Humulene (BioDeep_00000859309)

Main id: BioDeep_00000000984

 

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


trans,trans,trans-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene

化学式: C15H24 (204.18779039999998)
中文名称: α-石竹烯, 1,4,8-环十一碳烯，2,6,6,9-四甲基-（1E，4E，8E）
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C/C/1=C\CC/C(=C/CC(C)(C)/C=C/C1)/C
InChI: InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6+,13-7+,14-10+

描述信息

α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1].
α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1].

同义名列表

29 个代谢物同义名

trans,trans,trans-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene; 1,4,8-Cycloundecatriene, 2,6,6,9-tetramethyl-, (1E,4E,8E)-; 1,4,8-Cycloundecatriene, 2,6,6,9-tetramethyl-, (E,E,E)-; (1E,4E,8E)-2,6,6,9-tetramethyl-1,4,8-cycloundecatriene; (1E,4E,8E)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene; 2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene (E,E,E)-; (E,E,E)-2,6,6,9-tetramethyl-1,4,8-cycloundecatriene; 4-05-00-01171 (Beilstein Handbook Reference); (1E,4E,8E)-humula-1(11),4,8-triene; (1E,4E,8E)-alpha-humulene; nchembio.2007.29-comp16; .alpha.-Caryophyllene; 3,7,10-Humulatriene; alpha-caryophyllene; EINECS 229-816-7; α-Caryophyllene; alpha-humulene; LMPR01030034; 53675_FLUKA; BRN 3240075; 65907-25-7; CHEBI:5768; 19132-75-3; 6753-98-6; Humulene; C09684; α-Humulene; Humulene; 1,4,8-Cycloundecatriene, 2,6,6,9-tetramethyl-, (1E,4E,8E)-



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

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)

1743 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

  • Qianqian Cheng, Bin Lyu, Jingweng Hu, Zhiqiang Zhang, Yusheng Huang, Zhenhua Wang. Research on the antipruritic active ingredients of Mikania micrantha. Fitoterapia. 2024 Jan; 174(?):105837. doi: 10.1016/j.fitote.2024.105837. [PMID: 38286314]
  • 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]
  • Naglaa S Ashmawy, Haidy A Gad, Heba A S El-Nashar. Comparative Study of Essential Oils from Different Organs of Syzygium cumini (Pamposia) Based on GC/MS Chemical Profiling and In Vitro Antiaging Activity. Molecules (Basel, Switzerland). 2023 Nov; 28(23):. doi: 10.3390/molecules28237861. [PMID: 38067590]
  • Tuan Quoc Doan, Dien Dinh, Thang Nam Tran, Phu Quynh Dinh Nguyen, Chau Bao Hoai Nguyen, Nhan Trong Le, Hung Quoc Vo, Duc Viet Ho, Anh Le Tuan, Hoai Thi Nguyen, Isiaka A Ogunwande. Chemical composition and acetylcholinesterase inhibitory activity of essential oil from the leaves of Mitrephora poilanei Weeras. & R.M.K. Saunders. Natural product research. 2023 Jun; ?(?):1-5. doi: 10.1080/14786419.2023.2227989. [PMID: 37357615]
  • Xiuyin Chen, Mindy Y Wang, Cecilia H Deng, Ron A Beatson, Kerry R Templeton, Ross G Atkinson, Niels J Nieuwenhuizen. The hops (Humulus lupulus) genome contains a mid-sized terpene synthase family that shows wide functional and allelic diversity. BMC plant biology. 2023 May; 23(1):280. doi: 10.1186/s12870-023-04283-y. [PMID: 37231379]
  • Bei Cui, Tao Zheng, Ping Deng, Sheng Zhang, Zhong Zhao. Chemotaxonomic Variation in Volatile Component Contents in Ancient Platycladus orientalis Leaves with Different Tree Ages in Huangdi Mausoleum. Molecules (Basel, Switzerland). 2023 Feb; 28(5):. doi: 10.3390/molecules28052043. [PMID: 36903288]
  • Qi Guo, Qian-Qian Peng, Ying-Ying Chen, Ping Song, Xiao-Jun Ji, He Huang, Tian-Qiong Shi. High-yield α-humulene production in Yarrowia lipolytica from waste cooking oil based on transcriptome analysis and metabolic engineering. Microbial cell factories. 2022 Dec; 21(1):271. doi: 10.1186/s12934-022-01986-z. [PMID: 36566177]
  • Qi Guo, Ya-Wen Li, Fang Yan, Ke Li, Yue-Tong Wang, Chao Ye, Tian-Qiong Shi, He Huang. Dual cytoplasmic-peroxisomal engineering for high-yield production of sesquiterpene α-humulene in Yarrowia lipolytica. Biotechnology and bioengineering. 2022 10; 119(10):2819-2830. doi: 10.1002/bit.28176. [PMID: 35798689]
  • Nurul Huda Alwakil, Mohamad Suffian Mohamad Annuar, Mahanom Jalil. Synergistic Effects of Plant Growth Regulators and Elicitors on α-Humulene and Zerumbone Production in Zingiber zerumbet Smith Adventitious Root Cultures. Molecules (Basel, Switzerland). 2022 Jul; 27(15):. doi: 10.3390/molecules27154744. [PMID: 35897918]
  • Silvia Di Giacomo, Alessia Mariano, Marco Gullì, Caterina Fraschetti, Annabella Vitalone, Antonello Filippi, Luisa Mannina, Anna Scotto d'Abusco, Antonella Di Sotto. Role of Caryophyllane Sesquiterpenes in the Entourage Effect of Felina 32 Hemp Inflorescence Phytocomplex in Triple Negative MDA-MB-468 Breast Cancer Cells. Molecules (Basel, Switzerland). 2021 Nov; 26(21):. doi: 10.3390/molecules26216688. [PMID: 34771097]
  • Xue-Long Yan, Jun-Sang, Xu Zhang, Yan Lin, Qing-De Long, Qin-Feng Zhu, Shang-Gao Liao. Euphorboside A, a cytotoxic meroterpenoid glycoside with an unusual humulene-phloroglucinol skeleton from Euphorbia kansuensis. Fitoterapia. 2021 Sep; 153(?):104966. doi: 10.1016/j.fitote.2021.104966. [PMID: 34144143]
  • Karolina Połeć, Karolina Olechowska, Amanda Klejdysz, Michał Dymek, Rafał Rachwalik, Elżbieta Sikora, Katarzyna Hąc-Wydro. The influence of ergosterol on the action of the hop oil and its major terpenes on model fungi membranes. Towards understanding the mechanism of action of phytocompounds for food and plant protection. Chemistry and physics of lipids. 2021 08; 238(?):105092. doi: 10.1016/j.chemphyslip.2021.105092. [PMID: 34000279]
  • Eduardo Valarezo, Génesis Gaona-Granda, Vladimir Morocho, Luis Cartuche, James Calva, Miguel Angel Meneses. Chemical Constituents of the Essential Oil from Ecuadorian Endemic Species Croton ferrugineus and Its Antimicrobial, Antioxidant and α-Glucosidase Inhibitory Activity. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154608. [PMID: 34361759]
  • Sofia Milker, Anne Sydow, Ingrid Torres-Monroy, Guido Jach, Frederik Faust, Lea Kranz, Ljubov Tkatschuk, Dirk Holtmann. Gram-scale production of the sesquiterpene α-humulene with Cupriavidus necator. Biotechnology and bioengineering. 2021 07; 118(7):2694-2702. doi: 10.1002/bit.27788. [PMID: 33844284]
  • Fumin Wang, Yong-Lak Park, Michael Gutensohn. Glandular Trichome-Derived Mono- and Sesquiterpenes of Tomato Have Contrasting Roles in the Interaction with the Potato Aphid Macrosiphum euphorbiae. Journal of chemical ecology. 2021 Feb; 47(2):204-214. doi: 10.1007/s10886-021-01243-4. [PMID: 33447946]
  • Mohammad Firoznejhad, Abdollah Ghasemi Pirbalouti, Vahid Abdoosi, Atousa Aliahmadi. Chemical composition of essential oils from the underground parts of Glycyrrhiza echinata L. accessions growing wild in Northern Iran. Natural product research. 2021 Jan; 35(1):162-166. doi: 10.1080/14786419.2019.1616721. [PMID: 31165644]
  • Didjour Albert Kambiré, Acafou Thierry Yapi, Jean Brice Boti, Zana Adama Ouattara, Zanahi Félix Tonzibo, Jean-Jacques Filippi, Ange Bighelli, Félix Tomi. Two new eudesman-4α-ol epoxides from the stem essential oil of Laggera pterodonta from Côte d'Ivoire. Natural product research. 2020 Oct; 34(19):2765-2771. doi: 10.1080/14786419.2019.1586701. [PMID: 30908078]
  • Anh Duc Nguyen, Donghyuk Kim, Eun Yeol Lee. Unlocking the biosynthesis of sesquiterpenoids from methane via the methylerythritol phosphate pathway in methanotrophic bacteria, using α-humulene as a model compound. Metabolic engineering. 2020 09; 61(?):69-78. doi: 10.1016/j.ymben.2020.04.011. [PMID: 32387228]
  • T Soumya, P R Jayasree, M Deepak, P R Manish Kumar. Chemical composition, antioxidant and antiproliferative activities of essential oil from rhizome and leaves of Curcuma mutabilis Škorničk., M. Sabu & Prasanthk., endemic to Western Ghats of India. Natural product research. 2020 Aug; 34(16):2336-2340. doi: 10.1080/14786419.2018.1533826. [PMID: 30724591]
  • Amanda Moreno-Rodríguez, Rosario Santos-Castro, Josefina Vázquez-Medrano, Rafael E Quintanar-Zúñiga, Fernando A García-García, Luis B Hernández-Portilla, Cesar M Flores-Ortiz. Effect of jasmonic acid on major terpenes and density of glandular trichomes in Lippia graveolens kunth (Verbenaceae). Natural product research. 2020 Jul; 34(13):1942-1946. doi: 10.1080/14786419.2019.1566721. [PMID: 30724587]
  • Sonal Shah, Tushar Dhanani, Sonu Sharma, Raghuraj Singh, Satyanshu Kumar, Bhanu Kumar, Sharad Srivastava, Srikant Ghosh, Rajesh Kumar, Sanis Juliet. Development and Validation of a Reversed Phase High Performance Liquid Chromatography-Photodiode Array Detection Method for Simultaneous Identification and Quantification of Coumarin, Precocene-I, β-Caryophyllene Oxide, α-Humulene, and β-Caryophyllene in Ageratum Conyzoides Extracts and Essential Oils from Plants. Journal of AOAC International. 2020 Jun; 103(3):857-864. doi: 10.1093/jaoacint/qsz038. [PMID: 33241362]
  • Hye-In Jang, Ki-Jong Rhee, Yong-Bin Eom. Antibacterial and antibiofilm effects of α-humulene against Bacteroides fragilis. Canadian journal of microbiology. 2020 Jun; 66(6):389-399. doi: 10.1139/cjm-2020-0004. [PMID: 32073898]
  • Hao Chen, Jingquan Yuan, Ji Hao, Yanzhang Wen, Yibing Lv, Lu Chen, Xinzhou Yang. α-Humulene inhibits hepatocellular carcinoma cell proliferation and induces apoptosis through the inhibition of Akt signaling. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 Dec; 134(?):110830. doi: 10.1016/j.fct.2019.110830. [PMID: 31562948]
  • E A J Silva, E B B Estevam, T S Silva, H D Nicolella, R A Furtado, C C F Alves, E L Souchie, C H G Martins, D C Tavares, L C A Barbosa, M L D Miranda. Antibacterial and antiproliferative activities of the fresh leaf essential oil of Psidium guajava L. (Myrtaceae). Brazilian journal of biology = Revista brasleira de biologia. 2019 Oct; 79(4):697-702. doi: 10.1590/1519-6984.189089. [PMID: 30462815]
  • Abeer A Mohamed, Said I Behiry, Hosny A Younes, Nader A Ashmawy, Mohamed Z M Salem, Ofelia Márquez-Molina, Alberto Barbabosa-Pilego. Antibacterial activity of three essential oils and some monoterpenes against Ralstonia solanacearum phylotype II isolated from potato. Microbial pathogenesis. 2019 Oct; 135(?):103604. doi: 10.1016/j.micpath.2019.103604. [PMID: 31247257]
  • Michaela Šadibolová, Tomáš Zárybnický, Tomáš Smutný, Petr Pávek, Zdeněk Šubrt, Petra Matoušková, Lenka Skálová, Iva Boušová. Sesquiterpenes Are Agonists of the Pregnane X Receptor but Do Not Induce the Expression of Phase I Drug-Metabolizing Enzymes in the Human Liver. International journal of molecular sciences. 2019 Sep; 20(18):. doi: 10.3390/ijms20184562. [PMID: 31540101]
  • Alline L B Dias, Hellen R F Batista, Elisângela B B Estevam, Cassia C F Alves, Moacir R Forim, Heloiza D Nicolella, Ricardo A Furtado, Denise C Tavares, Thayna S Silva, Carlos H G Martins, Mayker L D Miranda. Chemical composition and in vitro antibacterial and antiproliferative activities of the essential oil from the leaves of Psidium myrtoides O. Berg (Myrtaceae). Natural product research. 2019 Sep; 33(17):2566-2570. doi: 10.1080/14786419.2018.1457664. [PMID: 29611435]
  • Gilcy George Kallivalappil, Girija Kuttan. Evaluation of the anti-inflammatory and urotoxicity ameliorative effects of γ-humulene containing active fraction of Emilia sonchifolia (L.) DC. Inflammopharmacology. 2019 Apr; 27(2):409-420. doi: 10.1007/s10787-017-0423-3. [PMID: 29224178]
  • Hai Ming Zhang, Shan Shan Guo, Bin Fan, Shu Shan Du, Yong Yan Wang, Zhi Wei Deng. Evaluation of efficacy of the essential oil from Ostericum viridiflorum (Turcz.) Kitagawa in control of stored product insects. Environmental science and pollution research international. 2019 Jan; 26(2):1406-1413. doi: 10.1007/s11356-018-3728-x. [PMID: 30426372]
  • Sandra Márcia Mazutti da Silva, Claudio Rodrigues Rezende Costa, Guilherme Martins Gelfuso, Eliete Neves Silva Guerra, Yanna Karla de Medeiros Nóbrega, Sueli Maria Gomes, Aline Pic-Taylor, Yris Maria Fonseca-Bazzo, Damaris Silveira, Pérola de Oliveira Magalhães. Wound Healing Effect of Essential Oil Extracted from Eugenia dysenterica DC (Myrtaceae) Leaves. Molecules (Basel, Switzerland). 2018 Dec; 24(1):. doi: 10.3390/molecules24010002. [PMID: 30577426]
  • Ekaterina Jeliazkova, Valtcho D Zheljazkov, Miroslava Kačániova, Tess Astatkie, Babu L Tekwani. Sequential Elution of Essential Oil Constituents during Steam Distillation of Hops (Humulus lupulus L.) and Influence on Oil Yield and Antimicrobial Activity. Journal of oleo science. 2018 Jul; 67(7):871-883. doi: 10.5650/jos.ess17216. [PMID: 29877222]
  • Raju Sripathi, Dharani Jayagopal, Subban Ravi. A study on the seasonal variation of the essential oil composition from Plectranthus hadiensis and its antibacterial activity. Natural product research. 2018 Apr; 32(7):871-874. doi: 10.1080/14786419.2017.1363748. [PMID: 28783957]
  • Giovanni Benelli, Mohan Rajeswary, Marimuthu Govindarajan. Towards green oviposition deterrents? Effectiveness of Syzygium lanceolatum (Myrtaceae) essential oil against six mosquito vectors and impact on four aquatic biological control agents. Environmental science and pollution research international. 2018 Apr; 25(11):10218-10227. doi: 10.1007/s11356-016-8146-3. [PMID: 27921244]
  • Thomas Krieg, Anne Sydow, Sonja Faust, Ina Huth, Dirk Holtmann. CO2 to Terpenes: Autotrophic and Electroautotrophic α-Humulene Production with Cupriavidus necator. Angewandte Chemie (International ed. in English). 2018 02; 57(7):1879-1882. doi: 10.1002/anie.201711302. [PMID: 29232490]
  • Giovanni Benelli, Marimuthu Govindarajan, Mohan Rajeswary, Baskaralingam Vaseeharan, Sami A Alyahya, Naiyf S Alharbi, Shine Kadaikunnan, Jamal M Khaled, Filippo Maggi. Insecticidal activity of camphene, zerumbone and α-humulene from Cheilocostus speciosus rhizome essential oil against the Old-World bollworm, Helicoverpa armigera. Ecotoxicology and environmental safety. 2018 Feb; 148(?):781-786. doi: 10.1016/j.ecoenv.2017.11.044. [PMID: 29190597]
  • Zhehao Jin, Moonhyuk Kwon, Ah-Reum Lee, Dae-Kyun Ro, Juraithip Wungsintaweekul, Soo-Un Kim. Molecular cloning and functional characterization of three terpene synthases from unripe fruit of black pepper (Piper nigrum). Archives of biochemistry and biophysics. 2018 01; 638(?):35-40. doi: 10.1016/j.abb.2017.12.011. [PMID: 29248443]
  • Linh Thuy Nguyen, Zuzana Myslivečková, Barbora Szotáková, Alena Špičáková, Kateřina Lněničková, Martin Ambrož, Vladimír Kubíček, Kristýna Krasulová, Pavel Anzenbacher, Lenka Skálová. The inhibitory effects of β-caryophyllene, β-caryophyllene oxide and α-humulene on the activities of the main drug-metabolizing enzymes in rat and human liver in vitro. Chemico-biological interactions. 2017 Dec; 278(?):123-128. doi: 10.1016/j.cbi.2017.10.021. [PMID: 29074051]
  • Abolfazl Shakeri, Javad Akhtari, Vahid Soheili, Seyedeh Faezeh Taghizadeh, Amirhossein Sahebkar, Rezvan Shaddel, Javad Asili. Identification and biological activity of the volatile compounds of Glycyrrhiza triphylla Fisch. & C.A.Mey. Microbial pathogenesis. 2017 Aug; 109(?):39-44. doi: 10.1016/j.micpath.2017.05.022. [PMID: 28526637]
  • Manel Boumaraf, Marianna Carbone, M Letizia Ciavatta, Samira Benyahia, Souad Ameddah, Ahmed Menad, Samir Benayache, Fadila Benayache, Margherita Gavagnin. Exploring the Bioactive Terpenoid Content of an Algerian Plant of the Genus Pulicaria: The ent-Series of Asteriscunolides. Journal of natural products. 2017 01; 80(1):82-89. doi: 10.1021/acs.jnatprod.6b00717. [PMID: 28032767]
  • Judith K Booth, Jonathan E Page, Jörg Bohlmann. Terpene synthases from Cannabis sativa. PloS one. 2017; 12(3):e0173911. doi: 10.1371/journal.pone.0173911. [PMID: 28355238]
  • Umberto Salvagnin, Silvia Carlin, Sergio Angeli, Urska Vrhovsek, Gianfranco Anfora, Mickael Malnoy, Stefan Martens. Homologous and heterologous expression of grapevine E-(β)-caryophyllene synthase (VvGwECar2). Phytochemistry. 2016 Nov; 131(?):76-83. doi: 10.1016/j.phytochem.2016.08.002. [PMID: 27561253]
  • Ming-Chi Wei, Jianbo Xiao, Yu-Chiao Yang. Extraction of α-humulene-enriched oil from clove using ultrasound-assisted supercritical carbon dioxide extraction and studies of its fictitious solubility. Food chemistry. 2016 Nov; 210(?):172-81. doi: 10.1016/j.foodchem.2016.04.076. [PMID: 27211636]
  • Haruhisa Kikuchi, Takehiro Nishimura, Eunsang Kwon, Junya Kawai, Yoshiteru Oshima. Development of a Terpenoid Alkaloid-like Compound Library Based on the Humulene Skeleton. Chemistry (Weinheim an der Bergstrasse, Germany). 2016 Oct; 22(44):15819-15825. doi: 10.1002/chem.201603224. [PMID: 27624861]
  • Marimuthu Govindarajan, Giovanni Benelli. α-Humulene and β-elemene from Syzygium zeylanicum (Myrtaceae) essential oil: highly effective and eco-friendly larvicides against Anopheles subpictus, Aedes albopictus, and Culex tritaeniorhynchus (Diptera: Culicidae). Parasitology research. 2016 Jul; 115(7):2771-8. doi: 10.1007/s00436-016-5025-2. [PMID: 27026503]
  • Jorge Triana, José Luis Eiroa, Manuel Morales, Francisco J Perez, Ignacio Brouard, José Quintana, Mercedes Ruiz-Estévez, Francisco Estévez, Francisco León. Sesquiterpenoids Isolated from Two Species of the Asteriscus Alliance. Journal of natural products. 2016 05; 79(5):1292-7. doi: 10.1021/acs.jnatprod.5b01013. [PMID: 27145162]
  • Marimuthu Govindarajan, Mohan Rajeswary, Subramanian Arivoli, Samuel Tennyson, Giovanni Benelli. Larvicidal and repellent potential of Zingiber nimmonii (J. Graham) Dalzell (Zingiberaceae) essential oil: an eco-friendly tool against malaria, dengue, and lymphatic filariasis mosquito vectors?. Parasitology research. 2016 May; 115(5):1807-16. doi: 10.1007/s00436-016-4920-x. [PMID: 26792432]
  • Ramesha H Jayaramaiah, Atul Anand, Supriya D Beedkar, Bhushan B Dholakia, Sachin A Punekar, Raviraj M Kalunke, Wasudeo N Gade, Hirekodathakallu V Thulasiram, Ashok P Giri. Functional characterization and transient expression manipulation of a new sesquiterpene synthase involved in β-caryophyllene accumulation in Ocimum. Biochemical and biophysical research communications. 2016 Apr; 473(1):265-271. doi: 10.1016/j.bbrc.2016.03.090. [PMID: 27005818]
  • Fatma Zohra Rahali, Myriam Lamine, Mahmoud Gargouri, Iness Bettaieb Rebey, Majdi Hammami, Ibtissem Hamrouni Sellami. Metabolite profiles of essential oils and molecular markers analysis to explore the biodiversity of Ferula communis: Towards conservation of the endemic giant fennel. Phytochemistry. 2016 Apr; 124(?):58-67. doi: 10.1016/j.phytochem.2016.01.012. [PMID: 26826740]
  • Rajesh K Joshi. Leucas aspera (Willd.) Link Essential Oil from India: β-Caryophyllene and 1-Octen-3-ol Chemotypes. Journal of chromatographic science. 2016 Mar; 54(3):295-8. doi: 10.1093/chromsci/bmv173. [PMID: 26620424]
  • Tarannum Naz, Joanne Packer, Ping Yin, Joseph J Brophy, Hans Wohlmuth, Dane E Renshaw, Joshua Smith, Yaegl Community Elders, Subramanyam R Vemulpad, Joanne F Jamie. Bioactivity and chemical characterisation of Lophostemon suaveolens--an endemic Australian Aboriginal traditional medicinal plant. Natural product research. 2016; 30(6):693-6. doi: 10.1080/14786419.2015.1038260. [PMID: 25942679]
  • Joseph J Brophy, John R Clarkson, Myrna A Deseo, Andrew J Ford, Douglas J Lawes, David N Leach. The Leaf Essential Oil of Eugenia reinwardtiana Growing in Australia. Natural product communications. 2015 Sep; 10(9):1611-4. doi: . [PMID: 26594771]
  • Chiaki Kuroda, Kou Inagaki, Xun Chao, Kyosuke Inoue, Yasuko Okamoto, Motoo Tori, Xun Gong, Ryo Hanai. Chemical and Genetic Diversity of Ligularia hodgsonii in China. Natural product communications. 2015 Jun; 10(6):823-6. doi: . [PMID: 26197490]
  • 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]
  • Emmanoel V Costa, Leociley R A Menezes, Suellen L A Rocha, Ingrid R S Baliza, Rosane B Dias, Clarissa A Gurgel Rocha, Milena B P Soares, Daniel P Bezerra. Antitumor Properties of the leaf essential oil of Zornia brasiliensis. Planta medica. 2015 May; 81(7):563-7. doi: 10.1055/s-0035-1545842. [PMID: 25856436]
  • Shanmugam Krishnamoorthy, Manivachagam Chandrasekaran, Gnanaprakasam Adaikala Raj, Mahalingam Jayaraman, Venugopalan Venkatesalu. Identification of chemical constituents and larvicidal activity of essential oil from Murraya exotica L. (Rutaceae) against Aedes aegypti, Anopheles stephensi and Culex quinquefasciatus (Diptera: Culicidae). Parasitology research. 2015 May; 114(5):1839-45. doi: 10.1007/s00436-015-4370-x. [PMID: 25697880]
  • Yi Cai, Feng-feng Xie, Ping-hua Yan, Ri-cheng Gan, Hua Zhu. [Volatile Oil Analysis of Piper hongkongense form Different Hatbitats by GC-MS]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Feb; 38(2):323-6. doi: ". [PMID: 26415410]
  • Rayane Cristine Santos da Silva, Paulo Milet-Pinheiro, Patrícia Cristina Bezerra da Silva, Alexandre Gomes da Silva, Marcia Vanusa da Silva, Daniela Maria do Amaral Ferraz Navarro, Nicácio Henrique da Silva. (E)-Caryophyllene and α-Humulene: Aedes aegypti Oviposition Deterrents Elucidated by Gas Chromatography-Electrophysiological Assay of Commiphora leptophloeos Leaf Oil. PloS one. 2015; 10(12):e0144586. doi: 10.1371/journal.pone.0144586. [PMID: 26650757]
  • Mitsuo Miyazawa, Yoshimi Nakashima, Hiroshi Nakahashi, Nobuyuki Hara, Hiroki Nakagawa, Atsushi Usami, Warinthorn Chavasiri. Volatile Compounds with Characteristic Odor of Essential Oil from Magnolia obovata Leaves by Hydrodistillation and Solvent-assisted Flavor Evaporation. Journal of oleo science. 2015; 64(9):999-1007. doi: 10.5650/jos.ess15114. [PMID: 26250428]
  • Pankaj Sharma, G C Shah. Composition and antioxidant activity of Senecio nudicaulis Wall. ex DC. (Asteraceae): a medicinal plant growing wild in Himachal Pradesh, India. Natural product research. 2015; 29(9):883-6. doi: 10.1080/14786419.2014.990904. [PMID: 25515495]
  • Saoussen Hammami, Ridha El Mokni, Khaled Faidi, Danilo Falconieri, Alessandra Piras, Silvia Procedda, Zine Mighri, Mohamed Hédi El Aouni. Chemical composition and antioxidant activity of essential oil from aerial parts of Teucrium flavum L. subsp. flavum growing spontaneously in Tunisia. Natural product research. 2015; 29(24):2336-40. doi: 10.1080/14786419.2015.1010162. [PMID: 25687213]
  • Kamala Jayanthi Pagadala Damodaram, Vivek Kempraj, Ravindra Mahadappa Aurade, Sowmya Bandhisara Rajasekhar, Ravindra Kothapalli Venkataramanappa, Bakthavatsalam Nandagopal, Abraham Verghese. Centuries of domestication has not impaired oviposition site-selection function in the silkmoth, Bombyx mori. Scientific reports. 2014 Dec; 4(?):7472. doi: 10.1038/srep07472. [PMID: 25503440]
  • N Shashiashvili, M Jokhadze, P Tushurashvili, A Bakuridze, D Berashvili. Analysis of Perilla nankinensis decne essential oil using gas chromatography coupled with time-of-flight mass spectrometry. Georgian medical news. 2014 Apr; ?(229):92-6. doi: ". [PMID: 24850613]
  • D Keerthi, C Geethu, R Aswati Nair, Padmesh Pillai. Metabolic profiling of Zingiber zerumbet following Pythium myriotylum infection: investigations on the defensive role of the principal secondary metabolite, zerumbone. Applied biochemistry and biotechnology. 2014 Mar; 172(5):2593-603. doi: 10.1007/s12010-013-0707-z. [PMID: 24414941]
  • Yu-Chiao Yang, Ming-Chi Wei, Show-Jen Hong. Ultrasound-assisted extraction and quantitation of oils from Syzygium aromaticum flower bud (clove) with supercritical carbon dioxide. Journal of chromatography. A. 2014 Jan; 1323(?):18-27. doi: 10.1016/j.chroma.2013.10.098. [PMID: 24290173]
  • Tran D Thang, Do N Dai, Ngo X Luong, Isiaka A Ogunwande. Constituents of essential oils from the leaves, stem barks and resins of Canarium parvum Leen., and Canarium tramdenanum Dai et Yakovl. (Burseracea) grown in Vietnam. Natural product research. 2014; 28(7):461-6. doi: 10.1080/14786419.2013.873435. [PMID: 24443833]
  • Megumi Iwasa, Toshiki Iwasaki, Toshirou Ono, Mitsuo Miyazawa. Chemical composition and major odor-active compounds of essential oil from PINELLIA TUBER (dried rhizome of Pinellia ternata) as crude drug. Journal of oleo science. 2014; 63(2):127-35. doi: 10.5650/jos.ess13092. [PMID: 24500103]
  • Nantiya Joycharat, Sonesay Thammavong, Supayang Piyawan Voravuthikunchai, Patimaporn Plodpai, Watcharapong Mitsuwan, Surasak Limsuwan, Sanan Subhadhirasakul. Chemical constituents and antimicrobial properties of the essential oil and ethanol extract from the stem of Aglaia odorata Lour. Natural product research. 2014; 28(23):2169-72. doi: 10.1080/14786419.2014.924934. [PMID: 24934340]
  • Mitsuru Satoh, Yoshio Satoh, Yasuhiro Anzai, Daisuke Ajisawa, Keiichi Matsuzaki, Mitsuko Makino, Yasuo Fujimotod. New humulenes from Hyptis incana (Labiatae). Natural product communications. 2013 Dec; 8(12):1665-8. doi: . [PMID: 24555267]
  • Vinícius Raphael de Almeida Borges, Ana Ferreira Ribeiro, Carina de Souza Anselmo, Lúcio Mendes Cabral, Valéria Pereira de Sousa. Development of a high performance liquid chromatography method for quantification of isomers β-caryophyllene and α-humulene in copaiba oleoresin using the Box-Behnken design. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Dec; 940(?):35-41. doi: 10.1016/j.jchromb.2013.09.024. [PMID: 24140654]
  • Chang-Qing Yang, Xiu-Ming Wu, Ju-Xin Ruan, Wen-Li Hu, Yin-Bo Mao, Xiao-Ya Chen, Ling-Jian Wang. Isolation and characterization of terpene synthases in cotton (Gossypium hirsutum). Phytochemistry. 2013 Dec; 96(?):46-56. doi: 10.1016/j.phytochem.2013.09.009. [PMID: 24074555]
  • Xinzheng Huang, Yutao Xiao, Tobias G Köllner, Wanna Zhang, Junxiang Wu, Juan Wu, Yuyuan Guo, Yongjun Zhang. Identification and characterization of (E)-β-caryophyllene synthase and α/β-pinene synthase potentially involved in constitutive and herbivore-induced terpene formation in cotton. Plant physiology and biochemistry : PPB. 2013 Dec; 73(?):302-8. doi: 10.1016/j.plaphy.2013.10.017. [PMID: 24184450]
  • Laura Vázquez-Araújo, Raquel Rodríguez-Solana, Sandra M Cortés-Diéguez, José M Domínguez. Use of hydrodistillation and headspace solid-phase microextraction to characterize the volatile composition of different hop cultivars. Journal of the science of food and agriculture. 2013 Aug; 93(10):2568-74. doi: 10.1002/jsfa.6078. [PMID: 23483584]
  • Z Laznik, S Trdan. An investigation on the chemotactic responses of different entomopathogenic nematode strains to mechanically damaged maize root volatile compounds. Experimental parasitology. 2013 Jul; 134(3):349-55. doi: 10.1016/j.exppara.2013.03.030. [PMID: 23562713]
  • Christelle Aurélie Maud Robert, Matthias Erb, Ivan Hiltpold, Bruce Elliott Hibbard, Mickaël David Philippe Gaillard, Julia Bilat, Jörg Degenhardt, Xavier Cambet-Petit-Jean, Ted Christiaan Joannes Turlings, Claudia Zwahlen. Genetically engineered maize plants reveal distinct costs and benefits of constitutive volatile emissions in the field. Plant biotechnology journal. 2013 Jun; 11(5):628-39. doi: 10.1111/pbi.12053. [PMID: 23425633]
  • Jian-Xu Li, Xin Fang, Qin Zhao, Ju-Xin Ruan, Chang-Qing Yang, Ling-Jian Wang, David J Miller, Juan A Faraldos, Rudolf K Allemann, Xiao-Ya Chen, Peng Zhang. Rational engineering of plasticity residues of sesquiterpene synthases from Artemisia annua: product specificity and catalytic efficiency. The Biochemical journal. 2013 May; 451(3):417-26. doi: 10.1042/bj20130041. [PMID: 23438177]
  • Miguel Angel Calleja, Jose María Vieites, Trinidad Montero-Meléndez, Trinidad Montero-Meterdez, María Isabel Torres, María José Faus, Angel Gil, Antonio Suárez. The antioxidant effect of β-caryophyllene protects rat liver from carbon tetrachloride-induced fibrosis by inhibiting hepatic stellate cell activation. The British journal of nutrition. 2013 Feb; 109(3):394-401. doi: 10.1017/s0007114512001298. [PMID: 22717234]
  • Tran D Thang, Le T Huong, Do N Dai, Isiaka A Ogunwande. A comparative analysis of essential oils of Goniothalamus macrocalyx Ban., Goniothalamus albiflorus Ban. and Goniothalamus tamirensis Pierre ex Fin. & Gagnep. from Vietnam. Natural product research. 2013; 27(21):1999-2005. doi: 10.1080/14786419.2013.814051. [PMID: 23822670]
  • Yuan Gao, Gang-Qiang Wang, Kun Wei, Ping Hai, Fei Wang, Ji-Kai Liu. Isolation and biomimetic synthesis of (±)-guajadial B, a novel meroterpenoid from Psidium guajava. Organic letters. 2012 Dec; 14(23):5936-9. doi: 10.1021/ol302849v. [PMID: 23163238]
  • Fengnian Yu, Sho Okamoto, Hisashi Harada, Kazuhisa Yamasaki, Norihiko Misawa, Ryutaro Utsumi. Zingiber zerumbet CYP71BA1 catalyzes the conversion of α-humulene to 8-hydroxy-α-humulene in zerumbone biosynthesis. Cellular and molecular life sciences : CMLS. 2011 Mar; 68(6):1033-40. doi: 10.1007/s00018-010-0506-4. [PMID: 20730551]
  • Ling Chai, Chao-Zhan Lin, Chen-Chen Zhu, Zhong-Xiang Zhao, Cui-Xian Zhang. [Analysis of the chemical constituents of essential oil from the leaves of Callicarpa integerrima]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2010 Mar; 33(3):382-5. doi: . [PMID: 20681304]
  • Alexandre P Rogerio, Edinéia L Andrade, Daniela F P Leite, Cláudia P Figueiredo, João B Calixto. Preventive and therapeutic anti-inflammatory properties of the sesquiterpene alpha-humulene in experimental airways allergic inflammation. British journal of pharmacology. 2009 Oct; 158(4):1074-87. doi: 10.1111/j.1476-5381.2009.00177.x. [PMID: 19438512]
  • Ping-Chuan Jiang, Jun Zhou, Bin Cao, Gui-Ning Wei, Kai-Jia He, Bu-Ming Liu. [Study on the volatile oil of Murraya exotica]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Aug; 32(8):1224-7. doi: . [PMID: 19960942]
  • Akinola O Ogunbinu, Guido Flamini, Pier L Cioni, Isiaka A Ogunwande, Sunday O Okeniyi. Essential oil constituents of Eclipta prostrata (L.) L. and Vernonia amygdalina Delile. Natural product communications. 2009 Mar; 4(3):421-4. doi: ". [PMID: 19413125]
  • Rosa Tundis, Monica R Loizzo, Marco Bonesi, Federica Menichini, Daniela Dodaro, Nicodemo G Passalacqua, Giancarlo Statti, Francesco Menichini. In vitro cytotoxic effects of Senecio stabianus Lacaita (Asteraceae) on human cancer cell lines. Natural product research. 2009; 23(18):1707-18. doi: 10.1080/14786410802194151. [PMID: 19921589]
  • Juliana Siqueira Chaves, Paulo César Leal, Luis Pianowisky, João B Calixto. Pharmacokinetics and tissue distribution of the sesquiterpene alpha-humulene in mice. Planta medica. 2008 Nov; 74(14):1678-83. doi: 10.1055/s-0028-1088307. [PMID: 18951339]
  • Somdej Kanokmedhakul, Kwanjai Kanokmedhakul, Ratsami Lekphrom. Bioactive constituents of the roots of Polyalthia cerasoides. Journal of natural products. 2007 Sep; 70(9):1536-8. doi: 10.1021/np070293a. [PMID: 17845001]
  • Elizabeth S Fernandes, Giselle F Passos, Rodrigo Medeiros, Fernanda M da Cunha, Juliano Ferreira, Maria M Campos, Luiz F Pianowski, João B Calixto. Anti-inflammatory effects of compounds alpha-humulene and (-)-trans-caryophyllene isolated from the essential oil of Cordia verbenacea. European journal of pharmacology. 2007 Aug; 569(3):228-36. doi: 10.1016/j.ejphar.2007.04.059. [PMID: 17559833]
  • Muriel Sylvestre, André Pichette, Serge Lavoie, Angélique Longtin, Jean Legault. Composition and cytotoxic activity of the leaf essential oil of Comptonia peregrina (L.) Coulter. Phytotherapy research : PTR. 2007 Jun; 21(6):536-40. doi: 10.1002/ptr.2095. [PMID: 17326040]
  • Giselle F Passos, Elizabeth S Fernandes, Fernanda M da Cunha, Juliano Ferreira, Luiz F Pianowski, Maria M Campos, João B Calixto. Anti-inflammatory and anti-allergic properties of the essential oil and active compounds from Cordia verbenacea. Journal of ethnopharmacology. 2007 Mar; 110(2):323-33. doi: 10.1016/j.jep.2006.09.032. [PMID: 17084568]
  • Leopold Jirovetz, Gerhard Buchbauer, Ivanka Stoilova, Albena Stoyanova, Albert Krastanov, Erich Schmidt. Chemical composition and antioxidant properties of clove leaf essential oil. Journal of agricultural and food chemistry. 2006 Aug; 54(17):6303-7. doi: 10.1021/jf060608c. [PMID: 16910723]
  • Alessandro Musenga, Anna Ferranti, Maria Addolorata Saracino, Salvatore Fanali, Maria Augusta Raggi. Simultaneous determination of aromatic and terpenic constituents of cloves by means of HPLC with diode array detection. Journal of separation science. 2006 Jun; 29(9):1251-8. doi: 10.1002/jssc.200600023. [PMID: 16833083]
  • Yong-Suk Kim, Dong-Hwa Shin. Volatile constituents from the leaves of Callicarpa japonica Thunb. and their antibacterial activities. Journal of agricultural and food chemistry. 2004 Feb; 52(4):781-7. doi: 10.1021/jf034936d. [PMID: 14969531]
  • Jian-hua Liu, Yu-qiong Gao, Xin Huo. [Studies on the chemical constituents of the volatile oil from Radix Cudramiae]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2003 Nov; 28(11):1047-9. doi: ". [PMID: 15615414]
  • Jean Legault, Wivecke Dahl, Eric Debiton, André Pichette, Jean-Claude Madelmont. Antitumor activity of balsam fir oil: production of reactive oxygen species induced by alpha-humulene as possible mechanism of action. Planta medica. 2003 May; 69(5):402-7. doi: 10.1055/s-2003-39695. [PMID: 12802719]
  • A P Rauter, I Branco, J Bermejo, A G González, M D García-Grávalos, A S Feliciano. Bioactive humulene derivatives from Asteriscus vogelii. Phytochemistry. 2001 Jan; 56(2):167-71. doi: 10.1016/s0031-9422(00)00304-6. [PMID: 11219809]
  • A Murakami, M Takahashi, S Jiwajinda, K Koshimizu, H Ohigashi. Identification of zerumbone in Zingiber zerumbet Smith as a potent inhibitor of 12-O-tetradecanoylphorbol-13-acetate-induced Epstein-Barr virus activation. Bioscience, biotechnology, and biochemistry. 1999 Oct; 63(10):1811-2. doi: 10.1271/bbb.63.1811. [PMID: 10586508]
  • W Zhang, H Chen. [Studies on the chemical constituents of essential oil from roots and rhizomes of Patrinia rupestris]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 1999 Aug; 22(8):403-4. doi: ". [PMID: 12571887]
  • G Q Zheng, P M Kenney, L K Lam. Sesquiterpenes from clove (Eugenia caryophyllata) as potential anticarcinogenic agents. Journal of natural products. 1992 Jul; 55(7):999-1003. doi: 10.1021/np50085a029. [PMID: 1402962]
  • S Fujita. [Miscellaneous contributions to the essential oils of plants from various territories. LI. On the components of essential oils of Torilis japonica (Houtt.) DC]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1990 Oct; 110(10):771-5. doi: 10.1248/yakushi1947.110.10_771. [PMID: 2074533]