Progesterone biotransformation by plant cell suspension cultures

Area of Science:

• Biochemistry
• Plant Science
• Steroid Metabolism

Background:

• Progesterone is a key steroid hormone.
• Plant cell cultures are increasingly used to study steroid metabolism.
• Understanding plant steroid biotransformation is crucial for various applications.

Purpose of the Study:

• To investigate the metabolic fate of progesterone in different plant cell cultures.
• To identify novel progesterone metabolites produced by Lycopersicon esculentum, Capsicum frutescens, and Vinca rosea.
• To characterize the stereospecificity of progesterone biotransformation in these plant systems.

Main Methods:

• Incubation of progesterone with cell cultures of Lycopersicon esculentum, Capsicum frutescens, and Vinca rosea.
• Identification and structural elucidation of progesterone metabolites using analytical techniques.
• Analysis of stereochemical outcomes of enzymatic reactions.

Main Results:

• Lycopersicon esculentum converted progesterone into 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.
• Capsicum frutescens yielded delta4-pregnene-20alpha-ol-3-one in high yield.
• Vinca rosea produced delta4-pregnene-20beta-ol-3-one and delta4-pregnene-14alpha-ol-3,20-dione.
• Stereospecific reduction of keto groups and double bonds, along with hydroxylation at C6, C11, and C14, were observed.
• The identified mono- and dihydroxylated progesterones are novel products from plant cell systems, indicating de novo hydroxylation.

Conclusions:

• Plant cell cultures exhibit diverse capabilities for progesterone metabolism.
• The study identified previously unreported hydroxylated progesterone metabolites.
• These findings highlight the potential of plant cell systems for steroid biotransformation and the discovery of novel compounds.