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A new view on the codonocarpine type alkaloids of Capparis decidua


Forster, Yvonne; Ghaffar, Abdul; Bienz, Stefan (2016). A new view on the codonocarpine type alkaloids of Capparis decidua. Phytochemistry, 128:50-59.

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 a,u-bis-adducts of spermidine with coumaric and/or ferulic acids, followed by phenol oxidation.

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 a,u-bis-adducts of spermidine with coumaric and/or ferulic acids, followed by phenol oxidation.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2016
Deposited On:03 Jun 2016 08:28
Last Modified:03 Jun 2016 08:28
Publisher:Pergamon
ISSN:0031-9422
Publisher DOI:https://doi.org/10.1016/j.phytochem.2016.03.019

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