Two Pairs of Enantiomeric Alkaloid Dimers from Macleaya cordata

• DOI: 10.1021/acs.orglett.5b02044
• Publication Date: 2015-08-11T10:29:40Z
• Authors: Chun-Mei Sai; Da-Hong Li; Chun-Mei Xue; Kai-Bo Wang; Ping Hu; Yue-Hu Pei; Jiao Bai; Yong-Kui Jing; Zhan-Lin Li; Hui-Ming Hua
• Keywords: Molecular Structure; Molecular Conformation; HL-60 Cells; Stereoisomerism; Plant Components, Aerial; Crystallography, X-Ray; 01 natural sciences; 0104 chemical sciences; Inhibitory Concentration 50; Alkaloids; Papaveraceae; Humans; Drug Screening Assays, Antitumor; Nuclear Magnetic Resonance, Biomolecular; Chromatography, High Pressure Liquid

Two pairs of enantiomeric alkaloid dimers, (±)-macleayins A (1) and B (2), representing a novel dimerization pattern two different types alkaloids via C–C σ-bond, were isolated from the aerial parts Macleaya cordata. The separation was achieved by chiral chromatography. Their structures stereochemistry determined analysis extensive spectroscopic data, electronic circular dichroism calculation, single-crystal X-ray diffraction data. (−)-Macleayin exhibits modest cytotoxic activity against HL-60 cell line with IC50 value 3.51 μM.