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一种大环内酯类化合物作为平菇菌株介导的含偕二甲基环己烷环的卤代内酯生物转化的意外产物。第1部分。

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

作者信息

Wińska Katarzyna, Mączka Wanda, Grabarczyk Małgorzata, Sugimoto Kenji, Matsuya Yuji, Szumny Antoni, Anioł Mirosław

机构信息

Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.

Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, 930-0194 Toyama, Japan.

出版信息

Molecules. 2016 Jun 30;21(7):859. doi: 10.3390/molecules21070859.

DOI:10.3390/molecules21070859
PMID:27376255
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6273929/
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.

摘要

本研究的目的是在两种卤代化合物δ-溴代和δ-碘代-γ-双环内酯1和2的生物转化过程中获得新化合物。出乎意料的是，平菇在产生羟基内酯2-羟基-4,4-二甲基-9-氧杂双环[4.3.0]壬烷-8-酮（3）的同时，还产生了其自身的代谢产物(3S,9S,15S)-(6E,12E)-3,9,15-三甲基-4,10,16-三氧杂环十六碳-6,12-二烯-1,5,8,11,14-五酮（4）。本文介绍的通过生物转化获得这种大环内酯4的方法，此前在文献中尚未有描述。据我们所知，该化合物迄今为止仅通过化学合成制备。这是关于平菇菌株生物合成该化合物可能性的首次报道。研究了温度、盐类、有机溶剂等影响平菇菌株产生这种大环内酯的条件和因素。发现卤代内酯以及碘化物、溴化物、铁和铜（2+）离子作为诱导剂时，大环内酯的产量最高。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/915a/6273929/7bfd776c22af/molecules-21-00859-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/915a/6273929/167c78f3f6c1/molecules-21-00859-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/915a/6273929/3eb1123045cd/molecules-21-00859-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/915a/6273929/7bfd776c22af/molecules-21-00859-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/915a/6273929/167c78f3f6c1/molecules-21-00859-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/915a/6273929/3eb1123045cd/molecules-21-00859-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/915a/6273929/7bfd776c22af/molecules-21-00859-sch002.jpg

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