Highly oxygenated and rearranged limonoids from the stem barks of Entandrophragma utile. (April 2020)

• Record Type: Journal Article
• Authors: Hu, Ya-Lin; Tian, Xiao-Meng; Wang, Cheng-Cheng; Olga, Quasie; Yan, Dan; Tang, Peng-Fei; Zhang, Li-Na; Luo, Jun; Kong, Ling-Yi
• Is Part Of: Phytochemistry. Volume 172(2020)
• Publication Date: 2020-04
• Subjects: Entandrophragma utile -- Meliaceae -- Limonoids -- Orthesters -- CD exciton chirality -- Multidrug resistance (MDR); Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2020.112282
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: 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 μ M with 6- to 19-fold enhancing effects. Graphical abstract: Image 1 Highlights: Twelve undescribed highly oxygenated and rearranged limonoids were isolated from Entandrophragma utile. Their structures were elucidated by NMR, CD exciton chirality, ECD calculations, single-crystal X-ray diffraction. Four compounds effectively reversed resistance in MCF-7/DOX cells.