Monamphilectine A, a potent antimalarial β-lactam from marine sponge Hymeniacidon sp: isolation, structure, semisynthesis, and bioactivity.
Monamphilectine A (1), a new diterpenoid β-lactam alkaloid showing potent antimalarial activity, was isolated in milligram quantities following bioassay-directed extraction of a Puerto Rican marine sponge Hymeniacidon sp. Its structure, established by interpretation of spectral data, was confirmed unequivocally by chemical interconversion and comparison of physical, chemical, and bioactivity data with the natural product. The one-step semisynthesis of monamphilectine A was based on a multicomponent Ugi reaction that also established its absolute stereostructure.
Department of Chemistry, University of Puerto Rico, P.O. Box 23346, UPR Station, San Juan, Puerto Rico 00931-3346.
Edward
E
Avilés
Abimael D
AD
Rodríguez
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000667:Ampicillin / Q000494:pharmacology; D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002228:Carbenicillin / Q000494:pharmacology; D002738:Chloroquine / Q000494:pharmacology; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004351:Drug Resistance / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D008386:Marine Biology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000187:drug effects; D011161:Porifera / Q000737:chemistry*; D047090:beta-Lactams / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
D000470:Alkaloids; D000962:Antimalarials; D004224:Diterpenes; D047090:beta-Lactams; D000667:Ampicillin; D002738:Chloroquine; D002228:Carbenicillin