beta-Bisabolene (BioDeep_00000011393)

 

Secondary id: BioDeep_00000016685, BioDeep_00000395680

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds


代谢物信息卡片


(-)-beta-bisabolene;(S)-(-)-6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene;(S)-1-methyl-4-(5-methyl-1-methylene-4-hexenyl)cyclohexene

化学式: C15H24 (204.18779039999998)
中文名称: β-红没药烯
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.21%

分子结构信息

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

描述信息

S-beta-Bisabolene is found in anise. S-beta-Bisabolene is a constituent of the essential oils of bergamot, lemon and wild carrot
Flavouring ingredient used singly or as mixed isomers. Component of FEMA 3331. See also 2,7,10-Bisabolatriene JHG85-W
β-Bisabolene is a?sesquiterpene isolated from?opoponax (Commiphora guidotti). β-Bisabolene, an anti-cancer agent, can be used for the study of breast cancer[1].
β-Bisabolene is a?sesquiterpene isolated from?opoponax (Commiphora guidotti). β-Bisabolene, an anti-cancer agent, can be used for the study of breast cancer[1].

同义名列表

17 个代谢物同义名

(-)-beta-bisabolene;(S)-(-)-6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene;(S)-1-methyl-4-(5-methyl-1-methylene-4-hexenyl)cyclohexene; (1S)-bisabola-4,7(11),10(15)-triene (4S)-1-methyl-4-(5-methyl-1-methylenehex-4-en-1-yl)cyclohexene; 1-Methyl-4-(5-methyl-1-methylene-4-hexenyl)cyclohexene, 9ci; 1-Methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene; 1-Methyl-4-(5-methyl-1-methylene-4-hexenyl)cyclohexene; (S)-beta-bisabolene; (-)-beta-bisabolene; l-beta-Bisabolene; beta-Bisabolene; beta-Bisabolen; b-Bisabolene; β-Bisabolene; Β-bisabolen; b-Bisabolen; b-Limene; (S)-beta-Bisabolene; beta-Bisabolene



数据库引用编号

22 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

17 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(14)

  • zealexin biosynthesis: 4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + NADPH + O2 ⟶ H2O + NADP+ + zealexin A1
  • zealexin biosynthesis: 4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + NADPH + O2 ⟶ H2O + NADP+ + zealexin A1
  • zealexin biosynthesis: 4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + NADPH + O2 ⟶ H2O + NADP+ + zealexin A1
  • zealexin biosynthesis: (2E,6E)-farnesyl diphosphate ⟶ (S)-β-bisabolene + diphosphate
  • zealexin biosynthesis: 4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + NADPH + O2 ⟶ H2O + NADP+ + zealexin A1
  • zealexin biosynthesis: 4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + NADPH + O2 ⟶ H2O + NADP+ + zealexin A1
  • zealexin biosynthesis: 4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + NADPH + O2 ⟶ H2O + NADP+ + zealexin A1
  • zealexin biosynthesis: O2 + [(4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)-cyclohex-1-en-1-yl] methanol + a reduced [NADPH-hemoprotein reductase] ⟶ (4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + H2O + an oxidized [NADPH-hemoprotein reductase]
  • zealexin biosynthesis: 4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + NADPH + O2 ⟶ H2O + NADP+ + zealexin A1
  • zealexin biosynthesis: H+ + NADPH + O2 + [4-(5,5-dimethylcyclohex-1-en-1-yl)-cyclohex-1-en-1-yl] methanol ⟶ 4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + H2O + NADP+
  • zealexin biosynthesis: 4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + NADPH + O2 ⟶ H2O + NADP+ + zealexin A1
  • zealexin biosynthesis: 4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + NADPH + O2 ⟶ H2O + NADP+ + zealexin A1
  • santalene biosynthesis II: (2E,6E)-farnesyl diphosphate ⟶ (-)-β-santalene + diphosphate
  • bisabolene biosynthesis (engineered): (2E,6E)-farnesyl diphosphate ⟶ (E)-α-bisabolene + diphosphate

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

174 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

  • Giusy Castagliuolo, Michela Di Napoli, Alessandro Vaglica, Natale Badalamenti, Dario Antonini, Mario Varcamonti, Maurizio Bruno, Anna Zanfardino, Giuseppe Bazan. Thymus richardii subsp. nitidus (Guss.) Jalas Essential Oil: An Ally against Oral Pathogens and Mouth Health. Molecules (Basel, Switzerland). 2023 Jun; 28(12):. doi: 10.3390/molecules28124803. [PMID: 37375358]
  • De-Sen Li, Lin-Lin Shi, Kai Guo, Shi-Hong Luo, Yan-Chun Liu, Yue-Gui Chen, Yan Liu, Sheng-Hong Li. A new sesquiterpene synthase catalyzing the formation of (R)-β-bisabolene from medicinal plant Colquhounia coccinea var. mollis and its anti-adipogenic and antibacterial activities. Phytochemistry. 2023 Apr; 211(?):113681. doi: 10.1016/j.phytochem.2023.113681. [PMID: 37080413]
  • Siwar Majdoub, Ridha El Mokni, Aliev Aslan Muradalievich, Alessandra Piras, Silvia Porcedda, Saoussen Hammami. Effect of pressure variation on the efficiency of supercritical fluid extraction of wild carrot (Daucus carota subsp. maritimus) extracts. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 Sep; 1125(?):121713. doi: 10.1016/j.jchromb.2019.121713. [PMID: 31323559]
  • Tiago J T de Souza, Sérgio A L Bordignon, Miriam A Apel. A Chemometrics Approach to the Investigation of the Intraspecific Variability of the Volatile Oil of Eupatorium tremulum from Southern Brazil. Journal of natural products. 2017 01; 80(1):45-52. doi: 10.1021/acs.jnatprod.6b00313. [PMID: 28098995]
  • Danae Kala Rodríguez Bardají, Jonas Joaquim Mangabeira da Silva, Thamires Chiquini Bianchi, Daniele de Souza Eugênio, Pollyanna Francielli de Oliveira, Luís Fernando Leandro, Hervé Louis Ghislain Rogez, Rodrigo Cassio Sola Venezianni, Sergio Ricardo Ambrosio, Denise Crispim Tavares, Jairo Kenupp Bastos, Carlos Henrique G Martins. Copaifera reticulata oleoresin: Chemical characterization and antibacterial properties against oral pathogens. Anaerobe. 2016 Aug; 40(?):18-27. doi: 10.1016/j.anaerobe.2016.04.017. [PMID: 27118478]
  • Syn Kok Yeo, Ahmed Y Ali, Olivia A Hayward, Daniel Turnham, Troy Jackson, Ifor D Bowen, Richard Clarkson. β-Bisabolene, a Sesquiterpene from the Essential Oil Extract of Opoponax (Commiphora guidottii), Exhibits Cytotoxicity in Breast Cancer Cell Lines. Phytotherapy research : PTR. 2016 Mar; 30(3):418-25. doi: 10.1002/ptr.5543. [PMID: 26666387]
  • Danielle Cardoso de Alencar, Maria Lúcia Belém Pinheiro, José Lamak da Silva Pereira, João Ernesto de Carvalho, Francinete Ramos Campos, Alessandra Freitas Serain, Ricardo Brunelli Tirico, Alvaro José Hernández-Tasco, Emmanoel Vilaça Costa, Marcos José Salvador. Chemical composition of the essential oil from the leaves of Anaxagorea brevipes (Annonaceae) and evaluation of its bioactivity. Natural product research. 2016; 30(9):1088-92. doi: 10.1080/14786419.2015.1101103. [PMID: 26586465]
  • Ana Carolina B C Rodrigues, Larissa M Bomfim, Sara P Neves, Leociley R A Menezes, Rosane B Dias, Milena B P Soares, Ana Paula N Prata, Clarissa A Gurgel Rocha, Emmanoel V Costa, Daniel P Bezerra. Antitumor Properties of the Essential Oil From the Leaves of Duguetia gardneriana. Planta medica. 2015 Jul; 81(10):798-803. doi: 10.1055/s-0035-1546130. [PMID: 26125546]
  • Idris Ajayi Oyemitan, Omotola Aanuoluwa Olayera, Akeeb Alabi, Luqman Adewale Abass, Christianah Abimbola Elusiyan, Adebola Omowumi Oyedeji, Moses Atanda Akanmu. Psychoneuropharmacological activities and chemical composition of essential oil of fresh fruits of Piper guineense (Piperaceae) in mice. Journal of ethnopharmacology. 2015 May; 166(?):240-9. doi: 10.1016/j.jep.2015.03.004. [PMID: 25771354]
  • Elzalina R Soares, Felipe M A da Silva, Richardson A de Almeida, Bruna R de Lima, Hector H F Koolen, Caroline C Lourenço, Marcos J Salvador, Adriana Flach, Luiz Antonio M A da Costa, Antonia Q L de Souza, Maria L B Pinheiro, Afonso D L de Souza. Chemical composition and antimicrobial evaluation of the essential oils of Bocageopsis pleiosperma Maas. Natural product research. 2015; 29(13):1285-8. doi: 10.1080/14786419.2014.996148. [PMID: 25562370]
  • Akbar Karami, Nematollah Dehghan-Mashtani. Composition of the essential oil of Stachys benthamiana Boiss. from the south of Iran. Natural product research. 2015; 29(15):1473-6. doi: 10.1080/14786419.2014.1003185. [PMID: 25605295]
  • Oladipupo A Lawal, Isiaka A Ogunwande, Atinuke F Salvador, Adetayo A Sanni, Andy R Opoku. Pachira glabra Pasq. essential oil: chemical constituents, antimicrobial and insecticidal activities. Journal of oleo science. 2014; 63(6):629-35. doi: 10.5650/jos.ess13179. [PMID: 24881772]
  • C Messaoud, H Chograni, M Boussaid. Chemical composition and antioxidant activities of essential oils and methanol extracts of three wild Lavandula L. species. Natural product research. 2012 Nov; 26(21):1976-84. doi: 10.1080/14786419.2011.635343. [PMID: 22117129]
  • 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]
  • Catherine Argyropoulou, Helen Skaltsa. Identification of essential oil components of Marrubium thessalum Boiss. & Heldr., growing wild in Greece. Natural product research. 2012; 26(7):593-9. doi: 10.1080/14786419.2010.535153. [PMID: 21827333]
  • Sunday O Okoh, Olayinka T Asekun, Oluwole B Familoni, Anthony J Afolayan. Composition and antioxidant activities of leaf and root volatile oils of Morinda lucida. Natural product communications. 2011 Oct; 6(10):1537-41. doi: ". [PMID: 22164802]
  • Danilo Falconieri, Alessandra Piras, Silvia Porcedda, Bruno Marongiu, Maria J Gonçalves, Célia Cabral, Carlos Cavaleiro, Ligia Salgueiro. Chemical composition and biological activity of the volatile extracts of Achillea millefolium. Natural product communications. 2011 Oct; 6(10):1527-30. doi: . [PMID: 22164800]
  • Cristina Herrero-Jáuregui, Miguel A Casado, Maria das Graças Bichara Zoghbi, Regina Célia Martins-da-Silva. Chemical variability of Copaifera reticulata Ducke oleoresin. Chemistry & biodiversity. 2011 Apr; 8(4):674-85. doi: 10.1002/cbdv.201000258. [PMID: 21480513]
  • Monika Tomczykowa, Katarzyna Leszczyńska, Michał Tomczyk, Elżbieta Tryniszewska, Danuta Kalemba. Composition of the essential oil of Bidens tripartita L. roots and its antibacterial and antifungal activities. Journal of medicinal food. 2011 Apr; 14(4):428-33. doi: 10.1089/jmf.2010.0066. [PMID: 21370967]
  • Zsuzsanna Pluhár, Szilvia Sárosi, Adrienn Pintér, Hella Simkó. Essential oil polymorphism of wild growing Hungarian thyme (Thymus pannonicus) populations in the Carpathian Basin. Natural product communications. 2010 Oct; 5(10):1681-6. doi: . [PMID: 21121273]
  • Masaki Fujisawa, Hisashi Harada, Hiromichi Kenmoku, Satoru Mizutani, Norihiko Misawa. Cloning and characterization of a novel gene that encodes (S)-beta-bisabolene synthase from ginger, Zingiber officinale. Planta. 2010 Jun; 232(1):121-30. doi: 10.1007/s00425-010-1137-6. [PMID: 20229191]
  • 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]
  • Hnia Chograni, Yosr Zaouali, Chayma Rajeb, Mohamed Boussaid. Essential oil variation among natural populations of Lavandula multifida L. (Lamiaceae). Chemistry & biodiversity. 2010 Apr; 7(4):933-42. doi: 10.1002/cbdv.200900201. [PMID: 20397226]
  • Qi Wang, Tzu-Hsuan Chen, Kenneth F Bastow, Kuo-Hsiung Lee, Dao-Feng Chen. Altaicalarins A-D, cytotoxic bisabolane sesquiterpenes from Ligularia altaica. Journal of natural products. 2010 Feb; 73(2):139-42. doi: 10.1021/np900489h. [PMID: 20073490]
  • Mohammad Bagher Gholivand, Mehdi Rahimi-Nasrabadi, Hossein Batooli, Abdolrasoul H Ebrahimabadi. Chemical composition and antioxidant activities of the essential oil and methanol extracts of Psammogeton canescens. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2010 Jan; 48(1):24-8. doi: 10.1016/j.fct.2009.09.007. [PMID: 19748545]
  • 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]
  • Jolanta Nazaruk, Danuta Kalemba. Chemical composition of the essential oils from the roots of Erigeron acris L. and Erigeron annuus (L.) Pers. Molecules (Basel, Switzerland). 2009 Jul; 14(7):2458-65. doi: 10.3390/molecules14072458. [PMID: 19633616]
  • Andrea Maxia, Bruno Marongiu, Alessandra Piras, Silvia Porcedda, Enrica Tuveri, Maria J Gonçalves, Carlos Cavaleiro, Ligia Salgueiro. Chemical characterization and biological activity of essential oils from Daucus carota L. subsp. carota growing wild on the Mediterranean coast and on the Atlantic coast. Fitoterapia. 2009 Jan; 80(1):57-61. doi: 10.1016/j.fitote.2008.09.008. [PMID: 18950693]
  • 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]
  • Tobias G Köllner, Christiane Schnee, Shenghong Li, Ales Svatos, Bernd Schneider, Jonathan Gershenzon, Jörg Degenhardt. Protonation of a neutral (S)-beta-bisabolene intermediate is involved in (S)-beta-macrocarpene formation by the maize sesquiterpene synthases TPS6 and TPS11. The Journal of biological chemistry. 2008 Jul; 283(30):20779-88. doi: 10.1074/jbc.m802682200. [PMID: 18524777]
  • Lexa G Matasyoh, Josphat C Matasyoh, Francis N Wachira, Miriam G Kinyua, Anne W Thairu Muigai, Titus K Mukiama. Antimicrobial activity of essential oils of Ocimum gratissimum L. From different populations of Kenya. African journal of traditional, complementary, and alternative medicines : AJTCAM. 2008 Jan; 5(2):187-93. doi: 10.4314/ajtcam.v5i2.31272. [PMID: 20161936]
  • 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]
  • Andréa M A Nascimento, Maria G L Brandão, Gabriel B Oliveira, Isabel C P Fortes, Edmar Chartone-Souza. Synergistic bactericidal activity of Eremanthus erythropappus oil or beta-bisabolene with ampicillin against Staphylococcus aureus. Antonie van Leeuwenhoek. 2007 Jul; 92(1):95-100. doi: 10.1007/s10482-006-9139-x. [PMID: 17235483]
  • 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]
  • Donata Ricci, Daniele Fraternale, Laura Giamperi, Anahi Bucchini, Francesco Epifano, Giovanni Burini, Massimo Curini. Chemical composition, antimicrobial and antioxidant activity of the essential oil of Teucrium marum (Lamiaceae). Journal of ethnopharmacology. 2005 Apr; 98(1-2):195-200. doi: 10.1016/j.jep.2005.01.022. [PMID: 15763383]
  • T Hernández, M Canales, J G Avila, A M García, A Martínez, J Caballero, A Romo de Vivar, R Lira. Composition and antibacterial activity of essential oil of Lantana achyranthifolia Desf. (Verbenaceae). Journal of ethnopharmacology. 2005 Jan; 96(3):551-4. doi: 10.1016/j.jep.2004.09.044. [PMID: 15619577]
  • Joyce Govinden-Soulange, Naresh Magan, Ameenah Gurib-Fakim, Anne Gauvin, Jaqueline Smadja, Hippolyte Kodja. Chemical composition and in vitro antimicrobial activities of the essential oils from endemic Psiadia species growing in mauritius. Biological & pharmaceutical bulletin. 2004 Nov; 27(11):1814-8. doi: 10.1248/bpb.27.1814. [PMID: 15516729]
  • Vijai K Agnihotri, Rajendra K Thappa, Baleshwar Meena, Bal K Kapahi, Rajendra K Saxena, Ghulam N Qazi, Shri G Agarwal. Essential oil composition of aerial parts of Angelica glauca growing wild in North-West Himalaya (India). Phytochemistry. 2004 Aug; 65(16):2411-3. doi: 10.1016/j.phytochem.2004.07.004. [PMID: 15381015]
  • Tobias G Köllner, Christiane Schnee, Jonathan Gershenzon, Jörg Degenhardt. The variability of sesquiterpenes emitted from two Zea mays cultivars is controlled by allelic variation of two terpene synthase genes encoding stereoselective multiple product enzymes. The Plant cell. 2004 May; 16(5):1115-31. doi: 10.1105/tpc.019877. [PMID: 15075399]
  • Frank Kjeldsen, Lars P Christensen, Merete Edelenbos. Changes in volatile compounds of carrots (Daucus carota L.) during refrigerated and frozen storage. Journal of agricultural and food chemistry. 2003 Aug; 51(18):5400-7. doi: 10.1021/jf030212q. [PMID: 12926889]
  • C R Benedict, J L Lu, D W Pettigrew, J Liu, R D Stipanovic, H J Williams. The cyclization of farnesyl diphosphate and nerolidyl diphosphate by a purified recombinant delta-cadinene synthase. Plant physiology. 2001 Apr; 125(4):1754-65. doi: 10.1104/pp.125.4.1754. [PMID: 11299356]
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