Bisabolene

• CAT Number: I023421
• CAS Number: 495-62-5
• Molecular Formula: C15H24
• Molecular Weight: 204.35
• Purity: 98%
• Synonyms: Bisabolene; Limene; Bisabolene (natural)
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4℃ for short term (days to weeks) or -20℃ for long term (months to years).
• IUPAC Name: (Z)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene
• InChI: InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14+
• InChIKey: XBGUIVFBMBVUEG-CCEZHUSRSA-N
• SMILES: C/C(C)=CCC/C(C)=C1CC=C(C)CC1

Bisabolene (Cat.No:I023421) is a sesquiterpene and can be extracted from oregano and other aromatic plants. It may be a potential anticancer agent that can induce apoptosis in A549 cancer cell line.

Reference

1: Jou YJ, Chen CJ, Liu YC, Way TD, Lai CH, Hua CH, Wang CY, Huang SH, Kao JY, Lin CW. Quantitative phosphoproteomic analysis reveals γ-bisabolene inducing p53-mediated apoptosis of human oral squamous cell carcinoma via HDAC2 inhibition and ERK1/2 activation. Proteomics. 2015 Oct;15(19):3296-309. doi: 10.1002/pmic.201400568. Epub 2015 Aug 13. PubMed PMID: 26194454.
2: Jou YJ, Hua CH, Lin CS, Wang CY, Wan L, Lin YJ, Huang SH, Lin CW. Anticancer Activity of γ-Bisabolene in Human Neuroblastoma Cells via Induction of p53-Mediated Mitochondrial Apoptosis. Molecules. 2016 May 7;21(5). pii: E601. doi: 10.3390/molecules21050601. PubMed PMID: 27164076.
3: Davies FK, Work VH, Beliaev AS, Posewitz MC. Engineering Limonene and Bisabolene Production in Wild Type and a Glycogen-Deficient Mutant of Synechococcus sp. PCC 7002. Front Bioeng Biotechnol. 2014 Jun 19;2:21. doi: 10.3389/fbioe.2014.00021. eCollection 2014. PubMed PMID: 25152894; PubMed Central PMCID: PMC4126464.
4: Aschenbrenner AK, Kwon M, Conrad J, Ro DK, Spring O. Identification and characterization of two bisabolene synthases from linear glandular trichomes of sunflower (Helianthus annuus L., Asteraceae). Phytochemistry. 2016 Apr;124:29-37. doi: 10.1016/j.phytochem.2016.01.009. Epub 2016 Feb 12. PubMed PMID: 26880289.
5: Phelan RM, Sekurova ON, Keasling JD, Zotchev SB. Engineering terpene biosynthesis in Streptomyces for production of the advanced biofuel precursor bisabolene. ACS Synth Biol. 2015 Apr 17;4(4):393-9. doi: 10.1021/sb5002517. Epub 2014 Jul 9. PubMed PMID: 25006988.
6: Parveen I, Wang M, Zhao J, Chittiboyina AG, Tabanca N, Ali A, Baerson SR, Techen N, Chappell J, Khan IA, Pan Z. Investigating sesquiterpene biosynthesis in Ginkgo biloba: molecular cloning and functional characterization of (E,E)-farnesol and α-bisabolene synthases. Plant Mol Biol. 2015 Nov;89(4-5):451-62. doi: 10.1007/s11103-015-0381-3. Epub 2015 Oct 6. PubMed PMID: 26442918.
7: Yeo SK, Ali AY, Hayward OA, Turnham D, Jackson T, Bowen ID, Clarkson R. β-Bisabolene, a Sesquiterpene from the Essential Oil Extract of Opoponax (Commiphora guidottii), Exhibits Cytotoxicity in Breast Cancer Cell Lines. Phytother Res. 2016 Mar;30(3):418-25. doi: 10.1002/ptr.5543. Epub 2015 Dec 15. PubMed PMID: 26666387.
8: Liu W, Liang KJ, Chiang CY, Lu MC, Su JH. New nitrogenous bisabolene-type sesquiterpenes from a formosan sponge Axinyssa sp. Chem Pharm Bull (Tokyo). 2014;62(4):392-4. Epub 2014 Jan 17. PubMed PMID: 24441415.
9: Hong YJ, Tantillo DJ. Branching out from the bisabolyl cation. Unifying mechanistic pathways to barbatene, bazzanene, chamigrene, chamipinene, cumacrene, cuprenene, dunniene, isobazzanene, iso-γ-bisabolene, isochamigrene, laurene, microbiotene, sesquithujene, sesquisabinene, thujopsene, trichodiene, and widdradiene sesquiterpenes. J Am Chem Soc. 2014 Feb 12;136(6):2450-63. doi: 10.1021/ja4106489. Epub 2014 Feb 3. PubMed PMID: 24490652.
10: Xi FM, Ma SG, Liu YB, Li L, Yu SS. Artaboterpenoids A and B, Bisabolene-Derived Sesquiterpenoids from Artabotrys hexapetalus. Org Lett. 2016 Jul 15;18(14):3374-7. doi: 10.1021/acs.orglett.6b01519. Epub 2016 Jun 24. PubMed PMID: 27341484.
11: Abdjul DB, Kanno SI, Yamazaki H, Ukai K, Namikoshi M. A dimeric urea of the bisabolene sesquiterpene from the Okinawan marine sponge Axinyssa sp. inhibits protein tyrosine phosphatase 1B activity in Huh-7 human hepatoma cells. Bioorg Med Chem Lett. 2016 Jan 15;26(2):315-317. doi: 10.1016/j.bmcl.2015.12.022. Epub 2015 Dec 8. PubMed PMID: 26711144.
12: Orellana-Paucar AM, Serruys AS, Afrikanova T, Maes J, De Borggraeve W, Alen J, León-Tamariz F, Wilches-Arizábala IM, Crawford AD, de Witte PA, Esguerra CV. Anticonvulsant activity of bisabolene sesquiterpenoids of Curcuma longa in zebrafish and mouse seizure models. Epilepsy Behav. 2012 May;24(1):14-22. doi: 10.1016/j.yebeh.2012.02.020. Epub 2012 Apr 5. PubMed PMID: 22483646.
13: Kirby J, Nishimoto M, Chow RW, Pasumarthi VN, Chan R, Chan LJ, Petzold CJ, Keasling JD. Use of nonionic surfactants for improvement of terpene production in Saccharomyces cerevisiae. Appl Environ Microbiol. 2014 Nov;80(21):6685-93. doi: 10.1128/AEM.02155-14. Epub 2014 Aug 22. PubMed PMID: 25149518; PubMed Central PMCID: PMC4249056.
14: Mao SC, Guo YW, van Soest R, Cimino G. Trans-dimer D, a novel dimeric sesquiterpene with a bis-bisabolene skeleton from a Hainan sponge Axinyssa variabilis. J Asian Nat Prod Res. 2011 Aug;13(8):770-5. doi: 10.1080/10286020.2011.588949. PubMed PMID: 21751848.
15: Bohlmann J, Crock J, Jetter R, Croteau R. Terpenoid-based defenses in conifers: cDNA cloning, characterization, and functional expression of wound-inducible (E)-alpha-bisabolene synthase from grand fir (Abies grandis). Proc Natl Acad Sci U S A. 1998 Jun 9;95(12):6756-61. PubMed PMID: 9618485; PubMed Central PMCID: PMC22624.
16: Fujisawa M, Harada H, Kenmoku H, Mizutani S, Misawa N. 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. Epub 2010 Mar 13. Erratum in: Planta. 2010 Jun;232(1):131. PubMed PMID: 20229191.
17: Nascimento AM, Brandão MG, Oliveira GB, Fortes IC, Chartone-Souza E. Synergistic bactericidal activity of Eremanthus erythropappus oil or beta-bisabolene with ampicillin against Staphylococcus aureus. Antonie Van Leeuwenhoek. 2007 Jul;92(1):95-100. Epub 2007 Jan 18. PubMed PMID: 17235483.
18: Vyvyan JR, Loitz C, Looper RE, Mattingly CS, Peterson EA, Staben ST. Synthesis of aromatic bisabolene natural products via palladium-catalyzed cross-couplings of organozinc reagents. J Org Chem. 2004 Apr 2;69(7):2461-8. PubMed PMID: 15049646.
19: Valdez-Calderón A, Torres-Valenci JM, Manríquez-Torres JJ, Velázquez-Jiménez R, Gómez-Hurtado MA, Román-Marín LU, Hernández-Hernández JD, Cerda-García-Rojas CM, Joseph-Nathan P. A new bisabolene from Stevia tomentosa. Nat Prod Commun. 2011 Sep;6(9):1225-8. PubMed PMID: 21941883.
20: Brézot P, Malosse C, Mori K, Renou M. Bisabolene epoxides in sex pheromone innezara viridula (L.) (Heteroptera: Pentatomidae): Role ofcis isomer and relation to specificity of pheromone. J Chem Ecol. 1994 Dec;20(12):3133-47. doi: 10.1007/BF02033716. PubMed PMID: 24241982.