New sesquiterpene lactone and neolignan glycosides with antioxidant and anti-inflammatory activities from the fruits of Illicium oligandrum

Phytochemical investigations of the fruits of illicium oligandrum resulted in a new sesquiterpene lactone, 3 beta-benzoyloxy-10-deoxyfloridanolide (1), and three new neolignan glycosides, including two dihydrobenzofuran neolignan glycosides, (7R,8S)-9-O-beta-D-XYIOpyranosyl-9' -O-alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (2) and (7R,8S)9-O-shikimoyl-4-O-beta-D-glucopyranosyldihydrodehydrodiconifer- yl alcohol (3) and one 8-0-4' neolignan glycoside, (7S,8R)-1-[4-O-(beta-D-glucopyranosyl)-3-methoxyphenyl]-2-[4-(3-hydroxypro- pyl)-2,6-dimethoxyphenoxy]-1,3-propanedioI (4), together with three known sesquiterpene lactones (5 - 7) and two known neolignan glycosides (8 and 9). Their structures were elucidated on the basis of 1D, 2D NMR, HR-MS and chemical evidence. Compounds 3 and 4 showed moderate antioxidant activity with the inhibitory rates 13.30 % and 9.30 % at 1.0 x 10(-5) M, respectively. Compounds 3 and 9 exhibited anti-inflammatory activity with the inhibitory rates 67.0% and 51.0% at 1.0 x 10(-5) M, respectively.