麦考吡喃酮：一种来自真菌物种的具有强效抗耐甲氧西林金黄色葡萄球菌活性的8,8'-联萘并吡喃酮
Mycopyranone: a 8,8'-binaphthopyranone with potent anti-MRSA activity from the fungus sp.
作者信息
Rivera-Chávez José, Caesar Lindsay, Garcia-Salazar Juan J, Raja Huzefa A, Cech Nadja B, Pearce Cedric J, Oberlies Nicholas H
机构信息
Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, North Carolina 27412, USA.
Mycosynthetix, Inc., Hillsborough, North Carolina, 27278, USA.
出版信息
Tetrahedron Lett. 2019 Feb 21;60(8):594-597. doi: 10.1016/j.tetlet.2019.01.029. Epub 2019 Jan 17.
A new 8,8'-binaphthopyranone (mycopyranone, ) was isolated from a solid fermentation of sp. (fungal strain MSX61662), and the structure was elucidated via analysis of the NMR and HRESIMS data. The axial chirality of was determined to be by ECD. The central chirality at C-4/C-4' was assigned through a modified Mosher's method, while the absolute configuration at C-3/C-3' was deduced based on analysis of the values and NOESY correlations. Compound was evaluated for its antimicrobial properties against SA1199 and a clinically relevant methicillin-resistant strain (MRSA USA300 LAC strain AH1263). Compound inhibited the growth of both strains in a concentration dependent manner with IC values in the low μM range. Molecular docking indicated that compound binds to the FtsZ (tubulin-like) protein in the same pocket as viriditoxin (), suggesting that targets bacterial cell division.
从一株曲霉属（真菌菌株MSX61662）的固体发酵产物中分离出一种新的8,8'-联萘并吡喃酮（霉菌吡喃酮），并通过对核磁共振和高分辨电喷雾电离质谱数据的分析阐明了其结构。通过电子圆二色光谱确定霉菌吡喃酮的轴手性为。通过改良的莫舍尔方法确定C-4/C-4'处的中心手性，而基于对化学位移值和核Overhauser效应光谱相关数据的分析推导C-3/C-3'处的绝对构型。评估了化合物对粪肠球菌SA1199和临床相关的耐甲氧西林金黄色葡萄球菌菌株（MRSA USA300 LAC菌株AH1263）的抗菌性能。化合物以浓度依赖性方式抑制这两种菌株的生长，其半数抑制浓度值在低微摩尔范围内。分子对接表明，化合物与绿胶霉素在相同的口袋中结合到FtsZ（微管蛋白样）蛋白上，这表明霉菌吡喃酮靶向细菌细胞分裂。
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