Abstract
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.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Animals
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification
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Antineoplastic Agents, Phytogenic / pharmacology*
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Artemia / drug effects
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Circular Dichroism
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Drug Screening Assays, Antitumor
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Furans / chemistry*
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Furans / isolation & purification
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Furans / pharmacology*
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Humans
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Lactones / chemistry*
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Lactones / pharmacology*
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Lethal Dose 50
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Magnetic Resonance Spectroscopy
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Models, Molecular
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Molecular Structure
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Stereoisomerism
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Structure-Activity Relationship
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Tetrahydrofolates / chemistry*
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Trees / chemistry*
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Tumor Cells, Cultured
Substances
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Antineoplastic Agents, Phytogenic
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Furans
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Lactones
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Tetrahydrofolates
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asiminocin
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bullatacin
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5,6,7,8-tetrahydrofolic acid