Oxidation of lynestrenol by the fungus Cunninghamella elegans

Abstract

Transformation of lynestrenol (19-nor-17α-pregn-4-en-20-yn-17β-ol) (1) was carried out by incubation with Cunninghamella elegans to obtain 19-nor-17α-pregn-4-en-20-yn-3-one-10β,17β-diol (2), 19-nor-17α-pregn-4-en-20-yn-3-one-6β,17β-diol (3), and 19-nor-17α-pregn-4-en-20-yn-3β,6β,17β-triol (4). Metabolite 4 was identified as a new compound. These metabolites were structurally characterised on the basis of spectroscopic techniques.

Keywords:

• microbial transformation
• oxidation
• Cunninghamella elegans
• lynestrenol (19-nor-17α-pregn-4-en-20-yn-17β-ol)
• 19-nor-17α-pregn-4-en-20-yn-3-one-10β,17β-diol
• 19-nor-17α-pregn-4-en-20-yn-3-one-6β,17β-diol
• 19-nor-17α-pregn-4-en-20-yn-3β,6β,17β-triol