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Sci. Pharm. 2014, 82(4), 835-846; doi:10.3797/scipharm.1404-02

Hydroxycinnamic Acid Derivatives Obtained from a Commercial Crataegus Extract and from Authentic Crataegus spp.

Univ. of Münster, Inst. of Pharm. Biology and Phytochemistry, Corrensstr. 48, D-48149 Münster, Germany
Part of the PhD thesis of U. Kuczkowiak, WWU Münster, Germany, 2000.
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Received: 9 April 2014 / Accepted: 21 August 2014 / Published: 21 August 2014
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Abstract

Eleven hydroxycinnamic acid derivatives were isolated from a 70% methanolic Crataegus extract (Crataegi folium cum flore) and partly verified and quantified for individual Crataegus species (C. laevigata, C. monogyna, C. nigra, C. pentagyna) by HPLC: 3-O-(E)-p-coumaroylquinic acid (1), 5-O-(E)-p-coumaroyl-quinic acid (2), 4-O-(E)-p-coumaroylquinic acid (3), 3-O-(E)-caffeoylquinic acid (4), 4-O-(E)-caffeoylquinic acid (5), 5-O-(E)-caffeoylquinic acid (6), 3,5-di-O-(E)-caffeoylquinic acid (7), 4,5-di-O-(E)-caffeoylquinic acid (8), (−)-2-O-(E)-caffeoyl-L-threonic acid (9), (−)-4-O-(E)-caffeoyl-L-threonic acid (10), and (−)-4-O-(E)-p-coumaroyl-L-threonic acid (11). Further, (−)-2-O-(E)-caffeoyl-D-malic acid (12) was isolated from C. submollis and also identified for C. pentagyna and C. nigra by co-chromatography. The isolates 10 and 11 were not found in the authentic fresh specimen, indicating that they may be formed during extraction by acyl migration from the 2-O-acylderivatives. Also, 9 and 11 are described here for the first time. All structures were assigned on the basis of their spectroscopic data (1H-, 13C-NMR, MS, optical rotation).
Keywords: Crataegus spp.; Rosaceae; Hydroxycinnamic acid derivatives; Hydroxycinnamoyl quinic acids; Hydroxycinnamoyl threonic acids Crataegus spp.; Rosaceae; Hydroxycinnamic acid derivatives; Hydroxycinnamoyl quinic acids; Hydroxycinnamoyl threonic acids
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

KUCZKOWIAK, U.; PETEREIT, F.; NAHRSTEDT, A. Hydroxycinnamic Acid Derivatives Obtained from a Commercial Crataegus Extract and from Authentic Crataegus spp.. Sci. Pharm. 2014, 82, 835-846.

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