Asimitrin and 4-hydroxytrilobin, new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis-tetrahydrofuran ring.
Bioactivity-directed fractionation of the seeds of Asimina triloba resulted in the isolation of asimitrin (1) and 4-hydroxytrilobin (2). Compound 1 represents an adjacent ring-hydroxylated bis-tetrahydrofuran (THF) acetogenin. Compound 2 has an adjacent bis-THF ring with two flanking hydroxyl groups and a alpha,beta-unsaturated gamma-lactone with a 4-hydroxyl group. Compounds 1 and 2 showed cytotoxic selectivity, with 100-10 000 times the potency of adriamycin against prostate adenocarcinoma (PC-3) and colon adenocarcinoma (HT-29) cell lines.
Kim
Eun Jung
EJ
Narcotic & Neuropharmacological Drug Division, Drug Evaluation Department, Korea Food and Drug Administration, Seoul 122-020, Korea.
Suh
Kyung Mi
KM
Kim
Dal Hwan
DH
Jung
Eun Joo
EJ
Seo
Chang Seob
CS
Son
Jong Keun
JK
Woo
Mi Hee
MH
McLaughlin
Jerry L
JL
D000818:Animals; D001156:Artemia / Q000187:drug effects; D031042:Asimina / Q000737:chemistry*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D042967:Electron Transport Complex I / Q000037:antagonists & inhibitors; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008396:Maryland; D015394:Molecular Structure; D012639:Seeds / Q000737:chemistry
C498487:4-hydroxytrilobin; D005663:Furans; D007783:Lactones; C498486:asimitrin; D042967:Electron Transport Complex I