Skip to main content
SpringerLink
Log in

A Review of the Application and Pharmacological Properties of α-Bisabolol and α-Bisabolol-Rich Oils

  • Review
  • Published:
Journal of the American Oil Chemists' Society

Abstract

α-Bisabolol is a naturally occurring sesquiterpene alcohol which was first isolated from Matricaria chamomilla (Asteraceae) in the twentieth century and has since been identified in other aromatic plants such as Eremanthus erythropappus, Smyrniopsis aucheri and Vanillosmopsis species. Recently, α-bisabolol was identified as a major constituent of Salvia runcinata essential oil, a plant indigenous to South Africa. The use of α-bisabolol or bisabolol-rich oil as an anti-inflammatory agent is ubiquitous. This compound also exhibits several other pharmacological properties such as analgesic, antibiotic and anticancer activities. Mutagenicity and genotoxicity of bisabolol have also been investigated. Due to the low toxicity associated with bisabolol the Food and Drug Administration (FDA) has granted this constituent with Generally Regarded as Safe (GRAS) status which has promoted its use as an active ingredient in several commercial products. This review aims to summarise the role of α-bisabolol in pharmacological and/or physiological processes and to discuss some of the possible mechanisms of action of this commercially important molecule.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Harrewijn P, Van Oosten MA, Piron PG (2001) Natural terpenoids as messengers: a multidisciplinary study of their production, biological functions, and practical applications. Kluwer, Boston

    Google Scholar 

  2. Hornby JM, Jensen EC, Lisec AD, Tasto JJ, Jahnke B, Shoemaker R, Dussault P, Nickerson KW (2001) Quorum sensing in the dimorphic fungus Candida albicans is mediated by farnesol. Appl Environ Microbiol 67:2982–2992

    Article  CAS  Google Scholar 

  3. Bauer K, Garbe D, Surburg H (1997) Common fragrance and flavor materials: preparation, properties and uses, 3rd edn. Wiley–VCH, New York

    Google Scholar 

  4. Harborne JB, Tomás-Barberán FA (1991) Ecological chemistry and biochemistry of plant terpenoids. Oxford University Press, New York

    Google Scholar 

  5. Brunke EJ, Hammaerschmidt FJ (1985) Constituents of the essential oil of Salvia stenophylla—first identification of the (+)-α-bisabolol in nature. In: Svendsen AB, Scheffer JJC (eds) Essential oils and aromatic plants. Martinus Nijhoff/Dr. Junk W Publishers, Dordrecht, pp 37–43

    Google Scholar 

  6. Gomes-Carneiro MR, Dias DMM, De-Oliveira ACAX, Paumgartten FJR (2005) Evaluation of mutagenic and antimutagenic activities of α-bisabolol in the Salmonella/microsome assay. Mutat Res 585:105–112

    CAS  Google Scholar 

  7. Isaac O, Thiemer K (1975) [Biochemical studies on camomile components/III. In vitro studies about the antipeptic activity of (−)-alpha-bisabolol (author’s transl)]. Arzneimittelforschung 25:1352–1354

    CAS  Google Scholar 

  8. Viljoen AM, Gono-Bwalya AB, Kamatou GPP, Başer KHC, Demirci B (2006) The essential oil composition and chemotaxonomy of Salvia stenophylla and its allies S. repens and S. runcinata. J Essent Oil Res 18:37–45

    CAS  Google Scholar 

  9. De Souza AT, Benazzi TL, Grings MB, Cabral V, da Silva EA, Cardozo-Filho L, Antunes OAC (2008) Supercritical extraction process and phase equilibrium of Candeia (Eremanthus erythropappus) oil using supercritical carbon dioxide. J Supercrit Fluids 47:182–187

    Article  Google Scholar 

  10. Madhavan BN (1999) Final report on the safety assessment of bisabolol. Int J Toxicol 18(Suppl. 3):33–40

    CAS  Google Scholar 

  11. Piochon M, Legault J, Gauthier C, Pichette A (2009) Synthesis and cytotoxicity evaluation of natural α-bisabolol b-d-fucopyranoside and analogues. Phytochemistry 70:228–236

    Article  CAS  Google Scholar 

  12. Sell CS (1999) Ingredients for the modern perfumery industry. In: Pybus DH, Sell CS (eds) The chemistry of fragrances. The Royal Society of Chemistry, UK

    Google Scholar 

  13. Perbellini L, Gottardo R, Caprini A, Bortolotti F, Mariotto S, Tagliaro F (2004) Determination of alpha-bisabolol in human blood by micro-HPLC–ion trap MS and head space-GC–MS methods. J Chromatogr B 812:373–377

    CAS  Google Scholar 

  14. Waleczek KJ, Cabral Marques HM, Hempel B, Schmidt PC (2003) Phase solubility studies of pure (2)-α-bisabolol and camomile essential oil with β-cyclodextrin. Eur J Pharm Biopharm 55:247–251

    Article  CAS  Google Scholar 

  15. Berry M (1995) The chamomiles. Pharm J 254:191–193

    Google Scholar 

  16. Kadir R, Barry BW (1991) α-Bisabolol, a possible safe penetration enhancer for dermal and transdermal therapeutics. Int J Pharm 70:87–94

    Article  CAS  Google Scholar 

  17. Baylac S, Racine P (2003) Inhibition of 5-lipoxygenase by essential oils and other natural fragrant extracts. Int J Aromather 13:138–142

    Article  Google Scholar 

  18. Van Zyl RL, Seatlholo ST, Van Vuuren SF, Viljoen AM (2006) The biological activities of 20 nature identical essential oil constituents. J Essent Oil Res 18:129–133

    Google Scholar 

  19. Siegenthaler G, Saurat JH, Ponec M (1988) Terminal differentiation in cultured human keratinocytes is associated with increased levels of cellular retinoic acid-binding protein. Exp Cell Res 178:114–126

    Article  CAS  Google Scholar 

  20. Zheng Y, Niyonsaba F, Ushio H, Ikeda S, Nagaoka I, Okumura K, Ogawa H (2008) Microbicidal protein psoriasin is a multifunctional modulator of neutrophil activation. Immunology 124:357–367

    Article  CAS  Google Scholar 

  21. Lopes NP, Kato MJ, Andrade EHA, Maia JGS, Yoshida M, Planchart AR, Katzin AM (1999) Antimalarial use of volatile oil from leaves of Virola surinamensis (Rol.) Warb. By Waiãpi Amazon Indians. J Ethnopharmacol 67:313–319

    Article  CAS  Google Scholar 

  22. Ultee A, Bennik MH, Moezelaar R (2002) The phenolic hydroxyl group of carvacrol is essential for action against the food-borne pathogen Bacillus cereus. Appl Environ Microbiol 68:1561–1568

    Article  CAS  Google Scholar 

  23. Tampieri MP, Galuppi R, Macchioni F, Carelle MS, Falcioni L, Cioni PL, Morelli I (2005) The inhibition of Candida albicans by selected essential oils and their major components. Mycopatholgia 159:339–345

    Article  CAS  Google Scholar 

  24. Duke JA, Bogenschutz-Godwin MJ, DuCellier J, Duke P-AK (2002) Handbook of medicinal herbs, 2nd edn. CRC Press, Boca Raton

    Google Scholar 

  25. Nuñez YO, Salabarria IS, Collado IG, Hernández-Galán R (2007) Sesquiterpenes from the wood of Juniperus lucayana. Phytochemistry 68:2409–2414

    Article  Google Scholar 

  26. Kamatou GPP, Viljoen AM, Lourens ACU, Başer KHC, Demirci B, Lindsey KL, Van Staden J, Steenkamp P (2005) The in vitro pharmacological activities and a chemical investigation of three South African Salvia species. J Ethnopharmacol 102:382–390

    Article  CAS  Google Scholar 

  27. Yonzon M, Dong JL, Yokochi T, Kawano Y, Nakahara T (2005) Antimicrobial activities of essential oils of Nepal. J Essent Oil Res 17:107–111

    Google Scholar 

  28. Morris JA, Khettry A, Seitz EW (1979) Anti-microbial activity or aroma chemicals and essential oils. J Am Oil Chem Soc 56:595–603

    Article  CAS  Google Scholar 

  29. Koch C, Reichling J, Kehm R, Sharaf MM, Zentgraf H, Schneele J, Schnitzler P (2008) Efficacy of anise oil, dwarf-pine oil and chamomile oil against thymidine-kinase-positive and thymidine-kinase-negative herpesviruses. J Pharm Pharmacol 60:1545–1550

    Article  CAS  Google Scholar 

  30. Koch C, Reichling J, Schneele J, Schnitzler P (2008) Inhibitory effect of essential oils against herpes simplex virus type 2. Phytomedicine 15:71–78

    Article  CAS  Google Scholar 

  31. Brehm-Stecher BF, Johnson EA (2003) Sensitization of Staphylococcus aureus and Escherichia coli to antibiotics by the sesquiterpenoids nerolidol, farnesol, bisabolol, and apritone. Antimicrob Agents Chemother 47:3357–3360

    Article  CAS  Google Scholar 

  32. Cornwell PA, Barry BW (1994) Sesquiterpene components of volatile oils as skin penetration enhancers for the hydrophilic permeant 5-fluorouracil. J Pharm Pharmacol 46:261–269

    CAS  Google Scholar 

  33. Aruoma OI (1998) Free radicals, oxidative stress and anti-oxidants in human health and disease. J Am Oil Chem Soc 75:199–212

    Article  CAS  Google Scholar 

  34. Ito N, Fukushima S, Tsuda H (1985) Carcinogenicity and modification of the carcinogenic response by BHA and BHT and other anti-oxidants. Crit Rev Toxicol 15:109–150

    Article  Google Scholar 

  35. Wanasundara UN, Shahidi F (1998) Anti-oxidant and pro-oxidant activity of green tea extract in marine oils. Food Chem 63:335–342

    Article  CAS  Google Scholar 

  36. Braga PC, Dal Sasso M, Fonti E, Culici M (2009) Antioxidant activity of bisabolol: inhibitory effects on chemiluminescence of human neutrophil bursts and cell-free systems. Pharmacology 83:110–115

    Article  CAS  Google Scholar 

  37. Safayhi H, Sabieraj J, Sailer E, Chamazulene AH (1994) An antioxidant-type inhibitor of leukotriene B4 formation. Planta Med 60:410–413

    Article  CAS  Google Scholar 

  38. Kim S, Lee J, Jung E, Huh S, Park J-O, Lee J-W, Byun SY, Park D (2008) Mecahnisms of depigmentation by α-bisabolol. J Dermatol Sci 52:219–222

    Article  CAS  Google Scholar 

  39. Kalia YN, Naik A, Garrison J, Guy RH (2007) Iontophoretic drug delivery. Adv Drug Deliv Rev 56:619–658

    Article  Google Scholar 

  40. Aqil M, Ahada A, Sultanaa Y, Ali A (2007) Status of terpenes as skin penetration enhancers. Drug Discov Today 12:1061–1067

    Article  CAS  Google Scholar 

  41. Williams AC, Barry BW (1991) Terpenes and the lipid-protein- partitioning theory of skin penetration enhancement. Pharm Res 8:17–24

    Article  CAS  Google Scholar 

  42. Food and Drug Administration. www.accessdata.fda.gov/scripts/crrh/cfdocs/cfcfr/CFRSearch.cfm?fr=182.20. Accessed 2009

  43. Monti D, Saettone MF, Giannaccini B, Galli-Angeli D (1995) Enhancement of transdermal penetration of dapiprazole through hairless mouse skin. J Control Release 33:71–77

    Article  CAS  Google Scholar 

  44. Torrado S, Torrado S, Agis A, Jimenez ME, Cadórniga R (1995) Effect of dissolution profile and (−)-alpha-bisabolol on the gastrotoxicity of acetylsalicylic acid. Pharmazie 50:141–143

    CAS  Google Scholar 

  45. Alvarez-Gonzalez I, Uc-Artigas E, Moreno LM, Madrigal-Bujaidar E (2006) Inhibitory effect of alpha-bisabolol on the genotoxic damage induced by daunorubicin in mouse. Toxicol Lett 164:S268

    Google Scholar 

  46. Cavalieri E, Mariotto S, Fabrizi C, Carcereri de Prati A, Gottado R, Leone S, Berra LV, Lauro GM, Ciampa AR, Suzuki H (2004) α-Bisabolol, a nontoxic compound, strongly induces apoptosis in glioma cells. Biochem Biophys Res Commun 315:589–594

    Article  CAS  Google Scholar 

  47. Darra E, Abdel-Azeim S, Manara A, Shoji K, Maréchal J-D, Mariotto S, Cavalieri E, Perbellini L, Pizza C, Perahia D, Crimi M, Suzuki H (2008) Insight into the apoptosis-inducing action of a-bisabolol towards malignant tumor cells: involvement of lipid rafts and bid. Arch Biochem Biophys 476:113–123

    Article  CAS  Google Scholar 

  48. Hernández-Ceruelos A, Sánchez-Gutiérrez M, Mojica-Villegas A, Chamorro-Cevallos G (2007) Chemoprotection of fertility by chamomile essential oil over the toxic effect. Toxicol Lett 172:S185–S186

    Article  Google Scholar 

  49. Furtado RF, De Lima MGA, Neto MA, Bezerra JNS, Silva EMG (2005) Atividade larvicida de óleos essenciais Contra Aedes aegypti L. (Diptera: Culicidae). Neotrop Entomol 34:843–847

    Article  CAS  Google Scholar 

  50. Niederhofer H (2009) Observational study: Matricaria chamomilla may improve some symptoms of attention-deficit hyper activity disorder. Phytomedicine 16:284–286

    Article  CAS  Google Scholar 

  51. Issac O (1979) Pharmacological investigations with compounds of chamomile. I. On the pharmacology of (−)-α-bisabolol and bisabolol oxides (review). Planta Med 35:118–124

    Article  Google Scholar 

  52. Villegas LF, Marçalo A, Martin J, Fernández ID, Maldonado H, Vaisberg AJ, Hammond GB (2001) (+)-epi-Alpha-bisabolol [correction of bisbolol] is the wound-healing principle of Peperomia galioides: investigation of the in vivo wound-healing activity of related terpenoids. J Nat Prod 64:1357–1359

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Pharmaceutical Sciences, Faculty of Science, Tshwane University of Technology, Private Bag X680, Pretoria, 0001, South Africa

    Guy P. P. Kamatou & Alvaro M. Viljoen

Authors
  1. Guy P. P. Kamatou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Alvaro M. Viljoen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alvaro M. Viljoen.

About this article

Cite this article

Kamatou, G.P.P., Viljoen, A.M. A Review of the Application and Pharmacological Properties of α-Bisabolol and α-Bisabolol-Rich Oils. J Am Oil Chem Soc 87, 1–7 (2010). https://doi.org/10.1007/s11746-009-1483-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-009-1483-3

Keywords

Search

Navigation