Discovery And Biological Activities Of Chalcones With NQO1 Induction Activities From Angelica Keiskei

Compounds that can react with glutathione (GSH) by Michael addition present good NQO1 induction activities. An LC-MS method, which GSH was used as substrate, was employed to reveal the compounds with NQO1 induction activities from Angelica keiskei. Some compounds, proposed as isobavachalcone, xanthoangelol and 4-hydroxyderricin, have NQO1 induction activities. To make the actual structures and bioactivities of these compounds clear, twenty-three compounds, including the three chalcones mentioned above and two new compounds 4-hydroxy-3,5,5-trimethyl-4-(1,2, 3-trihydroxybutyl)cyclohex-2-enone (18) and (Z)-2-(3-hydroxypent-l-ynyl)-3-(non-1-enyl)oxiran-2-ol (23), were isolated from the 95% ethanol extract of Angelica keiskei. The bioassay results suggested the three chalcones had notable NQO1 induction activities, verifying the reliability of the method LC-MS for revealing compounds with NQO1 induction activities. The radical scavenging andα-glucosidase inhibition activities of the isolated compounds were also tested. Compounds 1,2,17 and 18 could scavenge DPPH radical by more than 20%. Compounds 1,2,3,5,9,16,20 and 21 exhibited excellent a-glucosidase inhibition activities.