(2,4-cis and trans)-gigantecinone and 4-deoxygigantecin, bioactive nonadjacent bis-tetrahydrofuran Annonaceous acetogenins, from Goniothalamus giganteus

被引:8
作者
Alali, FQ [1 ]
Zhang, Y [1 ]
Rogers, L [1 ]
McLaughlin, JL [1 ]
机构
[1] PURDUE UNIV,SCH PHARM & PHARMACAL SCI,DEPT MED CHEM & MOL PHARMACOL,W LAFAYETTE,IN 47907
来源
JOURNAL OF NATURAL PRODUCTS | 1997年 / 60卷 / 09期
关键词
D O I
10.1021/np970211q
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two new acetogenins, (2,4-cis and trans)-gigantecinone (1), isolated as a mixture, and 4-deoxygigantecin (2), a known acetogenin whose absolute stereochemistry has not been determined previously, were isolated using activity-directed fractionation, from the bark of Goniothalamus giganteus. A key step in solving their absolute stereochemistries was the preparation of 1,4-diol formaldehyde acetal derivatives (1b and 2a). Using the advanced Mosher ester method and circular dichroism, the absolute stereochemistries of I and 2 were revealed and were found to be the same as that of gigantecin (3), which supports a common biogenetic origin. Both 1 and Ib showed potent and selective cytotoxicities against the PC-3 human prostate adenocarcinoma cell line. Against yellow fever mosquito larvae, 1 and 2 were more potent than rotenone in pesticidal activity. Longimicin C and a mixture of (2,4-cis and trans)-isoannonacin were also isolated for the first time from this species.
引用
收藏
页码:929 / 933
页数:5
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