Microbiological conversion of lapachol by various microorganisms.

Abstract

Oxydative cyclization of lapachol was attempted by feeding this compound into the culture broth of Beauveria sulfurescens and two ionophore-producing strains of Streptomyces albus and Streptomyces griseus. As a result, three compounds were obtained, lomatiol, lomatic acid and lomatiol acetate, only with B. sulfurescens and S. albus. The structures of these products were determinated by NMRand mass spectrometry. The stereochemistry is given by a comparison with butene analogs.

13C NMR of lapachol and some related naphthoquinones

“…I3C NMR chemical shift assignments have been reported for a number of naphthoquinones. '-* The results reported here are in agreement with those of McDonald et al ' for a-lapachone (6). However, all other sets of data previously reported for the compounds studied here contain some misassignments.…”

Transformation of Prenylated Isoflavone Luteone in a Rat Liver Homogenate

“…Luteone (1), one of the major prenylated isoflavones in lupins (Lupinus spp., Leguminosae), was mainly transformed into luteone hydrate (10) or luteone glycol (11) by A.jiavus, while 1 was metabolized to BC-I [( -)-2J, BC-2 (12) and 11 by B. cinerea. 1) It was suggested that these metabolites, except for 10, were formed via an epoxide intermediate.…”