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Secondary Metabolites and Cytotoxic Activities from the Stem Bark of Zanthoxylum nitidum
Author(s) -
Yang ChengHui,
Cheng MingJen,
Lee ShiowJu,
Yang ChengWei,
Chang HsunShuo,
Chen IhSheng
Publication year - 2009
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200800107
Subject(s) - chemistry , stereochemistry , phenanthridine , ether , cytotoxicity , two dimensional nuclear magnetic resonance spectroscopy , cancer cell lines , alkaloid , terpenoid , bark (sound) , organic chemistry , cancer cell , in vitro , biology , biochemistry , genetics , ecology , cancer
A dihydrobenzo[ c ]phenanthridine alkaloid, epizanthocadinanine A ( 1 ), together with 27 known compounds, including eight benzo[ c ]phenanthridines, i.e. , oxynitidine ( 2 ), oxyavicine ( 3 ), oxychelerythrine ( 4 ), dihydrochelerythrine ( 5 ), 6‐acetonyldihydrochelerythrine ( 6 ), norchelerythrine ( 7 ), decarine ( 8 ), and arnottianamide ( 9 ); two 2‐quinolones, i.e. , flindersine ( 10 ) and 4‐methoxy‐1‐methyl‐2‐quinolone ( 11 ); two furoquinolines, i.e. , skimmianine ( 12 ) and γ ‐fagarine ( 13 ); three aporphines, i.e. , liriodenine ( 14 ), N ‐acetyldehydroanonaine ( 15 ), and N ‐acetylanonaine ( 16 ); six lignans, i.e. , sesamin ( 17 ), episesamin ( 18 ), piperitol‐3,3‐dimethylallyl ether ( 19 ), xanthoxylol‐3,3‐dimethylallyl ether ( 20 ), savinin ( 21 ), and 2,3‐bis(3,4‐methylenedioxybenzyl)but‐2‐en‐4‐olide ( 22 ); three terpenoids, i.e. , α ‐cadinol ( 23 ), anticopalol ( 24 ), and spathulenol ( 25 ); one coumarin, i.e. , aesculetin dimethyl ether ( 26 ); and two steroids, i.e. , β ‐sitosterol ( 27 ) and β ‐sitostenone ( 28 ) were isolated from the stem bark of Zanthoxylum nitidum. Their structures were elucidated on the basis of extensive 1D‐ and 2D‐NMR as well as MS analyses. Moreover, the recently reported structures 2′ – 4′ of rhoifolines B and A, and ‘8‐methoxynorchelerythrine’, resp., isolated as new compounds from Z. rhoifolium and Z. nitidum , resp., could be assigned the revised structures 2 – 4 by reinvestigation of the spectroscopic data. In addition, the cytotoxicity of the isolates was evaluated on the MCF‐7, NCI‐H460, and SF‐268 cell lines. Among these isolates, liriodenine ( 14 ) was the most active compound against the MCF‐7, NCI‐H460, and SF‐268 cell lines with IC 50 values of 2.19, 2.38, and 3.19 μg/ml, resp.