Structure and stereochemistry of pectinolides A-C, novel antimicrobial and cytotoxic 5,6-dihydro-alpha-pyrones from Hyptis pectinata.
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 micrograms/ml. Compounds 1-3 exhibited significant cytotoxic activity (ED50 < 4 micrograms/ml) against a variety of tumor cell lines.
Pereda-Miranda
R
R
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, D.F.
Hernández
L
L
Villavicencio
M J
MJ
Novelo
M
M
Ibarra
P
P
Chai
H
H
Pezzuto
J M
JM
D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000302:isolation & purification* / Q000494:pharmacology; D000935:Antifungal Agents / Q000302:isolation & purification / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D006801:Humans; D007941:Leukemia P388 / Q000188:drug therapy; D051379:Mice; D011753:Pyrones / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D011753:Pyrones