New Sesquiterpene Lactone and Neolignan Glycosides with Antioxidant and Anti-Inflammatory Activities from the Fruits of Illicium oligandrum

Abstract

Phytochemical investigations of the fruits of Illicium oligandrum resulted in a new sesquiterpene lactone, 3β-benzoyloxy-10-deoxyfloridanolide (1), and three new neolignan glycosides, including two dihydrobenzofuran neolignan glycosides, (7R,8S)-9-O-β-D-xylopyranosyl-9′-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (2) and (7R,8S)-9-O-shikimoyl-4-O-β-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (3) and one 8-O-4′ neolignan glycoside, (7S,8R)-1-[4-O-(β-D-glucopyranosyl)-3-methoxyphenyl]-2-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]-1,3-propanediol (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 × 10^-5 M, respectively. Compounds 3 and 9 exhibited anti-inflammatory activity with the inhibitory rates 67.0 % and 51.0 % at 1.0 × 10^-5 M, respectively.

Key words

Illicium oligandrum - Illiciaceae - sesquiterpene lactones - neolignan glycosides - antioxidant activity - anti-inflammatory activity

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