| Literature DB >> 28029796 |
Jianjun Zhang1, Ryan R Hughes1, Meredith A Saunders1, Sherif I Elshahawi1, Larissa V Ponomareva1, Yinan Zhang1, Sydney R Winchester1, Samantha A Scott1, Manjula Sunkara1, Andrew J Morris1, Mark A Prendergast1, Khaled A Shaaban1, Jon S Thorson1.
Abstract
The assessment of glycosyl-scanning to expand the molecular and functional diversity of metabolites from the underground coal mine fire-associated Streptomyces sp. RM-14-6 is reported. Using the engineered glycosyltransferase OleD Loki and a 2-chloro-4-nitrophenylglycoside-based screen, six metabolites were identified as substrates of OleD Loki, from which 12 corresponding metabolite glycosides were produced and characterized. This study highlights the first application of the 2-chloro-4-nitrophenylglycoside-based screen toward an unbiased set of unique microbial natural products and the first reported application of the 2-chloro-4-nitrophenylglycoside-based transglycosylation reaction for the corresponding preparative synthesis of target glycosides. Bioactivity analysis (including antibacterial, antifungal, anticancer, and EtOH damage neuroprotection assays) revealed glycosylation to attenuate the neuroprotective potency of 4, while glycosylation of the structurally related inactive spoxazomicin C (3) remarkably invoked neuroprotective activity.Entities:
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Year: 2016 PMID： 28029796 PMCID： PMC5337260 DOI： 10.1021/acs.jnatprod.6b00949
Source DB: PubMed Journal: J Nat Prod ISSN： 0163-3864 Impact factor: 4.050