Seven undescribed compounds from the flower heads of Helianthus annuus L.

Abstract

Seven undescribed compounds, namely, 4-hydroxy-3-(2′-hydroxy-3′-methyl-1′-butenyl) acetophenone-1′-O-β-D-glucopyranoside (1), 4-hydroxy-3-((Z)-3′-hydroxy-3′-methyl-1′-butenyl) acetophenone-8-O-β-D-glucopyranoside (2), 4,6-hydroxy-3-((Z)-3′-hydroxy-3′-methyl-1′-butenyl) acetophenone-8-O-β-D-glucopyranoside (3), 4-hydroxy-3-((Z)-3′-hydroxy-3′-methyl-1′-butenyl) acetophenone-6-O-β-D-glucopyranoside (4), 2-hydroxymethylimino-3,4-dimethyl-7-hydroxy-6-methyl ketone-2H-chromon (5), annuolide A-15-O-β-D-glucopyranoside (6) and heliannuoside A (7), together with eighteen known compounds, were obtained from water extract of the flower heads of Helianthus annuus L. (Asteraceae). The structures of these compounds were elucidated based on spectroscopic analyses. Upon evaluation of the anti-inflammatory activity of compounds 1–9, 15–18, 21 and 24–25 by their effects on the release of NO in MH-S cells, compound 6 showed significant inhibition of NO secretion at 12.5 μM (P < 0.05) and 25 μM (P < 0.01) in a dose-dependent manner, and compound 18 showed inhibition of NO secretion at 25 μM (P < 0.05).