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Aldgamycins J–O, 16-Membered Macrolides with a Branched Octose Unit from Streptomycetes sp. and Their Antibacterial Activities

Author:
Wang, Chuan-Xi, Ding, Rong, Jiang, Shu-Tai, Tang, Jin-Shan, Hu, Dan, Chen, Guo-Dong, Lin, Feng, Hong, Kui, Yao, Xin-Sheng, Gao, Hao
Source:
Journal of natural products 2016 v.79 no.10 pp. 2446-2454
ISSN:
1520-6025
Subject:
Aspergillus niger, Candida albicans, Escherichia coli, Staphylococcus aureus, Streptomyces, X-ray diffraction, antibacterial properties, fungi, macrolides, spectroscopy, structure-activity relationships, sugars
Abstract:
Six new 16-membered macrolides with a rare branched octose unit, aldgamycins J–O (1–6), along with two known compounds, swalpamycin B (7) and chalcomycin (8), were isolated from Streptomyces sp. HK-2006-1. Their structures were determined by detailed spectroscopic and X-ray crystallographic analysis. Natural products containing branched sugar units are rare. Aldgaropyranose and decarboxylated aldgaropyranose are branched octoses, specifically aldgarose-type branched octose. Until now, only 11 compounds have been reported to contain an aldgarose-type branched octose. The discovery of aldgamycins J–O (1–6) adds new members of this type of natural product. All the compounds (1–8) herein were tested for antimicrobial activities against Gram-positive Staphylococcus aureus 209P, Gram-negative Escherichia coli ATCC0111, and two fungi, Candida albicans FIM709 and Aspergillus niger R330. Most of these compounds showed antibacterial activity against S. aureus. Their preliminary structure–activity relationships are proposed.
Agid:
5578730