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Planta Med 2010; 76(15): 1765-1772
DOI: 10.1055/s-0030-1249878
Analytical Studies
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Cotinus coggygria Wood: Novel Flavanone Dimer and Development of an HPLC/UV/MS Method for the Simultaneous Determination of Fourteen Phenolic Constituents

Diana S. Antal1 , 3 , Stefan Schwaiger1 , Ernst P. Ellmerer-Müller2 , Hermann Stuppner1
  • 1Institute of Pharmacy/Pharmacognosy, University of Innsbruck, Innsbruck, Austria
  • 2Institute of Organic Chemistry, University of Innsbruck, Innsbruck, Austria
  • 3Faculty of Pharmacy, University of Medicine and Pharmacy of Timisoara, Timisoara, Romania
Further Information

Publication History

received January 22, 2010 revised March 3, 2010

accepted March 30, 2010

Publication Date:
05 May 2010 (online)

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Abstract

Phytochemical investigations of Cotinus coggygria Scop. wood, a medicinal and tinctorial plant used since antiquity, resulted in the isolation and structure elucidation of the novel C-3/C-3′′ dimer of butin (3′,4′,7-trihydroxyflavanone) and other known compounds: gallic acid and its methyl ester; catechin; profisetinidins: fisetinidol-(4α→8)-(+)-catechin and epifisetinidol-(4β→8)-(+)-catechin; flavanonols: fustin and dihydroquercetagetin; flavanones: butin and eriodictyol; flavonols: fisetin and quercetin; the chalcone butein and the aurone sulfuretin. The isolated compounds were used for the development and validation of a HPLC-method which enables the determination of these bioactive substances in C. coggygria extracts. Separation was possible on an ether-linked phenyl column material, using as mobile phase mixtures of water, methanol, and acetonitrile with 0.02 % trifluoroacetic acid. Sensitivity, selectivity, linearity, precision, accuracy, and repeatability of the method were verified and assured suitability for its intended use. LC‐MS experiments performed in positive and negative electrospray ionization mode confirmed the identity of analytes and allowed unambiguous assignment of all peaks of interest. The analysis of different C. coggygria samples revealed that sulfuretin (0.38–0.69 %) and fustin (0.33–0.59 %) dominated, followed by dihydroquercetagetin (0.12–0.35 %), a rare flavanonol derivative with a 5,6,7-trihydroxysubstituted A-ring. The new natural compound C-3/C-3′′ flavanone dimer occurred in concentrations of 0.03–0.06 %; the two latter compounds could represent valuable markers for the identification and quality control of C. coggygria wood.

Key words

Cotinus coggygria - Anacardiaceae - HPLC‐DAD - LC‐MS - validation - biflavonoids

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Dr. Diana S. Antal

Department of Pharmaceutical Botany
Faculty of Pharmacy
University of Medicine and Pharmacy of Timisoara

Piata Eftimie Murgu 2

300041 Timisoara

Romania

Phone: + 40 2 56 49 46 04

Fax: + 40 2 56 22 04 79

Email: diana.antal@umft.ro

    www.thieme-connect.de/ejournals/toc/plantamedica