Planta Med 2009; 75 - PJ198
DOI: 10.1055/s-0029-1235003

A new facile and efficient synthesis of trans-(+)-sobrerol by biotransformation of α-pinene using extremophiles microorganisms

LA Vilaseca 1, J Quillaguamán 2, L Fuentes 1, O Sterner 3
  • 1Centro de Tecnología Agroindustrial, Facultad de Ciencias y Tecnología, Universidad Mayor de San Simón, Cochabamba, Bolivia
  • 2Centro de Biotecnología, Facultad de Ciencias y Tecnología, Universidad Mayor de San Simón, Cochabamba, Bolivia
  • 3Department of Organic Chemistry, University of Lund, Sweden

Trans-(+)-sobrerol is a hydroxyl containing monocyclic terpenoid resulting from the autoxidation of α-pinene in presence of air and water. It presents pharmacological properties as mucolytic agent and clinical trials have confirmed its efficacy in relieving obstructive symptoms in patients suffering from chronic bronchitics [1].

Synthetic pathways have been established to obtain trans-(+)-sobrerol but in general they consist of several steps and the overall yields are low with poor stereoselectivity [2].

Essential oils are rich mixtures of natural products, mainly terpenes, and are obtained from aromatic plants by steam distillation or hydrodistillation. Some terpenes are very useful starting materials for the synthesis of more complex molecules [3].

α-Pinene, a hydrocarbon monoterpene present in several essential oils, can be easily obtained by rectification. It has been transformed in products of more added value by chemical reactions but also by biotransformation using fungi species, resulting in complex mixtures of oxygenated compounds [4].

In this work, we report for the first time the use of extremophiles microorganisms for the biotransformation of α-pinene. This terpene was transformed by a halophilic bacterial strain belonging to the genus Jeotgalicoccus after cultivation in liquid medium under aerobic conditions at 30oC for 48h. GC analyses of the reaction mixture, after extraction in ethyl acetate, showed the presence of few components. The component present in the highest concentration was isolated and identified as trans-(+)-sobrerol by NMR spectroscopy.

Acknowledgements: We are grateful to SIDA-SAREC (Sweden) for financial support.

References: [1] Braga, P.C. et al. (1987) Int. J. Clin. Pharmacol. Res. 7:381–400.

[2] Wang, Q. et al. (2003) Synth. Comm. 33:2125–2134.

[3] Monteiro, J.L.F., Veloso, C.O. (2004) Top.Catal. 27:169–180.

[4] Lindmark-Henriksson, M. et al. (2003)J. Nat. Prod. 66:337–343.