5-alkylresorcinols from Hakea trifurcata that cleave DNA

被引:69
作者
Lytollis, W
Scannell, RT
An, HY
Murty, VS
Reddy, KS
Barr, JR
Hecht, SM
机构
[1] UNIV VIRGINIA,DEPT CHEM,CHARLOTTESVILLE,VA 22901
[2] UNIV VIRGINIA,DEPT BIOL,CHARLOTTESVILLE,VA 22901
关键词
D O I
10.1021/ja00156a004
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A dichloromethane extract of Hakea trifurcata that mediated relaxation of phi X174 replicative form DNA at micromolar concentrations in the presence of CU2+ was resolved into six active components by bioassay-guided fractionation. Five of the active principles were characterized structurally and shown to be 5-alkylresorcinol derivatives. These included 1,3-dihydroxy-5-tridecylbenzene (1), 1,3-dihydroxy-5-(cis-8'-pentadecenyl)benzene (2), 1,3-dihydroxy-5-[14'-(3'',5''-dihydroxyphenyl)-cis-6'-tetradecenyl]benzene (3), 1,3-dihyroxy-5-[1 4'-(3'',5''-dihydroxyphenyl)tetradecyl]benzene (4), and 1,3-dihydroxy-5-[16'-(3'',5''-dihydroxyphenyl)-cis-8'-hexadencenyl]benzene (5). The structures of these five natural principles were confirmed by total synthesis; compounds 1-5 were accessible from 3,5-dimethoxybenzaldehyde in overall yields of 59%, 27%, 15%, 16%, and 13%, respectively.
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收藏
页码:12683 / 12690
页数:8
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