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Structure elucidation and absolute configuration of metabolites from the soil-derived fungus Dictyosporium digitatum using spectroscopic and computational methods
Phytochemistry ( IF 3.2 ) Pub Date : 2020-05-01 , DOI: 10.1016/j.phytochem.2020.112278
Trong D Tran 1 , Brice A P Wilson 1 , Curtis J Henrich 2 , Karen L Wendt 3 , Jarrod King 3 , Robert H Cichewicz 3 , Alberto M Stchigel 4 , Andrew N Miller 5 , Barry R O'Keefe 6 , Kirk R Gustafson 1
Affiliation  

Following the discovery of a new class of compounds that inhibit the mucosa-associated lymphoid tissue lymphoma translocation 1 (MALT1) protease in a prior study, further chemical investigation of the Dictyosporium digitatum fungus resulted in the identification of 16 additional metabolites, including 12 undescribed compounds (1-12). The constitution and relative configuration of these new molecules were established by comprehensive NMR and HRMS analyses. Their absolute configurations were determined by employing Mosher's ester analysis and TDDFT ECD calculations. Two sesquiterpenes, dictyosporins A (1) and B (2), possess an undescribed eudesmen-type of structural scaffold. The ability of the isolated compounds to inhibit MALT1 proteolytic activity was evaluated, but none of them exhibited significant inhibition.

中文翻译:


使用光谱和计算方法解析土壤来源真菌指状网孢菌代谢物的结构和绝对构型



继在先前的研究中发现一类抑制粘膜相关淋巴组织淋巴瘤易位 1 (MALT1) 蛋白酶的新化合物后,对指状盘孢真菌的进一步化学研究导致鉴定出 16 种其他代谢物,其中包括 12 种未描述的化合物(1-12)。通过综合 NMR 和 HRMS 分析确定了这些新分子的构成和相对构型。它们的绝对构型是通过采用 Mosher 酯分析和 TDDFT ECD 计算确定的。两种倍半萜烯,即网孢菌素 A (1) 和 B (2),具有未描述的 eudesmen 型结构支架。评估了分离的化合物抑制 MALT1 蛋白水解活性的能力,但没有一个化合物表现出显着的抑制作用。
更新日期:2020-05-01
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