ABSTRACT
A new andirobin-type limonoid with modified furan ring, khaysenelide K (1), together with a known analogue (2), was isolated from the stem barks of Khaya senegalensis. The structure and absolute configuration of 1 were elucidated by a combination of 1D and 2D NMR, HRESIMS, and single-crystal X-ray diffraction using mirror Cu-Kα radiation. Compound 1 showed moderate NO inhibitory activity in LPS-activated RAW 264.7 macrophages with IC50 value of 27.74 ± 0.68 µM.[Formula: see text].
Subject(s)
Limonins , Meliaceae , Furans , Limonins/pharmacology , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
Six undescribed 1,8,9-phragmalin limonoid orthoesters (chukorthoesters A-F, 1-6) and two undescribed mexicanolide-type limonoids (ivorenoids H and I, 7 and 8), together with ten known limonoids, were isolated from the seeds of common wood-source and greening plants Chukrasia tabularis A. Juss. Their chemical structures were elucidated using HR-ESI-MS, 1D and 2D NMR spectroscopic analysis, and that of 1 along with absolute configuration was confirmed by X-ray diffraction experiment with Cu Kα radiation. Bioactivities screening indicated the limonoid orthoesters 1 and 2 shown reversing resistance in MCF-7/DOX cells at 10 µM (RF:4-5 folds).
Subject(s)
Limonins , Meliaceae , Drug Resistance, Multiple , Humans , Limonins/pharmacology , Molecular Structure , SeedsABSTRACT
Four new limonoids, toonayunnanaes F - I (1 - 4), and six known compounds (5 - 10) were isolated from the barks of Toona ciliata. Their structures were elucidated by thoroughly analyzing of NMR and HRMS data, and single-crystal X-ray diffraction of 1. The oxetane ring moiety in 1 was rare in limonoids and other natural products. Compound 1 showed nitric oxide (NO) inhibitory effect with an IC50 38.45 ± 0.41 µM in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages.
