Abstract
A resin-bound nitroso compound sequestered a single unexpected component from crude plant seed extracts. Several plants, including Piper nigrum, Eugenia caryophyllata, and Pimenta dioica, were extracted with organic solvent in the presence of a nitroso-containing resin. The nitroso resin selectively sequestered a single compound, β-caryophyllene, via a chemo- and regioselective ene reaction. The ene product was released from the resin, and proper selection of the solid-phase linker and cleavage cocktail allowed concomitant further transformation of the primary ene product to a novel functionalized polycycle. Preliminary studies indicate that the new hydroxylamine-containing natural product derivatives have antibiotic activity.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Acrylic Resins / chemistry
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Anti-Inflammatory Agents, Non-Steroidal / chemistry*
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Chromatography, High Pressure Liquid
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Complex Mixtures / chemistry
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Cyclohexenes / chemistry
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Hydroxylamines / chemistry
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Nitroso Compounds / chemistry
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Pimenta / chemistry*
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Piper nigrum / chemistry*
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Plant Extracts / chemistry*
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Polycyclic Sesquiterpenes
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Seeds / chemistry
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Sesquiterpenes / chemistry*
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Syzygium / chemistry*
Substances
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Acrylic Resins
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Anti-Inflammatory Agents, Non-Steroidal
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Complex Mixtures
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Cyclohexenes
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Hydroxylamines
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Nitroso Compounds
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Plant Extracts
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Polycyclic Sesquiterpenes
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Sesquiterpenes
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1,4-cyclohexadiene
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caryophyllene