The absolute configuration of adjacent bis-THF acetogenins and asiminocin, a novel highly potent asimicin isomer from Asimina triloba.
A novel acetogenin, asiminocin (1), was isolated by activity-directed fractionation from the stem bark of the paw paw tree, Asimina triloba. By spectral and chemical methods, 1 was identified as (30S)-hydroxy-4-deoxyasimicin. The absolute configuration of 1, along with those of previously reported acetogenins asimin, asiminacin, bullatin, (30S)-bullanin, and (30R) bullanin, was determined by Mosher ester methodology. Compound 1 was highly inhibitory to three human solid tumor cell lines with over a billion times the potency of adriamycin.
Zhao
G X
GX
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907, USA.
Chao
J F
JF
Zeng
L
L
Rieser
M J
MJ
McLaughlin
J L
JL
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001156:Artemia / Q000187:drug effects; D002942:Circular Dichroism; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D007783:Lactones / Q000737:chemistry* / Q000494:pharmacology*; D007928:Lethal Dose 50; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013763:Tetrahydrofolates / Q000737:chemistry*; D014197:Trees / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; D013763:Tetrahydrofolates; C100552:asiminocin; C061022:bullatacin; C030371:5,6,7,8-tetrahydrofolic acid