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Biotransformations of tocopherols by Streptomyces catenulae
B Rousseau1, L Dostal, J P Rosazza
1Division of Medicinal & Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City 52242, USA.
Abstract:
Streptomyces catenulae catalyzed the oxidation of alpha-tocopherol to alpha-tocopherolquinone. Nitrotocopherols isolated from S. catenulae grown in defined culture medium containing delta- and gamma-tocopherols are formed by a combination of enzymatic nitrate reduction to nitrite, and subsequent nonenzymatic acid-catalyzed nitration. The incorporation of 15N18O3-into nitrated tocopherols confirmed the origin of the nitrating species. Structures of chromatographically purified products obtained from S. catenulae transformations of tocopherols were deduced by spectral (mass spectrometry, 1H-, and 13C-nuclear magnetic resonance) analyses.