Benzolignanoid and Polyphenols from Origanum Vulgare

Abstract A new dihydrobenzodioxane derivative, origalignanol ( 10 ), together with nine polyphenolic compounds, salvianolic acid A ( 1 ), salvianolic acid C ( 2 ), lithospermic acid ( 3 ), apigenin 7‐ O ‐β‐ D ‐glucuronide ( 4 ), apigenin 7‐ O ‐β‐ D ‐(6″‐methyl)glucuronide ( 5 ), luteolin, ( 6 ), luteolin 7‐ O ‐β‐ D ‐glucopyranoside ( 7 ), luteolin 7‐ O ‐β‐ D ‐glucuronide ( 8 ), and luteolin 7‐ O ‐β‐ D ‐xylopyranoside ( 9 ), were isolated from the aqueous ethanolic extract of the aerial parts of Origanum vulgare for the first time. The structure of new compound 10 was determined on the basis of spectroscopic methods. Compound 5 is probably an artifact formed during the isolation. Compounds 1, 2 and 3 showed strong DPPH radical scavenging activity with an EC 50 of 7.2 ± 0.4, 9.6 ± 0.9, and 9.5 ± 0.7 μM, respectively, and protected rat hepatocytes from CCl 4 ‐damage at 100 μM.