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Molecules 2016, 21(7), 859; doi:10.3390/molecules21070859

A Macrosphelide as the Unexpected Product of a Pleurotus ostreatus Strain-Mediated Biotransformation of Halolactones Containing the gem-Dimethylcyclohexane Ring. Part 1

1
Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
2
Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, 930-0194 Toyama, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 28 April 2016 / Revised: 14 June 2016 / Accepted: 25 June 2016 / Published: 30 June 2016
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Abstract

The aim of the study was to obtain new compounds during biotransformation of two halocompounds, the δ-bromo and δ-iodo-γ-bicyclolactones 1 and 2. Unexpectedly Pleurotus ostreatus produced together with the hydroxylactone, 2-hydroxy-4,4-dimethyl-9-oxabicyclo[4.3.0]nonane-8-one (3), its own metabolite (3S,9S,15S)-(6E,12E)-3,9,15-trimethyl-4,10,16-trioxacyclohexa-deca-6,12-diene-1,5,8,11,14-pentaone (4). The method presented here, in which this macrosphelide 4 was obtained by biotransformation, has not been previously described in the literature. To the best of our knowledge, this compound has been prepared only by chemical synthesis to date. This is the first report on the possibility of the biosynthesis of this compound by the Pleurotus ostreatus strain. The conditions and factors, like temperature, salts, organic solvents, affecting the production of this macrosphelide by Pleurotus ostreatus strain were examined. The highest yield of macroshphelide production was noticed for halolactones, as well with iodide, bromide, iron and copper (2+) ions as inductors. View Full-Text
Keywords: macrosphelide; biotransformation; Pleurotus ostreatus; hydrolytic dehalogenation macrosphelide; biotransformation; Pleurotus ostreatus; hydrolytic dehalogenation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Wińska, K.; Mączka, W.; Grabarczyk, M.; Sugimoto, K.; Matsuya, Y.; Szumny, A.; Anioł, M. A Macrosphelide as the Unexpected Product of a Pleurotus ostreatus Strain-Mediated Biotransformation of Halolactones Containing the gem-Dimethylcyclohexane Ring. Part 1. Molecules 2016, 21, 859.

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