Plant Biotechnology

Electronic Journal of Biotechnology ISSN: 0717-3458 Vol. 10 No. 4, Issue of October 15, 2007
© 2007 by Pontificia Universidad Católica de Valparaíso -- Chile Received January 19, 2007 / Accepted May 8, 2007
DOI: 10.2225/vol10-issue4-fulltext-8
RESEARCH ARTICLE

Bioconversion of (+)- and (-)-alpha-pinene to (+)- and (-)-verbenone by plant cell cultures of Psychotria brachyceras and Rauvolfia sellowii 

Renata Pereira Limberger
Programa de Pós-Graduação em Ciências Farmacêuticas
Faculdade de Farmácia
Universidade Federal do Rio Grande do Sul
Av. Ipiranga 2752, 90.610.000
Porto Alegre, RS, Brazil
Tel: 55 51 33085297
Fax: 55 51 33085437
E-mail: renata@farmacia.ufrgs.br

Adriana Mendes Aleixo
Faculdade de Engenharia, Arquitetura e Urbanismo
Universidade Metodista de Piracicaba
Rodovia Santa Bárbara Iracemápolis Km 1, 13450-000
Santa Barbara D'oeste, SP, Brazil
Tel: 19 31241782
E-mail: amaleixo@unimep.br 

Arthur Germano Fett-Neto
Programa de Pós-Graduação em Biologia Celular e Molecular
Centro de Biotecnologia
Universidade Federal do Rio Grande do Sul
CP 15005 Agronomia, 91509-900
Porto Alegre, RS - Brazil
Tel: 51 33087642
Fax: 51 33087309
E-mail: fettneto@cbiot.ufrgs.br

Amélia T. Henriques*
Programa de Pós-Graduação em Ciências Farmacêuticas
Faculdade de Farmácia
Universidade Federal do Rio Grande do Sul
Av. Ipiranga 2752, 90.610.000
Porto Alegre, RS, Brazil
Tel: 55 51 33085417
Fax: 55 51 33085437
E-mail: amelia@farmacia.ufrgs.br

*Corresponding author

Financial support: CNPq, CAPES and FAPERGS.

Keywords: alpha-pinene, biotransformation, verbenol, verbenone.

Abbreviations:

2,4-D: 2,4-dichlorophenoxyacetic acid
EtOAc: ethyl acetate
GC: gas chromatography
GC-MS: gas chromatography-mass spectrometry
MS: Murashige and Skoog
NMR: Nuclear Magnetic Resonance Spectroscopy

Abstract
Full Text

This work describes the bioconversion of (-)- and (+)-alpha-pinene (2,6,6-trimethyl-bicyclo[3.1.1]hept-2-ene), targeted at the production of (-)- and (+)-verbenone (4,6,6-trimethyl-bicyclo (3.1.1) hept-3-en-2-one), respectively, using Psychotria brachyceras and Rauvolfia sellowii cell suspension cultures. P. brachyceras showed selectivity to (-)-alpha-pinene with 80.9% conversion (relative integrated area gas chromatography-mass spectrometry (GC-MS)) of (-)-verbenone in 10-day-incubation, whereas R. sellowii was able to convert both pinene enantiomers (37.6% conversion of (-)-verbenone in 7-day-incubation and 32.2% conversion of (+)-verbenone in 10-day-incubation). In both systems trans-verbenol was formed as main product and then slowly biocatalyzed to verbenone. Verbenone were also present among the autoxidation products during control experiments, but in much lower amounts and accompanied by several by-products, highlighting the usefulness of the biotransformation process.

Supported by UNESCO / MIRCEN network