Two new macrocyclic secondary metabolites, glycosyl-migrastatin (1) and 5-hydroxy-migrastatin (2), were isolated from a gut bacterium Kitasatospora sp. JL24 in dung beetle Onthophagus lenzii. Based on a comprehensive analysis of the NMR, MS, and UV spectroscopic data, the planar structures of 1 and 2 were successfully identified as new candidates for migrastatin. Compound 1 was the first glycosylated member of the migrastatin family. The absolute configuration of the sugar moiety was determined to be d-glucose through the analysis of coupling constants and ROESY correlations, followed by chromatographic chemical derivatization and comparison with authentic d- and l-glucose. Compound 2, identified as 5-hydroxy-migrastatin possessing an additional hydroxy group with a previously unreported chiral center, was assigned using Mosher's method through 19F NMR chemical shifts and confirmed with the modified Mosher's method. Genomic analysis of Kitasatospora sp. strain JL24 revealed a putative biosynthetic pathway involving an acyltransferase-less type I polyketide synthase biosynthetic gene cluster.

中文翻译：

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粪甲虫肠道 Kitasatospora sp 中糖基和 5-羟基 Migrastatins 的发现和结构解析。


从肠道细菌 Kitasatospora sp. 中分离出两种新的大环次级代谢产物：糖基-migrastatin (1) 和 5-羟基-migrastatin (2)。粪甲虫 Onthophagus lenzii 中的 JL24。基于对NMR、MS和UV光谱数据的综合分析，1和2的平面结构被成功鉴定为migrastatin的新候选物。化合物 1 是 migrastatin 家族的第一个糖基化成员。通过耦合常数和ROESY相关性分析，随后进行色谱化学衍生化并与真实的d-和l-葡萄糖进行比较，确定糖部分的绝对构型为d-葡萄糖。化合物 2 被鉴定为 5-羟基-migrastatin，具有额外的羟基和先前未报道的手性中心，使用 Mosher 方法通过 19F NMR 化学位移进行归属，并使用改进的 Mosher 方法进行确认。 Kitasatospora sp. 的基因组分析。菌株JL24揭示了一条假定的生物合成途径，涉及无酰基转移酶的I型聚酮合酶生物合成基因簇。