Cotinus coggygria wood: novel flavanone dimer and development of an HPLC/UV/MS method for the simultaneous determination of fourteen phenolic constituents.
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.
Antal
Diana S
DS
Institute of Pharmacy/Pharmacognosy, University of Innsbruck, Innsbruck, Austria. diana.antal@umft.ro
Schwaiger
Stefan
S
Ellmerer-Müller
Ernst P
EP
Stuppner
Hermann
H
D027926:Anacardiaceae / Q000737:chemistry*; D005591:Chemical Fractionation / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002853:Chromatography, Liquid; D044950:Flavanones / Q000737:chemistry* / Q000302:isolation & purification; D013058:Mass Spectrometry; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification; D015203:Reproducibility of Results; D014934:Wood / Q000737:chemistry*
D044950:Flavanones; D010936:Plant Extracts
J Nat Prod. 2000 Dec;63(12):1696-8
11141121
Chem Res Toxicol. 2001 Apr;14(4):398-408
11304128
J Sep Sci. 2006 May;29(8):1074-81
16830721
J Chromatogr A. 2004 Sep 17;1049(1-2):219-22
15499936
Planta Med. 2003 Oct;69(10):899-904
14648391
Arch Pharm Res. 2003 Jun;26(6):458-62
12877554
J Agric Food Chem. 2004 Sep 22;52(19):5863-8
15366833
Plant Cell Rep. 1990 May;8(12):711-3
24232923
Biochim Biophys Acta. 2002 Apr 15;1570(3):181-91
12020808
Plant Physiol. 2002 Apr;128(4):1173-9
11950966
J Chromatogr A. 2005 Dec 2;1097(1-2):148-56
16298194
Anal Bioanal Chem. 2009 Jun;394(3):871-82
19352635
Biochem J. 1960 Jul;76(1):17-23
16748820