Verbinone (BioDeep_00000000972)

 

Secondary id: BioDeep_00000398726

human metabolite PANOMIX_OTCML-2023 blood metabolite Volatile Flavor Compounds


代谢物信息卡片


Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R-cis)-

化学式: C10H14O (150.1044594)
中文名称: 马鞭草烯酮, 马苄烯酮, 马鞭草酮, (-)-马鞭烯酮
谱图信息: 最多检出来源 Homo sapiens(blood) 2.04%

分子结构信息

SMILES: CC1=CC(=O)C2CC1C2(C)C
InChI: InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3

描述信息

Verbenone, also known as verbenone, (1r)-isomer, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Verbenone is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Verbenone is a camphor, celery, and menthol tasting compound and can be found in a number of food items such as spearmint, cabbage, white cabbage, and rosemary, which makes verbenone a potential biomarker for the consumption of these food products. Verbenone is a natural organic compound classified as a terpene that is found naturally in a variety of plants. The chemical has a pleasant characteristic odor. Besides being a natural constituent of plants, it and its analogs are insect pheromones. In particular, verbenone when formulated in a long-lasting matrix has an important role in the control of bark beetles such as the mountain pine beetle and the Southern pine bark beetle .
4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one is a carbobicyclic compound that is bicyclo[3.1.1]heptane which is substituted by an oxo group at position 2 and by methyl groups at positions 4, 6 and 6, and which contains a double bond between positions 3 and 4. It is a carbobicyclic compound, a cyclic ketone and an enone.
Verbenone is a natural product found in Eucalyptus fasciculosa, Eucalyptus intertexta, and other organisms with data available.
Verbenone ((-)-Verbenone) is a natural terpene in leaves of the tree, Verbena officinalis[1]. Verbenone has anti-aggregation pheromone and interrupts the attraction of bark beetles to their aggregation pheromones[2].
Verbenone ((-)-Verbenone) is a natural terpene in leaves of the tree, Verbena officinalis[1]. Verbenone has anti-aggregation pheromone and interrupts the attraction of bark beetles to their aggregation pheromones[2].

同义名列表

35 个代谢物同义名

Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R-cis)-; Bicyclo[3.1.1]hept-3-en-2-one,4,6,6-trimethyl-, (1R,5R)-; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1R-cis)-; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1S,5S)-; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1R,5R)-; Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R)-; Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1S)-; (1R-cis)-4,6,6-Trimethylbicyclo(3.1.1)hept-3-ene-2-one; (-)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one; 2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-one; 2-Pinen-4-one, (1S,5S)-(-)-; (1s)-(-)-pin-2-en-4-one; verbenone, (1R)-isomer; verbenone, (1S)-isomer; verbenone, (+-)-isomer; (-)-cis-verbenone; (-)-2-Pinen-4-one; (S)-(-)-Verbenone; Verbenone (D,L-); Verbenone, (L)-; Verbenone, (d)-; VERBENONE,(DL); 2-Pinen-4-one; (S)-verbenone; dl-Verbenone; S-Verbenone; d-Verbenone; Verbinone; Verbenone; (-)-Verbenone; Verbenone; D-Verbenone; Verbenone; (-)-Verbenone



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)

27 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

  • Ahlem Bekhechi, Charaf Eddine Watheq Malti, Brahim Babali, Miloud Bouafia, Chahrazed Bekhechi, Joseph Casanova, Mathieu Paoli, Félix Tomi. Chemical Variability and Anti-Inflammatory Activity of Rosmarinus officinalis L. Leaf Essential Oil from Algerian Sahara. Chemistry & biodiversity. 2024 Apr; 21(4):e202302077. doi: 10.1002/cbdv.202302077. [PMID: 38388803]
  • Tobias Frühbrodt, Baoguo Du, Horst Delb, Tim Burzlaff, Jürgen Kreuzwieser, Peter H W Biedermann. Know When You Are Too Many: Density-Dependent Release of Pheromones During Host Colonisation by the European Spruce Bark Beetle, Ips typographus (L.). Journal of chemical ecology. 2023 Oct; ?(?):. doi: 10.1007/s10886-023-01453-y. [PMID: 37789096]
  • Antonio Raffo, Irene Baiamonte, Laura De Benedetti, Elisabetta Lupotto, Ilaria Marchioni, Nicoletta Nardo, Claudio Cervelli. Exploring volatile aroma and non-volatile bioactive compounds diversity in wild populations of rosemary (Salvia rosmarinus Schleid.). Food chemistry. 2023 Mar; 404(Pt A):134532. doi: 10.1016/j.foodchem.2022.134532. [PMID: 36242966]
  • Monica L Gaylord, Jackson P Audley, Joel D McMillin, Christopher J Fettig. Acetophenone and Green Leaf Volatiles Do Not Enhance the Efficacy of Verbenone for Inhibiting Attraction of Ips pini (Coleoptera: Curculionidae) to Pheromone-baited Traps in Northern Arizona. Journal of economic entomology. 2023 Feb; ?(?):. doi: 10.1093/jee/toad016. [PMID: 36744905]
  • Jaime-Andrés Becerra, Juan-Miguel González, Aída-Luz Villa. Comparison by Life-Cycle Assessment of Alternative Processes for Carvone and Verbenone Production. Molecules (Basel, Switzerland). 2022 Aug; 27(17):. doi: 10.3390/molecules27175479. [PMID: 36080248]
  • Qingjie Cao, Tuuli-Marjaana Koski, Huiping Li, Chi Zhang, Jianghua Sun. The effect of inactivation of aldehyde dehydrogenase on pheromone production by a gut bacterium of an invasive bark beetle, Dendroctonus valens. Insect science. 2022 Aug; ?(?):. doi: 10.1111/1744-7917.13101. [PMID: 36003004]
  • Hansel E González-Velasco, María S Pérez-Gutiérrez, Ángel J Alonso-Castro, Juan R Zapata-Morales, Perla Del C Niño-Moreno, Nimsi Campos-Xolalpa, Marco M González-Chávez. Anti-Inflammatory and Antinociceptive Activities of the Essential Oil of Tagetes parryi A. Gray (Asteraceae) and Verbenone. Molecules (Basel, Switzerland). 2022 Apr; 27(9):. doi: 10.3390/molecules27092612. [PMID: 35565963]
  • Jackson P Audley, Richard M Bostock, Steven J Seybold. Trap Assays of the Walnut Twig Beetle, Pityophthorus juglandis Blackman (Coleoptera: Curculionidae: Scolytinae), Reveal an Effective Semiochemical Repellent Combination. Journal of chemical ecology. 2020 Dec; 46(11-12):1047-1058. doi: 10.1007/s10886-020-01228-9. [PMID: 33106973]
  • 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]
  • Monique J Rivera, Xavier Martini, Derrick Conover, Agenor Mafra-Neto, Daniel Carrillo, Lukasz L Stelinski. Evaluation of semiochemical based push-pull strategy for population suppression of ambrosia beetle vectors of laurel wilt disease in avocado. Scientific reports. 2020 02; 10(1):2670. doi: 10.1038/s41598-020-59569-0. [PMID: 32060382]
  • María Pardo-Muras, Carolina G Puig, Nuria Pedrol. Cytisus scoparius and Ulex europaeus Produce Volatile Organic Compounds with Powerful Synergistic Herbicidal Effects. Molecules (Basel, Switzerland). 2019 Dec; 24(24):. doi: 10.3390/molecules24244539. [PMID: 31835831]
  • C X Wu, F Liu, S F Zhang, X B Kong, Z Zhang. Semiochemical Regulation of the Intraspecific and Interspecific Behavior of Tomicus yunnanensis and Tomicus minor during the Shoot-Feeding Phase. Journal of chemical ecology. 2019 Mar; 45(3):227-240. doi: 10.1007/s10886-019-01048-6. [PMID: 30796677]
  • Elena Drosopoulou, Dimitris Vlastos, Ioanna Efthimiou, Paraskevi Kyrizaki, Sofia Tsamadou, Maria Anagnostopoulou, Danai Kofidou, Maxim Gavriilidis, Despoina Mademtzoglou, Penelope Mavragani-Tsipidou. In vitro and in vivo evaluation of the genotoxic and antigenotoxic potential of the major Chios mastic water constituents. Scientific reports. 2018 08; 8(1):12200. doi: 10.1038/s41598-018-29810-y. [PMID: 30111795]
  • John A Byers, Yonatan Maoz, David Wakarchuk, Daniela Fefer, Anat Levi Zada. Inhibitory Effects of Semiochemicals on the Attraction of an Ambrosia Beetle Euwallacea nr. fornicatus to Quercivorol. Journal of chemical ecology. 2018 Jun; 44(6):565-575. doi: 10.1007/s10886-018-0959-8. [PMID: 29663165]
  • Qiong Hu, Gui-Shan Lin, Wen-Gui Duan, Min Huang, Fu-Hou Lei. Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters. Molecules (Basel, Switzerland). 2017 Oct; 22(10):. doi: 10.3390/molecules22101678. [PMID: 29023419]
  • Letian Xu, Min Lu, Dandan Xu, Li Chen, Jianghua Sun. Sexual variation of bacterial microbiota of Dendroctonus valens guts and frass in relation to verbenone production. Journal of insect physiology. 2016 12; 95(?):110-117. doi: 10.1016/j.jinsphys.2016.09.014. [PMID: 27677696]
  • Kenichi Tomi, Makiko Kitao, Norihiro Konishi, Hiroshi Murakami, Yasuki Matsumura, Takahiro Hayashi. Enantioselective GC-MS analysis of volatile components from rosemary (Rosmarinus officinalis L.) essential oils and hydrosols. Bioscience, biotechnology, and biochemistry. 2016 May; 80(5):840-7. doi: 10.1080/09168451.2016.1146066. [PMID: 26923429]
  • Haobin Hu, Xudong Zheng, Huaisheng Hu, Ruirui Wang, Yun Wu. Study on gas chromatography-mass spectrometry fingerprint of Acanthopanax brachypus. Journal of chromatographic science. 2014 Sep; 52(8):759-65. doi: 10.1093/chromsci/bmt137. [PMID: 24076562]
  • Nancy E Gillette, Sandra J Kegley, Sheryl L Costello, Sylvia R Mori, Jeffrey N Webster, Constance J Mehmel, David L Wood. Efficacy of verbenone and green leaf volatiles for protecting whitebark and limber pines from attack by mountain pine beetle (Coleoptera: Curculionidae: Scolytinae). Environmental entomology. 2014 Aug; 43(4):1019-26. doi: 10.1603/en12330. [PMID: 25003785]
  • M Hassine, A Zardi-Berguaoui, M Znati, G Flamini, H Ben Jannet, M A Hamza. Chemical composition, antibacterial and cytotoxic activities of the essential oil from the flowers of Tunisian Convolvulus althaeoides L. Natural product research. 2014; 28(11):769-75. doi: 10.1080/14786419.2013.879476. [PMID: 24498906]
  • Ji-Yeon Yang, Hoi-Seon Lee. Verbenone structural analogues isolated from Artemesia aucheri as natural acaricides against Dermatophagoides spp. and Tyrophagus putrescentiae. Journal of agricultural and food chemistry. 2013 Dec; 61(50):12292-6. doi: 10.1021/jf404849t. [PMID: 24295367]
  • Sergio López, Carmen Quero, Juan Carlos Iturrondobeitia, Angel Guerrero, Arturo Goldarazena. Electrophysiological and behavioural responses of Pityophthorus pubescens (Coleoptera: Scolytinae) to (E,E)-α-farnesene, (R)-(+)-limonene and (S)-(-)-verbenone in Pinus radiata (Pinaceae) stands in northern Spain. Pest management science. 2013 Jan; 69(1):40-7. doi: 10.1002/ps.3359. [PMID: 22764125]
  • Daniella K S Lima, Laudir J Ballico, Fernanda Rocha Lapa, Hilda P Gonçalves, Lauro Mera de Souza, Marcello Iacomini, Maria Fernanda de Paula Werner, Cristiane Hatsuko Baggio, Isabela Tiemy Pereira, Luisa Mota da Silva, Valdir A Facundo, Adair Roberto Soares Santos. Evaluation of the antinociceptive, anti-inflammatory and gastric antiulcer activities of the essential oil from Piper aleyreanum C.DC in rodents. Journal of ethnopharmacology. 2012 Jun; 142(1):274-82. doi: 10.1016/j.jep.2012.05.016. [PMID: 22588049]
  • Igor Jerković, Dajana Gašo-Sokač, Hrvoje Pavlović, Zvonimir Marijanović, Mirko Gugić, Ivana Petrović, Spomenka Kovač. Volatile organic compounds from Centaurium erythraea Rafn (Croatia) and the antimicrobial potential of its essential oil. Molecules (Basel, Switzerland). 2012 Feb; 17(2):2058-72. doi: 10.3390/molecules17022058. [PMID: 22349896]
  • E G Burbano, M G Wright, N E Gillette, S Mori, N Dudley, T Jones, M Kaufmann. Efficacy of traps, lures, and repellents for Xylosandrus compactus (Coleoptera: Curculionidae) and other ambrosia beetles on Coffea arabica plantations and Acacia koa nurseries in Hawaii. Environmental entomology. 2012 Feb; 41(1):133-40. doi: 10.1603/en11112. [PMID: 22525068]
  • Federica Pellati, Francesco Epifano, Nicoletta Contaldo, Giulia Orlandini, Lisa Cavicchi, Salvatore Genovese, Davide Bertelli, Stefania Benvenuti, Massimo Curini, Assunta Bertaccini, Maria Grazia Bellardi. Chromatographic methods for metabolite profiling of virus- and phytoplasma-infected plants of Echinacea purpurea. Journal of agricultural and food chemistry. 2011 Oct; 59(19):10425-34. doi: 10.1021/jf2025677. [PMID: 21830789]
  • Dorothea Kaufmann, Anudeep Kaur Dogra, Michael Wink. Myrtenal inhibits acetylcholinesterase, a known Alzheimer target. The Journal of pharmacy and pharmacology. 2011 Oct; 63(10):1368-71. doi: 10.1111/j.2042-7158.2011.01344.x. [PMID: 21899553]
  • Rafal Szmigielski, Marek Cieslak, Krzysztof J Rudziński, Barbara Maciejewska. Identification of volatiles from Pinus silvestris attractive for Monochamus galloprovincialis using a SPME-GC/MS platform. Environmental science and pollution research international. 2011 Aug; 19(7):2860-9. doi: 10.1007/s11356-012-0792-5. [PMID: 22322293]
  • M Martinez-Velazquez, R Rosario-Cruz, G Castillo-Herrera, J M Flores-Fernandez, A H Alvarez, E Lugo-Cervantes. Acaricidal effect of essential oils from Lippia graveolens (Lamiales: Verbenaceae), Rosmarinus officinalis (Lamiales: Lamiaceae), and Allium sativum (Liliales: Liliaceae) against Rhipicephalus (Boophilus) microplus (Acari: Ixodidae). Journal of medical entomology. 2011 Jul; 48(4):822-7. doi: 10.1603/me10140. [PMID: 21845941]
  • Angelike Triantafyllou, Alfiya Bikineyeva, Anna Dikalova, Rafal Nazarewicz, Stamatios Lerakis, Sergey Dikalov. Anti-inflammatory activity of Chios mastic gum is associated with inhibition of TNF-alpha induced oxidative stress. Nutrition journal. 2011 Jun; 10(?):64. doi: 10.1186/1475-2891-10-64. [PMID: 21645369]
  • Chia-Feng Kuo, Jeng-De Su, Chun-Hung Chiu, Chiung-Chi Peng, Chi-Huang Chang, Tzu-Ying Sung, Shiau-Huei Huang, Wen-Chin Lee, Charng-Cherng Chyau. Anti-inflammatory effects of supercritical carbon dioxide extract and its isolated carnosic acid from Rosmarinus officinalis leaves. Journal of agricultural and food chemistry. 2011 Apr; 59(8):3674-85. doi: 10.1021/jf104837w. [PMID: 21375325]
  • Ezekiel Green, Lawrence C Obi, Amidou Samie, Pascal O Bessong, Roland N Ndip. Characterization of n-Hexane sub-fraction of Bridelia micrantha (Berth) and its antimycobacterium activity. BMC complementary and alternative medicine. 2011 Apr; 11(?):28. doi: 10.1186/1472-6882-11-28. [PMID: 21481267]
  • Celia Diezel, Danny Kessler, Ian T Baldwin. Pithy protection: Nicotiana attenuata's jasmonic acid-mediated defenses are required to resist stem-boring weevil larvae. Plant physiology. 2011 Apr; 155(4):1936-46. doi: 10.1104/pp.110.170936. [PMID: 21300916]
  • Kevin J Dodds, Daniel R Miller. Test of nonhost angiosperm volatiles and verbenone to protect trap trees for Sirex noctilio (Hymenoptera: Siricidae) from attacks by bark beetles (Coleoptera: Scolytidae) in the northeastern United States. Journal of economic entomology. 2010 Dec; 103(6):2094-9. doi: 10.1603/ec10225. [PMID: 21309230]
  • Gary J Blomquist, Rubi Figueroa-Teran, Mory Aw, Minmin Song, Andrew Gorzalski, Nicole L Abbott, Eric Chang, Claus Tittiger. Pheromone production in bark beetles. Insect biochemistry and molecular biology. 2010 Oct; 40(10):699-712. doi: 10.1016/j.ibmb.2010.07.013. [PMID: 20727970]
  • Luis Sampedro, Xoaquín Moreira, Joan Llusia, Josep Peñuelas, Rafael Zas. Genetics, phosphorus availability, and herbivore-derived induction as sources of phenotypic variation of leaf volatile terpenes in a pine species. Journal of experimental botany. 2010 Oct; 61(15):4437-47. doi: 10.1093/jxb/erq246. [PMID: 20952630]
  • Wagner A Bernardes, Rodrigo Lucarini, Marcos G Tozatti, Lúzio G Bocalon Flauzino, Maria G M Souza, Isabel C C Turatti, Márcio L Andrade e Silva, Carlos H G Martins, Ademar A da Silva Filho, Wilson R Cunha. Antibacterial activity of the essential oil from Rosmarinus officinalis and its major components against oral pathogens. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2010 Sep; 65(9-10):588-93. doi: 10.1515/znc-2010-9-1009. [PMID: 21138060]
  • Qing-He Zhang, Fredrik Schlyter. Inhibition of predator attraction to kairomones by non-host plant volatiles for herbivores: a bypass-trophic signal. PloS one. 2010 Jun; 5(6):e11063. doi: 10.1371/journal.pone.0011063. [PMID: 20548795]
  • Yosei Tamaki, Takahito Tabuchi, Toshiyuki Takahashi, Kunio Kosaka, Takumi Satoh. Activated glutathione metabolism participates in protective effects of carnosic acid against oxidative stress in neuronal HT22 cells. Planta medica. 2010 May; 76(7):683-8. doi: 10.1055/s-0029-1240622. [PMID: 19941258]
  • Ester Innocent, Cosam C Joseph, Nicholas K Gikonyo, Mayunga H H Nkunya, Ahmed Hassanali. Constituents of the essential oil of Suregada zanzibariensis leaves are repellent to the mosquito, Anopheles gambiae s.s. Journal of insect science (Online). 2010; 10(?):57. doi: 10.1673/031.010.5701. [PMID: 20569134]
  • Martin N Andersson, Mattias C Larsson, Fredrik Schlyter. Specificity and redundancy in the olfactory system of the bark beetle Ips typographus: single-cell responses to ecologically relevant odors. Journal of insect physiology. 2009 Jun; 55(6):556-67. doi: 10.1016/j.jinsphys.2009.01.018. [PMID: 19233334]
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  • Pedro Romón, Juan Carlos Iturrondobeitia, Ken Gibson, B Staffan Lindgren, Arturo Goldarazena. Quantitative association of bark beetles with pitch canker fungus and effects of verbenone on their semiochemical communication in Monterey pine forests in Northern Spain. Environmental entomology. 2007 Aug; 36(4):743-50. doi: 10.1603/0046-225x(2007)36[743:qaobbw]2.0.co;2. [PMID: 17716465]
  • Jun-Hyung Tak, Hyun-Kyung Kim, Seung-Hwan Lee, Young-Joon Ahn. Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae). Pest management science. 2006 Jun; 62(6):551-7. doi: 10.1002/ps.1212. [PMID: 16602084]
  • Christopher J Fettig, Stephen R McKelvey, Dezene P W Huber. Nonhost angiosperm volatiles and verbenone disrupt response of western pine beetle, Dendroctonus brevicomis (Coleoptera: Scolytidae), to attractant-baited traps. Journal of economic entomology. 2005 Dec; 98(6):2041-8. doi: 10.1603/0022-0493-98.6.2041. [PMID: 16539131]
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