Additional bioactive annonaceous acetogenins from Asimina triloba (Annonaceae).
Trilobalicin (1), a new nonadjacent bis-THF ring annonaceous acetogenin, 2,4-cis- (2) and 2,4-trans-trilobacinone (3), the ketolactones of trilobacin, an adjacent bis-THF ring acetogenin, were isolated from the stem bark of Asimina triloba (L.) Dunal (Annonaceae). Their structures were established based on chemical and spectral evidence. The relative stereochemistry of 1 was determined as trans/threo/threo/trans/erythro from C-10 to C-22 by comparisons of NMR data with those of model compounds. Compound 1 is the first example of a nonadjacent bis-THF acetogenin being isolated from the title species and represents a new type of these compounds. Bioactivities of these new structures against brine shrimp larvae and six human solid tumor cell lines were determined, and cytotoxic selectivities were shown for the lung (A-549) and breast (MCF-7) cell lines with up to a million times the potency of adriamycin.
He
K
K
Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907, USA.
Zhao
G X
GX
Shi
G
G
Zeng
L
L
Chao
J F
JF
McLaughlin
J L
JL
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology*; D001156:Artemia; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D014197:Trees / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; C107228:trilobalicin; C074719:trilobacin; D015107:4-Butyrolactone