Transformation of steroids by Bacillus strains isolated from the foregut of water beetles (Coleoptera:Dytiscidae): I. Metabolism of androst-4-en-3,17-dione (AD).
Two Bacillus strains were isolated from the foregut of the water beetle Agabus affinis (Payk.) and tested for their steroid transforming ability. After incubation with androst-4-en-3,17-dione (AD), 13 different transformation products were detected. AD was hydroxylated at C6, C7, C11 and C14, resulting in formation of 6beta-, 7alpha-, 11alpha- and 14alpha-hydroxy-AD. One strain also produced small amounts of 6beta,14alpha-dihydroxy-AD. Partly, the 6beta-hydroxy group was further oxidized to the corresponding 6-oxo steroids. In addition, a specific reduction of the delta4-double bond was observed, leading to the formation of 5alpha-androstane derivatives. In minor yields the carbonyl functions at C3 and C17 were reduced leading to the formation of 3zeta-OH or 17beta-OH steroids. EI mass spectra of the trimethylsilyl and O-methyloxime trimethylsilyl ether derivatives of some transformation products are presented for the first time.
Schaaf
O
O
Universität Bayreuth, Lehrstuhl für Tierökologie II, Germany.
Dettner
K
K
D000731:Androstanes / Q000737:chemistry / Q000378:metabolism; D000735:Androstenedione / Q000378:metabolism*; D000818:Animals; D001407:Bacillus / Q000302:isolation & purification / Q000378:metabolism*; D001711:Biotransformation; D002849:Chromatography, Gas; D001517:Coleoptera / Q000382:microbiology*; D004064:Digestive System / Q000382:microbiology*; D006914:Hydroxysteroids / Q000737:chemistry / Q000378:metabolism; D007202:Indicators and Reagents; D015394:Molecular Structure
D000731:Androstanes; D006914:Hydroxysteroids; D007202:Indicators and Reagents; D000735:Androstenedione