(S)-p-Menth-1-en-4-ol (BioDeep_00000019609)

Main id: BioDeep_00000001095

 

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol

化学式: C10H18O (154.1358)
中文名称: (+)-萜品-4-醇, 4-萜烯醇, 4-香芹酚
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C)[C@]1(O)CCC(C)=CC1
InChI: InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3

描述信息

(S)-p-Menth-1-en-4-ol occurs in many essential oils, e.g. lavende
Occurs in many essential oils, e.g. lavender
Terpinen-4-ol (4-Carvomenthenol), a naturally occurring monoterpene, is the main bioactive component of tea-tree oil. Terpinen-4-ol suppresses inflammatory mediator production by activated human monocytes. Terpinen-4-ol significantly enhances the effect of several chemotherapeutic and biological agents[1][2][3].
Terpinen-4-ol (4-Carvomenthenol), a naturally occurring monoterpene, is the main bioactive component of tea-tree oil. Terpinen-4-ol suppresses inflammatory mediator production by activated human monocytes. Terpinen-4-ol significantly enhances the effect of several chemotherapeutic and biological agents[1][2][3].

同义名列表

13 个代谢物同义名

(1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol; (1S)-1-isopropyl-4-methylcyclohex-3-en-1-ol; (S)-1-Isopropyl-4-methyl-3-cyclohexen-1-ol; (S)-(+)-P-Menth-1-en-4-ol; (S)-p-Menth-1-en-4-ol; 4-Terpineol, (+/-)-; S-4-Carvomenthenol; (+)-terpinen-4-ol; Terpinen-4-ol; S-Origanol; 4-Carvomenthenol; Terpineol-4; 4-Carvomenthenol



数据库引用编号

20 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

0 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(0)

PharmGKB(0)

612 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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 ANXA5, BCL2, CASP3, CASP8, CCND1, HPGDS, MAPK14, MARVELD1, TYR
Peripheral membrane protein 4 ACHE, ANXA5, CYP1B1, GORASP1
Endoplasmic reticulum membrane 2 BCL2, CYP1B1
Nucleus 9 ACHE, BCL2, CASP3, CASP8, CCND1, MAPK14, MARVELD1, MPO, PCNA
cytosol 8 ANXA5, BCL2, CASP3, CASP8, CCND1, GPT, HPGDS, MAPK14
nuclear body 1 PCNA
centrosome 2 CCND1, PCNA
nucleoplasm 7 CASP3, CASP8, CCND1, HPGDS, MAPK14, MPO, PCNA
Cell membrane 3 ACHE, MARVELD1, TNF
Cytoplasmic side 1 GORASP1
lamellipodium 1 CASP8
Multi-pass membrane protein 1 MARVELD1
Golgi apparatus membrane 1 GORASP1
Synapse 1 ACHE
cell surface 2 ACHE, TNF
glutamatergic synapse 2 CASP3, MAPK14
Golgi apparatus 3 ACHE, ATRN, GORASP1
Golgi membrane 1 GORASP1
neuromuscular junction 1 ACHE
neuronal cell body 2 CASP3, TNF
sarcolemma 1 ANXA5
Lysosome 2 MPO, TYR
plasma membrane 4 ACHE, ATRN, MARVELD1, TNF
Membrane 5 ACHE, ANXA5, BCL2, CYP1B1, MARVELD1
extracellular exosome 5 ANXA5, ATRN, GPT, MPO, PCNA
endoplasmic reticulum 1 BCL2
extracellular space 7 ACHE, ATRN, CXCL8, IL10, IL6, MPO, TNF
perinuclear region of cytoplasm 2 ACHE, TYR
bicellular tight junction 1 CCND1
mitochondrion 4 BCL2, CASP8, CYP1B1, MAPK14
protein-containing complex 2 BCL2, CASP8
intracellular membrane-bounded organelle 4 CYP1B1, HPGDS, MPO, TYR
Microsome membrane 1 CYP1B1
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 ATRN, TYR
Secreted 4 ACHE, CXCL8, IL10, IL6
extracellular region 8 ACHE, ANXA5, CXCL8, IL10, IL6, MAPK14, MPO, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, CASP8
[Isoform 2]: Secreted 1 ATRN
Extracellular side 1 ACHE
Nucleus membrane 2 BCL2, CCND1
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, CCND1
external side of plasma membrane 2 ANXA5, TNF
Melanosome membrane 1 TYR
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cell projection, lamellipodium 1 CASP8
Membrane raft 1 TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 MARVELD1
focal adhesion 1 ANXA5
cis-Golgi network 1 GORASP1
basement membrane 1 ACHE
collagen-containing extracellular matrix 1 ANXA5
secretory granule 1 MPO
nuclear speck 1 MAPK14
Zymogen granule membrane 1 ANXA5
chromatin 1 PCNA
phagocytic cup 1 TNF
cytoskeleton 2 CASP8, MARVELD1
spindle pole 1 MAPK14
nuclear replication fork 1 PCNA
chromosome, telomeric region 1 PCNA
Lipid-anchor, GPI-anchor 1 ACHE
[Isoform 3]: Secreted 1 ATRN
Melanosome 1 TYR
cell body 1 CASP8
side of membrane 1 ACHE
replication fork 1 PCNA
myelin sheath 1 BCL2
azurophil granule 1 MPO
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
endoplasmic reticulum lumen 1 IL6
transcription repressor complex 1 CCND1
male germ cell nucleus 1 PCNA
azurophil granule lumen 1 MPO
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
vesicle membrane 1 ANXA5
nuclear lamina 1 PCNA
phagocytic vesicle lumen 1 MPO
synaptic cleft 1 ACHE
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
[Isoform 1]: Cell membrane 1 ATRN
cyclin-dependent protein kinase holoenzyme complex 2 CCND1, PCNA
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
cyclin D1-CDK4 complex 1 CCND1
PCNA complex 1 PCNA
PCNA-p21 complex 1 PCNA
replisome 1 PCNA
[Isoform H]: Cell membrane 1 ACHE
cyclin D1-CDK6 complex 1 CCND1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Jing Ren, Yi-Ming Wang, Shuai-Bing Zhang, Yang-Yong Lv, Huan-Chen Zhai, Shan Wei, Ping-An Ma, Yuan-Sen Hu. Terpinen-4-ol from tea tree oil prevents Aspergillus flavus growth in postharvest wheat grain. International journal of food microbiology. 2024 Jun; 418(?):110741. doi: 10.1016/j.ijfoodmicro.2024.110741. [PMID: 38733636]
  • Caroline Deweer, Karin Sahmer, Jérôme Muchembled. Anti-oomycete activities from essential oils and their major compounds on Phytophthora infestans. Environmental science and pollution research international. 2023 Oct; ?(?):. doi: 10.1007/s11356-023-29270-6. [PMID: 37779122]
  • Xinping Zhao, Hailong Wu, Shuaili Yue, Xin Chen, Yong Huang, Haiqun Cao, Min Liao. Role of CYP6MS subfamily enzymes in detoxification of Sitophilus zeamais after exposure to terpinen-4-ol and limonene. Pesticide biochemistry and physiology. 2023 Jun; 193(?):105426. doi: 10.1016/j.pestbp.2023.105426. [PMID: 37248004]
  • 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]
  • Anita Vidács, Erika Beáta Kerekes, Miklós Takó, Csaba Vágvölgyi, Judit Krisch. Eradication of multiple-species biofilms from food industrial and domestic surfaces using essential oils. Food science and technology international = Ciencia y tecnologia de los alimentos internacional. 2023 Mar; ?(?):10820132231165543. doi: 10.1177/10820132231165543. [PMID: 36959708]
  • Shanshan Gao, Xinlong Guo, Shumei Liu, Siying Li, Jiahao Zhang, Shuang Xue, Qingbo Tang, Kunpeng Zhang, Ruimin Li. Cytochrome P450 gene CYP6BQ8 mediates terpinen-4-ol susceptibility in the red flour beetle, Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae). Bulletin of entomological research. 2023 Jan; ?(?):1-11. doi: 10.1017/s0007485322000566. [PMID: 36636814]
  • Souad El Hafidi, Khadija Bakhy, Mohammed Ouhssine, Abderrahim Benzakour, Hamid Khamar, Joseph Casanova, Mathieu Paoli, Félix Tomi. Composition and Chemical Variability of the Essential Oil from Aerial Parts of Cladanthus scariosus, an Endemic Species to the Moroccan High Atlas. Chemistry & biodiversity. 2023 Jan; 20(1):e202201022. doi: 10.1002/cbdv.202201022. [PMID: 36520049]
  • Meilin Li, Shunlong Liu, Zhijuan Yin, Charlotte Bernigaud, Jacques Guillot, Fang Fang. Activity of terpenes derived from essential oils against Sarcoptes scabiei eggs. Parasites & vectors. 2021 Dec; 14(1):600. doi: 10.1186/s13071-021-05094-6. [PMID: 34886874]
  • Sahar Ghulam Mohyuddin, Aftab Qamar, Can-Ying Hu, Yun Li, Sheng-Wei Chen, Jia-Ying Wen, Ming-Long Bao, Xiang Hong Ju. Terpinen4-ol inhibits heat stress induced inflammation in colonic tissue by Activating Occludin, Claudin-2 and TLR4/NF-κB signaling pathway. International immunopharmacology. 2021 Oct; 99(?):107727. doi: 10.1016/j.intimp.2021.107727. [PMID: 34426115]
  • Zhenbiao Li, Yingying Wei, Zidan Cao, Shu Jiang, Yi Chen, Xingfeng Shao. The Jasmonic Acid Signaling Pathway is Associated with Terpinen-4-ol-Induced Disease Resistance against Botrytis cinerea in Strawberry Fruit. Journal of agricultural and food chemistry. 2021 Sep; 69(36):10678-10687. doi: 10.1021/acs.jafc.1c04608. [PMID: 34468130]
  • Yanyan Zhang, Li He, Mengxin Tu, Mei Huang, Yan Chen, Di Pan, Jianqing Peng, Xiangchun Shen. The ameliorative effect of terpinen-4-ol on ER stress-induced vascular calcification depends on SIRT1-mediated regulation of PERK acetylation. Pharmacological research. 2021 08; 170(?):105629. doi: 10.1016/j.phrs.2021.105629. [PMID: 34089864]
  • Tyler M Wilson, Ariel Poulson, Chris Packer, Richard E Carlson, R Michael Buch. Essential Oil Profile and Yield of Corolla, Calyx, Leaf, and Whole Flowering Top of Cultivated Lavandula angustifolia Mill. (Lamiaceae) from Utah. Molecules (Basel, Switzerland). 2021 Apr; 26(8):. doi: 10.3390/molecules26082343. [PMID: 33920647]
  • Anan Athipornchai, Rungnapha Kumpang, Suwanna Semsri. Potential Biological Activities of Clausena Essential Oils for the Treatment of Diabetes. Journal of oleo science. 2021; 70(11):1669-1676. doi: 10.5650/jos.ess19294. [PMID: 34732637]
  • Qian Xu, Luyun Zhang, Shuai Yu, Guangqing Xia, Junyi Zhu, Hao Zang. Chemical composition and biological activities of an essential oil from the aerial parts of Artemisia Gmelinii weber ex Stechm. Natural product research. 2021 Jan; 35(2):346-349. doi: 10.1080/14786419.2019.1627349. [PMID: 31177847]
  • Di Chen, Jingyi Wang, David A Sullivan, Wendy R Kam, Yang Liu. Effects of Terpinen-4-ol on Meibomian Gland Epithelial Cells In Vitro. Cornea. 2020 Dec; 39(12):1541-1546. doi: 10.1097/ico.0000000000002506. [PMID: 32947397]
  • Zhenbiao Li, Nan Wang, Yingying Wei, Xiurong Zou, Shu Jiang, Feng Xu, Hongfei Wang, Xingfeng Shao. Terpinen-4-ol Enhances Disease Resistance of Postharvest Strawberry Fruit More Effectively than Tea Tree Oil by Activating the Phenylpropanoid Metabolism Pathway. Journal of agricultural and food chemistry. 2020 Jun; 68(24):6739-6747. doi: 10.1021/acs.jafc.0c01840. [PMID: 32379969]
  • Min Liao, Su Shi, Hailong Wu, Qianqian Yang, Zeng Zhu, Jinjing Xiao, Yong Huang, Haiqun Cao. Effects of terpinen-4-ol fumigation on protein levels of detoxification enzymes in Tribolium confusum. Archives of insect biochemistry and physiology. 2020 Apr; 103(4):e21653. doi: 10.1002/arch.21653. [PMID: 31859418]
  • 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]
  • Yong Huang, Min Liao, Qianqian Yang, Su Shi, Jinjing Xiao, Haiqun Cao. Knockdown of NADPH-cytochrome P450 reductase and CYP6MS1 increases the susceptibility of Sitophilus zeamais to terpinen-4-ol. Pesticide biochemistry and physiology. 2020 Jan; 162(?):15-22. doi: 10.1016/j.pestbp.2019.07.008. [PMID: 31836049]
  • 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]
  • Yang Wang, Li-Ting Zhang, Yi-Xi Feng, Shan-Shan Guo, Xue Pang, Di Zhang, Zhu-Feng Geng, Shu-Shan Du. Insecticidal and repellent efficacy against stored-product insects of oxygenated monoterpenes and 2-dodecanone of the essential oil from Zanthoxylum planispinum var. dintanensis. Environmental science and pollution research international. 2019 Aug; 26(24):24988-24997. doi: 10.1007/s11356-019-05765-z. [PMID: 31240663]
  • Teresa Della Pepa, Hazem S Elshafie, Raffaele Capasso, Vincenzo De Feo, Ippolito Camele, Filomena Nazzaro, Maria Rosa Scognamiglio, Lucia Caputo. Antimicrobial and Phytotoxic Activity of Origanum heracleoticum and O. majorana Essential Oils Growing in Cilento (Southern Italy). Molecules (Basel, Switzerland). 2019 Jul; 24(14):. doi: 10.3390/molecules24142576. [PMID: 31315175]
  • Karolina Połeć, Aneta Wójcik, Michał Flasiński, Paweł Wydro, Marcin Broniatowski, Katarzyna Hąc-Wydro. The influence of terpinen-4-ol and eucalyptol - The essential oil components - on fungi and plant sterol monolayers. Biochimica et biophysica acta. Biomembranes. 2019 06; 1861(6):1093-1102. doi: 10.1016/j.bbamem.2019.03.015. [PMID: 30926362]
  • Asit Ray, Sudipta Jena, Basudeba Kar, Jeetendranath Patnaik, Pratap Chandra Panda, Sanghamitra Nayak. Chemical composition and antioxidant activities of essential oil of Hedychium greenii and Hedychium gracile from India. Natural product research. 2019 May; 33(10):1482-1485. doi: 10.1080/14786419.2017.1416384. [PMID: 29252004]
  • Yong Huang, Min Liao, Qianqian Yang, Jinjing Xiao, Zhaoyin Hu, Haiqun Cao. iTRAQ-based quantitative proteome revealed metabolic changes of Sitophilus zeamais in response to terpinen-4-ol fumigation. Pest management science. 2019 Feb; 75(2):444-451. doi: 10.1002/ps.5135. [PMID: 30039555]
  • Paola Brun, Giulia Bernabè, Raffaella Filippini, Anna Piovan. In Vitro Antimicrobial Activities of Commercially Available Tea Tree (Melaleuca alternifolia) Essential Oils. Current microbiology. 2019 Jan; 76(1):108-116. doi: 10.1007/s00284-018-1594-x. [PMID: 30421144]
  • Talha Ali Chohan, Tahir Ali Chohan, Lijun Zhou, Qianqian Yang, Liao Min, Haiqun Cao. Repellency, Toxicity, Gene Expression Profiling and In Silico Studies to Explore Insecticidal Potential of Melaleuca alternifolia Essential Oil against Myzus persicae. Toxins. 2018 Oct; 10(11):. doi: 10.3390/toxins10110425. [PMID: 30366370]
  • Emira Noumi, Abderrahmen Merghni, Mousa M Alreshidi, Ons Haddad, Gültekin Akmadar, Laura De Martino, Maha Mastouri, Ozgur Ceylan, Mejdi Snoussi, Abdulbasit Al-Sieni, Vincenzo De Feo. Chromobacterium violaceum and Pseudomonas aeruginosa PAO1: Models for Evaluating Anti-Quorum Sensing Activity of Melaleuca alternifolia Essential Oil and Its Main Component Terpinen-4-ol. Molecules (Basel, Switzerland). 2018 Oct; 23(10):. doi: 10.3390/molecules23102672. [PMID: 30336602]
  • Nelson Siu Kei Lam, Xin Xin Long, Robert C Griffin, Mu-Kai Chen, James Cg Doery. Can the tea tree oil (Australian native plant: Melaleuca alternifolia Cheel) be an alternative treatment for human demodicosis on skin?. Parasitology. 2018 10; 145(12):1510-1520. doi: 10.1017/s0031182018000495. [PMID: 29667560]
  • Noohi Nasim, Jay Krishna Behera, I Sriram Sandeep, V V RamaRao, Basudeba Kar, Antaryami Mishra, Sanghamitra Nayak, Sujata Mohanty. Phytochemical analysis of flower from Pandanus odorifer (Forssk.) Kuntze for industrial application. Natural product research. 2018 Oct; 32(20):2494-2497. doi: 10.1080/14786419.2017.1422184. [PMID: 29298498]
  • Yuetian Zhang, Ruizhang Feng, Lixia Li, Xun Zhou, Zhengwen Li, Renyong Jia, Xu Song, Yuanfeng Zou, Lizi Yin, Changliang He, Xiaoxia Liang, Wanhai Zhou, Qin Wei, Yonghua Du, Kuan Yan, Zili Wu, Zhongqiong Yin. The Antibacterial Mechanism of Terpinen-4-ol Against Streptococcus agalactiae. Current microbiology. 2018 Sep; 75(9):1214-1220. doi: 10.1007/s00284-018-1512-2. [PMID: 29804206]
  • Yong Huang, Min Liao, Qianqian Yang, Jinjing Xiao, Zhaoyin Hu, Lijun Zhou, Haiqun Cao. Transcriptome profiling reveals differential gene expression of detoxification enzymes in Sitophilus zeamais responding to terpinen-4-ol fumigation. Pesticide biochemistry and physiology. 2018 Jul; 149(?):44-53. doi: 10.1016/j.pestbp.2018.05.008. [PMID: 30033015]
  • Andreia R Bucci, Larissa Marcelino, Renata K Mendes, Augusto Etchegaray. The antimicrobial and antiadhesion activities of micellar solutions of surfactin, CTAB and CPCl with terpinen-4-ol: applications to control oral pathogens. World journal of microbiology & biotechnology. 2018 Jun; 34(6):86. doi: 10.1007/s11274-018-2472-1. [PMID: 29876752]
  • Wirginia Kukula-Koch, Wojciech Koch, Lidia Czernicka, Kazimierz Głowniak, Yoshinori Asakawa, Akemi Umeyama, Zbigniew Marzec, Takashi Kuzuhara. MAO-A Inhibitory Potential of Terpene Constituents from Ginger Rhizomes-A Bioactivity Guided Fractionation. Molecules (Basel, Switzerland). 2018 May; 23(6):. doi: 10.3390/molecules23061301. [PMID: 29844252]
  • Małgorzata Kucharska, Jadwiga A Szymańska, Wiktor Wesołowski, Elżbieta Bruchajzer, Barbara Frydrych. [Comparison of chemical composition of selected essential oils used in respiratory diseases]. Medycyna pracy. 2018 Mar; 69(2):167-178. doi: 10.13075/mp.5893.00673. [PMID: 29300393]
  • Rungarun Tisgratog, Chutipong Sukkanon, John P Grieco, Unchalee Sanguanpong, Kamlesh R Chauhan, Joel R Coats, Theeraphap Chareonviriyaphap. Evaluation of the Constituents of Vetiver Oil Against Anopheles minimus (Diptera: Culicidae), a Malaria Vector in Thailand. Journal of medical entomology. 2018 01; 55(1):193-199. doi: 10.1093/jme/tjx188. [PMID: 29029183]
  • 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]
  • Antonio Nei Santana Gondim, Aline Lara, Artur Santos-Miranda, Danilo Roman-Campos, Sandra Lauton-Santos, José Evaldo Rodrigues Menezes-Filho, Carla Maria Lins de Vasconcelos, Eduardo Antonio Conde-Garcia, Silvia Guatimosim, Jader S Cruz. (-)-Terpinen-4-ol changes intracellular Ca2+ handling and induces pacing disturbance in rat hearts. European journal of pharmacology. 2017 Jul; 807(?):56-63. doi: 10.1016/j.ejphar.2017.04.022. [PMID: 28435092]
  • Katarzyna Hąc-Wydro, Michał Flasiński, Marcin Broniatowski, Monika Sołtys. Studies on the Behavior of Eucalyptol and Terpinen-4-ol-Natural Food Additives and Ecological Pesticides-in Model Lipid Membranes. Langmuir : the ACS journal of surfaces and colloids. 2017 07; 33(27):6916-6924. doi: 10.1021/acs.langmuir.7b00774. [PMID: 28654274]
  • 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]
  • Fredrik Schubert, Katinka Pålsson, Ellen Santangelo, Anna-Karin Borg-Karlson. Sulfate turpentine: a resource of tick repellent compounds. Experimental & applied acarology. 2017 Jul; 72(3):291-302. doi: 10.1007/s10493-017-0145-7. [PMID: 28589297]
  • Aida Lahmar, Ahmed Bedoui, Imen Mokdad-Bzeouich, Zaineb Dhaouifi, Zahar Kalboussi, Imed Cheraif, Kamel Ghedira, Leila Chekir-Ghedira. Reversal of resistance in bacteria underlies synergistic effect of essential oils with conventional antibiotics. Microbial pathogenesis. 2017 May; 106(?):50-59. doi: 10.1016/j.micpath.2016.10.018. [PMID: 27815129]
  • Zineb Djerrad, Abderrahmane Djouahri, Leila Kadik. Variability of Pinus halepensis Mill. Essential Oils and Their Antioxidant Activities Depending on the Stage of Growth During Vegetative Cycle. Chemistry & biodiversity. 2017 Apr; 14(4):. doi: 10.1002/cbdv.201600340. [PMID: 27936295]
  • Shih-Yu Lee, Po-Yu Chen, Jung-Chun Lin, Nicholas S Kirkby, Ching-Huei Ou, Tsu-Chung Chang. Melaleuca alternifolia Induces Heme Oxygenase-1 Expression in Murine RAW264.7 Cells through Activation of the Nrf2-ARE Pathway. The American journal of Chinese medicine. 2017; 45(8):1631-1648. doi: 10.1142/s0192415x17500884. [PMID: 29121804]
  • Thirssa H Grando, Matheus D Baldissera, Lucas T Gressler, Mariângela Facco de Sá, Bruna N Bortoluzzi, Andressa S Schafer, Rafael C Ebling, Renata P Raffin, Roberto C V Santos, Lenita M Stefani, Rodrigo Vaucher, Marta L R Leal, Silvia G Monteiro. Melaleuca alternifolia anthelmintic activity in gerbils experimentally infected by Haemonchus contortus. Experimental parasitology. 2016 Nov; 170(?):177-183. doi: 10.1016/j.exppara.2016.09.004. [PMID: 27646626]
  • Katarzyna Hąc-Wydro, Karolina Szydło. The influence of environmentally friendly pesticide - Eucalyptol - alone and in combination with terpinen-4-ol - on model bacterial membranes. Colloids and surfaces. B, Biointerfaces. 2016 Oct; 146(?):918-23. doi: 10.1016/j.colsurfb.2016.07.044. [PMID: 27472454]
  • Alessandra Manzo, Loana Musso, Sara Panseri, Marcello Iriti, Sabrina Dallavalle, Enrico Catalano, Giorgio Scarì, Annamaria Giorgi. Screening of the chemical composition and bioactivity of Waldheimia glabra (Decne.) Regel essential oil. Journal of the science of food and agriculture. 2016 Jul; 96(9):3195-201. doi: 10.1002/jsfa.7499. [PMID: 26467601]
  • Guillermo E Marcial, Carla L Gerez, Martha Nuñez de Kairuz, Victoria Coll Araoz, Carola Schuff, Graciela Font de Valdez. Influence of oregano essential oil on traditional Argentinean cheese elaboration: Effect on lactic starter cultures. Revista Argentina de microbiologia. 2016 Jul; 48(3):229-235. doi: 10.1016/j.ram.2016.04.006. [PMID: 27577090]
  • Petar Knezevic, Verica Aleksic, Natasa Simin, Emilija Svircev, Aleksandra Petrovic, Neda Mimica-Dukic. Antimicrobial activity of Eucalyptus camaldulensis essential oils and their interactions with conventional antimicrobial agents against multi-drug resistant Acinetobacter baumannii. Journal of ethnopharmacology. 2016 Feb; 178(?):125-36. doi: 10.1016/j.jep.2015.12.008. [PMID: 26671210]
  • Marimuthu Govindarajan, Mohan Rajeswary, S L Hoti, Giovanni Benelli. Larvicidal potential of carvacrol and terpinen-4-ol from the essential oil of Origanum vulgare (Lamiaceae) against Anopheles stephensi, Anopheles subpictus, Culex quinquefasciatus and Culex tritaeniorhynchus (Diptera: Culicidae). Research in veterinary science. 2016 Feb; 104(?):77-82. doi: 10.1016/j.rvsc.2015.11.011. [PMID: 26850541]
  • Cheng-Fang Wang, Kai Yang, Chun-Xue You, Wen-Juan Zhang, Shan-Shan Guo, Zhu-Feng Geng, Shu-Shan Du, Yong-Yan Wang. Chemical Composition and Insecticidal Activity of Essential Oils from Zanthoxylum dissitum Leaves and Roots against Three Species of Storage Pests. Molecules (Basel, Switzerland). 2015 May; 20(5):7990-9. doi: 10.3390/molecules20057990. [PMID: 25946557]
  • Raimunda Sâmia Nogueira Brilhante, Natalya Fechine Silva, Francisca Jakelyne de Farias Marques, Débora de Souza Collares Maia Castelo-Branco, Rita Amanda Chaves de Lima, Angela Donato Maia Malaquias, Erica Pacheco Caetano, Giovanna Riello Barbosa, Zoilo Pires de Camargo, Anderson Messias Rodrigues, André Jalles Monteiro, Tereza de Jesus Pinheiro Gomes Bandeira, Rossana de Aguiar Cordeiro, José Júlio Costa Sidrim, José Luciano Bezerra Moreira, Marcos Fábio Gadelha Rocha. In vitro inhibitory activity of terpenic derivatives against clinical and environmental strains of the Sporothrix schenkii complex. Medical mycology. 2015 Feb; 53(2):93-8. doi: 10.1093/mmy/myu085. [PMID: 25541558]
  • Wen-Juan Zhang, Kai Yang, Chun-Xue You, Ying Wang, Cheng-Fang Wang, Yan Wu, Zhu-Feng Geng, Yang Su, Shu-Shan Du, Zhi-Wei Deng. Bioactivity of essential oil from Artemisia stolonifera (Maxim.) Komar. and its main compounds against two stored-product insects. Journal of oleo science. 2015; 64(3):299-307. doi: 10.5650/jos.ess14187. [PMID: 25757434]
  • Elisabeth Mantil, Grace Daly, Tyler J Avis. Effect of tea tree (Melaleuca alternifolia) oil as a natural antimicrobial agent in lipophilic formulations. Canadian journal of microbiology. 2015 Jan; 61(1):82-8. doi: 10.1139/cjm-2014-0667. [PMID: 25515896]
  • D C Cabrera, G L S Gomes, A Flach, L A M A da Costa, G R Rosa, N F de Moura. Evaluation of climatic factors on the yield and chemical composition of the essential oil of Myrocarpus frondosus. Natural product research. 2015; 29(7):667-70. doi: 10.1080/14786419.2014.976642. [PMID: 25421822]
  • 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]
  • Sladjana Malic, Rachael P C Jordan, Mark G J Waters, David J Stickler, David W Williams. Biocide activity against urinary catheter pathogens. Antimicrobial agents and chemotherapy. 2014; 58(2):1192-4. doi: 10.1128/aac.01106-13. [PMID: 24247129]
  • L L Silva, Q I Garlet, S C Benovit, G Dolci, C A Mallmann, M E Bürger, B Baldisserotto, S J Longhi, B M Heinzmann. Sedative and anesthetic activities of the essential oils of Hyptis mutabilis (Rich.) Briq. and their isolated components in silver catfish (Rhamdia quelen). Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2013 Sep; 46(9):771-9. doi: 10.1590/1414-431x20133013. [PMID: 24068193]
  • K Chooluck, R P Singh, K Sathirakul, H Derendorf. Plasma and dermal pharmacokinetics of terpinen-4-ol in rats following intravenous administration. Die Pharmazie. 2013 Feb; 68(2):135-40. doi: . [PMID: 23469686]
  • Atsuhiko Nakamura, Mitsuo Miyazawa. Evaluation of volatiles from Ampelopsis brevipedunculata var. heterophylla using GC-olfactometry, GC-MS and GC-pulsed flame photometric detector. Journal of oleo science. 2013; 62(9):645-55. doi: 10.5650/jos.62.645. [PMID: 24005009]
  • Kotchaphan Chooluck, Rajendra P Singh, Korbtham Sathirakul, Hartmut Derendorf. Dermal pharmacokinetics of Terpinen-4-ol following topical administration of Zingiber cassumunar (plai) oil. Planta medica. 2012 Nov; 78(16):1761-6. doi: 10.1055/s-0032-1315262. [PMID: 23027380]
  • Dwijendra Singh, T R S Kumar, Vivek K Gupt, Pushplata Chaturvedi. Antimicrobial activity of some promising plant oils, molecules and formulations. Indian journal of experimental biology. 2012 Oct; 50(10):714-7. doi: ". [PMID: 23214265]
  • Sita Luvangadio Lukoki Vunda, Ismael Pretto Sauter, Samuel Paulo Cibulski, Paulo Michel Roehe, Sérgio A Loreto Bordignon, Marilise Brittes Rott, Miriam A Apel, Gilsane Lino von Poser. Chemical composition and amoebicidal activity of Croton pallidulus, Croton ericoides, and Croton isabelli (Euphorbiaceae) essential oils. Parasitology research. 2012 Sep; 111(3):961-6. doi: 10.1007/s00436-012-2918-6. [PMID: 22526294]
  • Katherine A Hammer, Kathryn A Heel. Use of multiparameter flow cytometry to determine the effects of monoterpenoids and phenylpropanoids on membrane polarity and permeability in staphylococci and enterococci. International journal of antimicrobial agents. 2012 Sep; 40(3):239-45. doi: 10.1016/j.ijantimicag.2012.05.015. [PMID: 22795655]
  • Erich Schmidt, Jürgen Wanner, Martina Hiiferl, Leopold Jirovetz, Gerhard Buchbauer, Velizar Gochev, Tania Girova, Albena Stoyanova, Margit Geissler. Chemical composition, olfactory analysis and antibacterial activity of Thymus vulgaris chemotypes geraniol, 4-thujanol/terpinen-4-ol, thymol and linalool cultivated in southern France. Natural product communications. 2012 Aug; 7(8):1095-8. doi: . [PMID: 22978238]
  • P J James, J T Callander. Bioactivity of tea tree oil from Melaleuca alternifolia against sheep lice (Bovicola ovis Schrank) in vitro. Veterinary parasitology. 2012 Jul; 187(3-4):498-504. doi: 10.1016/j.vetpar.2012.02.004. [PMID: 22398149]
  • Sabrine Attia, Kaouthar L Grissa, Anne C Mailleux, Stéphanie Heuskin, Georges Lognay, Thierry Hance. Acaricidal activities of Santolina africana and Hertia cheirifolia essential oils against the two-spotted spider mite (Tetranychus urticae). Pest management science. 2012 Jul; 68(7):1069-76. doi: 10.1002/ps.3269. [PMID: 22407653]
  • Li-ming Sun, Chen-lu Zhang, Ping Li. Characterization, antibiofilm, and mechanism of action of novel PEG-stabilized lipid nanoparticles loaded with terpinen-4-ol. Journal of agricultural and food chemistry. 2012 Jun; 60(24):6150-6. doi: 10.1021/jf3010405. [PMID: 22640226]
  • Olfa Baâtour, Imen Tarchoune, Hela Mahmoudi, Nawel Nassri, Wissal Abidi, Rym Kaddour, Ghaith Hamdaoui, Mouhiba Ben Nasri-Ayachi, Mohtar Lachaâl, Brahim Marzouk. Culture conditions and salt effects on essential oil composition of sweet marjoram (Origanum majorana) from Tunisia. Acta pharmaceutica (Zagreb, Croatia). 2012 Jun; 62(2):251-61. doi: 10.2478/v10007-012-0019-9. [PMID: 22750822]
  • Ibrahim Taga, Christopher Q Lan, Illimar Altosaar. Plant essential oils and mastitis disease: their potential inhibitory effects on pro-inflammatory cytokine production in response to bacteria related inflammation. Natural product communications. 2012 May; 7(5):675-82. doi: . [PMID: 22799106]
  • Alessandra Piras, Antonella Rosa, Bruno Marongiu, Angela Atzeri, M Assunta Dessì, Danilo Falconieri, Silvia Porcedda. Extraction and separation of volatile and fixed oils from seeds of Myristica fragrans by supercritical CO₂: chemical composition and cytotoxic activity on Caco-2 cancer cells. Journal of food science. 2012 Apr; 77(4):C448-53. doi: 10.1111/j.1750-3841.2012.02618.x. [PMID: 22429024]
  • 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]
  • C Morcia, M Malnati, V Terzi. In vitro antifungal activity of terpinen-4-ol, eugenol, carvone, 1,8-cineole (eucalyptol) and thymol against mycotoxigenic plant pathogens. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2012; 29(3):415-22. doi: 10.1080/19440049.2011.643458. [PMID: 22257275]
  • Ram Swaroop Verma, Rajendra Chandra Padalia, Amit Chauhan. Volatile constituents of Origanum vulgare L., 'thymol' chemotype: variability in North India during plant ontogeny. Natural product research. 2012; 26(14):1358-62. doi: 10.1080/14786419.2011.602017. [PMID: 22011270]
  • O Gudaitytė, P R Venskutonis, R Maždžierienė. Distribution and chemical polymorphism of the essential oils of Achillea cartilaginea growing wild in Lithuania. Natural product research. 2012; 26(8):722-30. doi: 10.1080/14786419.2010.551642. [PMID: 22011043]
  • G Tewari, C Pande, G Kharkwal, S Singh, C Singh. Phytochemical study of essential oil from the aerial parts of Coleus aromaticus Benth. Natural product research. 2012; 26(2):182-5. doi: 10.1080/14786419.2011.574135. [PMID: 22060194]
  • Hugo J de Boer, Vichith Lamxay, Lars Björk. Steam sauna and mother roasting in Lao PDR: practices and chemical constituents of essential oils of plant species used in postpartum recovery. BMC complementary and alternative medicine. 2011 Dec; 11(?):128. doi: 10.1186/1472-6882-11-128. [PMID: 22171719]
  • Pratibha Nand, Sushma Drabu, Rajinder K Gupta. Antimicrobial investigation of Linum usitatissimum for the treatment of acne. Natural product communications. 2011 Nov; 6(11):1701-4. doi: . [PMID: 22224292]
  • 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]
  • Olfa Baâtour, Rym Kaddour, Hela Mahmoudi, Imen Tarchoun, Iness Bettaieb, Nawel Nasri, Sabah Mrah, Ghaith Hamdaoui, Mokhtar Lachaâl, Brahim Marzouk. Salt effects on Origanum majorana fatty acid and essential oil composition. Journal of the science of food and agriculture. 2011 Nov; 91(14):2613-20. doi: 10.1002/jsfa.4495. [PMID: 21800320]
  • Ming-Hua Jiang, Li Yang, Liang Zhu, Jin-Hua Piao, Jian-Guo Jiang. Comparative GC/MS analysis of essential oils extracted by 3 methods from the bud of Citrus aurantium L. var. amara Engl. Journal of food science. 2011 Nov; 76(9):C1219-25. doi: 10.1111/j.1750-3841.2011.02421.x. [PMID: 22416680]
  • Niaz Ali, Ghayour Ahmed, Syed Wadood Ali Shah, Ismail Shah, Mehreen Ghias, Imran Khan. Acute toxicity, brine shrimp cytotoxicity and relaxant activity of fruits of callistemon citrinus curtis. BMC complementary and alternative medicine. 2011 Oct; 11(?):99. doi: 10.1186/1472-6882-11-99. [PMID: 22024247]
  • C Njume, A J Afolayan, E Green, R N Ndip. Volatile compounds in the stem bark of Sclerocarya birrea (Anacardiaceae) possess antimicrobial activity against drug-resistant strains of Helicobacter pylori. International journal of antimicrobial agents. 2011 Oct; 38(4):319-24. doi: 10.1016/j.ijantimicag.2011.05.002. [PMID: 21752604]
  • Yusei Kashima, Hidehiko Yamaki, Takuya Suzuki, Mitsuo Miyazawa. Insecticidal effect and chemical composition of the volatile oil from Bergenia ligulata. Journal of agricultural and food chemistry. 2011 Jul; 59(13):7114-9. doi: 10.1021/jf201401j. [PMID: 21639116]
  • Adeleke A Kasali, Oladipupo A Lawal, Adeolu O Eshilokun, Abayomi A Olaniyan, Andy R Opoku, William N Setzer. Citrus essential oil of Nigeria. Part V: Volatile constituents of sweet orange leaf oil (Citrus sinensis). Natural product communications. 2011 Jun; 6(6):875-8. doi: ". [PMID: 21815430]
  • B A Santos, D Roman-Campos, M S Carvalho, F M F Miranda, D C Carneiro, P H Cavalcante, E A F Cândido, L Xavier Filho, J S Cruz, A N S Gondim. Cardiodepressive effect elicited by the essential oil of Alpinia speciosa is related to L-type Ca²+ current blockade. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2011 May; 18(7):539-43. doi: 10.1016/j.phymed.2010.10.015. [PMID: 21112750]
  • Ian E Cock, Liisa Kukkonen. An examination of the medicinal potential of Scaevola spinescens: Toxicity, antibacterial, and antiviral activities. Pharmacognosy research. 2011 Apr; 3(2):85-94. doi: 10.4103/0974-8490.81955. [PMID: 21772751]
  • Christopher I Keeling, Sabrina Weisshaar, Steven G Ralph, Sharon Jancsik, Britta Hamberger, Harpreet K Dullat, Jörg Bohlmann. Transcriptome mining, functional characterization, and phylogeny of a large terpene synthase gene family in spruce (Picea spp.). BMC plant biology. 2011 Mar; 11(?):43. doi: 10.1186/1471-2229-11-43. [PMID: 21385377]
  • Donatella Pietrella, Letizia Angiolella, Elisabetta Vavala, Anna Rachini, Francesca Mondello, Rino Ragno, Francesco Bistoni, Anna Vecchiarelli. Beneficial effect of Mentha suaveolens essential oil in the treatment of vaginal candidiasis assessed by real-time monitoring of infection. BMC complementary and alternative medicine. 2011 Feb; 11(?):18. doi: 10.1186/1472-6882-11-18. [PMID: 21356078]
  • Antonio Jacinto Demuner, Luiz Claudio Almeida Barbosa, Cassia Gonçalves Magalhaes, Cleber Jose da Silva, Celia Regina Alvares Maltha, Antonio Lelis Pinheiro. Seasonal variation in the chemical composition and antimicrobial activity of volatile oils of three species of Leptospermum (Myrtaceae) grown in Brazil. Molecules (Basel, Switzerland). 2011 Jan; 16(2):1181-91. doi: 10.3390/molecules16021181. [PMID: 21270734]
  • Rhl Souza, Msp Cardoso, Ct Menezes, Jp Silva, Dp De Sousa, Js Batista. Gastroprotective activity of α-terpineol in two experimental models of gastric ulcer in rats. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences. 2011; 19(4):277-81. doi: . [PMID: 22615669]
  • Deepa Bisht, Chandan S Chanotiya. 2-undecanone rich leaf essential oil from Zanthoxylum armatum. Natural product communications. 2011 Jan; 6(1):111-4. doi: . [PMID: 21366058]
  • Tavleen S Mann, Garikapati D Kiran Babu, Shailja Guleria, Bikram Singh. Comparison of Eucalyptus cinerea essential oils produced by hydrodistillation and supercritical carbon dioxide extraction. Natural product communications. 2011 Jan; 6(1):107-10. doi: . [PMID: 21366057]
  • Aleksandra Budzyńska, Marzena Wieckowska-Szakiel, Beata Sadowska, Danuta Kalemba, Barbara Rózalska. Antibiofilm activity of selected plant essential oils and their major components. Polish journal of microbiology. 2011; 60(1):35-41. doi: . [PMID: 21630572]
  • Anil Pareek, Manish Suthar, Garvendra S Rathore, Vijay Bansal. Feverfew (Tanacetum parthenium L.): A systematic review. Pharmacognosy reviews. 2011 Jan; 5(9):103-10. doi: 10.4103/0973-7847.79105. [PMID: 22096324]
  • N J Yob, S Mohd Jofrry, M M R Meor Mohd Affandi, L K Teh, M Z Salleh, Z A Zakaria. Zingiber zerumbet (L.) Smith: A Review of Its Ethnomedicinal, Chemical, and Pharmacological Uses. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):543216. doi: 10.1155/2011/543216. [PMID: 21584247]
  • R S Verma, R C Padalia, C S Chanotiya, A Chauhan. Chemical investigation of the essential oil of Thymus linearis (Benth. ex Benth) from western Himalaya, India. Natural product research. 2010 Dec; 24(20):1890-6. doi: 10.1080/14786411003754322. [PMID: 21108114]
  • Shuhua Wu, Krupa B Patel, Leland J Booth, Jordan P Metcalf, Hsueh-Kung Lin, Wenxin Wu. Protective essential oil attenuates influenza virus infection: an in vitro study in MDCK cells. BMC complementary and alternative medicine. 2010 Nov; 10(?):69. doi: 10.1186/1472-6882-10-69. [PMID: 21078173]
  • Silvana A Rodriguez, Ana P Murray. Antioxidant activity and chemical composition of essential oil from Atriplex undulata. Natural product communications. 2010 Nov; 5(11):1841-4. doi: ". [PMID: 21213996]