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Article

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

by
Ulrich KUCZKOWIAK
,
Frank PETEREIT
* and
Adolf NAHRSTEDT
*
Univ. of Münster, Inst. of Pharm. Biology and Phytochemistry, Corrensstr. 48, D-48149 Münster, Germany
*
Authors to whom correspondence should be addressed.
Part of the PhD thesis of U. Kuczkowiak, WWU Münster, Germany, 2000.
Sci. Pharm. 2014, 82(4), 835-846; https://doi.org/10.3797/scipharm.1404-02
Submission received: 9 April 2014 / Accepted: 21 August 2014 / Published: 21 August 2014

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

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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. https://doi.org/10.3797/scipharm.1404-02

AMA Style

KUCZKOWIAK U, PETEREIT F, NAHRSTEDT A. Hydroxycinnamic Acid Derivatives Obtained from a Commercial Crataegus Extract and from Authentic Crataegus spp. Scientia Pharmaceutica. 2014; 82(4):835-846. https://doi.org/10.3797/scipharm.1404-02

Chicago/Turabian Style

KUCZKOWIAK, Ulrich, Frank PETEREIT, and Adolf NAHRSTEDT. 2014. "Hydroxycinnamic Acid Derivatives Obtained from a Commercial Crataegus Extract and from Authentic Crataegus spp." Scientia Pharmaceutica 82, no. 4: 835-846. https://doi.org/10.3797/scipharm.1404-02

APA Style

KUCZKOWIAK, U., PETEREIT, F., & NAHRSTEDT, A. (2014). Hydroxycinnamic Acid Derivatives Obtained from a Commercial Crataegus Extract and from Authentic Crataegus spp. Scientia Pharmaceutica, 82(4), 835-846. https://doi.org/10.3797/scipharm.1404-02

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