Transformation of 5-ene steroids by the fungus Aspergillus tamarii KITA: mixed molecular fate in lactonization and hydroxylation pathways with identification of a putative 3beta-hydroxy-steroid dehydrogenase/Delta5-Delta4 isomerase pathway

Biochimica Et Biophysica Acta
A Christy HunterSalomé-Juliette Koussoroplis

Abstract

The fungus Aspergillus tamarii metabolizes progesterone to testololactone in high yield through a sequential four step enzymatic pathway which, has demonstrated flexibility in handling a range of steroidal probes. These substrates have revealed that subtle changes in the molecular structure of the steroid lead to significant changes in route of metabolism. It was therefore of interest to determine the metabolism of a range of 5-ene containing steroidal substrates. Remarkably the primary route of 5-ene steroid metabolism involved a 3beta-hydroxy-steroid dehydrogenase/Delta(5)-Delta(4) isomerase (3beta-HSD/isomerase) enzyme(s), generating 3-one-4-ene functionality and identified for the first time in a fungus with the ability to handle both dehydroepiansdrosterone (DHEA) as well as C-17 side-chain containing compounds such as pregnenolone and 3beta-hydroxy-16alpha,17alpha-epoxypregn-5-en-20-one. Uniquely in all the steroids tested, 3beta-HSD/isomerase activity only occurred following lactonization of the steroidal ring-D. Presence of C-7 allylic hydroxylation, in either epimeric form, inhibited 3beta-HSD/isomerase activity and of the substrates tested, was only observed with DHEA and its 13alpha-methyl analogue. In contrast to pr...Continue Reading

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Citations

Nov 12, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alina Świzdor
Mar 5, 2016·Environmental Science & Technology·Jodi L SangsterShannon L Bartelt-Hunt
Nov 16, 2014·Daru : Journal of Faculty of Pharmacy, Tehran University of Medical Sciences·Tahereh HosseinabadiFarzad Kobarfard
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May 6, 2011·Chemical Reviews·Hannes LeischPeter C K Lau
Apr 27, 2010·Current Opinion in Endocrinology, Diabetes, and Obesity

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