Two new epimeric pairs of acetogenins bearing a carbonyl group from Annona cherimolia seeds.
Further studies on the seeds of Annona cherimolia have led to the isolation of two pairs of Annonaceous acetogenins, a mixture of epimers of annomolon A (1) and 34-epi-annomolon A (1'), and a mixture of epimers of annomolon B (2) and 34-epi-annomolon B (2'), containing a rare gamma-hydroxymethyl-gamma-lactone moiety and a carbonyl group. Their structures were elucidated on the basis of spectroscopic and chemical methods, and their absolute stereochemistry was solved by preparing their respective per-Mosher ester derivatives. These acetogenins showed substantial cytotoxicity, comparable to that of adriamycin, against a human pancreatic tumor cell line (MIA PaCa-2).
College of Pharmacy, Yeungnam University, Gyeongsan, 712-749, Korea.
Jong Keun
JK
Son
Dal Hwan
DH
Kim
Mi Hee
MH
Woo
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001156:Artemia / Q000187:drug effects; D002140:California; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D007659:Ketones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007659:Ketones