title: Selective molecular sequestration with concurrent natural product functionalization and derivatization: from crude natural product extracts to a single natural product derivative in one step.
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.
authors: Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556, USA.
authors: Viktor
authors: V
authors: Krchňák
authors: Jaroslav
authors: J
authors: Zajíček
authors: Patricia A
authors: PA
authors: Miller
authors: Marvin J
authors: MJ
authors: Miller
mesh_terms: D000180:Acrylic Resins / Q000737:chemistry; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D045424:Complex Mixtures / Q000737:chemistry; D053138:Cyclohexenes / Q000737:chemistry; D006898:Hydroxylamines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry; D027841:Pimenta / Q000737:chemistry*; D029222:Piper nigrum / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry*; D000081223:Polycyclic Sesquiterpenes; D012639:Seeds / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry*; D027842:Syzygium / Q000737:chemistry*
chemical_list: D000180:Acrylic Resins; D000894:Anti-Inflammatory Agents, Non-Steroidal; D045424:Complex Mixtures; D053138:Cyclohexenes; D006898:Hydroxylamines; D009603:Nitroso Compounds; D010936:Plant Extracts; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C048401:1,4-cyclohexadiene; C024714:caryophyllene