STRUCTURE AND STEREOCHEMISTRY OF PECTINOLIDES AC, NOVEL ANTIMICROBIAL AND CYTOTOXIC 5,6-DIHYDRO-ALPHA-PYRONES FROM HYPTIS-PECTINATA

被引：85

作者：

PEREDAMIRANDA, R ^{[1
]}

HERNANDEZ, L ^{[1
]}

VILLAVICENCIO, MJ ^{[1
]}

NOVELO, M ^{[1
]}

IBARRA, P ^{[1
]}

CHAI, HY ^{[1
]}

PEZZUTO, JM ^{[1
]}

机构：

[1] UNIV ILLINOIS, COLL PHARM, DEPT MED CHEM & PHARMACOGNOSY, CHICAGO, IL 60612 USA

来源：

JOURNAL OF NATURAL PRODUCTS | 1993年 / 56卷 / 04期

关键词：

D O I：

10.1021/np50094a019

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

By bioactivity-directed fractionation, three new antimicrobial and cytotoxic 5,6-dihydro-alpha-pyrones, pectinolides A-C, have been isolated from Hyptis pectinata (Lamiaceae). The absolute stereochemistry of pectinolide A [1] was established as 6S-[(3S-acetyloxy)-1Z-heptenyl]-5S-(acetyloxy)-5,6-dihydro-2H-pyran-2-one, on the basis of spectral, chiroptical, and chemical evidence. The structures of pectinolides B [2] and C [3] were determined as the monodeacetylated forms of 1 by comparison of their spectral data and chemical correlation with the prototype compound. Staphylococcus aureus and Bacillus subtilis were sensitive to pectinolide A [1] in the concentration range of 6.25-12.5 mug/ml. Compounds 1-3 exhibited significant cytotoxic activity (ED50<4 mug/ml) against a variety of tumor cell lines.

引用

页码：583 / 593

页数：11

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