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Biotransformation of natural and synthetic isoflavonoids by two recombinant microbial enzymes.
Appl Environ Microbiol. 2003 Sep; 69(9):5045-50.AE

Abstract

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.

Authors+Show Affiliations

Laboratorio de Microbiología Molecular y Biotecnología Ambiental, Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso, Chile. michael.seeger@qui.utfsm.clNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

12957885

Citation

Seeger, Michael, et al. "Biotransformation of Natural and Synthetic Isoflavonoids By Two Recombinant Microbial Enzymes." Applied and Environmental Microbiology, vol. 69, no. 9, 2003, pp. 5045-50.
Seeger M, González M, Cámara B, et al. Biotransformation of natural and synthetic isoflavonoids by two recombinant microbial enzymes. Appl Environ Microbiol. 2003;69(9):5045-50.
Seeger, M., González, M., Cámara, B., Muñoz, L., Ponce, E., Mejías, L., Mascayano, C., Vásquez, Y., & Sepúlveda-Boza, S. (2003). Biotransformation of natural and synthetic isoflavonoids by two recombinant microbial enzymes. Applied and Environmental Microbiology, 69(9), 5045-50.
Seeger M, et al. Biotransformation of Natural and Synthetic Isoflavonoids By Two Recombinant Microbial Enzymes. Appl Environ Microbiol. 2003;69(9):5045-50. PubMed PMID: 12957885.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Biotransformation of natural and synthetic isoflavonoids by two recombinant microbial enzymes. AU - Seeger,Michael, AU - González,Myriam, AU - Cámara,Beatriz, AU - Muñoz,Liliana, AU - Ponce,Emilio, AU - Mejías,Lorenzo, AU - Mascayano,Carolina, AU - Vásquez,Yesseny, AU - Sepúlveda-Boza,Silvia, PY - 2003/9/6/pubmed PY - 2004/1/13/medline PY - 2003/9/6/entrez SP - 5045 EP - 50 JF - Applied and environmental microbiology JO - Appl. Environ. Microbiol. VL - 69 IS - 9 N2 - 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. SN - 0099-2240 UR - https://www.unboundmedicine.com/medline/citation/12957885/Biotransformation_of_natural_and_synthetic_isoflavonoids_by_two_recombinant_microbial_enzymes_ L2 - http://aem.asm.org/cgi/pmidlookup?view=long&pmid=12957885 DB - PRIME DP - Unbound Medicine ER -