Humulene (BioDeep_00000859309)

Main id: BioDeep_00000000984

 

PANOMIX_OTCML-2023


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
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

27 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



数据库引用编号

14 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)

616 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]
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