Chemical investigation of drug-like compounds from the Australian tree, Neolitsea dealbata

Trong D Tran; N B Pham; G Fechner; R J Quinn

doi:10.1016/j.bmcl.2010.07.100

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Chemical investigation of drug-like compounds from the Australian tree, Neolitsea dealbata

Journal article

Peer reviewed

Chemical investigation of drug-like compounds from the Australian tree, Neolitsea dealbata

Trong D Tran, N B Pham, G Fechner and R J Quinn

Bioorganic & Medicinal Chemistry Letters, Vol.20(19), pp.5859-5863

2010

DOI: https://doi.org/10.1016/j.bmcl.2010.07.100

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Abstract

aporphine alkaloids

neolitsea dealbata

drug-like natural products

cytotoxicity

Two of the four parameters in the 'rule of five', molecular weight and log P, 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-Nβ-oxide (4). Physico-chemical property evaluation demonstrated all alkaloids had no Lipinski violation. Compound 1 inhibited selectively against cervical cancer cells (HeLa) with an IC50 of 4.0 μM. © 2010 Elsevier Ltd. All rights reserved.

Details

Title: Chemical investigation of drug-like compounds from the Australian tree, Neolitsea dealbata
Authors: Trong D Tran (Author) - Griffith University
N B Pham (Author) - Griffith University
G Fechner (Author) - Griffith University
R J Quinn (Author) - Griffith University
Publication details: Bioorganic & Medicinal Chemistry Letters, Vol.20(19), pp.5859-5863
Publisher: Pergamon
DOI: 10.1016/j.bmcl.2010.07.100
ISSN: 0960-894X
Organisation Unit: Centre for Bioinnovation; University of the Sunshine Coast, Queensland; School of Science and Engineering - Legacy; School of Science, Technology and Engineering
Language: English
Record Identifier: 99451193202621
Output Type: Journal article

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