New aurone epoxide and auronolignan from the heartwood of Cotinus coggygria Scop

• Published in: Natural product research Vol. 33; no. 19; pp. 2837 - 2844
• Main Authors: Novakovic, Miroslav, Djordjevic, Iris, Todorovic, Nina, Trifunovic, Snezana, Andjelkovic, Boban, Mandic, Boris, Jadranin, Milka, Vuckovic, Ivan, Vajs, Vlatka, Milosavljevic, Slobodan, Tesevic, Vele
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 02-10-2019; Taylor & Francis Ltd
• Subjects: Column chromatography; cotinignan A; Cotinus coggygria; Cotinus coggygria Scop; Dichloromethane; Dihydroxybenzoic acid; Flavonoids; High performance liquid chromatography; Liquid chromatography; Metabolites; NMR; Nuclear magnetic resonance; Secondary metabolites; semipreparative HPLC; Silica; Silica gel; Silicon dioxide; NMR; cotinignan A; semipreparative HPLC; flavonoids; Scop
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2018.1508141

New aurone epoxide, 2,10-oxy-10-methoxysulfuretin (14), and new auronolignan (15), named cotinignan A, were isolated by silica gel column and semipreparative HPLC chromatography from the methylene chloride/methanol extract of Cotinus coggygria Scop. heartwood. In addition, thirteen known secondary metabolites namely sulfuretin, 2,3-trans-fustin, fisetin, butin, butein, taxifolin, eriodictyol, 3',5,5',7-tetrahydroxyflavanone, 3',4',7-trihydroxyflavone, 3-O-methyl-2,3-trans-fustin, 3-O-galloyl-2,3-trans-fustin, β-resorcylic acid and 3-O-β-sitosterol glucoside were isolated as well. Their structures were elucidated by 1D and 2D NMR, HR-ESI-MS, IR and UV. Ten out of eleven isolated flavonoids possess 7, 3' and 4' hydroxy groups. These structural features could be considered as chemotaxonomic characteristic of flavonoids from C. coggygria. Cotinignan A (15) represents new subclass of secondary metabolites - auronolignans.