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Chromatographic Separation of the Codonocarpine Type Alkaloids from the Root Bark of Capparis decidua   

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Original research article

A brief version of this protocol appeared in:
Phytochemistry
Aug 2016

Abstract

Various parts of the caper tree Capparis decidua have found application in traditional medicine. The isolation and structural elucidation of the codonocarpine type alkaloids contained in the root bark, however, is not trivial and has probably led to misinterpretation in the past. This protocol describes the extraction and chromatographic separation of the four major alkaloids of the root bark of Capparis decidua. The delivered samples of cadabicine, codonocarpine, isocodonocarpine and capparidisinine were suitable for their unambiguous structural elucidation by NMR, MS and MS/MS.

Keywords: Capparis decidua, Capparaceae, Spermidine alkaloid, Cadabicine, Codonocarpine, Isocodonocarpine, Capparidisinine, Chromatographic separation

Background

The tree Capparis decidua is widely distributed in the arid regions of Africa, the Middle East and Southern Asia, where various parts of the plant are commonly used in local folk medicines for the treatment of various disorders. The root bark, for example, is applied as anthelmintic and purgative, and it has been shown that its alcoholic extract possesses significant antibacterial and antifungal activities (Singh et al., 2011; Singh and Singh, 2011; Tlili et al., 2011; Mohammed et al., 2015).

Ahmad et al. (1985; 1986; 1987; 1989; Arif, 1986) intensively studied the root bark extract of Capparis decidua and published several structures of codonocarpine type alkaloids. Some of these structures did not fit with our understanding of the biosynthesis of such alkaloids. Further, we were not convinced that the given analytic data and its interpretation gives unambiguous proof for the structural claims (Bienz et al., 2002). Therefore, we initiated our own investigation. We developed a protocol for the extraction and chromatographic separation of codonocarpine type alkaloids and could isolate three alkaloid fractions that allowed the identification and structural elucidation of the four major spermidine alkaloids of the root bark of Capparis decidua: cadabicine (1), codonocarpine (2), isocodonocarpine (3), and capparidisinine (4) (Figure 1) (Forster et al., 2016).


Figure 1. The four major codonocarpine type alkaloids found in the root bark of Capparis decidua. (1) Cadabicine; (2) Codonocarpine; (3) Isocodonocarpine; and (4) Capparidisinine.

The isolation and structure elucidation of alkaloids is not trivial. The class of alkaloids, defined as nitrogen containing organic compounds from natural sources with a most basic character, comprises more than 10,000 compounds. As the properties and structures of alkaloids differ strongly from compound to compound, there is no general way to isolate them. Nevertheless, most alkaloids exist naturally in their protonated form. Hence, the methanolic extraction of dried and crushed plant material is often applied. As alkaloids usually possess amino and other functional groups that could react with solvents and additives, as well as with CO2 or oxygen from air, the formation of artefacts is prevented as far as possible by the choice of appropriate conditions. In general, artefacts can be recognized by comparing the analytical data of the isolated fractions and the original sample. Therefore, some of the original sample should always be kept as reference material (Hesse, 2000).

Copyright: © 2017 The Authors; exclusive licensee Bio-protocol LLC.
How to cite: Forster, Y., Ghaffar, A. and Bienz, S. (2017). Chromatographic Separation of the Codonocarpine Type Alkaloids from the Root Bark of Capparis decidua. Bio-protocol 7(4): e2144. DOI: 10.21769/BioProtoc.2144.
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