Abstract：
:A series of 3α,5-cycloandrostane analogues with a range of functionality (6α and 6β alcohols and ketone) at carbon 6 were tested in the endogenous lactonization pathway in Aspergillus tamarii KITA. This metabolic route converts progesterone to testololactone in high yield through a four step enzymatic pathway. To date, no studies have looked at the effect of steroids devoid of polar functionality at carbon 3 and their subsequent metabolic fate by fungi which contain Baeyer-Villiger monooxygenases. Incubation of all of the cycloandrostane analogues resulted in lactonization of ring-D irrespective of C-6 stereochemistry or absence of C-3 functionality. Presence of 6β-hydroxy group and the C-17 ketone was required in order for these analogues to undergo hydroxylation at C-15β position. All metabolites were isolated by column chromatography and were identified by (1)H, (13)C NMR, DEPT analysis and other spectroscopic data.
journal_name
Phytochemistryjournal_title
Phytochemistryauthors
Hunter AC,Patel S,Dedi C,Dodd HT,Bryce RAdoi
10.1016/j.phytochem.2015.09.003subject
Has Abstractpub_date
2015-11-01 00:00:00pages
19-25eissn
0031-9422issn
1873-3700pii
S0031-9422(15)30082-0journal_volume
119pub_type
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