Journals / Turkish Journal of Chemistry / 2010 / Cilt: 34 - Sayı: 6

Biotransformation of danazol by Fusarium solani and Gibberella fujikuorii, and prolyl endopeptidase inhibition studies of transformed products

Pages
945–952
DOI
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Abstract

Biotransformation of danazol (17b-hydroxy-17a-pregna-2,4-dien-20-yno-[2,3-d] isoxazole) (1) on fermentation with Fusarium solani yielded 17b-hydroxy-2-(hydroxymethyl)-17a -pregn-4-en-20-yn-3-one (2) and 17b -hydroxy-2-(hydroxymethyl)-17a-pregna-1,4-dien-20-yn-3-one (3), while the fermentation of 1 with Gibberella fujikuorii yielded compound 2 only. The structures of these compounds were deduced on the basis of modern spectroscopic techniques. Prolyl endopeptidase inhibition activities of danazol (1) and its transformed products 2 and 3 are also studied.

Özet

Biotransformation of danazol (17b-hydroxy-17a-pregna-2,4-dien-20-yno-[2,3-d] isoxazole) (1) on fermentation with Fusarium solani yielded 17b-hydroxy-2-(hydroxymethyl)-17a -pregn-4-en-20-yn-3-one (2) and 17b -hydroxy-2-(hydroxymethyl)-17a-pregna-1,4-dien-20-yn-3-one (3), while the fermentation of 1 with Gibberella fujikuorii yielded compound 2 only. The structures of these compounds were deduced on the basis of modern spectroscopic techniques. Prolyl endopeptidase inhibition activities of danazol (1) and its transformed products 2 and 3 are also studied.

Keywords: Biotransformation, danazol, Fusarium solani, Gibberella fujikuorii, prolyl endopeptidase (PEP) inhibition assay