determined by varying the content of the cross-linking agent. It was shown that the films made in this way are stable in a range of organic solvents and could be useful as semipermeable or membrane materials for use in liquid organic media. The permeability of the polymer films in question to 1-phenylethanol and mandelic acid was studied. The results obtained are discussed along with the data from the DSC, TGA, and powder X-ray diffraction studies of the properties of the synthesized metathesis homo- and copolymers.

Schinus terebinthifolius Raddi, popularly known as "Pink pepper", is a plant native to Brazil. The objective of this work was to analyze the chemical composition and the antioxidant and antibacterial potential of essential oils (EOs) from the leaves, fruits and twigs of S. terebinthifolius, aiming for their application in food safety. EOs were obtained by hydrodistillation and the chemical composition was determined by gas chromatography coupled to mass spectrometry. Phenolic compounds were quantified and antioxidant activity was evaluated using three different methods. The antibacterial activity was determined by the broth microdilution method against foodborne bacteria. In the chemical analysis, 22 compounds were identified in the leaves, 13 compounds in the fruits and 37 compounds in the twigs, revealing the presence of the main compounds germacrene D (12.04%, 15.78%, 20,41%), caryophyllene (15.97%, 3.12%, 11.73%), α-pinene (11.6%, 17.16%, 2.99%), β-pinene (5.68%, 43.34%, 5.60%) and γ-gurjunene (16,85%, 3,15%) respectively. EOs showed better antioxidant potential using the β-carotene/linoleic acid method with 40.74, 61.52 and 63.65% oxidation inhibition for leaves, fruits and twigs, respectively. The EO from the leaves showed greater antibacterial potential against Escherichia coli and Staphylococcus aureus with a minimum inhibitory concentration (MIC) of 0.62 mg mL−1, a value lower than the MIC of sodium nitrite (5.00 mg mL−1), the antimicrobial standard synthetic. The activities of pink pepper EOs suggest their potential as a biopreservative in foods. [ABSTRACT FROM AUTHOR]

Turpentine is a renewable and resourceful forest product. The deep processing and utilization of turpentine, particularly its primary component β-pinene, has garnered widespread attention. This study aimed to synthesize 40 derivatives of β-pinene, including nopinone, 3-cyanopyridines of nopinone, myrtanyl acid, myrtanyl acylthioureas, and myrtanyl amides. We assessed the antiviral activities of these β-pinene derivatives against influenza virus A/Puerto Rico/8/34 (H1N1) using the 3-(4,5-dimetylthiazol-2-yl)-2,5-diphenyltetrazolium bromide method. The β-pinene derivatives were used before and after cellular infection with the influenza virus to evaluate their preventive and therapeutic effects against the H1N1 virus. The results showed that only compound 10o exhibited a preventive effect against the H1N1 virus with a half-maximal inhibitory concentration (IC50) value of 47.6 μmol/L. Among the compounds, 4e, 4i, and 4l demonstrated therapeutic effects against cellular infection, with compound 4e displaying the most potent therapeutic effect (IC50 = 17.5 μmol/L), comparable to the positive control ribavirin. These findings indicated that certain β-pinene derivatives exhibited in vitro antiviral activity against the H1N1 influenza A virus, warranting further investigation as potential anti-influenza agents. [ABSTRACT FROM AUTHOR]

The needle and cone essential oils of Pinus fenzeliana Hand-Mazz. (Pinus kwangtungensis Chun & Tsiang) collected in Hang Kia-Pa Co Nature Reserve, Hoa Binh province were obtained by hydrodistillation and analyzed by a combination of GC-FID, GC-MS and NMR (Gas Chromatography/Gas Chromatography-Mass Spectrometry/Nuclear Magnetic Resonance (NMR) analysis). The oil yields were 0.2% and 0.37% respectively (v/w on dry weight basis). Twenty-seven compounds were detected in both needle and cone oils, accounting for 98.0% and 98.2% of the whole composition, respectively. The main components identified in the needle oil were α-pinene (20.7%), β-pinene (11.3%), δ-3-carene (32.2%), limonene (8.0%) and E-β-caryophyllene (7.1%). The cone oil contained mainly α-pinene (19.3%), β-pinene (45.4%), δ-3-carene (3.5%), limonene (12.7%) and E-β-caryophyllene (3.4%). This is the first report on the chemical composition of the cone essential oil of P. fenzeliana from Vietnam. [ABSTRACT FROM AUTHOR]

This study sought to examine hitherto unresearched relationships between serum terpenes and the prevalence of dyslipidemia. Serum terpenes such as limonene, α-pinene, and β-pinene from the 2013–2014 National Health and Nutrition Examination Survey (NHANES) were used as independent variables in this cross-sectional study. Continuous lipid variables included total cholesterol (TC), high-density lipoprotein cholesterol (HDL-C), non-HDL-C, triglycerides (TG), low-density lipoprotein cholesterol (LDL-C), residual cholesterol (RC), and apolipoprotein B (Apo B). Binary lipid variables (elevated TC, ≥5.18 mmol/L; lowered HDL-C, <1.04 mmol/L in men, and <1.30 mmol/L in women; elevated non-HDL-C, ≥4.2 mmol/L; elevated TG, ≥1.7 mmol/L; elevated LDL-C, ≥3.37 mmol/L; elevated RC, ≥1.0 mmol/L; and elevated Apo B, ≥1.3 g/L) suggest dyslipidemia. The relationships between the mixture of serum terpenes with lipid variables were investigated using weighted quantile sum (WQS) regression and Bayesian kernel machine regression (BKMR). The study for TC, HDL-C, and non-HDL-C included a total of 1,528 people, whereas the analysis for TG, LDL-C, RC, and Apo B comprised 714 participants. The mean age of the overall participants was 47.69 years, and 48.77% were male. We found that tertiles of serum terpene were positively associated with binary (elevated TC, non-HDL-C, TG, LDL-C, RC, Apo B, and lowered HDL-C) and continuous (TC, non-HDL-C, TG, LDL-C, RC, and Apo B, but not HDL-C) serum lipid variables. WQS regression and BKMR analysis revealed that the mixture of serum terpenes was linked with the prevalence of dyslipidemia. According to our data, the prevalence of dyslipidemia was correlated with serum concentrations of three terpenes both separately and collectively. [ABSTRACT FROM AUTHOR]

The present investigation was carried out for a comparative volatile study and aroma profiling of Hedychium flavescens. The headspace gas chromatography mass spectrometry (GC-MS) analysis of flowers (HS-F) and rhizome (HS-R); GC-MS analysis of flower essential oil (EO-F), flower absolute (AB-F) and rhizome essential oil (EO-R) revealed 27, 19, 19, 15 and 12 compounds which constitute 96.22%, 96.93% 97.43%, 86.79% and 97.62% composition, respectively. The identification results demonstrated that flowers and rhizome were rich in β-pinene, 1,8-cineol, linalool and E-β-caryohyllene components. β-Pinene was the most abundant component in HS-R (38.99%), EO-R (26.61%); linalool in HF-F (25.34%) and EO-F (25.99%) and ρ-vinyl-guaiacol in AB-F (32.19%), respectively. The aroma profile of H. flavescens was dominated with floral and jasmine (flowers); spicy, earthy and herbal (EO-F); floral and balsamic (AB-F); herbal, pungent, spicy and earthy (rhizome and EO-R) notes. Based on aroma profile, AB-F was evaluated as potential ingredient for perfume industry. [ABSTRACT FROM AUTHOR]

Eucalyptus (Myrtaceae) is a genus of extremely varied blooming trees that produce valuable essential oil as well as hard and durable heartwood. The primary sources of eucalyptus oil are the leaves of Eucalyptus globulus, E. citriodora, E. tereticornis. The essential oil is isolated by hydro-distillation and is used as a medication, antibacterial, repellent, flavouring agent and in aromatherapy. Monoterpenes like 1,8-cineole, α-pinene, β-pinene and limonene are the major components of the oil. The present study was planned to do the quantitative analysis of essential oil in Eucalyptus tereticornis leaves by qNMR as an alternate analytical technique in addition to more commonly used GC–MS. The method was validated with respect to selectivity, linearity, accuracy, precision and robustness. The developed method can be used to analyse Eucalyptus oil from diverse species as they also contain these volatiles but in different ratios. [ABSTRACT FROM AUTHOR]

Background and objectives: The oleo-gum resin from Ferula gummosa Bioss. is commercially important. Variability of geographic location has shown a deep effect on essential oil of different genus of plants. Thus, evaluation of oleo-gum resin of Ferula gummosa from different locations is important for further studies. In the present study, phytochemicals profile of essential oil of oleo-gum resins from F. gummosa in different geographic location and various bioclimates of Iran, were studied. Methods: The oleo-gum resin of F. gummosa was collected from different regions of Iran. The essential oils of the samples were extracted by Clevenger apparatus and were analyzed by GC-MS. Results: The highest amount of essential oil compared was observed in the samples from Damghan area (24.0%), Firuzkuh area (22%) and Kalat-e-Naderi area (22%). The variability in the oil composition of different samples exhibited a notable difference in monoterpenes content from 39.15 % to 87.48%. Based on GC-MS analysis, the major components were β-pinene (5.11-63.80 %), sabinene (3.37-30.69%), α-pinene (4.43-12.72%) and δ-carene (2.38-10.23 %). The highest concentrations of β-pinene (63.80%) and sabinene (30.69%) were observed in the Shiraz and Torbat-e-Jam essential oils, respectively. The highest amounts of α-pinene (12.72%) and δ-carene (10.23%) were recorded in Firuzkuh and Shiraz areas, respectively. Conclusion: Significant variation in the component of the essential oils from different oleo-gum resins can be used to improve the knowledge about the endemic medicinal plants.

The essential oils (EOs) of Guatteria schomburgkiana (Gsch) and Xylopia frutescens (Xfru) (Annonaceae) were obtained by hydrodistillation, and their chemical composition was evaluated by gas chromatography-mass spectrometry (GC/MS). Herbicide activity was measured by analyzing the seed germination percentage and root and hypocotyl elongation of two invasive species: Mimosa pudica and Senna obtusifolia. The highest yield was obtained for the EO of Xfru (1.06%). The chemical composition of Gsch was characterized by the presence of the oxygenated sesquiterpenes spathulenol (22.40%) and caryophyllene oxide (14.70%). Regarding the EO of Xfru, the hydrocarbon monoterpenes α-pinene (35.73%) and β-pinene (18.90%) were the components identified with the highest concentrations. The germination of seeds of S. obtusifolia (13.33 ± 5.77%) showed higher resistance than that of seeds of M. pudica (86.67 ± 5.77%). S. obtusifolia was also more sensitive to the EO of Xfru in terms of radicle (55.22 ± 2.72%) and hypocotyl (71.12 ± 3.80%) elongation, while M. pudica showed greater sensitivity to the EO of Gsch. To screen the herbicidal activity, the molecular docking study of the major and potent compounds was performed against 4-hydroxyphenylpyruvate dioxygenase (HPPD) protein. Results showed good binding affinities and attributed the strongest inhibitory activity to δ-cadinene for the target protein. This work contributes to the study of the herbicidal properties of the EOs of species of Annonaceae from the Amazon region. [ABSTRACT FROM AUTHOR]

Polymers based on renewable monomers are projected to have a significant role in the sustainable economy, even in the near future. Undoubtedly, the cationically polymerizable β-pinene, available in considerable quantities, is one of the most promising bio-based monomers for such purposes. In the course of our systematic investigations related to the catalytic activity of TiCl4 on the cationic polymerization of this natural olefin, it was found that the 2-chloro-2,4,4-trimethylpentane (TMPCl)/TiCl4/N,N,N′,N′-tetramethylethylenediamine (TMEDA) initiating system induced efficient polymerization in dichloromethane (DCM)/hexane (Hx) mixture at both −78 °C and room temperature. At −78 °C, 100% monomer conversion was observed within 40 min, resulting in poly(β-pinene) with relatively high Mn (5500 g/mol). The molecular weight distributions (MWD) were uniformly shifted towards higher molecular weights (MW) in these polymerizations as long as monomer was present in the reaction mixture. However, chain–chain coupling took place after reaching 100% conversion, i.e., under monomer-starved conditions, resulting in considerable molecular weight increase and MWD broadening at −78 °C. At room temperature, the polymerization rate was lower, but chain coupling did not occur. The addition of a second feed of monomer in the polymerization system led to increasing conversion and polymers with higher MWs at both temperatures. 1H NMR spectra of the formed polymers indicated high in-chain double-bond contents. To overcome the polarity decrease by raising the temperature, polymerizations were also carried out in pure DCM at room temperature and at −20 °C. In both cases, rapid polymerization occurred with nearly quantitative yields, leading to poly(β-pinene)s with Mns in the range of 2000 g/mol. Strikingly, polymerization by TiCl4 alone, i.e., without any additive, also occurred with near complete conversion at room temperature within a few minutes, attributed to initiation by adventitious protic impurities. These results convincingly prove that highly efficient carbocationic polymerization of the renewable β-pinene can be accomplished with TiCl4 as catalyst under both cryogenic conditions, applied widely for carbocationic polymerizations, and the environmentally benign, energy-saving room temperature, i.e., without any additive and cooling or heating. These findings enable TiCl4-catalyzed eco-friendly manufacturing of poly(β-pinene)s, which can be utilized in various applications, and in addition, subsequent derivatizations could result in a range of high-added-value products. [ABSTRACT FROM AUTHOR]

Background: Rabbitbrush (Ericameria nauseosa) is a conspicuous member of plant communities in the deserts of western North America. The plant is an important winter forage for several ungulates in the region and has been used in Native American ethnopharmacology. Methods: Several specimens were collected from North Central Utah (8 samples) and Southwestern Idaho (6 samples). The essential oils were obtained by hydrodistillation and analyzed by gas chromatographic techniques. The data were analyzed using agglomerative hierarchical cluster analysis (HCA), principal component analysis (PCA), and Pearson correlation analysis. Results: Essential oil yields ranged from 0.030% to 2.011%. The major components in the essential oils were β-phellandrene (1.8%-56.5%), β-pinene (0.%3-23.3%), limonene (0.7%-22.3%), and (Z)-β-ocimene (0.0%-29.3%). With the exception of 1 sample from Utah, the essential oils showed greater than 50% similarity in composition. There were significant differences in percentages of some components, however. Sabinene, β-phellandrene, cosmene, 1,3,8- p -menthatriene, terpinen-4-ol, and β-eudesmol concentrations were higher in the Idaho samples while myrcene, limonene, geranyl acetate, (E)-β-caryophyllene, γ-curcumene, germacrene D, α-muurolene, γ-cadinene, and δ-cadinene concentrations were significantly higher in the Utah samples. Chiral gas chromatography–mass spectrometry showed the chiral monoterpenoids to be dominated by the (−)-enantiomers, but there were some differences in enantiomeric distribution in the essential oils from Utah compared to those from Idaho. Conclusion: The essential oil compositions in this work are qualitatively similar to those reported previously. However, there were quantitative differences in chemical composition and enantiomeric distributions between the Utah samples and the Idaho samples. Additional research is needed to compare essential oil composition from other geographical locations in western North America. [ABSTRACT FROM AUTHOR]

The effect of intercropping of hyssop (Hyssopus officinalis L.) from Lamiaceae with a medicinal legume, that is, fenugreek (Trigonella foenum-graecum L.) on the hyssop essential oil was investigated. The highest herbage and essential oil yields of hyssop were produced from sole cropping and also intercropped hyssop with fenugreek (3:1 ratio); however, the highest antioxidant activity was obtained from the intercropped hyssop with fenugreek (1:3 ratio). The highest contents of the major constituents in the hyssop essential oil such as cis- and trans-pinocamphone and β-pinene were obtained from sole cropped of hyssop and the intercropping of hyssop with fenugreek (3:1 ratio). In conclusion, the intercropping of hyssop with fenugreek can increase biodiversity and efficiency of using resources. Therefore, this strategy could be considered in order to recommend in simultaneous production of secondary metabolites in the herbs like hyssop in an agricultural land. [ABSTRACT FROM AUTHOR]

In this work, the essential oils (EOs) from leaves and flowers of Rhododendron spinuliferum and Rhododendron spiciferum were extracted by hydrodistillation, chemical compositions of EOs were analyzed by GC-MS and GC-FID. For R. spinuliferum and R. spiciferum, α- and β-pinene were common major compounds. It provided an opportunity to test the potential synergistic effect of α- and β-pinene among EOs. Firstly, four EOs and two major compounds (α- and β-pinene) exhibited fumigant, contact and repellent activities to three stored-product insects. To the red flour beetle, leaves of both species exhibited stronger contact toxicity than flowers did. This trend was diverse to the booklouse. Furthermore, binary mixture bioassays of α- and β-pinene were performed following natural proportions. Results of multiple linear regression showed that α-pinene, trans-β-farnesene and bornyl acetate were responsible for the contact toxicity to the red flour beetle and booklouse with diverse contribution. [ABSTRACT FROM AUTHOR]

To achieve a product with a high quantity and quality of active substance in the main and valuable medicinal and aromatic plants like hyssop (Hyssopus officinalis L.) under semiarid conditions requires the use of novel agronomic technics. The effects of the foliar application of salicylic acid (SA) and proline were investigated on the hyssop growth and phytochemical traits at the field conditions during two experimental years. The experiment was performed as a factorial in a completely randomized block design (RCBD), in which irrigation treatment (optimum and reduced irrigation) and the foliar application (control, the foliar applications of SA and proline). The volatile oils from the aerial parts harvested at the flowering were analyzed by GC-FID and GC/MS. Results indicated that water deficit stress significantly affected some physiological and phytochemical characteristics of hyssop. In general, the amounts of proline and chlorophyll (a, b, and total), the volatile oil content, and the concentrations of the major constituents of the volatile oil improved under water deficit stress. The highest values of the volatile oil content and the concentrations of the major constituents of the volatile oil including β-pinene (24.59%), trans-pinocamphene (14.20%), cis-pinocamphene (65.57%), and myrtenol (6.95%) were obtained from the plants treated with deficit irrigation × foliar spraying of SA. In conclusion, the foliar-spraying of SA could decrease the harmful impacts of water deficit on the concentrations of the main compounds in the volatile oil, and it is recommended for the stability of the active substance yield of H. officinalis in a semiarid climate. [ABSTRACT FROM AUTHOR]

The genus Kaempferia (Zingiberaceae) is well-known for its diverse phytochemical constituents and characteristic essential oil. Kaempferia champasakensis was firstly described in 2008 by Chayan Picheansoonthon and Supachai Koonterm in Champasak province of Southern Laos. To date, little is known about phytochemical components and pharmacological activities of the plant. In the present study, the extraction of essential oil from K. champasakensis leaves as well as Gas Chromatography - Mass Spectrometry (GC/MS) profile were investigated. The major components in essential oil extracted from K. champasakensis leaves were determined as β-caryophyllene (16.07%), β-elemenone (14.53%), β-pinene (13.80%), germacrone (9.85%), myrcene (9.46%) and diisooctyl phthalate (8.62%). This is the first report on chemical constituents of essential oil extracted from the leaves of K. champasakensis. [ABSTRACT FROM AUTHOR]

Schinus terebinthifolius Raddi, popularly known as “Pink pepper”, is a plant native to Brazil. The objective of this work was to analyze the chemical composition and the antioxidant and antibacterial potential of essential oils (EOs) from the leaves, fruits and twigs of S. terebinthifolius, aiming for their application in food safety. EOs were obtained by hydrodistillation and the chemical composition was determined by gas chromatography coupled to mass spectrometry. Phenolic compounds were quantified and antioxidant activity was evaluated using three different methods. The antibacterial activity was determined by the broth microdilution method against foodborne bacteria. In the chemical analysis, 22 compounds were identified in the leaves, 13 compounds in the fruits and 37 compounds in the twigs, revealing the presence of the main compounds germacrene D (12.04%, 15.78%, 20,41%), caryophyllene (15.97%, 3.12%, 11.73%), α-pinene (11.6%, 17.16%, 2.99%), β-pinene (5.68%, 43.34%, 5.60%) and γ-gurjunene (16,85%, 3,15%) respectively. EOs showed better antioxidant potential using the β-carotene/linoleic acid method with 40.74, 61.52 and 63.65% oxidation inhibition for leaves, fruits and twigs, respectively. The EO from the leaves showed greater antibacterial potential against Escherichia coli and Staphylococcus aureus with a minimum inhibitory concentration (MIC) of 0.62 mg mL−1, a value lower than the MIC of sodium nitrite (5.00 mg mL−1), the antimicrobial standard synthetic. The activities of pink pepper EOs suggest their potential as a biopreservative in foods.

Liquidambar formosana Hance is a pinene-rich deciduous plant species in the Altingiaceae family that is used as a medicinal plant in China. However, the regulatory mechanisms underlying α-pinene and β-pinene biosynthesis in L. formosana leaves remain unknown. Here, a joint analysis of the volatile compounds and transcriptomes of L. formosana leaves was performed to comprehensively explore the terpene synthase (TPS) that may participate in α-pinene and β-pinene biosynthesis. Headspace solid-phase microextraction (HS-SPME) and gas chromatography–mass spectrometry (GC–MS) jointly detected volatile L. formosana leaves. Trees with high and low levels of both α-pinene and β-pinene were defined as the H group and L group, respectively. RNA sequencing data revealed that DXR (1-deoxy-D-xylulose-5-phosphate reductoisomerase), HDS [(E)-4-hydroxy-3-methylbut-2-eny-l-diphosphate synthase], and TPS may be the major regulators of monoterpenoid biosynthesis. We identified three TPSs (LfTPS1, LfTPS2, and LfTPS3), which are highly homologous to α-pinene and β-pinene synthases of other species in phylogenetic analysis. Four TPS genes (LfTPS1, LfTPS2, LfTPS4, LfTPS5) may be critically involved in the biosynthesis and regulation of α-pinene and β-pinene in L. formosana. Bioinformatic and transcriptomic results were verified using quantitative real-time PCR. We identified LfTPS1, LfTPS2 as candidate genes for α-pinene and β-pinene biosynthesis that significantly improve the yield of beneficial terpenoids. [ABSTRACT FROM AUTHOR]

Cockroaches are urban pests that are very difficult to control. Using repellents is a green, safe and effective strategy for their control. In order to find novel cockroach repellents, the repellent activity of 45 bridged-ring terpenoid derivatives synthesized from β-pinene against Blattella germanica was tested. The relationship between the molecular structure of these bridged-ring terpenoid derivatives and their repellent activity against Blattella germanica was also analysed. The results show that some of the bridged-ring terpenoid derivatives exhibit good repellent activity against Blattella germanica, and six compounds (RR = 60.44–87.32%) show higher repellent activity against Blattella germanica than DEET (RR = 54.77%), making them promising for development as new cockroach repellents. Quantitative structure–activity relationship (QSAR) analysis revealed that the HOMO-1 energy, Kier and Hall index (order 2), Balaban index, and relative positive charged surface area of bridged-ring terpenoid derivatives have effects on repellent activity against Blattella germanica. The present study may provide a theoretical basis for the high-value use of β-pinene and can be helpful to the development of novel repellents against Blattella germanica. [ABSTRACT FROM AUTHOR]

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[Display omitted] • One-pot transformation of β-pinene to myrtanal using a tandem approach with two catalysts. • Metal-modified mesoporous catalysts transform β-pinene into valuable fine chemicals. • MgO+Fe/SBA-15 catalysts achieved a 63 % myrtanal yield and 60 % H 2 O 2 efficiency. • Total acidity and acid site density are key descriptors of catalytic activity. • Reusability and no Fe leaching were observed for the synthesis of myrtanal. Metal-modified heterogeneous catalysts based on mesoporous supports such as MCM-41 and SBA-15 were prepared and evaluated in the one-pot tandem transformation of β-pinene, along with MgO. This route involves epoxidation with H 2 O 2 followed by the subsequent isomerization of the epoxide, yielding myrtanal as the major product; this aldehyde has wide-ranging applications as a fine chemical in fragrances, flavors, and as a precursor for pharmaceutical products. Several metals (Sn, Fe, Cu, Co) were anchored onto the supports by wetness impregnation methodology and the solids were thoroughly characterized using ICP/OES, XRD, N 2 physisorption, TEM-EDX, pyridine-FTIR, NH 3 -TPD, and XPS techniques. Among these catalysts, Fe (5.07 wt%)/SBA-15 (FeS1) exhibited the highest yield to myrtanal (63 %) with a H 2 O 2 efficiency of up to 60 %; this catalyst had a total acidity of 138 μmol g−1, a surface area of 496 m2 g−1, a pore volume of 0.96 cm3 g−1, and an acid site density of 0.28 μmol m−2. Myrtanal selectivity was also high with Sn-based catalysts, while it was poor with Cu-based materials and the null activity of Co catalysts. Total Lewis acidity and acid site density were identified as suitable kinetic descriptors of catalytic data, owing to their crucial role in the ring-opening of monoterpene epoxides. The most active catalyst showed reusability without considerable loss of substrate conversion or selectivity towards myrtanal. Additionally, no leaching of Fe was observed. Based on materials characterization and catalytic results, a plausible reaction pathway was proposed for the one-pot tandem transformation of β-pinene towards myrtanal. [ABSTRACT FROM AUTHOR]

Abstract In this paper, the chemical constituents, larvicidal and antimicrobial activities of hydrodistilled essential oils from Zingiber castaneum Škorničk. & Q.B. Nguyễn and Zingiber nitens M.F. Newman were reported. The main constituents of Z. castaneum leaf were bicyclogermacrene (24.8%), germacrene D (12.9%), cis-β-elemene (11.2%) and β-pinene (10.3%), while sabinene (22.9%) and camphene (21.2%) were the significant compounds in the rhizome. However, the dominant compounds in the leaf of Z. nitens includes β-pinene (45.8%) and α-pinene (10.7%). Terpinen-4-ol (77.9%) was the most abundant compound of the rhizome. Z. castaneum rhizome oil displayed larvicidal activity against Aedes aegypti and Culex quinquefasciatus with LC50 values of 121.43 and 88.86 µg/mL, respectively, at 24 h. The leaf oil exhibited activity with LC50 values of 39.30 µg/mL and 84.97 µg/mL, respectively. Also, the leaf and rhizome oils of Z. nitens displayed greater larvicidal action towards Ae. aegypti with LC50 values of 17.58 µg/mL and 29.60 µg/mL, respectively. Only the rhizome oil displayed toxicity against Cx. quinquefasciatus with LC50 value of 64.18 µg/mL. All the studied essential oils inhibited the growth of Pseudomonas aeruginosa ATCC25923 with minimum inhibitory concentration (MIC) value of 50.0 µg/mL. This paper provides information on the larvicidal and antimicrobial potentials of Z. castaneum and Z. nitens essential oils.

This research aimed to identify the volatile compounds of essential oils found in the rhizomes and leaves of Zingiber monophyllum Gagnep. This is the first phytochemical investigation of this species. Essential oils from the rhizomes and leaves of Z. monophyllum were obtained by hydrodistillation and analyzed by gas chromatography coupled with mass spectrometry (GC/MS). Twenty-three compounds accounting for 90.9% of the rhizome oils were identified, while there were seventeen volatile components corresponding to 91.8% in the leaf oil. The major constituents of rhizome and leaf oils were β-pinene (44.9% and 29.8%), borneol (5.2% and 3.1%), α-pinene (4.1% and 1.8%), and myrtenal (3.2% and 4.0%). However, larger amounts of dihydroedulan I (21.7%), n-hexadecanol (7.0%), and α-copaene (6.5%) were found in the leaf oil only. [ABSTRACT FROM AUTHOR]

Recently, spices have attracted the attention of scientists and agrochemical companies for their potential as insecticidal and acaricidal agents, and even as repellents to replace synthetic compounds that are labeled with detrimental impacts on environment and human and animal health. In this framework, the aim of this study was to evaluate the insecticidal potential of the essential oils (EOs) obtained from three Cameroonian aromatic plants, namely Monodora myristica (Gaertn.) Dunal, Xylopia aethiopica (Dunal) A. Rich., and Aframomum citratum (J. Pereira) K. Schum. They were produced by hydrodistillation, with yields of 3.84, 4.89, and 0.85%, respectively. The chemical composition was evaluated by GC-MS analysis. The EOs and their major constituents (i.e., geraniol, sabinene, α-pinene, p-cymene, α-phellandrene, and β-pinene) were tested against the polyphagous moth pest, i.e., Spodoptera littoralis (Boisd.), the common housefly, Musca domestica L., and the filariasis and arbovirus mosquito vector, Culex quinquefasciatus Say. Our results showed that M. myristica and X. aethiopica EOs were the most effective against M. domestica adults, being effective on both males (22.1 µg adult−1) and females (LD50: 29.1 µg adult−1). The M. myristica EO and geraniol showed the highest toxicity on S. littoralis, with LD50(90) values of 29.3 (123.5) and 25.3 (83.2) µg larva−1, respectively. Last, the EOs from M. myristica and X. aethiopica, as well as the major constituents p-cymene and α-phellandrene, were the most toxic against C. quinquefasciatus larvae. The selected EOs may potentially lead to the production of cheap and effective botanical insecticides for African smallholders, although the development of effective formulations, a safety evaluation, and an in-depth study of their efficacy on different insect species are needed. [ABSTRACT FROM AUTHOR]

Pinewood nematode, Bursaphelenchus xylophilus, a pine-parasitic nematode, poses a serious threat to pine trees globally, causing pine wilt disease. When dispersal-stage juvenile 4 (dauer, JIV, a durable stage) of B. xylophilus enters the new pine, it transforms into a propagative adult (dauer moulting) and reproduces quickly. Our previous studies have found that pine-volatile β-pinene promotes dauer moulting of B. xylophilus; however, this mechanism is not clear. Here, this study is attempting to unravel the molecular process underlying dauer moulting of B. xylophilus through signal chemical tests and transcriptome analysis. The results showed that β-pinene could promote dauer moulting of B. xylophilus, while other common dauer moulting signals, such as dafachronic acid (DA), part of the TGF/insulin signal pathway, were inoperative. Moreover, the JIV soaked in 1% β-pinene for only 6 h could transform into adults at a significant rate. Therefore, the transcriptomes of JIV soaked in 1% β-pinene for 6 h were sequenced. It was found that 15,556 genes were expressed; however, only 156 genes were expressed differentially and enriched in the metabolism of xenobiotics, peroxisome, fatty acid metabolism, and carbon metabolism, indicating that energy metabolism was active at the early stage of dauer moulting. With a stricter parameter, the number of differential genes fell to 19, including 4 sterol hydroxylase, 5 dehydrogenase, 2 glucuronosyltransferase, 5 nuclear-related factor, 1 calcium-binding protein, 1 nitrogen metabolic regulation protein, and 1 cystathionine gamma-lyase. These results indicated that dauer moulting of B. xylophilus into adults might not be regulated by the TGF-β/insulin signal pathway but by another new signal pathway related to the 19 differential genes which need more exploration. Our results contribute to the understanding of the molecular mechanisms behind dauer moulting and may be useful in reducing pine wilt disease by suppressing this moulting to cut the life cycle of B. xylophilus. [ABSTRACT FROM AUTHOR]

Theoretical calculations of optical rotation (OR), although important to predict absolute configurations (ACs) and corroborate experiments, require efficient methodology able to reproduce enantiomer specificity and real OR values. Also, troublesome molecules are recurring in the literature, such as (S)‐methyloxirane and (1R,5R)‐β‐pinene. This study evaluates DFT functionals B3LYP, CAM‐B3LYP, ωB97X‐D, M06‐2X, and PBE0 considering basis sets aug‐cc‐pVDZ, aug‐cc‐pVTZ, 6‐311++G(2d,p), and 6‐311++G(3df,2p) in OR prediction of 42 rigid organic molecules assessing cases with wrong enantiomeric determination comparing to available experimental data at wavelengths 355, 589, and 633 nm. Functionals CAM‐B3LYP and ωB97X‐D with aug‐cc‐pVTZ are indicated here to reproduce experimental values more accurately considering fewer number of wrong AC predictions, normalized RMSD values below 0.70, and a good approximation to experimental values in hierarchical cluster analysis. Methyloxirane AC was reproduced in CAM‐B3LYP and PBE0, with [α]355=6.94 for CAM‐B3LYP/aug‐cc‐pVTZ close to experimental value [α]355=7.49±0.30. Good results were found for AC of β‐pinene in M06‐2X, CAM‐B3LYP, and ωB97X‐D while the latter in 6‐311++G(3df,2p) obtained OR values of [α]589=3.44 and [α]689=4.20 close to experimental values [α]589=2.8 and [α]689=4.66±0.60. The two molecules aforementioned are, for the first time, reported to give valid theoretical OR values in such simple methodologies. OR calculations were all performed after geometry optimization at the same level of theory, and analysis of different functional combinations for each step in β‐pinene showed it can interfere with AC prediction even in rigid molecules. [ABSTRACT FROM AUTHOR]

A new library of pinane-based 1,4-amino alcohols was synthesised and utilised as chiral ligands in enantioselective diethylzinc addition to benzaldehyde. Aldol condensation of (+)-nopinone, derived from (–)-β-pinene, with 2-pyridinecarboxaldehyde gave the key intermediate α,β-unsaturated ketone, which was transformed in diastereoselective reduction, followed by hydrogenation, resulting in 1,4-amino alcohols. On the other hand, epoxidation of the α,β-unsaturated ketone, followed by reduction and then hydrogenation of the pyridine ring, afforded a mixture of 4-amino-2,3-epoxy-1-ols. Stereoselective hydride reduction of the epoxy ketone and subsequent condensation of the resulting products with substituted benzyl bromides provided quaternary ammonium salts, which were subjected to hydride reduction and then hydrogenation, affording 4-amino-2,3-epoxy-1-ol derivatives containing an N -benzylpiperidine moiety. The inhibition of nucleophile-initiated opening of the oxirane ring was interpreted by a systematic series- of comparative Hartree–Fock modelling study using the 6-31+G(d,p) basis set. The antiproliferative activities of 4-amino-2,3-epoxy--1-ol derivatives were examined, and structure–activity relationships were studied from the aspects of the stereochemistry of the oxirane ring, saturation, and substituent effects on the piperidine ring system. [ABSTRACT FROM AUTHOR]

Diabetes mellitus is a major global health concern in the current scenario which is chiefly characterized by the rise in blood sugar levels or hyperglycemia. In the context, DPP4 enzyme plays a critical role in glucose homeostasis. DPP4 targets and inactivates incretin hormones such as glucagon-like peptide-1 (GLP-1) and gastric inhibitory polypeptide (GIP) as physiological substrates, which are essential to regulate the amount of insulin that is secreted after eating. Since the inactivation of incretins occurs, the hyperglycemic conditions continue to rise, and result in adverse physiological conditions linked with diabetes mellitus. Hence, inhibition of DPP4 has been the center of focus in the present antidiabetic studies. Although few DPP4 inhibitor drugs, such as alogliptin, saxagliptin, linagliptin, and sitagliptin, are available, their adverse effects on human metabolism are undeniable. Therefore, it becomes essential for the phytochemical intervention of the disease using computational methods prior to performing in vitro and in vivo studies. In this regard, we used an in-silico approach involving molecular docking, molecular dynamics simulations, and binding free energy calculations to investigate the inhibitory potential of Ocimum tenuiflorum phytocompounds against DPP4. In this regard, three phytocompounds (1S-α-pinene, β-pinene, and dehydro-p-cymene) from O. tenuiflorum have been discovered as the potential inhibitors of the DPP4 protein. To summarize, from our in-silico experiment outcomes, we propose dehydro-p-cymene as the potential lead inhibitor of DPP4 protein, thereby discovering new a phytocompound for the effective management of hyperglycemia and diabetes mellitus. The reported compound can be taken for in vitro and in vivo analyses in near future. [ABSTRACT FROM AUTHOR]

Introduction: Monoterpenes, a subset of the terpene family composed of two isoprene units, have garnered significant attention in research circles owing to their potential medicinal benefits. Recent experimental studies indicate that they might exert positive effects on bone health. Nevertheless, the impact of monoterpenes exposure on bone health remains unexplored in humans., Methods: We examined 748 adults (age ≥ 40 years) from the National Health and Nutrition Examination Survey (NHANES) 2013-2014 to explore the correlation between three monoterpenes (α-pinene, β-pinene, and limonene), bone mineral density (BMD) in the total lumbar spine and proximal femur, FRAX ® scores, and prior bone fracture history., Results and Discussion: Our analysis unveiled a significant inverse association between a one-unit increase in the natural logarithm (ln) of α-pinene and limonene and total proximal femur BMD (ß = -0.027, S.E. = 0.008, P = 0.004 and ß = -0.019, S.E. = 0.007, P = 0.016, respectively). As serum α-pinene levels ascended across quintiles, there was a notable decrease in total proximal femur BMD ( P for trend = 0.025). The inverse relationship between ln α-pinene levels and total proximal femur BMD was more pronounced in women, especially pre-menopausal women. Compared to subjects with α-pinene and limonene levels at or below the 50 th percentiles, those exceeding this threshold exhibited the lowest mean value of total proximal femur BMD (0.8628 g/cm2, S.E. = 0.026, P = 0.009). However, the trend was not statistically significant ( P = 0.070). Additionally, all three monoterpenes were linked to a higher prevalence of previous spine fractures, whereas β-pinene showed a reduced incidence of other types of fractures. In this comprehensive survey of American adults aged 40 and above, higher serum levels of α-pinene and limonene correlated with decreased total proximal femur BMD. Furthermore, our findings suggest a potential combined effect of α-pinene and limonene on total proximal femur BMD. Further investigation is essential to elucidate the clinical relevance and causative nature of our findings., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2024 Fang, Wang and Lin.)

Aiming to valorise the Atlantic Rainforest biodiversity in Santa Catarina, the chemical characterisation of the essential oils (EOs) from leaves of Vernonanthura montevidensis (Spreng.) H. Rob. is described for the first time. Fresh leaves collected in the year 2014 and 2015, were submitted to hydrodistillation to give pale blue EOs in yields of 0.21 and 0.19%, respectively. The EOs were characterised by GC-MS and GC-FID semi- and quantitative methods. The monoterpene β-pinene was the major constituent in both samples reaching a maximum of 26.3%. The monoterpene α-pinene and the sesquiterpene β-caryophyllene, were also among the major constituents in both samples. By means of the extracted ion chromatogram procedure, it was possible to detect chamazulene, which was associated with the pale blue colour of the essential oils. In the in vitro antimollicute assays, the essential oil was moderately active against Mycoplasma genitalium and M. pneumoniae with MIC values of 250 µg mL−1. [ABSTRACT FROM AUTHOR]

Introduction: Streptococcus mutans has been known to play a major role in dental caries development. This tooth decay is the most common oral disease affecting people in the world. Hence, discovering the new herbal antibacterial agent seems to become more promising yet challenging. One of natural antibacterial source is the peel of Citrus aurantifolia, as it may contain antibacterial active compounds against pathogenic oral microbes. This study was aimed to isolate antibacterial compound from essential oil of Citrus aurantifolia and to analyse its antibacterial activity against oral Streptococcus mutans ATCC 25175. Methods: Type of research was laboratory experimental. The essential oil was isolated from peel of Citrus aurantifolia by hydro-distillation technique and further isolation of antibacterial compounds was conducted by combination column chromatography using organic solvent, and the structure was determined by UV-Vis, infrared (IR), 1D NMR of 1H-, 13C-NMR and DEPT 135° in CDCl3 spectrometers methods. The antibacterial activity was tested against Streptococcus mutans ATCC 25175 using the Kirby-Bauer method. Results: 0.75% yield was obtained from the essential oil of peel Citrus aurantifolia and after purification, an antibacterial compound was identified as β-pinene with the molecular formula C10H16. Furthermore, the β-pinene from peel of Citrus aurantifolia exerted inhibition growth against Streptococcus mutans at concentration of 2000, 1000, and 500 ppm by showing respectively, inhibition values of 13.0, 11.9, and 11.6 mm on paper disk. Conclusion: In the present study, the essential oil of Citrus aurantifolia peel is proven to contain prospective antibacterial compound (β-pinene) that potentially can be used as natural antibacterial alternative choice to manage oral disease associated with Streptococcus mutans infection.

Polymers based on renewable monomers are projected to have a significant role in the sustainable economy, even in the near future. Undoubtedly, the cationically polymerizable β-pinene, available in considerable quantities, is one of the most promising bio-based monomers for such purposes. In the course of our systematic investigations related to the catalytic activity of TiCl4 on the cationic polymerization of this natural olefin, it was found that the 2-chloro-2,4,4-trimethylpentane (TMPCl)/TiCl4/N,N,N′,N′-tetramethylethylenediamine (TMEDA) initiating system induced efficient polymerization in dichloromethane (DCM)/hexane (Hx) mixture at both −78 °C and room temperature. At −78 °C, 100% monomer conversion was observed within 40 min, resulting in poly(β-pinene) with relatively high Mn (5500 g/mol). The molecular weight distributions (MWD) were uniformly shifted towards higher molecular weights (MW) in these polymerizations as long as monomer was present in the reaction mixture. However, chain–chain coupling took place after reaching 100% conversion, i.e., under monomer-starved conditions, resulting in considerable molecular weight increase and MWD broadening at −78 °C. At room temperature, the polymerization rate was lower, but chain coupling did not occur. The addition of a second feed of monomer in the polymerization system led to increasing conversion and polymers with higher MWs at both temperatures. 1H NMR spectra of the formed polymers indicated high in-chain double-bond contents. To overcome the polarity decrease by raising the temperature, polymerizations were also carried out in pure DCM at room temperature and at −20 °C. In both cases, rapid polymerization occurred with nearly quantitative yields, leading to poly(β-pinene)s with Mns in the range of 2000 g/mol. Strikingly, polymerization by TiCl4 alone, i.e., without any additive, also occurred with near complete conversion at room temperature within a few minutes, attributed to initiation by adventitious protic impurities. These results convincingly prove that highly efficient carbocationic polymerization of the renewable β-pinene can be accomplished with TiCl4 as catalyst under both cryogenic conditions, applied widely for carbocationic polymerizations, and the environmentally benign, energy-saving room temperature, i.e., without any additive and cooling or heating. These findings enable TiCl4-catalyzed eco-friendly manufacturing of poly(β-pinene)s, which can be utilized in various applications, and in addition, subsequent derivatizations could result in a range of high-added-value products.

The essential oils (EOs) of Guatteria schomburgkiana (Gsch) and Xylopia frutescens (Xfru) (Annonaceae) were obtained by hydrodistillation, and their chemical composition was evaluated by gas chromatography-mass spectrometry (GC/MS). Herbicide activity was measured by analyzing the seed germination percentage and root and hypocotyl elongation of two invasive species: Mimosa pudica and Senna obtusifolia. The highest yield was obtained for the EO of Xfru (1.06%). The chemical composition of Gsch was characterized by the presence of the oxygenated sesquiterpenes spathulenol (22.40%) and caryophyllene oxide (14.70%). Regarding the EO of Xfru, the hydrocarbon monoterpenes α-pinene (35.73%) and β-pinene (18.90%) were the components identified with the highest concentrations. The germination of seeds of S. obtusifolia (13.33 ± 5.77%) showed higher resistance than that of seeds of M. pudica (86.67 ± 5.77%). S. obtusifolia was also more sensitive to the EO of Xfru in terms of radicle (55.22 ± 2.72%) and hypocotyl (71.12 ± 3.80%) elongation, while M. pudica showed greater sensitivity to the EO of Gsch. To screen the herbicidal activity, the molecular docking study of the major and potent compounds was performed against 4-hydroxyphenylpyruvate dioxygenase (HPPD) protein. Results showed good binding affinities and attributed the strongest inhibitory activity to δ-cadinene for the target protein. This work contributes to the study of the herbicidal properties of the EOs of species of Annonaceae from the Amazon region.

Essential oils are volatile oil-like liquids with a characteristic strong smell and taste. They are formed in plants and are then extracted. Essential oils have extremely strong physiological and pharmacological properties, which are used in the medicine, cosmetics, and food industries. In this study, the molecules caryophyllene oxide, β-pinene, 1,8-cineol, α-cubebene, and β-caryophyllene, which are the molecules with the highest contents in the essential oil of the plant mentioned in the title, were selected and theoretical calculations describing their interactions with water were performed. Because oil–water mixtures are very important in biology and industry and are ubiquitous in nature, quantum chemical calculations for binary mixtures of water with caryophyllene oxide, β-pinene, 1,8-cineol, α-cubebene, and β-caryophyllene were performed using the density functional theory (DFT)/B3LYP method with a basis of 6–31 G (d, p). Molecular structures, HOMO–LUMO energies, electronic properties, reactivity (ELF, LOL, and Fukui), and NCI-RDG and molecular electrostatic potential (MEP) on surfaces of the main components of Phlomis bruguieri Desf. essential oil were calculated and described.

Terpenes constitute a major part of secondary metabolites secreted by plants in the rhizosphere. However, their specific functions in fungal–plant interactions have not been investigated thoroughly. In this study we investigated the role of monoterpenes in interactions between oilseed rape (Brassica napus) and the soilborne pathogen Verticillium longisporum. We identified seven monoterpenes produced by B. napus, and production of α‐pinene, β‐pinene, 3‐carene, and camphene was significantly increased upon fungal infection. Among them, β‐pinene was chosen for further analysis. Transcriptome analysis of V. longisporum on exposure to β‐pinene resulted in identification of two highly expressed pleotropic drug transporters paralog genes named VlAbcG1a and VlAbcG1b. Overexpression of VlAbcG1a in Saccharomyces cerevisiae increased tolerance to β‐pinene, while deletion of the VlAbcG1a homologous gene in Verticillium dahliae resulted in mutants with increased sensitivity to certain monoterpenes. Furthermore, the VlAbcG1a overexpression strain displayed an increased tolerance to β‐pinene and increased virulence in tomato plants. Data from this study give new insights into the roles of terpenes in plant–fungal pathogen interactions and the mechanisms fungi deploy to cope with the toxicity of these secondary metabolites. [ABSTRACT FROM AUTHOR]