Further C-15-acyl phragmalin derivatives from Chukrasia tabularis A. Juss. (September 2015)

• Record Type: Journal Article
• Authors: Luo, Jun; Zhang, Hong-Jian; Quasie, Olga; Shan, Si-Ming; Zhang, Yang-Mei; Kong, Ling-Yi
• Is Part Of: Phytochemistry. Volume 117(2015:Sep.)
• Page Start: 410
• Page End: 416
• Publication Date: 2015-09
• Subjects: Chukrasia tabularis A. Juss. -- Meliaceae -- C-15 enolic acyl phragmalin -- UV-guided isolation -- Absolute configuration; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2015.05.014
• Languages: English
• ISSNs: 0031-9422

Abstract

Graphical abstract: Sixteen phragmalins with three types of enolic acyl substituents at C-15 were isolated from the seeds of Chukrasia tabularis A. Juss. One of these (compound1 ) had its structure determined by NMR and X-ray diffraction analysis, while the others were determined via NMR, HR-MS, and CD spectra. Highlights: Sixteen phragmalins with three kinds of enolic acyl substituents at C-15 were isolated. UV-guided separation based on the characteristic double UV absorptions (210 and 270 nm). The configuration of one of the phragmalins was confirmed by X-ray crystallographic and CD spectrum analyses. Abstract: Relying on characteristic double UV absorptions (210 and 270 nm), sixteen phragmalins with three types of enolic acyl substituents at C-15 were isolated directly from EtOH extracts of the seeds of Chukrasia tabularis A. Juss. Eight of these compounds possessed a C-15-acetyl phragmalin skeleton, and the basic carbon skeleton and absolute configuration of one of these was determined by NMR and X-ray diffraction analysis, while the structures of the other phragmalins were determined via NMR, HR-MS, and CD spectra. Additionally, all of the isolates were tested for inhibition against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages and cytotoxicity in SMMC-7721, MCF-7 and U2OS tumor cells.