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

Abstract

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.

Keywords.:

• Cotinus coggygria Scop
• flavonoids
• cotinignan A
• semipreparative HPLC
• NMR

Acknowledgements

The authors are grateful to Prof. M. Veljic, Faculty of Biology, University of Belgrade, Serbia, for the taxonomic determination of the plant species.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

The authors acknowledge their gratitude to the Ministry of Science and Technological Development of Serbia for financial support, Project No. 172053.