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Formicolides A and B, Antioxidative and Antiangiogenic 20-Membered Macrolides from a Wood Ant Gut Bacterium.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-09-05 , DOI: 10.1021/acs.jnatprod.0c00772
Joon Soo An 1 , Ji Yun Lee 1 , Eunji Kim 1 , Hyungju Ahn 1 , Yong-Joon Jang 2 , Bora Shin 1 , Sunghoon Hwang 1 , Jongheon Shin 1 , Yeo Joon Yoon 1 , Sang Kook Lee 1 , Dong-Chan Oh 1
Affiliation  

Two new macrolides, formicolides A (1) and B (2), were isolated from Streptomyces sp. BA01, a gut bacterial strain of the wood ant (Formica yessensis). Their 20-membered macrocyclic lactone structures were established using NMR and mass spectrometric data. The relative configurations of the formicolides were determined by J-based configuration analysis utilizing ROESY, HETLOC, and HECADE NMR spectroscopic data. Genomic and bioinformatics analysis of the bacterial strain enabled us to identify the type-I polyketide synthase pathway employing a trans-acyltransferase system. The absolute configurations of 1 and 2 are proposed based on detailed analysis of the sequences of the ketoreductases in the modular gene cluster and statistical comparative analysis of the experimental NMR chemical shifts and quantum mechanical calculations. Formicolides A and B (1 and 2) induced quinone reductase activity in murine Hepa-1c1c7 cells and antiangiogenic activity by suppression of tube formation in human umbilical vein endothelial cells.

中文翻译:

Formicolides A 和 B,来自木蚂蚁肠道细菌的抗氧化和抗血管生成 20 元大环内酯。

Streptomyces sp.中分离出两种新的大环内酯类,formicolides A ( 1 ) 和 B ( 2 ) 。BA01,木蚂蚁(Formica yessensis)的肠道细菌菌株。它们的 20 元大环内酯结构是使用 NMR 和质谱数据建立的。使用 ROESY、HETLOC 和 HECADE NMR 光谱数据,通过基于J的配置分析确定了甲内酯的相对构型。细菌菌株的基因组和生物信息学分析使我们能够鉴定采用酰基转移酶系统的 I 型聚酮化合物合酶途径。12的绝对构型提出基于模块化基因簇中酮还原酶序列的详细分析以及实验核磁共振化学位移和量子力学计算的统计比较分析。Formicolides A 和 B(12)通过抑制人脐静脉内皮细胞中的管形成来诱导鼠 Hepa-1c1c7 细胞中的醌还原酶活性和抗血管生成活性。
更新日期:2020-09-25
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