title: A new view on the codonocarpine type alkaloids of Capparis decidua.
abstract: Several spermidine alkaloids are described in literature as constituents of the root bark of Capparis decidua. Since some of the proposed structures, however, are in conflict with the expected biosynthetic paths, an extract of the root bark of the plant was re-investigated. Four major spermidine alkaloids of the codonocarpine type were identified and their structures elucidated: of the four compounds, isocodonocarpine was described previously for C. decidua and cadabicine was proposed as a possible constituent as well. Codonocarpine was found for the first time in an extract of C. decidua but was previously isolated from a closely related plant. Capparidisinine, finally, is an alkaloid with a structure that has never been described before. The structures of the four alkaloids are substantiated by NMR and MS data, and the four compounds are in logical agreement with biosynthetic considerations: they would arise from α,ω-bis-adducts of spermidine with coumaric and/or ferulic acids, followed by phenol oxidation.
authors.affiliation: Department of Chemistry, Section A, University of Zurich, Winterthurerstrasse 190, CH-8057, Zurich, Switzerland. Electronic address: yvonne.forster@chem.uzh.ch.
authors.forename: Yvonne
authors.initials: Y
authors.lastname: Forster
authors.affiliation: Department of Chemistry, Baghdad-ul-Jadeed Campus, The Islamia University of Bahawalpur, Pakistan. Electronic address: aghaffarswl@hotmail.com.
authors.forename: Abdul
authors.initials: A
authors.lastname: Ghaffar
authors.affiliation: Department of Chemistry, Section A, University of Zurich, Winterthurerstrasse 190, CH-8057, Zurich, Switzerland. Electronic address: stefan.bienz@chem.uzh.ch.
authors.forename: Stefan
authors.initials: S
authors.lastname: Bienz
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification*; D031484:Capparis / Q000737:chemistry*; D026121:Indole Alkaloids; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010636:Phenols / Q000737:chemistry / Q000378:metabolism; D010936:Plant Extracts / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D013095:Spermidine / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D026121:Indole Alkaloids; D010636:Phenols; D010936:Plant Extracts; C000614030:codonocarpine; D013095:Spermidine
keywords: Capparaceae; Capparis decidua; Codonocarpine; Spermidine alkaloid; Structure elucidation