alpha-Terpineol (BioDeep_00000007671)

 

Secondary id: BioDeep_00000265659, BioDeep_00000396317, BioDeep_00000396759, BioDeep_00000405580, BioDeep_00000638371, BioDeep_00000858371

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2-(4-Methylcyclohex-3-enyl)propan-2-ol (alpha-terpineol)

化学式: C10H18O (154.1357578)
中文名称: (+)-α-松油醇, α-萜品醇, 松脂醇, alpha-松油醇
谱图信息: 最多检出来源 Homo sapiens(feces) 0.16%

分子结构信息

SMILES: C1C(=CC[C@H](C1)C(O)(C)C)C
InChI: InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3

描述信息

alpha-Terpineol (CAS: 98-55-5) is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers of terpineol, alpha-, beta-, and gamma-terpineol, with the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. Terpineol has a pleasant odour similar to lilac and is a common ingredient in perfumes, cosmetics, and flavours. alpha-Terpineol is occasionally found as a volatile component in urine. It is a water-soluble component of Melaleuca alternifolia Cheel, the tea tree oil (TTO). alpha-Terpineol is a likely mediator of the in vitro and in vivo activity of the TTO as an agent that could control C. albicans vaginal infections. Purified alpha-terpineol can suppress pro-inflammatory mediator production by activated human monocytes. alpha-Terpineol is able to impair the growth of human M14 melanoma cells and appear to be more effective on their resistant variants, which express high levels of P-glycoprotein in the plasma membrane, overcoming resistance to caspase-dependent apoptosis exerted by P-glycoprotein-positive tumour cells (PMID:5556886, 17083732, 11131302, 15009716).
Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. (R)-alpha-Terpineol is found in many foods, some of which are mentha (mint), sweet marjoram, lovage, and cardamom.
α-Terpineol is isolated from Eucalyptus globulus Labill, exhibits strong antimicrobial activity against periodontopathic and cariogenic bacteria[1]. α-Terpineol possesses antifungal activity against T. mentagrophytes, and the activity might lead to irreversible cellular disruption[2].
α-Terpineol is isolated from Eucalyptus globulus Labill, exhibits strong antimicrobial activity against periodontopathic and cariogenic bacteria[1]. α-Terpineol possesses antifungal activity against T. mentagrophytes, and the activity might lead to irreversible cellular disruption[2].

同义名列表

43 个代谢物同义名

2-(4-Methylcyclohex-3-enyl)propan-2-ol (alpha-terpineol); (1R)-alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanol; (R)-alpha,alpha,4-Trimethylcyclohex-3-ene-1-methanol; alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanol; 2-[(1R)-4-Methylcyclohex-3-en-1-yl]propan-2-ol; (1R)-Α,α,4-trimethyl-3-cyclohexene-1-methanol; (1R)-a,a,4-trimethyl-3-cyclohexene-1-methanol; (R)-Α,α,4-trimethylcyclohex-3-ene-1-methanol; (R)-a,a,4-Trimethylcyclohex-3-ene-1-methanol; (R)-2-(4-Methyl-3-cyclohexenyl)isopropanol; 2-(4-Methyl-3-cyclohexen-1-yl)-2-propanol; 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol; alpha-terpineol, sodium salt; (R)-(+)-α-Terpineol; (S)-(-)-p-menth-1-en-8-ol; (R)-(+)-alpha-Terpineol; (6R)-P-Menth-1-en-8-ol; (+)-p-Menth-1-en-8-ol; (R)-P-Menth-1-en-8-ol; Terpineol schlechthin; (+)-alpha-terpineol; (R)-alpha-Terpineol; DL-alpha-terpineol; p-menth-1-en-8-ol; D-alpha-terpineol; L-alpha-TERPINEOL; 1-alpha-terpineol; alpha-Terpineole; alpha-Terpinenol; (+)-Α-terpineol; alpha-terpineol; (+)-a-Terpineol; (R)-a-Terpineol; (S)-Α-terpineol; (S)-a-Terpineol; (R)-Α-terpineol; alpha-Terpinol; Lily OF valley; α-Terpineol; a-Terpineol; TERPINEOLS; Terpineol; Terpenol



数据库引用编号

30 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

PharmGKB(0)

589 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • M Shiraiwa, T Fang, J Wei, Psj Lakey, Bch Hwang, K C Edwards, S Kapur, Jem Mena, Y-K Huang, M A Digman, S A Weichenthal, S Nizkorodov, M T Kleinman. Chemical and Cellular Formation of Reactive Oxygen Species from Secondary Organic Aerosols in Epithelial Lining Fluid. Research report (Health Effects Institute). 2023 Dec; ?(215):1-56. doi: ". [PMID: 38420854]
  • Wenhui Zeng, Tong Chen, Yong Chen, Xun Yan, Wenjing Wu, Shijun Zhang, Zhiqiang Li. α-Terpineol affects social immunity, increasing the pathogenicity of entomopathogenic nematodes to subterranean termites (Isoptera). Pesticide biochemistry and physiology. 2023 Nov; 196(?):105621. doi: 10.1016/j.pestbp.2023.105621. [PMID: 37945257]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Xiujuan Pan, He Xiao, Xinping Hu, Zhi Long Liu. Insecticidal activities of the essential oil of Rhynchanthus beesianus rhizomes and its constituents against two species of grain storage insects. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2023 Jan; 78(1-2):83-89. doi: 10.1515/znc-2022-0017. [PMID: 36130869]
  • Azize Demirpolat. Chemical Composition of Essential Oils of Seven Polygonum Species from Turkey: A Chemotaxonomic Approach. Molecules (Basel, Switzerland). 2022 Dec; 27(24):. doi: 10.3390/molecules27249053. [PMID: 36558187]
  • Valtcho D Zheljazkov, Giuseppe Micalizzi, Solomon Yilma, Charles L Cantrell, Amber Reichley, Luigi Mondello, Ivanka Semerdjieva, Tzenka Radoukova. Melissa officinalis L. as a Sprout Suppressor in Solanum tuberosum L. and an Alternative to Synthetic Pesticides. Journal of agricultural and food chemistry. 2022 Nov; 70(44):14205-14219. doi: 10.1021/acs.jafc.2c05942. [PMID: 36306427]
  • Majid Mohammadhosseini, Alessandro Venditti, Behnam Mahdavi, Mohammad Reza Kianasab, Reyhaneh Shirazi. Profiling of the essential oil compositions from the flowers and leaves of Tanacetum fisherae Aitch. & Hemsl., an endemic plant in Kerman province, Iran. Natural product research. 2022 Oct; 36(20):5347-5352. doi: 10.1080/14786419.2021.1924711. [PMID: 33977845]
  • Emanuel Tenório Paulino, Amanda Karine Barros Ferreira Rodrigues, Maria Luiza Dal Pont Machado, Kelly Rayane Vital de Oliveira, Alessando César Bernardino, Lucindo José Quintans-Júnior, Aldeídia Pereira Oliveira, Êurica Adélia Nogueira Ribeiro. Alpha-terpineol prevents myocardial damage against isoproterenol-MI induced in Wistar-Kyoto rats: new possible to promote cardiovascular integrity. Life sciences. 2022 Feb; 290(?):120087. doi: 10.1016/j.lfs.2021.120087. [PMID: 34740575]
  • Guodong Zheng, Yingxin Chao, Mengshi Liu, Yuhua Yang, Dedong Zhang, Kanghui Wang, Yiwen Tao, Jianye Zhang, Yongmei Li, Minyan Wei. Evaluation of dynamic changes in the bioactive components in Citri Reticulatae Pericarpium (Citrus reticulata 'Chachi') under different harvesting and drying conditions. Journal of the science of food and agriculture. 2021 Jun; 101(8):3280-3289. doi: 10.1002/jsfa.10957. [PMID: 33222189]
  • José Manuel Pineda-Ríos, Juan Cibrián-Tovar, Luis Martín Hernández-Fuentes, Rosa María López-Romero, Lauro Soto-Rojas, Jesús Romero-Nápoles, Celina Llanderal-Cázares, Luis F Salomé-Abarca. α-Terpineol: An Aggregation Pheromone in Optatus palmaris (Coleoptera: Curculionidae) (Pascoe, 1889) Enhanced by Its Host-Plant Volatiles. Molecules (Basel, Switzerland). 2021 May; 26(10):. doi: 10.3390/molecules26102861. [PMID: 34065875]
  • Sunil Kumar Bose, Karuna Sharma, Sanjay Chhibber, Kusum Harjai. Therapeutic potential of nanolipoidal α-terpineol in combating keratitis induced by Pseudomonas aeruginosa in the murine model. International journal of pharmaceutics. 2021 Feb; 594(?):120175. doi: 10.1016/j.ijpharm.2020.120175. [PMID: 33338569]
  • Any Carolina Cardoso Guimarães Vasconcelos, Daniel Fernando Pereira Vasconcelos, Felipe Rodolfo Pereira da Silva, Luiz Felipe de Carvalho França, Even Herlany Pereira Alves, David Di Lenardo, Larissa Dos Santos Pessoa, Hélio Mateus Silva Nascimento, André Dos Santos Carvalho, Francisca Beatriz de Melo Sousa, André Luiz Dos Reis Barbosa, Jand-Venes Rolim Medeiros, Pedro Duarte Novaes, Flávia Sammartino Mariano, Bruno Dos Santos Lima, Adriano Antunes de Souza Araujo, Lucindo José Quintans Júnior, Aldeídia Pereira de Oliveira. Alpha-terpineol complexed with beta-cyclodextrin reduces damages caused by periodontitis in rats. Journal of periodontal research. 2020 Dec; 55(6):877-886. doi: 10.1111/jre.12780. [PMID: 32583890]
  • Xin-Sheng Liu, Bo Gao, Xin-Lu Li, Wan-Nan Li, Zi-An Qiao, Lu Han. Chemical Composition and Antimicrobial and Antioxidant Activities of Essential Oil of Sunflower (Helianthus annuus L.) Receptacle. Molecules (Basel, Switzerland). 2020 Nov; 25(22):. doi: 10.3390/molecules25225244. [PMID: 33187052]
  • Rosa M Ojeda-Amador, Giuseppe Fregapane, María Desamparados Salvador. Influence of cultivar and technological conditions on the volatile profile of virgin pistachio oils. Food chemistry. 2020 May; 311(?):125957. doi: 10.1016/j.foodchem.2019.125957. [PMID: 31864191]
  • Nicole G H Leferink, Kara E Ranaghan, Jaime Battye, Linus O Johannissen, Sam Hay, Marc W van der Kamp, Adrian J Mulholland, Nigel S Scrutton. Taming the Reactivity of Monoterpene Synthases To Guide Regioselective Product Hydroxylation. Chembiochem : a European journal of chemical biology. 2020 04; 21(7):985-990. doi: 10.1002/cbic.201900672. [PMID: 31682055]
  • Anand Kumar Chaudhari, Vipin Kumar Singh, Abhishek Kumar Dwivedy, Somenath Das, Neha Upadhyay, Akanksha Singh, Mumtaz S Dkhar, Highland Kayang, Bhanu Prakash, Nawal Kishore Dubey. Chemically characterised Pimenta dioica (L.) Merr. essential oil as a novel plant based antimicrobial against fungal and aflatoxin B1 contamination of stored maize and its possible mode of action. Natural product research. 2020 Mar; 34(5):745-749. doi: 10.1080/14786419.2018.1499634. [PMID: 30421964]
  • Carla Maria Mariano Fernandez, Maurício Ferreira da Rosa, Ana Claudia Aparecida Mariano Fernandez, Wanessa de Campos Bortolucci, Fabiana Borges Padilha Ferreira, Giani Andrea Linde, Nelson Barros Colauto, Márcia Regina Simões, Viviane da Silva Lobo, Zilda Cristiani Gazim. Essential oil and fractions isolated of Laurel to control adults and larvae of cattle ticks. Natural product research. 2020 Mar; 34(5):731-735. doi: 10.1080/14786419.2018.1495637. [PMID: 30445842]
  • Dlzar A Kheder, Omar A M Al-Habib, Gianluca Gilardoni, Giovanni Vidari. Components of Volatile Fractions from Eucalyptus camaldulensis Leaves from Iraqi-Kurdistan and Their Potent Spasmolytic Effects. Molecules (Basel, Switzerland). 2020 Feb; 25(4):. doi: 10.3390/molecules25040804. [PMID: 32069801]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Joel Ljunggren, Felipe Borrero-Echeverry, Amrita Chakraborty, Tobias U T Lindblom, Erik Hedenström, Maria Karlsson, Peter Witzgall, Marie Bengtsson. Yeast Volatomes Differentially Affect Larval Feeding in an Insect Herbivore. Applied and environmental microbiology. 2019 11; 85(21):. doi: 10.1128/aem.01761-19. [PMID: 31444202]
  • J Tyler Ramsey, Yin Li, Yukitomo Arao, Ajanta Naidu, Laurel A Coons, Alejandro Diaz, Kenneth S Korach. Lavender Products Associated With Premature Thelarche and Prepubertal Gynecomastia: Case Reports and Endocrine-Disrupting Chemical Activities. The Journal of clinical endocrinology and metabolism. 2019 11; 104(11):5393-5405. doi: 10.1210/jc.2018-01880. [PMID: 31393563]
  • Chuanbo Zhang, Man Li, Guang-Rong Zhao, Wenyu Lu. Alpha-Terpineol production from an engineered Saccharomyces cerevisiae cell factory. Microbial cell factories. 2019 Sep; 18(1):160. doi: 10.1186/s12934-019-1211-0. [PMID: 31547812]
  • Nilufar Z Mamadalieva, Fadia S Youssef, Mohamed L Ashour, Sobirdjan A Sasmakov, Antonio Tiezzi, Shahnoz S Azimova. Chemical composition, antimicrobial and antioxidant activities of the essential oils of three Uzbek Lamiaceae species. Natural product research. 2019 Aug; 33(16):2394-2397. doi: 10.1080/14786419.2018.1443088. [PMID: 29468889]
  • Mohamed E I Badawy, Gehan I Kh Marei, Entsar I Rabea, Nehad E M Taktak. Antimicrobial and antioxidant activities of hydrocarbon and oxygenated monoterpenes against some foodborne pathogens through in vitro and in silico studies. Pesticide biochemistry and physiology. 2019 Jul; 158(?):185-200. doi: 10.1016/j.pestbp.2019.05.008. [PMID: 31378356]
  • Q Kong, L Zhang, P An, J Qi, X Yu, J Lu, X Ren. Antifungal mechanisms of α-terpineol and terpene-4-alcohol as the critical components of Melaleuca alternifolia oil in the inhibition of rot disease caused by Aspergillus ochraceus in postharvest grapes. Journal of applied microbiology. 2019 Apr; 126(4):1161-1174. doi: 10.1111/jam.14193. [PMID: 30614164]
  • Yueting Chen, Yuanyuan Weng, Min Zhou, Yiyu Meng, Jialu Liu, Lin Yang, Zhaojiang Zuo. Linalool- and α-terpineol-induced programmed cell death in Chlamydomonas reinhardtii. Ecotoxicology and environmental safety. 2019 Jan; 167(?):435-440. doi: 10.1016/j.ecoenv.2018.10.062. [PMID: 30368137]
  • Yutian Zhang, Diying Li, Zhuo Wang, Wanting Zang, Pan Rao, Yunxiang Liang, Yuxia Mei. Alpha-terpineol affects synthesis and antitumor activity of triterpenoids from Antrodia cinnamomea mycelia in solid-state culture. Food & function. 2018 Dec; 9(12):6517-6525. doi: 10.1039/c8fo02079e. [PMID: 30474680]
  • Daniel Vázquez-Sánchez, Juliana Antunes Galvão, Marina Rodrigues Mazine, Eduardo Micotti Gloria, Marília Oetterer. Control of Staphylococcus aureus biofilms by the application of single and combined treatments based in plant essential oils. International journal of food microbiology. 2018 Dec; 286(?):128-138. doi: 10.1016/j.ijfoodmicro.2018.08.007. [PMID: 30099281]
  • Silan Chen, Tiefeng Zheng, Chaolin Ye, Wulan Huannixi, Zumulati Yakefu, Yiyu Meng, Xin Peng, Zhengfeng Tian, Junhao Wang, Yuandan Ma, Youyou Yang, Zhongqing Ma, Zhaojiang Zuo. Algicidal properties of extracts from Cinnamomum camphora fresh leaves and their main compounds. Ecotoxicology and environmental safety. 2018 Nov; 163(?):594-603. doi: 10.1016/j.ecoenv.2018.07.115. [PMID: 30077157]
  • Donato Colangelo, Fabrizio Torchio, Dante Marco De Faveri, Milena Lambri. The use of chitosan as alternative to bentonite for wine fining: Effects on heat-stability, proteins, organic acids, colour, and volatile compounds in an aromatic white wine. Food chemistry. 2018 Oct; 264(?):301-309. doi: 10.1016/j.foodchem.2018.05.005. [PMID: 29853380]
  • Elena Drosopoulou, Dimitris Vlastos, Ioanna Efthimiou, Paraskevi Kyrizaki, Sofia Tsamadou, Maria Anagnostopoulou, Danai Kofidou, Maxim Gavriilidis, Despoina Mademtzoglou, Penelope Mavragani-Tsipidou. In vitro and in vivo evaluation of the genotoxic and antigenotoxic potential of the major Chios mastic water constituents. Scientific reports. 2018 08; 8(1):12200. doi: 10.1038/s41598-018-29810-y. [PMID: 30111795]
  • Negin Khomarlou, Parviz Aberoomand-Azar, Ardalan Pasdaran Lashgari, Hamid Tebyanian, Ali Hakakian, Reza Ranjbar, Seyed Abdolmajid Ayatollahi. Essential oil composition and in vitro antibacterial activity of Chenopodium album subsp. striatum. Acta biologica Hungarica. 2018 Jun; 69(2):144-155. doi: 10.1556/018.69.2018.2.4. [PMID: 29888667]
  • Giovanni Benelli, Mohan Rajeswary, Periasamy Vijayan, Sengamalai Senthilmurugan, Naiyf S Alharbi, Shine Kadaikunnan, Jamal M Khaled, Marimuthu Govindarajan. Boswellia ovalifoliolata (Burseraceae) essential oil as an eco-friendly larvicide? Toxicity against six mosquito vectors of public health importance, non-target mosquito fishes, backswimmers, and water bugs. Environmental science and pollution research international. 2018 Apr; 25(11):10264-10271. doi: 10.1007/s11356-017-8820-0. [PMID: 28332087]
  • Jiao Xie, Lili Deng, Yahan Zhou, Shixiang Yao, Kaifang Zeng. Analysis of changes in volatile constituents and expression of genes involved in terpenoid metabolism in oleocellosis peel. Food chemistry. 2018 Mar; 243(?):269-276. doi: 10.1016/j.foodchem.2017.09.142. [PMID: 29146338]
  • Wanping Zhu, Xia Liu, Yuji Wang, Yeling Tong, Yongzhou Hu. Discovery of a novel series of α-terpineol derivatives as promising anti-asthmatic agents: Their design, synthesis, and biological evaluation. European journal of medicinal chemistry. 2018 Jan; 143(?):419-425. doi: 10.1016/j.ejmech.2017.07.068. [PMID: 29202404]
  • Gulden Dogan, Nazan Kara, Eyup Bagci, Seher Gur. Chemical composition and biological activities of leaf and fruit essential oils from Eucalyptus camaldulensis. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2017 Oct; 72(11-12):483-489. doi: 10.1515/znc-2016-0033. [PMID: 28640755]
  • Wen-Wan Chao, Chia-Chi Su, Hsin-Yi Peng, Su-Tze Chou. Melaleuca quinquenervia essential oil inhibits α-melanocyte-stimulating hormone-induced melanin production and oxidative stress in B16 melanoma cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2017 Oct; 34(?):191-201. doi: 10.1016/j.phymed.2017.08.024. [PMID: 28899502]
  • Abdullah H Alluhayb, Brian A Logue. The analysis of aroma/flavor compounds in green tea using ice concentration linked with extractive stirrer. Journal of chromatography. A. 2017 Oct; 1518(?):8-14. doi: 10.1016/j.chroma.2017.08.049. [PMID: 28882342]
  • Sirajudheen Anwar, Rebecca A Crouch, Nasser A Awadh Ali, Mohamed A Al-Fatimi, William N Setzer, Ludger Wessjohann. Hierarchical cluster analysis and chemical characterisation of Myrtus communis L. essential oil from Yemen region and its antimicrobial, antioxidant and anti-colorectal adenocarcinoma properties. Natural product research. 2017 Sep; 31(18):2158-2163. doi: 10.1080/14786419.2016.1277346. [PMID: 28068844]
  • Kaoutar Aboukhalid, Chaouki Al Faiz, Ahmed Douaik, Mohamed Bakha, Karolina Kursa, Monika Agacka-Mołdoch, Nathalie Machon, Félix Tomi, Abdeslam Lamiri. Influence of Environmental Factors on Essential Oil Variability in Origanum compactum Benth. Growing Wild in Morocco. Chemistry & biodiversity. 2017 Sep; 14(9):. doi: 10.1002/cbdv.201700158. [PMID: 28556574]
  • Miao Wang, Dongyu Gu, Haoquan Li, Qi Wang, Jie Kang, Tingting Chu, Hong Guo, Yi Yang, Jing Tian. Rapid prediction and identification of lipase inhibitors in volatile oil from Pinus massoniana L. needles. Phytochemistry. 2017 Sep; 141(?):114-120. doi: 10.1016/j.phytochem.2017.06.002. [PMID: 28609696]
  • Hui Feng, Patricia A Skinkis, Michael C Qian. Pinot noir wine volatile and anthocyanin composition under different levels of vine fruit zone leaf removal. Food chemistry. 2017 Jan; 214(?):736-744. doi: 10.1016/j.foodchem.2016.07.110. [PMID: 27507532]
  • Birgit Piechulla, Richard Bartelt, Anne Brosemann, Uta Effmert, Harro Bouwmeester, Frank Hippauf, Wolfgang Brandt. The α-Terpineol to 1,8-Cineole Cyclization Reaction of Tobacco Terpene Synthases. Plant physiology. 2016 12; 172(4):2120-2131. doi: 10.1104/pp.16.01378. [PMID: 27729471]
  • Shanshan Guo, Zhufeng Geng, Wenjuan Zhang, Junyu Liang, Chengfang Wang, Zhiwei Deng, Shushan Du. The Chemical Composition of Essential Oils from Cinnamomum camphora and Their Insecticidal Activity against the Stored Product Pests. International journal of molecular sciences. 2016 Nov; 17(11):. doi: 10.3390/ijms17111836. [PMID: 27827929]
  • Xiaofeng Dong, Makiko Kashio, Guangda Peng, Xinyue Wang, Makoto Tominaga, Tatsuhiko Kadowaki. Isoform-specific modulation of the chemical sensitivity of conserved TRPA1 channel in the major honeybee ectoparasitic mite, Tropilaelaps mercedesae. Open biology. 2016 06; 6(6):. doi: 10.1098/rsob.160042. [PMID: 27307515]
  • Do N Dai, Tran D Thang, Isiaka A Ogunwande, Oladipupo A Lawal. Study on essential oils from the leaves of two Vietnamese plants: Jasminum subtriplinerve C.L. Blume and Vitex quinata (Lour) F.N. Williams. Natural product research. 2016; 30(7):860-4. doi: 10.1080/14786419.2015.1071364. [PMID: 26313766]
  • Brigitte Lukas, Corinna Schmiderer, Johannes Novak. Essential oil diversity of European Origanum vulgare L. (Lamiaceae). Phytochemistry. 2015 Nov; 119(?):32-40. doi: 10.1016/j.phytochem.2015.09.008. [PMID: 26454793]
  • Guangda Peng, Makiko Kashio, Tomomi Morimoto, Tianbang Li, Jingting Zhu, Makoto Tominaga, Tatsuhiko Kadowaki. Plant-Derived Tick Repellents Activate the Honey Bee Ectoparasitic Mite TRPA1. Cell reports. 2015 Jul; 12(2):190-202. doi: 10.1016/j.celrep.2015.06.025. [PMID: 26146083]
  • Da-Cheng Wang, Da-Ren Qiu, Li-Na Shi, Hong-Yu Pan, Ya-Wei Li, Jin-Zhu Sun, Ying-Jie Xue, Dong-Sheng Wei, Xiang Li, Ya-Mei Zhang, Jian-Chun Qin. Identification of insecticidal constituents of the essential oils of Dahlia pinnata Cav. against Sitophilus zeamais and Sitophilus oryzae. Natural product research. 2015; 29(18):1748-51. doi: 10.1080/14786419.2014.998218. [PMID: 25563135]
  • Ryota Motooka, Atsushi Usami, Hiroshi Nakahashi, Satoshi Koutari, Satoshi Nakaya, Ryoyu Shimizu, Kaoru Tsuji, Shinsuke Marumoto, Mitsuo Miyazawa. Characteristic odor components of essential oils from Eurya japonica. Journal of oleo science. 2015; 64(5):577-84. doi: 10.5650/jos.ess14225. [PMID: 25843279]
  • Mohaddese Mahboubi, Nastaran Kazempour, Atefeh Mahboubi. The efficacy of essential oils as natural preservatives in vegetable oil. Journal of dietary supplements. 2014 Dec; 11(4):334-46. doi: 10.3109/19390211.2014.887603. [PMID: 24552253]
  • Taravat Azanchi, Hamed Shafaroodi, Jinous Asgarpanah. Anticonvulsant activity of Citrus aurantium blossom essential oil (neroli): involvment of the GABAergic system. Natural product communications. 2014 Nov; 9(11):1615-8. doi: ". [PMID: 25532295]
  • Zhen-Ming Lu, Yan Geng, Hua-Xiang Li, Qing Sun, Jin-Song Shi, Zheng-Hong Xu. Alpha-terpineol promotes triterpenoid production of Antrodia cinnamomea in submerged culture. FEMS microbiology letters. 2014 Sep; 358(1):36-43. doi: 10.1111/1574-6968.12545. [PMID: 25053476]
  • M N M Nogueira, S G Aquino, C Rossa Junior, D M P Spolidorio. Terpinen-4-ol and alpha-terpineol (tea tree oil components) inhibit the production of IL-1β, IL-6 and IL-10 on human macrophages. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2014 Sep; 63(9):769-78. doi: 10.1007/s00011-014-0749-x. [PMID: 24947163]
  • Hassan Sabik, Allaoua Achouri, Maria Alfaro, Marylène Pelletier, Denis Belanger, Michel Britten, Patrick Fustier. Study of chemical stability of lemon oil components in sodium caseinate-lactose glycoconjugate-stabilized oil-in-water emulsions using solid-phase microextraction-gas chromatography. Food & function. 2014 Jul; 5(7):1495-505. doi: 10.1039/c4fo00016a. [PMID: 24832672]
  • N A Vyry Wouatsa, Laxminarain Misra, R Venkatesh Kumar. Antibacterial activity of essential oils of edible spices, Ocimum canum and Xylopia aethiopica. Journal of food science. 2014 May; 79(5):M972-7. doi: 10.1111/1750-3841.12457. [PMID: 24758511]
  • René F Ramos Alvarenga, Baojie Wan, Taichi Inui, Scott G Franzblau, Guido F Pauli, Birgit U Jaki. Airborne antituberculosis activity of Eucalyptus citriodora essential oil. Journal of natural products. 2014 Mar; 77(3):603-10. doi: 10.1021/np400872m. [PMID: 24641242]
  • Li Li, Chaofeng Shi, Zhongqiong Yin, Renyong Jia, Lianci Peng, Shuai Kang, Zhengwen Li. Antibacterial activity of α-terpineol may induce morphostructural alterations in Escherichia coli. Brazilian journal of microbiology : [publication of the Brazilian Society for Microbiology]. 2014; 45(4):1409-13. doi: 10.1590/s1517-83822014000400035. [PMID: 25763048]
  • Di Sotto Antonella, Durazzi Federico, Sarpietro Maria Grazia, Mazzanti Gabriela. Antimutagenic and antioxidant activities of some bioflavours from wine. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Oct; 60(?):141-6. doi: 10.1016/j.fct.2013.07.042. [PMID: 23891760]
  • Najia Herzi, Jalloul Bouajila, Séverine Camy, Sylvie Cazaux, Mehrez Romdhane, Jean Stéphane Condoret. Comparison between supercritical CO2 extraction and hydrodistillation for two species of eucalyptus: yield, chemical composition, and antioxidant activity. Journal of food science. 2013 May; 78(5):C667-72. doi: 10.1111/1750-3841.12113. [PMID: 23551200]
  • You-Jin Choi, Woo-Cheol Sim, Hyun Kyu Choi, Seung-Ho Lee, Byung-Hoon Lee. α-Terpineol induces fatty liver in mice mediated by the AMP-activated kinase and sterol response element binding protein pathway. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 May; 55(?):129-36. doi: 10.1016/j.fct.2012.12.025. [PMID: 23274539]
  • R Belaqziz, F Bahri, A Romane, S Antoniotti, X Fernandez, E Duñach. Essential oil composition and antibacterial activity of the different parts of Thymus maroccanus Ball: an endemic species in Morocco. Natural product research. 2013; 27(18):1700-4. doi: 10.1080/14786419.2013.768989. [PMID: 23425125]
  • Yongjian Xie, Qiuying Huang, Chaoliang Lei. Bioassay-guided isolation and identification of antitermitic active compound from the leaf of Chinese cedar (Cryptomeria fortunei Hooibrenk). Natural product research. 2013; 27(22):2137-9. doi: 10.1080/14786419.2013.778850. [PMID: 23521318]
  • Aline Augusti Boligon, Thiago Guilherme Schwanz, Mariana Piana, Rose Vanessa Bandeira, Janaína Kieling Frohlich, Thiele Faccim de Brum, Marina Zadra, Margareth Linde Athayde. Chemical composition and antioxidant activity of the essential oil of Tabernaemontana catharinensis A. DC. leaves. Natural product research. 2013; 27(1):68-71. doi: 10.1080/14786419.2011.653971. [PMID: 22273350]
  • Xun Hu, Richard Gunawan, Daniel Mourant, Yi Wang, Caroline Lievens, Weerawut Chaiwat, Liping Wu, Chun-Zhu Li. Esterification of bio-oil from mallee (Eucalyptus loxophleba ssp. gratiae) leaves with a solid acid catalyst: Conversion of the cyclic ether and terpenoids into hydrocarbons. Bioresource technology. 2012 Nov; 123(?):249-55. doi: 10.1016/j.biortech.2012.07.073. [PMID: 22940326]
  • Regina Karousou, Chrysa Efstathiou, Diamanto Lazari. Chemical diversity of wild growing Origanum majorana in Cyprus. Chemistry & biodiversity. 2012 Oct; 9(10):2210-7. doi: 10.1002/cbdv.201100375. [PMID: 23081921]
  • Nallely E Sandoval-Montemayor, Abraham García, Elizabeth Elizondo-Treviño, Elvira Garza-González, Laura Alvarez, María del Rayo Camacho-Corona. Chemical composition of hexane extract of Citrus aurantifolia and anti-Mycobacterium tuberculosis activity of some of its constituents. Molecules (Basel, Switzerland). 2012 Sep; 17(9):11173-84. doi: 10.3390/molecules170911173. [PMID: 22992784]
  • Chokri Messaoud, Abdelmonoem Laabidi, Mohamed Boussaid. Myrtus communis L. infusions: the effect of infusion time on phytochemical composition, antioxidant, and antimicrobial activities. Journal of food science. 2012 Sep; 77(9):C941-7. doi: 10.1111/j.1750-3841.2012.02849.x. [PMID: 22888790]
  • Inès Ellouze, Manef Abderrabba, Nassereddine Sabaou, Florence Mathieu, Ahmed Lebrihi, Jalloul Bouajila. Season's variation impact on Citrus aurantium leaves essential oil: chemical composition and biological activities. Journal of food science. 2012 Sep; 77(9):T173-80. doi: 10.1111/j.1750-3841.2012.02846.x. [PMID: 22897411]
  • Makson G B de Oliveira, Rosemarie B Marques, Michele F de Santana, Amanda B D Santos, Fabíola A Brito, Emiliano O Barreto, Damião P De Sousa, Fernanda R C Almeida, Daniel Badauê-Passos, Angelo R Antoniolli, Lucindo J Quintans-Júnior. α-terpineol reduces mechanical hypernociception and inflammatory response. Basic & clinical pharmacology & toxicology. 2012 Aug; 111(2):120-5. doi: 10.1111/j.1742-7843.2012.00875.x. [PMID: 22380944]
  • Anke Fähnrich, Anne Brosemann, Laura Teske, Madeleine Neumann, Birgit Piechulla. Synthesis of 'cineole cassette' monoterpenes in Nicotiana section Alatae: gene isolation, expression, functional characterization and phylogenetic analysis. Plant molecular biology. 2012 Aug; 79(6):537-53. doi: 10.1007/s11103-012-9933-y. [PMID: 22669744]
  • Wei-Cai Zeng, Zeng Zhang, Hong Gao, Li-Rong Jia, Qiang He. Chemical composition, antioxidant, and antimicrobial activities of essential oil from pine needle (Cedrus deodara). Journal of food science. 2012 Jul; 77(7):C824-9. doi: 10.1111/j.1750-3841.2012.02767.x. [PMID: 22757704]
  • Ling Chai, Bu-Ming Liu, Xiao Lin, Qi-Xiu Li, Mao-Xiang Lai. [Analysis of compositions of the essential oil from Curcuma aromatica by gas chromatography-mass spectrometry]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2012 Jul; 35(7):1102-4. doi: ". [PMID: 23252275]
  • Mohammad Moradi, Massoud Kaykhaii, Ali Reza Ghiasvand, Shahriar Shadabi, Alinazar Salehinia. Comparison of headspace solid-phase microextraction, headspace single-drop microextraction and hydrodistillation for chemical screening of volatiles in Myrtus communis L. Phytochemical analysis : PCA. 2012 Jul; 23(4):379-86. doi: 10.1002/pca.1368. [PMID: 22069217]
  • Hassan Sereshti, Ahmad Rohanifar, Sadjad Bakhtiari, Soheila Samadi. Bifunctional ultrasound assisted extraction and determination of Elettaria cardamomum Maton essential oil. Journal of chromatography. A. 2012 May; 1238(?):46-53. doi: 10.1016/j.chroma.2012.03.061. [PMID: 22483097]
  • Nae Hyung Ryu, Kyung-Ran Park, Sung-Moo Kim, Hyung-Mun Yun, Dongwoo Nam, Seok-Geun Lee, Hyeung-Jin Jang, Kyoo Seok Ahn, Sung-Hoon Kim, Bum Sang Shim, Seung-Hoon Choi, Ashik Mosaddik, Somi K Cho, Kwang Seok Ahn. A hexane fraction of guava Leaves (Psidium guajava L.) induces anticancer activity by suppressing AKT/mammalian target of rapamycin/ribosomal p70 S6 kinase in human prostate cancer cells. Journal of medicinal food. 2012 Mar; 15(3):231-41. doi: 10.1089/jmf.2011.1701. [PMID: 22280146]
  • Ivana Bonaccorsi, Danilo Sciarrone, Luisa Schipilliti, Paola Dugo, Luigi Mondello, Giovanni Dugo. Multidimensional enantio gas chromtography/mass spectrometry and gas chromatography-combustion-isotopic ratio mass spectrometry for the authenticity assessment of lime essential oils (C. aurantifolia Swingle and C. latifolia Tanaka). Journal of chromatography. A. 2012 Feb; 1226(?):87-95. doi: 10.1016/j.chroma.2011.10.038. [PMID: 22088669]
  • Seng-Sung Cheng, Chun-Ya Lin, Min-Jay Chung, Shang-Tzen Chang. Chemical composition and antitermitic activity against Coptotermes formosanus Shiraki of Cryptomeria japonica leaf essential oil. Chemistry & biodiversity. 2012 Feb; 9(2):352-8. doi: 10.1002/cbdv.201100243. [PMID: 22344910]
  • Ranil Waliwitiya, Peter Belton, Russell A Nicholson, Carl A Lowenberger. Plant terpenoids: acute toxicities and effects on flight motor activity and wing beat frequency in the blow fly Phaenicia sericata. Journal of economic entomology. 2012 Feb; 105(1):72-84. doi: 10.1603/ec10381. [PMID: 22420258]
  • Chen-Lung Ho, Yu-Chang Su. Composition, antioxidant and antimicrobial activities of the leaf essential oil of Machilus japonica from Taiwan. Natural product communications. 2012 Jan; 7(1):109-12. doi: ". [PMID: 22428261]
  • M Rahimi-Nasrabadi, F Ahmadi, H Batooli. Essential oil composition of Eucalyptus procera Dehnh. leaves from central Iran. Natural product research. 2012; 26(7):637-42. doi: 10.1080/14786419.2010.541875. [PMID: 21861767]
  • Hanieh Azimi, Mehrnaz Fallah-Tafti, Maliheh Karimi-Darmiyan, Mohammad Abdollahi. A comprehensive review of vaginitis phytotherapy. Pakistan journal of biological sciences : PJBS. 2011 Nov; 14(21):960-6. doi: 10.3923/pjbs.2011.960.966. [PMID: 22514885]
  • Anke Fähnrich, Katrin Krause, Birgit Piechulla. Product variability of the 'cineole cassette' monoterpene synthases of related Nicotiana species. Molecular plant. 2011 Nov; 4(6):965-84. doi: 10.1093/mp/ssr021. [PMID: 21527560]
  • Maria Graça Miguel, Maria Dulce Antunes. Is propolis safe as an alternative medicine?. Journal of pharmacy & bioallied sciences. 2011 Oct; 3(4):479-95. doi: 10.4103/0975-7406.90101. [PMID: 22219581]
  • Carmen Formisano, Daniela Rigano, Felice Senatore, Franco Piozzi, Nelly Apostolides Arnold. Analysis of essential oils from Scutellaria orientalis ssp. alpina and S. utriculata by GC and GC-MS. Natural product communications. 2011 Sep; 6(9):1347-50. doi: . [PMID: 21941912]
  • Sung-Tong Chin, Bussayarat Maikhunthod, Philip J Marriott. Universal method for online enrichment of target compounds in capillary gas chromatography using in-oven cryotrapping. Analytical chemistry. 2011 Sep; 83(17):6485-92. doi: 10.1021/ac200973z. [PMID: 21766796]
  • Rafal Szmigielski, Marek Cieslak, Krzysztof J Rudziński, Barbara Maciejewska. Identification of volatiles from Pinus silvestris attractive for Monochamus galloprovincialis using a SPME-GC/MS platform. Environmental science and pollution research international. 2011 Aug; 19(7):2860-9. doi: 10.1007/s11356-012-0792-5. [PMID: 22322293]
  • Angelike Triantafyllou, Alfiya Bikineyeva, Anna Dikalova, Rafal Nazarewicz, Stamatios Lerakis, Sergey Dikalov. Anti-inflammatory activity of Chios mastic gum is associated with inhibition of TNF-alpha induced oxidative stress. Nutrition journal. 2011 Jun; 10(?):64. doi: 10.1186/1475-2891-10-64. [PMID: 21645369]
  • Wei-Cai Zeng, Rui-Xue Zhu, Li-Rong Jia, Hong Gao, Yue Zheng, Qun Sun. Chemical composition, antimicrobial and antioxidant activities of essential oil from Gnaphlium affine. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Jun; 49(6):1322-8. doi: 10.1016/j.fct.2011.03.014. [PMID: 21414372]
  • Laura W Juan, Alejandro Lucia, Eduardo N Zerba, Leonel Harrand, Martin Marco, Hector M Masuh. Chemical composition and fumigant toxicity of the essential oils from 16 species of Eucalyptus against Haematobia irritans (Diptera: Muscidae) adults. Journal of economic entomology. 2011 Jun; 104(3):1087-92. doi: 10.1603/ec09431. [PMID: 21735933]
  • Khalijah Awang, Halijah Ibrahim, Devi Rosmy Syamsir, Mastura Mohtar, Rasadah Mat Ali, Nor Azah Mohamad Ali. Chemical constituents and antimicrobial activity of the leaf and rhizome oils of Alpinia pahangensis Ridl., an endemic wild ginger from peninsular Malaysia. Chemistry & biodiversity. 2011 Apr; 8(4):668-73. doi: 10.1002/cbdv.201000225. [PMID: 21480512]
  • Jason E Ham, J Raymond Wells. Surface chemistry of a pine-oil cleaner and other terpene mixtures with ozone on vinyl flooring tiles. Chemosphere. 2011 Apr; 83(3):327-33. doi: 10.1016/j.chemosphere.2010.12.036. [PMID: 21237482]
  • Mohammad Bagher Hassanpouraghdam. α-Pinene- and β-myrcene-rich volatile fruit oil of Cupressus arizonica Greene from northwest Iran. Natural product research. 2011 Mar; 25(6):634-9. doi: 10.1080/14786419.2010.531479. [PMID: 21409725]
  • Ameur Elaissi, Hanène Medini, Monique Simmonds, Frederic Lynen, Farhat Farhat, Rachid Chemli, Fethia Harzallah-Skhiri, Mohamed Larbi Khouja. Variation in volatile leaf oils of seven eucalyptus species harvested from Zerniza arboreta (Tunisia). Chemistry & biodiversity. 2011 Feb; 8(2):362-72. doi: 10.1002/cbdv.201000103. [PMID: 21337508]
  • Ameur Elaissi, Hanène Medini, Mohamed Larbi Khouja, Monique Simmonds, Frederic Lynen, Farhat Farhat, Rachid Chemli, Fethia Harzallah-Skhiri. Variation in volatile leaf oils of five Eucalyptus species harvested from Jbel Abderrahman arboreta (Tunisia). Chemistry & biodiversity. 2011 Feb; 8(2):352-61. doi: 10.1002/cbdv.201000102. [PMID: 21337507]
  • Chokri Messaoud, Mohamed Boussaid. Myrtus communis berry color morphs: a comparative analysis of essential oils, fatty acids, phenolic compounds, and antioxidant activities. Chemistry & biodiversity. 2011 Feb; 8(2):300-10. doi: 10.1002/cbdv.201000088. [PMID: 21337502]
  • A J Mossi, R L Cansian, N Paroul, G Toniazzo, J V Oliveira, M K Pierozan, G Pauletti, L Rota, A C A Santos, L A Serafini. Morphological characterisation and agronomical parameters of different species of Salvia sp. (Lamiaceae). Brazilian journal of biology = Revista brasleira de biologia. 2011 Feb; 71(1):121-9. doi: 10.1590/s1519-69842011000100018. [PMID: 21437408]
  • Chen-Lung Ho, Kuang-Ping Hsu, Yen-Hsueh Tseng, Eugene I-Chen Wang, Pei-Chun Liao, Ju-Ching Chou, Chien-Nan Lin, Yu-Chang Su. Composition and antimicrobial activities of the leaf essential oil of Machilus kusanoi from Taiwan. Natural product communications. 2011 Feb; 6(2):267-70. doi: ". [PMID: 21425691]
  • Hamzeh Amiri. The in vitro antioxidative properties of the essential oils and methanol extracts of Satureja macrosiphonia Bornm. Natural product research. 2011 Feb; 25(3):232-43. doi: 10.1080/14786410903374694. [PMID: 20623422]