Asitrilobins A and B: cytotoxic mono-THF annonaceous acetogenins from the seeds of Asimina triloba.
The seeds of Asimina triloba have yielded two novel cytotoxic mono-tetrahydrofuran (THF) Annonaceous acetogenins, asitrilobins A (1) and B (2). In addition, annonacin, asimin and asiminacin, which are known, and annomontacin and xylomaticin, which are known but are new in this species, were obtained. Compounds 1 and 2 have a relative stereochemical relationship of erythro/cis/threo across the mono-THF ring with its two flanking hydroxyls and they, thus, represent a new type of acetogenin. Their structures were established on the basis of chemical and spectral evidence. 1 and 2 showed potent bioactivities in the brine shrimp lethality test (BST) and among six human solid tumor cell lines with notable selectivity for the pancreatic cell line (MIA PaCa-2) at ten to one-hundred times the potency of adriamycin.
Woo
M H
MH
Department of Pharmacy, College of Pharmacy, Catholic University of Taegu-Hyosung, Kyongsan, South Korea.
Kim
D H
DH
McLaughlin
J L
JL
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology* / Q000633:toxicity; D033364:Decapoda / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000302:isolation & purification* / Q000494:pharmacology* / Q000633:toxicity; D006801:Humans; D007783:Lactones / Q000302:isolation & purification* / Q000494:pharmacology* / Q000633:toxicity; D012639:Seeds / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D018675:Toxicity Tests; D014197:Trees / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; C120122:asitrilobin A; C120123:asitrilobin B