Asitrilobins C and D: two new cytotoxic mono-tetrahydrofuran annonaceous acetogenins from Asimina triloba seeds.
Two new bioactive mono-tetrahydrofuran (THF) gamma-lactone acetogenins, asitrilobins C (1) and D (2), were isolated from the seeds of Asimina triloba (Annonaceae) by directing the fractionation with brine shrimp lethality. Compounds 1 and 2 have a relative stereochemical relationship of threo/trans/threo across the mono-THF ring with its two flanking hydroxyls. Their structures were established on the basis of chemical and spectral evidence. Compounds 1 and 2 showed selective cytotoxicity comparable with adriamycin for the breast carcinoma (MCF-7) and the colon adenocarcinoma (HT-29) cell lines.
Woo
M H
MH
Department of Pharmacy, College of Pharmacy, Catholic University of Taegu-Hyosung, Kyongsan, South Korea.
Chung
S O
SO
Kim
D H
DH
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000302:isolation & purification*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D010944:Plants / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry*; D013057:Spectrum Analysis; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; C417193:asitrilobin C; C417194:asitrilobin D; D015107:4-Butyrolactone