Terpinolene (BioDeep_00000004341)

 

Secondary id: BioDeep_00000638382, BioDeep_00000859513, BioDeep_00001867725

human metabolite Endogenous


代谢物信息卡片


1-methyl-4-(propan-2-ylidene)cyclohexene p-mentha-1,4(8)-diene

化学式: C10H16 (136.1251936)
中文名称: 萜品油烯
谱图信息: 最多检出来源 Ailuropoda melanoleuca(feces) 1.19%

分子结构信息

SMILES: C1CC(=C(C)C)CC=C1C
InChI: InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3

描述信息

Terpinolene (TPO), also known as alpha-terpinolene or isoterpinene, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, terpinolene is considered to be an isoprenoid lipid molecule. Terpinolene is a very hydrophobic monoterpenoid, practically insoluble in water, and relatively neutral. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes in plants is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Terpinolene is one of the constituents of turpentine and an isomer of terpinene. It appears colourless to pale yellow liquid. Alpha-terpinolene has been identified as an abundant monoterpene in the essential oil of Cannabis sativa plants (PMID:6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Although common in cannabis cultivars, terpinolene is typically found in relatively low amounts. On the other hand, the concentration of terpinolene can be has high as 30\\% of the essential oil. It is thought that terpinolene offers a mildly sedative effect and can reduce anxiety (PMID:28826544 ). In particular, terpinolene is a central nervous system depressant that has been shown to induce drowsiness (PMID:23339024 ). Terpinolene has been demonstrated to prevent LDL oxidation and is of potential interest in the treatment of atherogenesis and coronary artery disease (PMID:28826544 ). Terpinolene exhibits antifungal and larvicidal properties (PMID:28826544 ). Terpinolene is also an effective anti-microbial agent, particularly against E coli and Staphylococcus bacteria (PMID:16402540 ). Terpinolene is also employed as a fragrence ingredient in lotions, insect repellents (similar to other terpenes), perfumes, and soaps. Terpinolene is also a constituent of many other essential oils e. g. Citrus, Mentha, Juniperus, Myristica species. Parsnip oil (Pastinaca sativa) in particular, is a major source (40-70\\%). Terpinolene is a sweet, citrus, and fresh tasting compound. It produces a floral, woody or herbal aroma reminiscent of pine needles. In addition to being found in various plant essential oils, terpinolene is found in a few different foods and spices, such as allspice, apples, sage, rosemary, parsnips, nutmegs, and wild carrots and in a lower concentration in sweet bay, star anises, turmerics, apricots, cumins, evergreen blackberries, red bell peppers, and caraway.
Constituent of many essential oils e.g. Citrus, Mentha, Juniperus, Myristica subspecies Parsnip oil (Pastinaca sativa) is a major source (40-70\\%). Flavouring ingredient. Terpinolene is found in many foods, some of which are coriander, ceylon cinnamon, pine nut, and caraway.

同义名列表

24 个代谢物同义名

1-methyl-4-(propan-2-ylidene)cyclohexene p-mentha-1,4(8)-diene; Cyclohexene, 3-methyl-6-(1-methylethylidene)- (9ci); 1-Methyl-4-(1-methylethylidene)cyclohexene, 9ci; 1-methyl-4-(1-methylethylidene)-1-cyclohexene; 1-methyl-4-(propan-2-ylidene)cyclohex-1-ene; 1-Methyl-4-(1-methylethylidene)-cyclohexene; 1-methyl-4-(1-methylethylidene)cyclohexene; 1-Methyl-4-(propan-2-ylidene)cyclohexene; 1-Methyl-4-isopropylidene-1-cyclohexene; 4-Isopropylidene-1-methyl-cyclohexene; 4-isopropylidene-1-methylcyclohexene; p-Mentha-1,4(8)-diene; 1,4(8)-p-menthadiene; alpha -Terpinolene; alpha-Terpinolene; 1,4(8)-Terpadiene; delta-Terpinene; Α-terpinolene; a-Terpinolene; isoterpinene; TERPINOLENE; δ-Terpinene; Terpinolen; FEMA 3046



数据库引用编号

19 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

11 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(3)

INOH(0)

PlantCyc(5)

COVID-19 Disease Map(0)

PathBank(1)

PharmGKB(0)

823 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

  • John Staton Laws, Scott D Smid. Characterizing cannabis-prevalent terpenes for neuroprotection reveal a role for α and β-pinenes in mitigating amyloid β-evoked neurotoxicity and aggregation in vitro. Neurotoxicology. 2024 Jan; 100(?):16-24. doi: 10.1016/j.neuro.2023.12.004. [PMID: 38070653]
  • 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]
  • Yukun Song, Panpan Zhang, Qiang Jiao, Ruili Gu, Lingxuan Qu, Shan Huang, Xiao Wang, Yue Liu, Yong Lai, Shen Ding, Yuanyuan Chen, Mingwan Li, Dangquan Zhang. Contribution of Constituents in Rosemary-Magnolia Compound Essential Oil to Antibacterial, Antioxidant and Cytotoxicity Bioactivities Revealed by Grey Correlation Analysis. Chemistry & biodiversity. 2023 Apr; ?(?):e202201179. doi: 10.1002/cbdv.202201179. [PMID: 37027518]
  • Kaitlin Urso, William Vizuete, Ryan Moravec, Andrey Khlystov, Alicia Frazier, Glenn Morrison. Indoor Monoterpene Emission Rates from Commercial Cannabis Cultivation Facilities in Colorado. Journal of the Air & Waste Management Association (1995). 2023 Feb; ?(?):. doi: 10.1080/10962247.2023.2175741. [PMID: 36730104]
  • Arkadeep Mukherjee, Young-Ho Ahn. Terpinolene as an enhancer for ultrasonic disinfection of multi-drug-resistant bacteria in hospital wastewater. Environmental science and pollution research international. 2022 May; 29(23):34500-34514. doi: 10.1007/s11356-022-18611-6. [PMID: 35037151]
  • Isis Oliveira Menezes, Jackelyne Roberta Scherf, Anita Oliveira Brito Pereira Bezerra Martins, Andreza Guedes Barbosa Ramos, Jullyana de Souza Siqueira Quintans, Henrique Douglas Melo Coutinho, Jaime Ribeiro-Filho, Irwin Rose Alencar de Menezes. Biological properties of terpinolene evidenced by in silico, in vitro and in vivo studies: A systematic review. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Dec; 93(?):153768. doi: 10.1016/j.phymed.2021.153768. [PMID: 34634744]
  • Yiwei Zhou, Farhat Abbas, Zhidong Wang, Yunyi Yu, Yuechong Yue, Xinyue Li, Rangcai Yu, Yanping Fan. HS-SPME-GC-MS and Electronic Nose Reveal Differences in the Volatile Profiles of Hedychium Flowers. Molecules (Basel, Switzerland). 2021 Sep; 26(17):. doi: 10.3390/molecules26175425. [PMID: 34500858]
  • Seon-Mi Seo, Jae-Woo Lee, Jonghyun Shin, Jun-Hyung Tak, Jinho Hyun, Il-Kwon Park. Development of cellulose nanocrystal-stabilized Pickering emulsions of massoia and nutmeg essential oils for the control of Aedes albopictus. Scientific reports. 2021 06; 11(1):12038. doi: 10.1038/s41598-021-91442-6. [PMID: 34103581]
  • Â V Pinto, J C de Oliveira, C A Costa de Medeiros, S L Silva, F O Pereira. Potentiation of antifungal activity of terbinafine by dihydrojasmone and terpinolene against dermatophytes. Letters in applied microbiology. 2021 Mar; 72(3):292-298. doi: 10.1111/lam.13371. [PMID: 32790923]
  • 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]
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  • Stephan R Rakotonandrasana, Delphin J R Rabehaja, Mathieu Paoli, Dominique de Rocca Serra, Charles Andrianjara, Ange Bighelli, Panja A R Ramanoelina, Félix Tomi. Chemical composition of the essential oils from the aerial parts of two Malagasy endemic species (Apiaceae): Billburttia capensoides Sales & Hedge and Billburttia vaginoides Sales & Hedge. Natural product research. 2019 Apr; 33(8):1200-1203. doi: 10.1080/14786419.2018.1457669. [PMID: 29611714]
  • Christine C Chiu, Christopher I Keeling, Hannah M Henderson, Joerg Bohlmann. Functions of mountain pine beetle cytochromes P450 CYP6DJ1, CYP6BW1 and CYP6BW3 in the oxidation of pine monoterpenes and diterpene resin acids. PloS one. 2019; 14(5):e0216753. doi: 10.1371/journal.pone.0216753. [PMID: 31071168]
  • Stephane L Ngahang Kamte, Farahnaz Ranjbarian, Kevin Cianfaglione, Stefania Sut, Stefano Dall'Acqua, Maurizio Bruno, Fariba Heshmati Afshar, Romilde Iannarelli, Giovanni Benelli, Loredana Cappellacci, Anders Hofer, Filippo Maggi, Riccardo Petrelli. Identification of highly effective antitrypanosomal compounds in essential oils from the Apiaceae family. Ecotoxicology and environmental safety. 2018 Jul; 156(?):154-165. doi: 10.1016/j.ecoenv.2018.03.032. [PMID: 29549739]
  • Jun-Yu Liang, Shan-Shan Guo, Wen-Juan Zhang, Zhu-Feng Geng, Zhi-Wei Deng, Shu-Shan Du, Ji Zhang. Fumigant and repellent activities of essential oil extracted from Artemisia dubia and its main compounds against two stored product pests. Natural product research. 2018 May; 32(10):1234-1238. doi: 10.1080/14786419.2017.1331227. [PMID: 28532258]
  • Emanuele Pallozzi, Ilaria Lusini, Lucia Cherubini, Ramilla A Hajiaghayeva, Paolo Ciccioli, Carlo Calfapietra. Differences between a deciduous and a conifer tree species in gaseous and particulate emissions from biomass burning. Environmental pollution (Barking, Essex : 1987). 2018 Mar; 234(?):457-467. doi: 10.1016/j.envpol.2017.11.080. [PMID: 29207297]
  • Alessandra Piras, Hanen Marzouki, Andrea Maxia, Arianna Marengo, Silvia Porcedda, Danilo Falconieri, Maria José Gonçalves, Carlos Cavaleiro, Ligia Salgueiro. Chemical characterisation and biological activity of leaf essential oils obtained from Pistacia terebinthus growing wild in Tunisia and Sardinia Island. Natural product research. 2017 Nov; 31(22):2684-2689. doi: 10.1080/14786419.2017.1289204. [PMID: 28278668]
  • Amanda Padovan, Andras Keszei, Yasmin Hassan, Sandra T Krause, Tobias G Köllner, Jörg Degenhardt, Jonathan Gershenzon, Carsten Külheim, William J Foley. Four terpene synthases contribute to the generation of chemotypes in tea tree (Melaleuca alternifolia). BMC plant biology. 2017 Oct; 17(1):160. doi: 10.1186/s12870-017-1107-2. [PMID: 28978322]
  • Gabriel Garcia, Adrien Garcia, Marc Gibernau, Ange Bighelli, Félix Tomi. Chemical compositions of essential oils of five introduced conifers in Corsica. Natural product research. 2017 Jul; 31(14):1697-1703. doi: 10.1080/14786419.2017.1285299. [PMID: 28278672]
  • Rayane C Albino, Prissila C Oliveira, Francisco Prosdocimi, Osman F da Silva, Humberto R Bizzo, Paola E Gama, Cássia M Sakuragui, Carolina Furtado, Danilo R de Oliveira. Oxidation of monoterpenes in Protium heptaphyllum oleoresins. Phytochemistry. 2017 Apr; 136(?):141-146. doi: 10.1016/j.phytochem.2017.01.013. [PMID: 28143669]
  • Koki Fujita, Ryo Kambe, Ransika De Alwis, Tatsuya Yagi, Yuji Tsutsumi. Airborne Monoterpenes Emitted from a Cupressus lusitanica Cell Culture Induce a Signaling Cascade that Produces β-Thujaplicin. Journal of chemical ecology. 2016 Aug; 42(8):814-820. doi: 10.1007/s10886-016-0739-2. [PMID: 27596215]
  • E M A Macedo, W C Santos, B P Sousa, E M Lopes, C A Piauilino, F V M Cunha, D P Sousa, F A Oliveira, F R C Almeida. Association of terpinolene and diclofenac presents antinociceptive and anti-inflammatory synergistic effects in a model of chronic inflammation. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2016 Jun; 49(7):. doi: 10.1590/1414-431x20165103. [PMID: 27332775]
  • Marcelo Felipe Rodrigues da Silva, Patrícia Cristina Bezerra-Silva, Camila Soledade de Lira, Bheatriz Nunes de Lima Albuquerque, Afonso Cordeiro Agra Neto, Emmanuel Viana Pontual, Jefferson Rodrigues Maciel, Patrícia Maria Guedes Paiva, Daniela Maria do Amaral Ferraz Navarro. Composition and biological activities of the essential oil of Piper corcovadensis (Miq.) C. DC (Piperaceae). Experimental parasitology. 2016 Jun; 165(?):64-70. doi: 10.1016/j.exppara.2016.03.017. [PMID: 26993082]
  • Mariela Pontin, Rubén Bottini, José Luis Burba, Patricia Piccoli. Allium sativum produces terpenes with fungistatic properties in response to infection with Sclerotium cepivorum. Phytochemistry. 2015 Jul; 115(?):152-60. doi: 10.1016/j.phytochem.2015.02.003. [PMID: 25819001]
  • Gun Woong Lee, Sungbeom Lee, Moon-Soo Chung, Yeon Sim Jeong, Byung Yeoup Chung. Rice terpene synthase 20 (OsTPS20) plays an important role in producing terpene volatiles in response to abiotic stresses. Protoplasma. 2015 Jul; 252(4):997-1007. doi: 10.1007/s00709-014-0735-8. [PMID: 25430981]
  • Rodrigo Alonso, Federico J Berli, Rubén Bottini, Patricia Piccoli. Acclimation mechanisms elicited by sprayed abscisic acid, solar UV-B and water deficit in leaf tissues of field-grown grapevines. Plant physiology and biochemistry : PPB. 2015 Jun; 91(?):56-60. doi: 10.1016/j.plaphy.2015.03.011. [PMID: 25885355]
  • Detlef Ulrich, Thomas Nothnagel, Hartwig Schulz. Influence of cultivar and harvest year on the volatile profiles of leaves and roots of carrots (Daucus carota spp. sativus Hoffm.). Journal of agricultural and food chemistry. 2015 Apr; 63(13):3348-56. doi: 10.1021/acs.jafc.5b00704. [PMID: 25797828]
  • Seyed Mehdi Razavi, Ameneh Ravansalar, Shahabeddin Mirinejad. The investigation on phytochemicals from Ferulago angulata (Schlecht) Boiss, indigenous to central parts of Iran. Natural product research. 2015; 29(21):2037-40. doi: 10.1080/14786419.2015.1017725. [PMID: 25743037]
  • Koki Fujita, Yasufumi Bunyu, Ken'ich Kuroda, Tatsuya Ashitani, Jun Shigeto, Yuji Tsutsumi. A novel synthetic pathway for tropolone ring formation via the olefin monoterpene intermediate terpinolene in cultured Cupressus lusitanica cells. Journal of plant physiology. 2014 May; 171(8):610-4. doi: 10.1016/j.jplph.2013.12.016. [PMID: 24709152]
  • Hoang D Trung, Tran D Thang, Pham H Ban, Tran M Hoi, Do N Dai, Isiaka A Ogunwande. Terpene constituents of the leaves of five Vietnamese species of Clausena (Rutaceae). Natural product research. 2014; 28(9):622-30. doi: 10.1080/14786419.2014.888555. [PMID: 24617735]
  • Elanur Aydin, Hasan Türkez, Sener Taşdemir. Anticancer and antioxidant properties of terpinolene in rat brain cells. Arhiv za higijenu rada i toksikologiju. 2013 Sep; 64(3):415-24. doi: 10.2478/10004-1254-64-2013-2365. [PMID: 24084350]
  • 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]
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  • Ricardo M Montanari, Luiz C A Barbosa, Antonio J Demuner, Cleber J Silva, Nelio J Andrade, Fyaz M D Ismail, Maria C A Barbosa. Exposure to Anacardiaceae volatile oils and their constituents induces lipid peroxidation within food-borne bacteria cells. Molecules (Basel, Switzerland). 2012 Aug; 17(8):9728-40. doi: 10.3390/molecules17089728. [PMID: 22893019]
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  • Mariana Gil, Mariela Pontin, Federico Berli, Rubén Bottini, Patricia Piccoli. Metabolism of terpenes in the response of grape (Vitis vinifera L.) leaf tissues to UV-B radiation. Phytochemistry. 2012 May; 77(?):89-98. doi: 10.1016/j.phytochem.2011.12.011. [PMID: 22277733]
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