Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens.
Saccharomyces cerevisiae (dry baker's yeast) and Pseudomonas fluorescens were used to convert trans-ferulic acid into 4-hydroxy-3-methoxystyrene in 96 and 89% yields, respectively. The metabolites were isolated by solid-phase extraction and analyzed by thin-layer chromatography and high-performance liquid chromatography. The identities of the metabolites were determined by 1H- and 13C-nuclear magnetic resonance spectroscopy and by mass spectrometry. The mechanism of the decarboxylation of ferulic acid was investigated by measuring the degree and position of deuterium incorporated into the styrene derivative from D2O by mass spectrometry and by both proton and deuterium nuclear magnetic resonance spectroscopies. Resting cells of baker's yeast reduced ferulic acid to 4-hydroxy-3-methoxyphenylpropionic acid in 54% yield when incubations were under an argon atmosphere.
Division of Medicinal and Natural Products Chemsitry, College of Pharmacy, University of Iowa, Iowa City 52242.
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Z
Huang
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Dostal
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JP
Rosazza
D001711:Biotransformation; D003373:Coumaric Acids / Q000378:metabolism*; D003470:Culture Media / Q000737:chemistry; D003903:Deuterium; D017666:Deuterium Oxide; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000378:metabolism; D011551:Pseudomonas fluorescens / Q000378:metabolism*; D012441:Saccharomyces cerevisiae / Q000378:metabolism*; D014867:Water
D003373:Coumaric Acids; D003470:Culture Media; D014867:Water; D006139:Guaiacol; C014245:4-vinylguaiacol; D003903:Deuterium; C004999:ferulic acid; D017666:Deuterium Oxide