title: Asitrilobins A and B: cytotoxic mono-THF annonaceous acetogenins from the seeds of Asimina triloba.
abstract: 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.
authors.affiliation: Department of Pharmacy, College of Pharmacy, Catholic University of Taegu-Hyosung, Kyongsan, South Korea.
authors.forename: M H
authors.initials: MH
authors.lastname: Woo
authors.forename: D H
authors.initials: DH
authors.lastname: Kim
authors.forename: J L
authors.initials: JL
authors.lastname: McLaughlin
mesh_terms: 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
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; C120122:asitrilobin A; C120123:asitrilobin B