Progesterone biotransformation by plant cell suspension cultures

Abstract

Progesterone was converted to 5alpha-pregnane-3alpha-ol-20-one, delta4-pregnene-20alpha-ol-3-one, delta4-pregnene-14alpha-ol-3,20-dione, delta4-pregnene-7beta,14alpha-diol-3,20-dione, and delta4-pregnene-6beta,11alpha-diol-3,20-dione by cell cultures of Lycopersicon esculentum. Cell cultures of Capsicum frutescens (green) metabolized progesterone to delta4-pregnene-20alpha-ol-3-one in very high yield, and Vinca rosea yielded delta4-pregnene-20beta-ol-3-one and delta4-pregnene-14alpha-ol-3,20-dione. A stereospecific reduction of the keto groups and a double bond and stereospecific introduction of hydroxyl groups at the 6, 11, and 14 positions have been observed. The mono- and dihydroxylated progesterones have not previously been reported as metabolic products of progesterone by plant cell systems and represent de novo hydroxylation of a nonglycosylated steroid.

Naturally occurring progesterone in loblolly pine (Pinus taeda L.): A major steroid precursor of environmental androgens

“…Janeczko and Skoczowski [28] reviewed the literature regarding sex hormones in plants and reported that androgens and progesterone are present in approximately 80% of the plant species studied, suggesting that industrial milling of other plant species could contribute to the environmental androgen load. Cultured plant cells in suspensions from Lycopersicon esculentum, Capsicum frutescens , and Vinca rosea have been shown to biotransform progesterone to a number of Δ 4 ‐pregnene hydroxylated androgens [29], although not as rapidly as certain bacteria do. Progesterone in plants may be involved in a natural defense response against parasites, as suggested for isoflavonoids that inhibit nematode infection in alfalfa [30].…”