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Applied and Environmental Microbiology, September 2003, p. 5045-5050, Vol. 69, No. 9
0099-2240/03/$08.00+0     DOI: 10.1128/AEM.69.9.5045-5050.2003
Copyright © 2003, American Society for Microbiology. All Rights Reserved.

Biotransformation of Natural and Synthetic Isoflavonoids by Two Recombinant Microbial Enzymes

Michael Seeger,1* Myriam González,1 Beatriz Cámara,1 Liliana Muñoz,1 Emilio Ponce,1 Lorenzo Mejías,2,{dagger} Carolina Mascayano,2 Yesseny Vásquez,2 and Silvia Sepúlveda-Boza2

Laboratorio de Microbiología Molecular y Biotecnología Ambiental, Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso,1 Laboratorio de Química Médica y Ensayos Biológicos, Facultad de Ciencias Médicas, Universidad de Santiago de Chile, Santiago, Chile2

Received 17 March 2003/ Accepted 4 June 2003

Isolation and synthesis of isoflavonoids has become a frequent endeavor, due to their interesting biological activities. The introduction of hydroxyl groups into isoflavonoids by the use of enzymes represents an attractive alternative to conventional chemical synthesis. In this study, the capabilities of biphenyl-2,3-dioxygenase (BphA) and biphenyl-2,3-dihydrodiol 2,3-dehydrogenase (BphB) of Burkholderia sp. strain LB400 to biotransform 14 isoflavonoids synthesized in the laboratory were investigated by using recombinant Escherichia coli strains containing plasmid vectors expressing the bphA1A2A3A4 or bphA1A2A3A4B genes of strain LB400. The use of BphA and BphB allowed us to biotransform 7-hydroxy-8-methylisoflavone and 7-hydroxyisoflavone into 7,2',3'-trihydroxy-8-methylisoflavone and 7,3',4'-trihydroxyisoflavone, respectively. The compound 2'-fluoro-7-hydroxy-8-methylisoflavone was dihydroxylated by BphA at ortho-fluorinated and meta positions of ring B, with concomitant dehalogenation leading to 7,2',3',-trihydroxy-8-methylisoflavone. Daidzein (7,4'-dihydroxyisoflavone) was biotransformed by BphA, generating 7,2',4'-trihydroxyisoflavone after dehydration. Biotransformation products were analyzed by gas chromatography-mass spectrometry and nuclear magnetic resonance techniques.

* Corresponding author. Mailing address: Departamento de Química, Universidad Técnica Federico Santa María, Av. España 1680, Valparaíso, Chile. Phone: (56) 32-654236. Fax: (56) 32-654782. E-mail: michael.seeger{at}qui.utfsm.cl.

{dagger} Present address: Institut für Organische Chemie und Makromolekulare Chemie, Düsseldorf, Germany.

Applied and Environmental Microbiology, September 2003, p. 5045-5050, Vol. 69, No. 9
0099-2240/03/$08.00+0     DOI: 10.1128/AEM.69.9.5045-5050.2003
Copyright © 2003, American Society for Microbiology. All Rights Reserved.



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