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Highly oxygenated and rearranged limonoids from the stem barks of Entandrophragma utile
Phytochemistry ( IF 3.2 ) Pub Date : 2020-04-01 , DOI: 10.1016/j.phytochem.2020.112282
Ya-Lin Hu 1 , Xiao-Meng Tian 1 , Cheng-Cheng Wang 1 , Quasie Olga 1 , Dan Yan 1 , Peng-Fei Tang 1 , Li-Na Zhang 1 , Jun Luo 1 , Ling-Yi Kong 1
Affiliation  

Seventeen highly oxygenated and rearranged limonoids, including nine previously undescribed phragmalin-type limonoids with 1,8,9- and 8,9,30-orthesters (entanutilins C-K, 1-9), three undescribed limonoids with rare rearranged-6/6/7/5 skeleton (entanutilins L-N, 10-12), and 5 known limonoids, were isolated from the stem barks of Entandrophragma utile from Ghana (Africa). Their structures including absolute configurations were elucidated based on comprehensive spectroscopic analyses, such as HRESIMS, 1D/2D-NMR, CD exciton chirality method, time-dependent density functional theory (TDDFT)/ECD calculations, and single-crystal X-ray diffraction. Bioactivity screenings suggested that some of these compounds effectively reversed resistance in MCF-7/DOX cells at a nontoxic concentration of 30 μM with 6- to 19-fold enhancing effects.

中文翻译:

来自 Entandrophragma utile 茎皮的高度氧化和重排的柠檬苦素

17 种高度含氧和重排的柠檬苦素,包括 9 种以前未描述的具有 1,8,9-和 8,9,30-邻位的 phragmalin 型柠檬苦素(entanutilins CK,1-9),三种未描述的具有罕见重排的柠檬苦素 - 6/6/ 7/5 骨架(entanutilins LN,10-12)和 5 种已知的柠檬苦素类化合物是从来自加纳(非洲)的 Entandrophragma utile 的茎皮中分离出来的。基于综合光谱分析,如 HRESIMS、1D/2D-NMR、CD 激子手性方法、时间相关密度泛函理论 (TDDFT)/ECD 计算和单晶 X 射线衍射,阐明了它们的结构,包括绝对构型。生物活性筛选表明,其中一些化合物以 30 μM 的无毒浓度有效逆转 MCF-7/DOX 细胞中的耐药性,并具有 6 至 19 倍的增强作用。
更新日期:2020-04-01
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