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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2024 · IF 3.8

Vapor–Liquid Equilibrium of Monoterpene-Sesquiterpene System Containing Resin Acid

Shufen Wang,Jinrou Wei,Hongzhao Xie,Xiaopeng Chen,Jie zhen Liang,Xiaojie Wei,Jie Huang,Linlin Wang

The phase equilibrium relationships of resin systems are indispensable for resin tapping, distillation, and investigating the release of terpenes in biogenic volatile organic compounds (BVOCs). Herein, we obtained the vapor–liquid equilibrium (VLE) data of monoterpene-sesquiterpene systems that contain resin acid by a headspace gas chromatography (HS-GC). There is no azeotropic behavior between terpenes, and abietic acid was found to inhibit the volatilization and separation of terpenes. Furthermore, the saturated vapor pressure of the systems almost triples when the experimental temperature increases from 313.15 to 333.15 K, which may exacerbate terpene emissions in ecosystems. Additionally, the thermodynamic consistency of the VLE values was confirmed by van Ness test, and the experimental data were correlated using NRTL, UNIQUAC, and Wilson activity coefficient models, while the Conductor-like Screening Model for Real Solvents (COSMO-RS) model was utilized for predictions. All of the data satisfy thermodynamic consistency, and the correlation results and prediction results demonstrate good adherence of the activity coefficient models to experimental values and the positive capacity of COSMO-RS in predicting the VLE relationship for the pine resin systems, respectively.

CAS / MDL: 80-56-8 475-20-7
研究领域: 生态学 · 化学工程 · 植物学
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Journal of Essential Oil Bearing Plants · 2019 · IF 0.688

Chemical Composition of Leaf Essential Oil of Cinnamomum porrectum (Roxb.) Kosterm

Fengying Qiu,Haikuan Yang,Ting Zhang,Xindong Wang,Shifang Wen,Xiaohua Su

Cinnamomum porrectum (Roxb.) Kosterm is an important plant which produces natural essential oil. In this study, essential oil was hydro-distilled from leaves of five different samples of C. porrectum which were randomly selected in a C. porrectum forest in Guangdong Province of China, and identified by Gas Chromatography Mass Spectrometry (GC/MS). The results revealed that the average yield of essential oil was 1.12 % (v/w). A total of 65 compounds were identified from five samples, and 31 of which were reported for the first time in leaf essential oil of C. porrectum. High contents of monoterpenes and sesquiterpenes were found in the leaves of C. porrectum. The main components of essential oil were linalool (79.4 %), elemol (38.1 %), eucalyptol (35.6 %), β-caryophyllene (34.6 %), camphor (33.2 %), α-eudesmol (26.5 %), citral (23.5 %) and L-α- Terpineol (22.0 %). Different types of high-value compounds were found to be present in the five selected samples of C. porrectum oil, and the difference of essential oil components in individual leaves was remarkable. The various breeding techniques can be utilization based on different chemical types of leaf essential oil to exploit the plant to its full potential.

研究领域: 植物学 · 化学生态学 · 药用植物研究
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MOLECULES · 2020 ·Vol. 25 ·期 14 ·3302 · IF 3.267

Silage Fermentation: A Potential Biological Approach for the Long-Term Preservation and Recycling of Polyphenols and Terpenes in Globe Artichoke (Cynara scolymus L.) By-Products

Zhuoyan Fan,Kai Chen,Lingyin Ban,Yu Mao,Caiyun Hou,Jingming Li

An economic and effective method for storage is necessary to make full use of the nature of active components in artichoke by-products and ease environmental pressure. In this paper, the potential of silage fermentation for the preservation and recycling of polyphenols and terpenes in artichoke by-products is evaluated. The silage of artichoke by-products is characterized by lactic acid bacteria fermentation. Silage distinctly increases the abundance of lactic acid bacteria in artichoke by-products, such asLactobacillus,Lactococcus,Serratia, andWeissella, and greatly increases the abundance ofFirmicutes. The improvement of the microorgan structure and composition is of great significance for the quality of artichoke by-products. Polyphenols in the stems and leaves of artichokes are preserved well in silage. Among the 18 polyphenol compounds detected by high performance liquid chromatography coupled with triple quadrupole tandem mass spectrometry (HPLC-QqQ-MS/MS), the contents of 11 phenolic acids and four flavonoids increased significantly. For terpenes detected by gas chromatography-mass spectrometry (GC-MS), the contents of four pentacyclic triterpenoids increased significantly, while two sterols were kept stable in the silage process. Silage is a potential biotechnology for the long-term preservation of bioactive components, such as polyphenols and terpenes in artichoke by-products, and the results provide a scientific basis for the efficient utilization of by-products.Keywords:globe artichoke by-product;silage;polyphenol;terpene;lactic acid bacteria

CAS / MDL: 544-76-3
研究领域: 植物学 · 食品科学 · 微生物学
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TREES-STRUCTURE AND FUNCTION · 2021 ·Vol. 36 ·期 2 ·711-721 · IF 2.529

Monoterpene emissions and their protection effects on adult Cinnamomum camphora against high temperature

Xu Chenyi,Ma Yuandan,Tian Zhengfeng,Luo Qingyun,Zheng Tiefeng,Wang Bin,Zuo Zhaojiang

Key message The four chemotypes of adult C. camphora released different monoterpenes which protected these plants against high temperature by lowering ROS levels and maintaining photosynthetic abilities. Abstract High temperature seriously impacts plant growth and development, and terpenes are believed to improve plant thermotolerance through indoor experiments using seedlings. To uncover the actual protection effects of monoterpenes on outdoor adult plants, we investigated the monoterpene emissions, reactive oxygen species (ROS) metabolism, and photosynthetic abilities in four chemotypes of adult Cinnamomum camphora that were blocked monoterpene synthesis by fosmidomycin (Fos) under high temperature in summer (the mean highest temperature at about 38.2 °C). Eucalyptol (EuL), linalool (Lnl), borneol (BeL), and camphor (CmR) chemotypes of C. camphora released an abundance of monoterpenes, with eucalyptol, linalool, endo-borneol, and camphor as the typical monoterpene, respectively. When the four chemotypes of C. camphora were treated with Fos, their monoterpene emission was inhibited remarkably, with disappearance of some monoterpenes. In that case, the content of O 2 − , H 2 O 2 , and thiobarbituric acid reactive substance (TBARS) in the four chemotypes of C. camphora significantly increased although antioxidant enzyme activities remarkably increased, and the photosynthetic abilities significantly decreased by declining the quantum production and electron transport in photosystem II and increasing the dissipation of absorbed light energy. Among the four chemotypes, monoterpenes might play the maximum roles in CmR lowering ROS levels and in EuL maintaining photosynthesis. It can be speculated that monoterpenes can protect adult C. camphora against high temperature by lowering ROS levels and maintaining photosynthetic abilities.

研究领域: 植物生理学 · 环境科学
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Parasites & Vectors · 2021 ·Vol. 14 ·期 1 ·1-6 · IF 3.876

Activity of terpenes derived from essential oils against Sarcoptes scabiei eggs

Li Meilin,Liu Shunlong,Yin Zhijuan,Bernigaud Charlotte,Guillot Jacques,Fang Fang

Background The limited ovicidal activity of currently available acaricides is a significant obstacle to efficacious scabies treatment. Several essential oils or their respective components have proved to be active against the eggs of arthropods, mainly lice and ticks. Information on the activity of these oils and/or components against the eggs of mites remains very limited. The aim of this study was to assess the activity of six terpenes (carvacrol, eugenol, geraniol, citral, terpinen-4-ol and linalool) commonly found in essential oils against the eggs of Sarcoptes scabiei . Methods Sarcoptes eggs were exposed to paraffin oil containing 1, 2.5, or 5% of each terpene tested. After a 12-h exposure period, the eggs were washed and placed in paraffin oil for hatching. Embryonic development following treatment was assessed every day to determine the stage of developmental arrest. Results The median effective concentration to obtain 50% egg mortality (EC 50 ) was 0.5, 0.9, 2.0, 4.8, 5.1 and 9.8% for carvacrol, eugenol, geraniol, citral, terpinen-4-ol and linalool, respectively. The microscopic images of eggs after each treatment indicated that these six terpenes may act by penetrating through the aeropyles on the egg surface. Conclusions In conclusion, carvacrol, eugenol and geraniol possess significant ovicidal activities, which should be considered as promising ovicidal agents for the treatment of scabies. Graphical Abstract

CAS / MDL: 120-51-4 8012-95-1
研究领域: 寄生虫学 · 皮肤病学 · 药理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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SEPARATION AND PURIFICATION TECHNOLOGY · 2025 · IF 9

Purification of crude tea tree oil through enrichment of terpinen-4-ol by in-situ formation of deep eutectic solvent

Lijiao Yu,Lihong Deng,Jieyu Wu,Subhan Mahmood,Ke Yuan,Haoran Wu,Xiaodong Wang,Jing Zhang,Shun Yao

As a key component in tea tree oil (TTO), terpinen-4-ol exhibits ideal physiological activities. However, the high content of terpenes in crude TTO makes it challenging to enrich terpineol-4-ol. In this study, molecular simulations combined with experimental methods were used to select the optimal hydrogen bond acceptor (HBA), tetrabutylammonium chloride (TBAC), which forms a deep eutectic solvent (DES) with terpinen-4-ol in situ. Combined with necessary post-treatment process, it provided a feasible way for purification of TTO. Related DESs were prepared and characterized, and their main properties were also investigated. When the amount of TBAC was three times that of terpinen-4-ol, the formation of hydrogen bonds became more pronounced. At this point, the DES achieved its highest distribution coefficient for terpinen-4-ol (D t  = 15.02), as well as superior selectivity for terpinen-4-ol (S t/c  = 24.59, S t/γ  = 57.69). Water as the back-extractant and n-hexane as the auxiliary extractant facilitated the deep purification of terpinen-4-ol. Response surface analysis and experimental results confirmed that the optimal enrichment conditions were 30 min of enrichment time, an enrichment temperature of 60℃, and 0.5 g/g of n-hexane dosage. The back-enrichment and recovery of TBAC also proved to be satisfactory, and when applied to real tea oil, the developed method achieved over 90 % enrichment efficiency for terpinen-4-ol.

研究领域: 化学工程 · 植物化学
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PLANT CELL AND ENVIRONMENT · 2024 · IF 6

Linalool and 1,8-Cineole as Constitutive Disease-Resistant Factors of Norway Spruce Against Necrotrophic Pathogen Heterobasidion Parviporum

Kai Wang,Wenzi Ren,Liang Hong,Qingao Wang,Rajendra Ghimire,Matti Haapanen,Minna Kivimäenpää,Pengfei Wu,Xiangqing Ma,Fred O. Asiegbu

Norway spruce is an important coniferous species in boreal forests. Root and stem rot diseases caused by the necrotrophic pathogen Heterobasidion parviporum threaten the wood production of Norway spruce which necessitates the search for durable control and management strategies. Breeding for resistant traits is considered a viable long-term strategy. However, identification of potential resistant traits and markers remains a major challenge. In this study, short-term disease resistance screening was conducted using 218 Norway spruce clones from 17 families. Disease resistance was evaluated based on the size of necrosis lesion length following infection with the pathogen. A subset of needles/branches from clones with small (partial resistant) or large (susceptible) lesions were used for terpene analysis and transcriptomic profiling. The results revealed that the content of monoterpene linalool and 1,8-cineole and their respective encoded genes were significantly more abundant and highly expressed in the partial resistant group. Furthermore, linalool and 1,8-cineole were demonstrated to have inhibitory effect on the growth of the pathogen H. parviporum , with morphological distortion of the hyphae. RNAseq analysis revealed that transcript of pathogen genes involved in the regulation of carbohydrate metabolism and stress responses were significantly decreased in presence of the terpenes. The results suggest the relevance of monoterpenes together with jasmonic acid precursor and some genes involved in phenylpropanoid biosynthesis, as constitutive tolerance factors for Norway spruce tolerance against necrotrophic pathogen. The high level of necrosis related cell death gene expression might be factors critical for host susceptibility and disease development.

CAS / MDL: 78-70-6
研究领域: 植物学 · 分子生物学 · 林学
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Journal of Environmental Sciences · 2024 · IF 5.9

Comparative studies of the NOx impacts on the photooxidation mechanisms of isomeric monoterpenes of β-pinene and limonene

Yingqi Zhao,Zhaoyan Zhang,Ya Zhao,Chong Wang,Hua Xie,Jiayue Yang,Weiqing Zhang,Guorong Wu,Gang Li,Ling Jiang,Xueming Yang

It is highly challenging to precisely compare the impacts of anthropogenic pollutants on the photooxidation of isomeric volatile organic compounds with respect to molecular compositions and particle number/mass concentrations of secondary organic aerosols (SOAs). In this study, we conducted a series of well-defined indoor chamber experiments to compare the effects of NO x (NO and NO 2 ) on the photooxidation of isomeric monoterpenes of β -pinene and limonene. For the photooxidation of β -pinene with NO x , the increase of the initial concentrations of NO ([NO] 0 ) shows a monotonous suppression of the particle mass concentration, whereas the increase of [NO 2 ] 0 shows a monotonous enhancement of the particle mass concentration. For the photooxidation of limonene with NO x , the increase of [NO] 0 exhibits a monotonous suppression of the particle mass concentration, whereas the increase of [NO 2 ] 0 shows a parabolic trend of the particle mass concentration. Utilizing a newly developed vacuum ultraviolet free electron laser (VUV-FEL), the online threshold photoionization mass spectrometry reveals a series of novel compounds at molecular weight (MW) = 232 and 306 for the β -pinene + NO x system and MW = 187, 261, 280, and 306 for the limonene + NO x system. The molecular structures and formation pathways of these species were inferred, which led to the prediction of the diversity and difference of SOA products (i.e., ester and peroxide accretion products) formed from different monoterpene precursors. To improve the predictions of future air quality, it is recommended that climate models should incorporate the NO x -driven diurnal photooxidation of monoterpenes for SOA formation mechanisms.

研究领域: 大气化学 · 环境科学
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ADSORPTION SCIENCE & TECHNOLOGY · 2021 · IF 4.232

Influence of Terpenic Oil on Flotation Behavior of Sphalerite and Implication for the Selective Separation

Bo Yang,Xian Xie,Xiong Tong,Lingyun Huang

Terpenic oil (TO) is commonly used as a flotation frother for the selective separation of sulfide minerals. As a frother, most reports have mainly focused on its effect on froth stability and froth entrainment, whereas its influence on the floatability of sulfide minerals has received little attention. In this work, the influence of TO on the flotation behavior of sphalerite was investigated by using microflotation tests, contact angle and zeta potential measurements, and FT-IR and SEM-EDS analyses. Microflotation tests conducted in a modified Hallimond tube indicated that compared with the collector potassium butyl xanthate (KBX), the flotation recovery of sphalerite was significantly increased when TO was added to the pulp, but the recovery of Cu-activated sphalerite with the addition of TO was lower than that with the addition of KBX. Contact angle measurements demonstrated that the contact angle of sphalerite was distinctly increased by the addition of TO, but the contact angle of sphalerite treated with TO was lower than that treated with KBX after Cu activation. Zeta potential measurements demonstrated that the zeta potential of sphalerite particles was slightly decreased when treated with TO, and the isoelectric point (IEP) was decreased from 3.3 to 3.1 due to the interaction of TO with sphalerite particles. FT-IR and SEM-EDS confirmed that TO could be adsorbed on the sphalerite surface on the formation of the oil film due to its low solubility, thereby increasing the surface hydrophobicity of the sphalerite. In addition, the TO absorbed on the surface acts as a bridging role and promotes the hydrophobic agglomeration of sphalerite particles. These results suggest that except for froth entrainment, the influence of TO on the flotation behavior of sphalerite may be another reason for the misreporting of sphalerite in concentrates.

研究领域: 矿物加工工程 · 材料科学与工程
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INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES · 2023 ·Vol. 24 ·期 8 ·7320 · IF 5.6

Creation of New Oregano Genotypes with Different Terpene Chemotypes via Inter- and Intraspecific Hybridization

Meiyu Sun,Ningning Liu,Jiahui Miao,Yanan Zhang,Yuanpeng Hao,Jinzheng Zhang,Hui Li,Hongtong Bai,Lei Shi

Oregano is a medicinal and aromatic plant of value in the pharmaceutical, food, feed additive, and cosmetic industries. Oregano breeding is still in its infancy compared with traditional crops. In this study, we evaluated the phenotypes of 12 oregano genotypes and generated F1progenies by hybridization. The density of leaf glandular secretory trichomes and the essential oil yield in the 12 oregano genotypes varied from 97–1017 per cm2and 0.17–1.67%, respectively. These genotypes were divided into four terpene chemotypes: carvacrol-, thymol-, germacrene D/β-caryophyllene-, and linalool/β-ocimene-type. Based on phenotypic data and considering terpene chemotypes as the main breeding goal, six oregano hybrid combinations were performed. Simple sequence repeat (SSR) markers were developed based on unpublished whole-genome sequencing data ofOriganum vulgare, and 64 codominant SSR primers were screened on the parents of the six oregano combinations. These codominant primers were used to determine the authenticity of 40 F1lines, and 37 true hybrids were identified. These 37 F1lines were divided into six terpene chemotypes: sabinene-, β-ocimene-, γ-terpinene-, thymol-, carvacrol-, andp-cymene-type, four of which (sabinene-, β-ocimene-, γ-terpinene-, andp-cymene-type) were novel (i.e., different from the chemotypes of parents). The terpene contents of 18 of the 37 F1lines were higher than those of their parents. The above results lay a strong foundation for the creating of new germplasm resources, constructing of genetic linkage map, and mapping quantitative trait loci (QTLs) of key horticultural traits, and provide insights into the mechanism of terpenoid biosynthesis in oregano.Keywords:oregano;essential oil;terpene chemotypes;hybrid;F1lines;SSR molecular marker

研究领域: 植物学 · 遗传学 · 药用植物学
✓ 已验证 DOI PubMed 高影响因子
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NEW JOURNAL OF CHEMISTRY · 2024 ·Vol. 48 ·期 10 ·4580-4588 · IF 2.7

Polymerization of α-pinene catalyzed by Lewis acidic deep eutectic solvents

Ningning Ji,Fengli Yu,Bing Yuan,Congxia Xie,Shitao Yu

A series of low-cost Lewis acidic deep eutectic solvents (DESs) was synthesized and applied for the first time for catalyzing the polymerization of α-pinene to produce terpene resins. The DES catalyst of [AlCl3]3[CPL] prepared via the self-assembly of AlCl3 and caprolactam (CPL) exhibited the highest catalytic activity, and polymerization conditions were optimized by a single-factor method: 15 g α-pinene, 3 g catalyst, 1 g initiator, −5 °C reaction temperature, and 4 h reaction time. Under these conditions, the softening point of the terpene resin reached (annular spheroid method) 118.3 °C, the acid value was 0.22 mg KOH g−1, and the depth of color (Fe–Co method) was 5. The structure of [AlCl3]3[CPL] was characterized using FT-IR, 1H-NMR, and UV-vis spectroscopy. GPC measure showed that the number-average molecular weight of the terpene resin was 510, the weight-average molecular weight was 776, and the polydispersity index was 1.523. TG results indicated that the terpene resin had favorable thermal stability. After the reaction, the product and the catalyst could be automatically divided into two phases, which was beneficial for recycling the catalyst. The results revealed that [AlCl3]3[CPL] exhibited good recyclability.

CAS / MDL: 60-35-5
研究领域: 化学工程 · 材料科学
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2024 · IF 3.8

Experimental and Molecular Insights into Efficient Deterpenation of Essential Oil Intensified by Extraction with Deep Eutectic Solvent

Lexuan Zhao,Hongye Cheng,Zhiwen Qi

Deep eutectic solvents (DESs) have been widely utilized to intensify separations by adjusting their structures and properties, particularly in extractive deterpenation of essential oils as green alternatives to conventional organic solvents. In this work, experimental and molecular insights into efficient deterpenation intensified by a DES containing tetrabutylammonium bromide (TBAB) and levulinic acid (LEA) were investigated with citral extraction from lemon essential oil as a case study. DES formation and preferred liquid operating window were determined through solid–liquid equilibrium; an excellent extraction performance was observed at varying citral concentrations via liquid–liquid equilibria. Extraction process was simulated with a well-correlated nonrandom two-liquid model, and a 7-fold concentration of terpenoids was achieved under optimal conditions. Fourier transform infrared spectra and molecular dynamics simulations elucidated the DES formation and extraction mechanisms. Hydrogen-bonding interactions primarily mediated by −COOH group of LEA and Br– anion of TBAB resulted in lower freezing points of DES, thereby enhancing extraction performance. The results provide valuable insights into the practical applications of DESs in separating structurally similar natural products.

CAS / MDL: 1643-19-2 629-50-5
研究领域: 化学工程 · 天然产物分离
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