Zingiberene (BioDeep_00000000721)

 

Secondary id: BioDeep_00000860053

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds natural product


代谢物信息卡片


(S-(R*,S*))-5-(1,5-Dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene

化学式: C15H24 (204.18779039999998)
中文名称: α-姜烯, 姜烯
谱图信息: 最多检出来源 Viridiplantae(plant) 0.45%

分子结构信息

SMILES: CC(=CCC[C@@H]([C@H]1C=CC(=CC1)C)C)C
InChI: InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-10,14-15H,5,7,11H2,1-4H3

描述信息

Zingiberene is 2-Methylcyclohexa-1,3-diene in which a hydrogen at the 5 position is substituted (R configuration) by a 6-methyl-hept-5-en-2-yl group (S configuration). It is a sesquiterpene found in the dried rhizomes of Indonesian ginger, Zingiber officinale. It is a sesquiterpene and a cyclohexadiene. It is an enantiomer of an ent-zingiberene.
Zingiberene is a natural product found in Chaerophyllum azoricum, Helichrysum odoratissimum, and other organisms with data available.
Constituent of ginger oiland is) also from wild thyme (Thymus serpyllum), long pepper (Piper longum) and kua (Curcuma zedoaria). Zingiberene is found in many foods, some of which are cloves, pepper (spice), ginger, and turmeric.
Zingiberene is found in anise. Zingiberene is a constituent of ginger oil. Also from wild thyme (Thymus serpyllum), long pepper (Piper longum) and kua (Curcuma zedoaria)

同义名列表

25 个代谢物同义名

(S-(R*,S*))-5-(1,5-Dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene; 1,3-CYCLOHEXADIENE, 5-((1S)-1,5-DIMETHYL-4-HEXEN-1-YL)-2-METHYL-, (5R)-; [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene; 1,3-Cyclohexadiene, 5-[(1S)-1,5-dimethyl-4-hexenyl]-2-methyl-, (5R)-; (5R)-2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene; (5R)-5-[(1S)-1,5-dimethyl-4-hexenyl]-2-methyl-1,3-cyclohexadiene; (5r)-2-methyl-5-[(2s)-6-methylhept-5-en-2yl] cyclohexa-1,3-diene; (R)-2-Methyl-5-((S)-6-methylhept-5-en-2-yl)cyclohexa-1,3-diene; 2-methyl-5-(6-methylhept-5-en-2-yl)cyclohexa-1,3-diene; 5-(1,5-Dimethyl-4-hexenyl)-2-methyl-1,3-cyclohexadiene; (-)-Zingiberene; l-Zingiberene; -Zingiberene; .alpha.-Sesquiphellandrene; Zingiberene from ginger; (-)-alpha-zingiberene; alpha -Zingibirene; alpha -Zingiberene; alpha-zingiberene; UNII-8XOC63EI5F; (-)-Zingiberene; a-Zingiberene; l-Zingiberene; Zingiberene; 8XOC63EI5F; Zingiberene; alpha-Zingiberene



数据库引用编号

23 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)

160 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

  • Bruno Antonio Ferreira, Ricardo Ferreira Silva, Francyelle Borges Rosa de Moura, Carolina Tannús Narduchi, Simone Ramos Deconte, Patricia Sartorelli, Tatiana Carla Tomiosso, João Henrique Ghilardi Lago, Fernanda de Assis Araújo. α-zingiberene, a sesquiterpene from essential oil from leaves of Casearia sylvestris, suppresses inflammatory angiogenesis and stimulates collagen deposition in subcutaneous implants in mice. Natural product research. 2022 Nov; 36(22):5858-5862. doi: 10.1080/14786419.2021.2019729. [PMID: 34961386]
  • Vidya Devanathadesikan Seshadri, Atif Abdulwahab A Oyouni, Waleed M Bawazir, Suliman A Alsagaby, Khalaf F Alsharif, Ashraf Albrakati, Osama M Al-Amer. Zingiberene exerts chemopreventive activity against 7,12-dimethylbenz(a)anthracene-induced breast cancer in Sprague-Dawley rats. Journal of biochemical and molecular toxicology. 2022 Oct; 36(10):e23146. doi: 10.1002/jbt.23146. [PMID: 35698847]
  • Heba A S El-Nashar, Mai Adel, Mohamed El-Shazly, Ibrahim S Yahia, Hamdy S El Sheshtawy, Adel A Almalki, Nehal Ibrahim. Chemical Composition, Antiaging Activities and Molecular Docking Studies of Essential Oils from Acca sellowiana (Feijoa). Chemistry & biodiversity. 2022 Sep; 19(9):e202200272. doi: 10.1002/cbdv.202200272. [PMID: 35938449]
  • Sebastian Zabel, Wolfgang Brandt, Andrea Porzel, Benedikt Athmer, Stefan Bennewitz, Petra Schäfer, Ruy Kortbeek, Petra Bleeker, Alain Tissier. A single cytochrome P450 oxidase from Solanum habrochaites sequentially oxidizes 7-epi-zingiberene to derivatives toxic to whiteflies and various microorganisms. The Plant journal : for cell and molecular biology. 2021 03; 105(5):1309-1325. doi: 10.1111/tpj.15113. [PMID: 33617106]
  • Xin Wang, Yi Shen, Kiran Thakur, Jinzhi Han, Jian-Guo Zhang, Fei Hu, Zhao-Jun Wei. Antibacterial Activity and Mechanism of Ginger Essential Oil against Escherichia coli and Staphylococcus aureus. Molecules (Basel, Switzerland). 2020 Aug; 25(17):. doi: 10.3390/molecules25173955. [PMID: 32872604]
  • Jingru Sun, Guanghong Cui, Xiaohui Ma, Zhilai Zhan, Ying Ma, Zhongqiu Teng, Wei Gao, Yanan Wang, Tong Chen, Changjiangsheng Lai, Yujun Zhao, Jinfu Tang, Huixin Lin, Ye Shen, Wen Zeng, Juan Guo, Luqi Huang. An integrated strategy to identify genes responsible for sesquiterpene biosynthesis in turmeric. Plant molecular biology. 2019 Oct; 101(3):221-234. doi: 10.1007/s11103-019-00892-0. [PMID: 31203559]
  • 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]
  • I P Lima, J T V Resende, J R F Oliveira, M V Faria, N C V Resende, R B Lima Filho. Indirect selection of industrial tomato genotypes rich in zingiberene and resistant to Tuta absoluta Meyrick. Genetics and molecular research : GMR. 2015 Nov; 14(4):15081-9. doi: 10.4238/2015.november.24.16. [PMID: 26634470]
  • Hong-bing Zhao, Zhi-hui Wang, Fang He, Han Meng, Jian-hua Peng, Ji-lian Shi. [Analysis of Volatile Oils from Different Processed Products of Zingiber officinale Rhizome by GC-MS]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Apr; 38(4):723-6. doi: . [PMID: 26672336]
  • Le T Huong, Do N Dai, Tran D Thang, Tran T Bach, Isiaka A Ogunwande. Volatile constituents of Amomum maximum Roxb and Amomum microcarpum C. F. Liang & D. Fang: two Zingiberaceae grown in Vietnam. Natural product research. 2015; 29(15):1469-72. doi: 10.1080/14786419.2014.1003064. [PMID: 25600992]
  • Diego Dinis Bou, João Henrique G Lago, Carlos R Figueiredo, Alisson L Matsuo, Rafael C Guadagnin, Marisi G Soares, Patricia Sartorelli. Chemical composition and cytotoxicity evaluation of essential oil from leaves of Casearia sylvestris, its main compound α-zingiberene and derivatives. Molecules (Basel, Switzerland). 2013 Aug; 18(8):9477-87. doi: 10.3390/molecules18089477. [PMID: 23966073]
  • Michael Gutensohn, Irina Orlova, Thuong T H Nguyen, Rachel Davidovich-Rikanati, Mario G Ferruzzi, Yaron Sitrit, Efraim Lewinsohn, Eran Pichersky, Natalia Dudareva. Cytosolic monoterpene biosynthesis is supported by plastid-generated geranyl diphosphate substrate in transgenic tomato fruits. The Plant journal : for cell and molecular biology. 2013 Aug; 75(3):351-63. doi: 10.1111/tpj.12212. [PMID: 23607888]
  • Challa Ravi Kiran, Ashok Kumar Chakka, K P Padmakumari Amma, A Nirmala Menon, M M Sree Kumar, V V Venugopalan. Influence of cultivar and maturity at harvest on the essential oil composition, oleoresin and [6]-gingerol contents in fresh ginger from northeast India. Journal of agricultural and food chemistry. 2013 May; 61(17):4145-54. doi: 10.1021/jf400095y. [PMID: 23570262]
  • Petra M Bleeker, Rossana Mirabella, Paul J Diergaarde, Arjen VanDoorn, Alain Tissier, Merijn R Kant, Marcel Prins, Martin de Vos, Michel A Haring, Robert C Schuurink. Improved herbivore resistance in cultivated tomato with the sesquiterpene biosynthetic pathway from a wild relative. Proceedings of the National Academy of Sciences of the United States of America. 2012 Dec; 109(49):20124-9. doi: 10.1073/pnas.1208756109. [PMID: 23169639]
  • In Hee Cho, Hyun Jeong Lee, Young-Suk Kim. Differences in the volatile compositions of ginseng species (Panax sp.). Journal of agricultural and food chemistry. 2012 Aug; 60(31):7616-22. doi: 10.1021/jf301835v. [PMID: 22804575]
  • Niko S Radulović, Marko Z Mladenović, Nevenka D Ethorđević. Chemotypification of Astrantia major L. (Apiaceae): essential-oil and lignan profiles of fruits. Chemistry & biodiversity. 2012 Jul; 9(7):1320-37. doi: 10.1002/cbdv.201100430. [PMID: 22782878]
  • Jianbo Lin, Jun Dou, Jiangling Xu, Haji Akber Aisa. Chemical composition, antimicrobial and antitumor activities of the essential oils and crude extracts of Euphorbia macrorrhiza. Molecules (Basel, Switzerland). 2012 May; 17(5):5030-9. doi: 10.3390/molecules17055030. [PMID: 22555293]
  • Jack D Williams, Ayman M Saleh, Dom N Acharya. Composition of the essential oil of wild growing Artemisia vulgaris from Erie, Pennsylvania. Natural product communications. 2012 May; 7(5):637-40. doi: . [PMID: 22799096]
  • Pramod Kumar Singh, Indu Pal Kaur. Synbiotic (probiotic and ginger extract) loaded floating beads: a novel therapeutic option in an experimental paradigm of gastric ulcer. The Journal of pharmacy and pharmacology. 2012 Feb; 64(2):207-17. doi: 10.1111/j.2042-7158.2011.01397.x. [PMID: 22221096]
  • Xiaofeng Zhuang, Tobias G Köllner, Nan Zhao, Guanglin Li, Yifan Jiang, Liucun Zhu, Jianxin Ma, Jörg Degenhardt, Feng Chen. Dynamic evolution of herbivore-induced sesquiterpene biosynthesis in sorghum and related grass crops. The Plant journal : for cell and molecular biology. 2012 Jan; 69(1):70-80. doi: 10.1111/j.1365-313x.2011.04771.x. [PMID: 21880075]
  • Kottarapat Jeena, Vijayastelter B Liju, Ramadasan Kuttan. A preliminary 13-week oral toxicity study of ginger oil in male and female Wistar rats. International journal of toxicology. 2011 Dec; 30(6):662-70. doi: 10.1177/1091581811419023. [PMID: 21960667]
  • Kwang-Hee Lee, Beom-Su Kim, Ki-Suk Keum, Hyeon-Hee Yu, Young-Hoi Kim, Byoung-Soo Chang, Ji-Young Ra, Hae-Dalma Moon, Bo-Ra Seo, Na-Young Choi, Yong-Ouk You. Essential oil of Curcuma longa inhibits Streptococcus mutans biofilm formation. Journal of food science. 2011 Nov; 76(9):H226-30. doi: 10.1111/j.1750-3841.2011.02427.x. [PMID: 22416707]
  • Petra M Bleeker, Eleni A Spyropoulou, Paul J Diergaarde, Hanne Volpin, Michiel T J De Both, Philipp Zerbe, Joerg Bohlmann, Vasiliki Falara, Yuki Matsuba, Eran Pichersky, Michel A Haring, Robert C Schuurink. RNA-seq discovery, functional characterization, and comparison of sesquiterpene synthases from Solanum lycopersicum and Solanum habrochaites trichomes. Plant molecular biology. 2011 Nov; 77(4-5):323-36. doi: 10.1007/s11103-011-9813-x. [PMID: 21818683]
  • José Fernando Caroprese Araque, María Isabel Parra Garcés, Dagoberto Arrieta Prieto, Elena Stashenko. [Microscopic anatomy and volatile secondary metabolites at three stages of development of the inflorescences of Lantana camara (Verbenaceae)]. Revista de biologia tropical. 2011 Mar; 59(1):473-86. doi: . [PMID: 21516661]
  • Hyung-In Moon, Sang-Buem Cho, Soo-Ki Kim. Composition and immunotoxicity activity of essential oils from leaves of Zingiber officinale Roscoe against Aedes aegypti L. Immunopharmacology and immunotoxicology. 2011 Mar; 33(1):201-4. doi: 10.3109/08923973.2010.495393. [PMID: 20568951]
  • Da-Hai Yang, Christian Hettenhausen, Ian T Baldwin, Jianqiang Wu. BAK1 regulates the accumulation of jasmonic acid and the levels of trypsin proteinase inhibitors in Nicotiana attenuata's responses to herbivory. Journal of experimental botany. 2011 Jan; 62(2):641-52. doi: 10.1093/jxb/erq298. [PMID: 20937731]
  • Petra M Bleeker, Paul J Diergaarde, Kai Ament, Stefan Schütz, Bettina Johne, Jan Dijkink, Henk Hiemstra, René de Gelder, Michiel T J de Both, Maurice W Sabelis, Michel A Haring, Robert C Schuurink. Tomato-produced 7-epizingiberene and R-curcumene act as repellents to whiteflies. Phytochemistry. 2011 Jan; 72(1):68-73. doi: 10.1016/j.phytochem.2010.10.014. [PMID: 21074818]
  • 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]
  • Isiaka A Ogunwande, Tameka M Walker, Anita Bansal, William N Setzer, Emmanuel E Essien. Essential oil constituents and biological activities of Peristrophe bicalyculata and Borreria verticillata. Natural product communications. 2010 Nov; 5(11):1815-8. doi: . [PMID: 21213989]
  • Hannah R Vasanthi, R P Parameswari. Indian spices for healthy heart - an overview. Current cardiology reviews. 2010 Nov; 6(4):274-9. doi: 10.2174/157340310793566172. [PMID: 22043203]
  • Jin-Ho Kang, Guanghui Liu, Feng Shi, A Daniel Jones, Randolph M Beaudry, Gregg A Howe. The tomato odorless-2 mutant is defective in trichome-based production of diverse specialized metabolites and broad-spectrum resistance to insect herbivores. Plant physiology. 2010 Sep; 154(1):262-72. doi: 10.1104/pp.110.160192. [PMID: 20668059]
  • Nicole M van Dam, Bao-Li Qiu, Cornelis A Hordijk, Louise E M Vet, Jeroen J Jansen. Identification of biologically relevant compounds in aboveground and belowground induced volatile blends. Journal of chemical ecology. 2010 Sep; 36(9):1006-16. doi: 10.1007/s10886-010-9844-9. [PMID: 20737198]
  • Megha Saraswat, Palla Suryanarayana, Paduru Yadagiri Reddy, Madhoosudan A Patil, Nagalla Balakrishna, Geereddy Bhanuprakash Reddy. Antiglycating potential of Zingiber officinalis and delay of diabetic cataract in rats. Molecular vision. 2010 Aug; 16(?):1525-37. doi: . [PMID: 20806076]
  • Ahmed Hassan El-Ghorab, Muhammad Nauman, Faqir Muhammad Anjum, Shahzad Hussain, Muhammad Nadeem. A comparative study on chemical composition and antioxidant activity of ginger (Zingiber officinale) and cumin (Cuminum cyminum). Journal of agricultural and food chemistry. 2010 Jul; 58(14):8231-7. doi: 10.1021/jf101202x. [PMID: 20590154]
  • Nitin P Kurade, Vikas Jaitak, Vijay K Kaul, Om P Sharma. Chemical composition and antibacterial activity of essential oils of Lantana camara, Ageratum houstonianum and Eupatorium adenophorum. Pharmaceutical biology. 2010 May; 48(5):539-44. doi: 10.3109/13880200903193336. [PMID: 20645797]
  • Jin-Ho Kang, Feng Shi, A Daniel Jones, M David Marks, Gregg A Howe. Distortion of trichome morphology by the hairless mutation of tomato affects leaf surface chemistry. Journal of experimental botany. 2010 Feb; 61(4):1053-64. doi: 10.1093/jxb/erp370. [PMID: 20018901]
  • Hai-Yan Lu, Fang Liu, Shu-De Zhu, Qing Zhang. [Effects of azadirachtin on rice plant volatiles induced by Nilaparvata lugens]. Ying yong sheng tai xue bao = The journal of applied ecology. 2010 Jan; 21(1):197-202. doi: . [PMID: 20387443]
  • M Khushtar, V Kumar, K Javed, Uma Bhandari. Protective Effect of Ginger oil on Aspirin and Pylorus Ligation-Induced Gastric Ulcer model in Rats. Indian journal of pharmaceutical sciences. 2009 Sep; 71(5):554-8. doi: 10.4103/0250-474x.58195. [PMID: 20502577]
  • Marcelo Lattarulo Campos, Marcílio de Almeida, Mônica Lanzoni Rossi, Adriana Pinheiro Martinelli, Celso Gaspar Litholdo Junior, Antonio Figueira, Fátima Teresinha Rampelotti-Ferreira, José Djair Vendramim, Vagner Augusto Benedito, Lázaro Eustáquio Pereira Peres. Brassinosteroids interact negatively with jasmonates in the formation of anti-herbivory traits in tomato. Journal of experimental botany. 2009; 60(15):4347-61. doi: 10.1093/jxb/erp270. [PMID: 19734261]
  • Kunyou Zhan, Chao Wang, Kun Xu, Hongzong Yin. [Analysis of volatile and non-volatile compositions in ginger oleoresin by gas chromatography-mass spectrometry]. Se pu = Chinese journal of chromatography. 2008 Nov; 26(6):692-6. doi: . [PMID: 19253546]
  • Rachel Davidovich-Rikanati, Efraim Lewinsohn, Einat Bar, Yoko Iijima, Eran Pichersky, Yaron Sitrit. Overexpression of the lemon basil alpha-zingiberene synthase gene increases both mono- and sesquiterpene contents in tomato fruit. The Plant journal : for cell and molecular biology. 2008 Oct; 56(2):228-238. doi: 10.1111/j.1365-313x.2008.03599.x. [PMID: 18643974]
  • Preeti Dohare, Puja Garg, Uma Sharma, N R Jagannathan, Madhur Ray. Neuroprotective efficacy and therapeutic window of curcuma oil: in rat embolic stroke model. BMC complementary and alternative medicine. 2008 Sep; 8(?):55. doi: 10.1186/1472-6882-8-55. [PMID: 18826584]
  • Julien Paolini, Elodie Nasica, Jean-Marie Desjobert, Alain Muselli, Antoine-François Bernardini, Jean Costa. Analysis of volatile constituents isolated by hydrodistillation and headspace solid-phase microextraction from Adenostyles briquetii Gamisans. Phytochemical analysis : PCA. 2008 May; 19(3):266-76. doi: 10.1002/pca.1047. [PMID: 17994535]
  • Filomena Conforti, Federica Menichini, Monica R Loizzo, A Giancarlo Statti, Antonio Rapisarda, Francesco Menichini, Peter J Houghton. Antioxidant, alpha-amylase inhibitory and brine-shrimp toxicity studies on Centaurea centaurium L. methanolic root extract. Natural product research. 2008; 22(16):1457-66. doi: 10.1080/14786410802098071. [PMID: 19023809]
  • Chao Zhao, Hua-guo Chen, Li Cheng, Xin Zhou, Zai-bo Yang, Yi-sha Zhang. [Analysis of volatile oil in herb of pimpinella candolleana by SPME-GC-MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Sep; 32(17):1759-62. doi: . [PMID: 17992994]
  • N Y Qin, F Q Yang, Y T Wang, S P Li. Quantitative determination of eight components in rhizome (Jianghuang) and tuberous root (Yujin) of Curcuma longa using pressurized liquid extraction and gas chromatography-mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2007 Jan; 43(2):486-92. doi: 10.1016/j.jpba.2006.07.034. [PMID: 16930909]
  • S Chrubasik, M H Pittler, B D Roufogalis. Zingiberis rhizoma: a comprehensive review on the ginger effect and efficacy profiles. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2005 Sep; 12(9):684-701. doi: 10.1016/j.phymed.2004.07.009. [PMID: 16194058]
  • George F Antonious, Tejinder S Kochhar. Zingiberene and curcumene in wild tomato. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2003 Jul; 38(4):489-500. doi: 10.1081/pfc-120021668. [PMID: 12856930]
  • J Li, J Lu. [Study on chemical constituents of Dendranthema morifolium by GC-MS]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2001 Sep; 24(9):642-3. doi: . [PMID: 11799772]
  • . . . . doi: . [PMID: 17440821]