Chemical investigation of drug-like compounds from the Australian tree, Neolitseadealbata.
Two of the four parameters in the 'rule of five', molecular weight and logP, which can be detected and predicted by mass spectrometry and compound retention on reversed-phase HPLC, were used as guidelines in natural product isolation. A new aporphine alkaloid, (6aR)-normecambroline (1), was isolated from the bark of Neolitsea dealbata (R. Br.) Merr. Its structure was determined on the basis of NMR, MS and CD analysis. It is the first time the absolute configuration of the roemerine-N-oxide was assigned for both roemerine-N(α)-oxide (3) and roemerine-N(β)-oxide (4). Physico-chemical property evaluation demonstrated all alkaloids had no Lipinski violation. Compound 1 inhibited selectively against cervical cancer cells (HeLa) with an IC(50) of 4.0 μM.
Tran
Trong D
TD
Eskitis Institute, Griffith University, Brisbane, QLD 4111, Australia.
Pham
Ngoc B
NB
Fechner
Gregory
G
Quinn
Ronald J
RJ
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D001060:Aporphines / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D001315:Australia; D045744:Cell Line, Tumor; D002942:Circular Dichroism; D006801:Humans; D019770:Lauraceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation
D000470:Alkaloids; D001060:Aporphines; C556100:normecambroline