Camphene (BioDeep_00000004167)

 

Secondary id: BioDeep_00000015179, BioDeep_00001867723

natural product human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


3,3-Dimethyl-2-methylidenebicyclo[2.2.1]heptane

化学式: C10H16 (136.1251936)
中文名称: 莰烯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.71%

分子结构信息

SMILES: C=C1C2CCC(C2)C1(C)C
InChI: InChI=1/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3

描述信息

Camphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, 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. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Camphene is nearly insoluble in water but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It exists as a flammable, white solid that has a minty, citrus, eucalyptus odor. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and in food additives for flavouring. In the mid-19th century it was used as a fuel for lamps, but this was limited by its explosiveness. Camphene exists in all eukaryotes, ranging from yeast to plants to humans. Camphene can be found in a number of food items such as dill, carrots, caraway, hyssop, lemon, orange, nutmeg seed, parsley, sage, thyme, turmeric and fennel, which makes camphene a potential biomarker for the consumption of these food products. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. Camphene is one of several monoterpenes that are found in cannabis plants (PMID:6991645 ).
Camphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, 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. Camphene is a camphor, fir needle, and herbal tasting compound and can be found in a number of food items such as cardamom, yellow bell pepper, common thyme, and coriander, which makes camphene a potential biomarker for the consumption of these food products. Camphene can be found primarily in feces and saliva. Camphene exists in all eukaryotes, ranging from yeast to humans. Camphene is a bicyclic monoterpene. It is nearly insoluble in water, but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and as a food additive for flavoring. Its mid-19th century use as a fuel for lamps was limited by its explosiveness .

同义名列表

9 个代谢物同义名

3,3-Dimethyl-2-methylidenebicyclo[2.2.1]heptane; 2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane; 2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane; 3,3-Dimethyl-2-methylenenorcamphane; 2,2-Dimethyl-3-methylenenorbornane; 3,3-Dimethyl-2-methylenenorbornane; (+)-Camphene; Comphene; CAMPHENE



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

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)

483 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

  • Borislava Lechkova, Niko Benbassat, Diana Karcheva-Bahchevanska, Kalin Ivanov, Lyudmil Peychev, Zhivko Peychev, Stanislav Dyankov, Yoana Georgieva-Dimova, Krasimir Kraev, Stanislava Ivanova. A Comparison between Bulgarian Tanacetum parthenium Essential Oil from Two Different Locations. Molecules (Basel, Switzerland). 2024 Apr; 29(9):. doi: 10.3390/molecules29091969. [PMID: 38731460]
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  • Ruinan Yang, Dongzhen Li, Shancheng Yi, Yi Wei, Manqun Wang. Odorant-binding protein 19 in Monochamus alternatus involved in the recognition of a volatile strongly emitted from ovipositing host pines. Insect science. 2023 Jun; ?(?):. doi: 10.1111/1744-7917.13238. [PMID: 37358042]
  • Tianming Zhao, Chao Ma, Guofei Zhu. Chemical Composition and Biological Activities of Essential Oils from the Leaves, Stems, and Roots of Kadsura coccinea. Molecules (Basel, Switzerland). 2021 Oct; 26(20):. doi: 10.3390/molecules26206259. [PMID: 34684838]
  • Assia Zeghib, Claude-Alain Calliste, Alain Simon, Rim Charfeddine, Mahjoub Aouni, Jean-Luc Duroux, Ahmed Kabouche, Zahia Kabouche. Chemical composition and biological potential of Thymus Willdenowii Boiss. & Reut. essential oil. Natural product research. 2021 Mar; 35(5):845-848. doi: 10.1080/14786419.2019.1602830. [PMID: 30990332]
  • Suji Baek, Jisu Kim, Byung Seok Moon, Sun Mi Park, Da Eun Jung, Seo Young Kang, Sang Ju Lee, Seung Jun Oh, Seung Hae Kwon, Myung Hee Nam, Hye Ok Kim, Hai Jeon Yoon, Bom Sahn Kim, Kang Pa Lee. Camphene Attenuates Skeletal Muscle Atrophy by Regulating Oxidative Stress and Lipid Metabolism in Rats. Nutrients. 2020 Dec; 12(12):. doi: 10.3390/nu12123731. [PMID: 33287349]
  • Elaine C D Gonçalves, Gabriela M Baldasso, Maíra A Bicca, Rodrigo S Paes, Raffaele Capasso, Rafael C Dutra. Terpenoids, Cannabimimetic Ligands, beyond the Cannabis Plant. Molecules (Basel, Switzerland). 2020 Mar; 25(7):. doi: 10.3390/molecules25071567. [PMID: 32235333]
  • Yi-Xi Feng, Yang Wang, Zhu-Feng Geng, Di Zhang, Borjigidai Almaz, Shu-Shan Du. Contact toxicity and repellent efficacy of Valerianaceae spp. to three stored-product insects and synergistic interactions between two major compounds camphene and bornyl acetate. Ecotoxicology and environmental safety. 2020 Mar; 190(?):110106. doi: 10.1016/j.ecoenv.2019.110106. [PMID: 31877546]
  • Nilufar Z Mamadalieva, Fadia S Youssef, Mohamed L Ashour, Sobirdjan A Sasmakov, Antonio Tiezzi, Shahnoz S Azimova. Chemical composition, antimicrobial and antioxidant activities of the essential oils of three Uzbek Lamiaceae species. Natural product research. 2019 Aug; 33(16):2394-2397. doi: 10.1080/14786419.2018.1443088. [PMID: 29468889]
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  • 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]
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  • Aphrodite Tsaballa, Alexandros Nikolaidis, Foteini Trikka, Codruta Ignea, Sotirios C Kampranis, Antonios M Makris, Anagnostis Argiriou. Use of the de novo transcriptome analysis of silver-leaf nightshade (Solanum elaeagnifolium) to identify gene expression changes associated with wounding and terpene biosynthesis. BMC genomics. 2015 Jul; 16(?):504. doi: 10.1186/s12864-015-1738-3. [PMID: 26149407]
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  • Robin D Couch, Allyson Dailey, Fatima Zaidi, Karl Navarro, Christopher B Forsyth, Ece Mutlu, Phillip A Engen, Ali Keshavarzian. Alcohol induced alterations to the human fecal VOC metabolome. PloS one. 2015; 10(3):e0119362. doi: 10.1371/journal.pone.0119362. [PMID: 25751150]
  • S L Slinski, F Zakharov, T R Gordon. The Effect of Resin and Monoterpenes on Spore Germination and Growth in Fusarium circinatum. Phytopathology. 2015 Jan; 105(1):119-25. doi: 10.1094/phyto-02-14-0027-r. [PMID: 25163010]
  • Marija Karapandzova, Gjose Stefkova, Ivana Cvetkovikj, Elena Trajkovska-Dokik, Ana Kaftandzieva, Svetlana Kulevanova. Chemical composition and antimicrobial activity of the essential oils of Pinus peuce (Pinaceae) growing wild in R. Macedonia. Natural product communications. 2014 Nov; 9(11):1623-8. doi: . [PMID: 25532297]
  • 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]
  • Effie Hanlidou, Regina Karousou, Diamanto Lazari. Essential-oil diversity of Salvia tomentosa Mill. in Greece. Chemistry & biodiversity. 2014 Aug; 11(8):1205-15. doi: 10.1002/cbdv.201300408. [PMID: 25146764]
  • Sohee Kim, Youngshim Choi, Seoyoon Choi, Yeji Choi, Taesun Park. Dietary camphene attenuates hepatic steatosis and insulin resistance in mice. Obesity (Silver Spring, Md.). 2014 Feb; 22(2):408-17. doi: 10.1002/oby.20554. [PMID: 23818423]
  • Sandeep B Rajput, S Mohan Karuppayil. Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans. SpringerPlus. 2013 Dec; 2(1):26. doi: 10.1186/2193-1801-2-26. [PMID: 23449869]
  • Thitiya Mangprayool, Sajeera Kupittayanant, Nuannoi Chudapongse. Participation of citral in the bronchodilatory effect of ginger oil and possible mechanism of action. Fitoterapia. 2013 Sep; 89(?):68-73. doi: 10.1016/j.fitote.2013.05.012. [PMID: 23685048]
  • Abdolkarim Chehregani, Morteza Atri, Somayeh Yousefi, Zahra Albooyeh, Fariba Mohsenzadeh. Essential oil variation in the populations of Artemisia spicigera from northwest of Iran: chemical composition and antibacterial activity. Pharmaceutical biology. 2013 Feb; 51(2):246-52. doi: 10.3109/13880209.2012.717631. [PMID: 23126238]
  • Asia Begum, Subarda Sandhya, Syed Shaffath Ali, Kombath Ravindran Vinod, Swapna Reddy, David Banji. An in-depth review on the medicinal flora Rosmarinus officinalis (Lamiaceae). Acta scientiarum polonorum. Technologia alimentaria. 2013 Jan; 12(1):61-73. doi: . [PMID: 24584866]
  • Marija Jug-Dujaković, Mihailo Ristić, Dejan Pljevljakušić, Zora Dajić-Stevanović, Zlatko Liber, Katarina Hančević, Tomislav Radić, Zlatko Satović. High diversity of indigenous populations of dalmatian sage (Salvia officinalis L.) in essential-oil composition. Chemistry & biodiversity. 2012 Oct; 9(10):2309-23. doi: 10.1002/cbdv.201200131. [PMID: 23081929]
  • Ji-Hyun Kim, Hyo-Jung Lee, Soo-Jin Jeong, Min-Ho Lee, Sung-Hoon Kim. Essential oil of Pinus koraiensis leaves exerts antihyperlipidemic effects via up-regulation of low-density lipoprotein receptor and inhibition of acyl-coenzyme A: cholesterol acyltransferase. Phytotherapy research : PTR. 2012 Sep; 26(9):1314-9. doi: 10.1002/ptr.3734. [PMID: 22275303]
  • Nasser A Awadh Ali, Martina Wursterb, Annika Denkert, Norbert Arnold, Iman Fadail, Gamal Al-Didamony, Ulrike Lindequist, Ludger Wessjohann, William N Setzer. Chemical composition, antimicrobial, antioxidant and cytotoxic activity of essential oils of Plectranthus cylindraceus and Meriandra benghalensis from Yemen. Natural product communications. 2012 Aug; 7(8):1099-102. doi: . [PMID: 22978239]
  • Mirjana Marcetić, Dragana Bozić, Marina Milenković, Branislava Lakusić, Nada Kovacević. Chemical composition and antimicrobial activity of essential oil of different parts of Seseli rigidum. Natural product communications. 2012 Aug; 7(8):1091-4. doi: . [PMID: 22978237]
  • 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]
  • Subhash C Joshi, Chandra S Mathela. Antioxidant and antibacterial activities of the leaf essential oil and its constituents furanodienone and curzerenone from Lindera pulcherrima (Nees.) Benth. ex hook. f. Pharmacognosy research. 2012 Apr; 4(2):80-4. doi: 10.4103/0974-8490.94721. [PMID: 22518079]
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  • Brijesh Kumar Singh, Madhulika Tripathi, Bhushan P Chaudhari, Pramod K Pandey, Poonam Kakkar. Natural terpenes prevent mitochondrial dysfunction, oxidative stress and release of apoptotic proteins during nimesulide-hepatotoxicity in rats. PloS one. 2012; 7(4):e34200. doi: 10.1371/journal.pone.0034200. [PMID: 22509279]
  • Ippolito Camele, Luciana Altieri, Laura De Martino, Vincenzo De Feo, Emilia Mancini, Gian Luigi Rana. In vitro control of post-harvest fruit rot fungi by some plant essential oil components. International journal of molecular sciences. 2012; 13(2):2290-2300. doi: 10.3390/ijms13022290. [PMID: 22408454]
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