Annonaceous acetogenins: a review.
The Annonaceous acetogenins are a series of apparently polyketide-derived fatty acid derivatives that possess tetrahydrofuran rings and a methylated gamma-lactone (sometimes rearranged to a methyl ketolactone) with various hydroxyl, acetoxyl, and/or ketoxyl groups along the hydrocarbon chain. They exhibit a broad range of potent biological activities (cytotoxicity, antitumor, antimalarial, antimicrobial, immunosuppressant, antifeedant, and pesticidal). The sources, isolation, chemistry, biogenesis, and biological actions of these compounds, published to date, are tabulated and discussed. Strategies for structural elucidation are reviewed, and structural revisions and refinements are suggested for some of the previously published compounds.
Rupprecht
J K
JK
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907.
Hui
Y H
YH
McLaughlin
J L
JL
D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification; D055598:Chemical Phenomena; D002621:Chemistry; D005227:Fatty Acids / Q000096:biosynthesis / Q000302:isolation & purification / Q000494:pharmacology; D005663:Furans / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D007783:Lactones / Q000302:isolation & purification / Q000494:pharmacology; D015394:Molecular Structure; D010575:Pesticides / Q000302:isolation & purification; D010944:Plants / Q000032:analysis
D000972:Antineoplastic Agents, Phytogenic; D005227:Fatty Acids; D005663:Furans; D007783:Lactones; D010575:Pesticides; C018674:tetrahydrofuran