Studies On The Chemical Constituents And Bioactivity From The Fruits And Stem Barks Of Illicium Oligandrum Merr.et Chun

Illicium oligandrum Merr. et Chun is a toxic species of the genus Illicium in thefamily Magnoliaeeae. This plant is mainly distributed in Southern China, such asGuang-xi, Yun-nan Provinces, and used in forlk medicine for relieving pain andrheumatoid arthritis. In our investigations, the petroleum ether and CHCl₃ parts of theethanol extraction of the fruits and stem barks exhibited weak cytotoxic activity. TheEtOAc and n-BuOH parts showed significant antioxidant activity. Based on thebioactivities, isolations of chemical constituents from the fruits and stem barks of I.oligandrum were carded out. As a result, 40 (1-40) compounds were isolated from thefruits and 11 (41-51) compounds were isolated from the stem barks of I. Oligandrum.They were attributed to sesquiterpene lactones (7, 8, 9, 10^*, 48, 51^*), lignans (4, 5, 6,11, 27, 28^*, 29^*, 30, 31, 32^*, 33, 34, 35), flavonoids (13, 14, 15, 16, 17, 18, 19, 20, 21,22, 23), phenolics (12, 24, 25, 26, 38, 39, 40) and prenylated C₆-C₃ compounds (41,42^*, 43^*, 44^*, 45^*, 46, 47, 49^*, 50^*), respectively. Among them, 11 were newcompounds (with^*) and 3 of them possessed new carbon skeletons (43^*, 44^*, 45^*).On the basis of chemical and spectral analysies, their structures were elueidateded asfollowes: cis-1, 8-terpine-diol (1), aurantiamide (2), 3, 4-isopropylidenedioxyshikimicacid (3), (1R,2S, 5R,6S)-2,6-di-(4-hydroxyphenyl)-dioxabicyclo[3,3,0]octane (4),(1R,2S,5R,6S)-6-(4-hydroxy-3-methoxyphenyl)-2-(3,4-dihydroxyphenyl)-3,7-dioxabic-yclo [3,3,0] octane (5), (1R, 2S, 5R, 6R)-2,6-di-(4-hydroxyphenyl)-3,7-dioxabicyclo[3, 3, 0]octane (6), pseudoanisatin (7), 4,7-hemiketal ofpseudoanisatin (8),dunnianin (9), 3β-benzoyl-oxy-10-deoxyfloridanolide (10^*), (7R,8S) 9-O-shikimoyl-4-O-β-D-glucopyranosyldihydro dehydrodiconiferyl alcohol (11), 4-hydroxy-phenethylalcohol (12), kaempferol (13), quercetin (14), quercetin-3-O-β-D-galactopyranoside(15),isorhamnetin-3-O-β-D-glucopyranoside(16), quercetin-3-O-α-L-arabinopyrano-side (17), quercetin-3-O-α-L-rhamnopyranoside (18), dihydroquercetin-3-O-α-L-rhamnopyranoside (19), dihydrokaempferol-3-O-α-L-rhamnopyranoside (20), quercetin-3-O-α-L-rhamno pyranosyl(1→6)β-D-glucopyranoside (21), kaempferol-3-O-α-L-rhamno pyranosyl (1→6)β-D-glucopyranoside (22), isorhamnetin-3-O-α-L-rhamn opyranosyl (1→6)β-D-glucopyranoside (23), 3,4-di-methoxyl-benzoicacid (24), 2,4-di-methoxylbenzoic acid (25), gallic acid (26), icariside E₄ (27), (7R, 8S)9-O-β-D-xylopyranosyl-9'-O-α-L-rhamnopyranosyl (1→6)β-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (28^*), (7R,8S) 9-O-shikimoyl-4-O-β-D-gluco-pyranosyldihydrodehydrodiconiferyl alcohol (29^*), (7R,8S) dihydrodehydrodiconiferylalcohol-4-O-β-D-glucopyranoside (30), (7S, 8R) erythro-7, 9, 9'-trihydroxy-3, 3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (31), (7S, 8R) 1-[4-O-(β-D-glucopyranosyl)-3-methoxyphenyl]-2-[4-(3-hydroxypropyl)-2,6-di-methoxyphenoxy]-1, 3-propanediol (32^*), icariside E₃ (33), 1-O-(β-D-glucopyranosyl)-2-[2-methoxy-4-(ω-hydroxypropyl)-phenoxy]-propan-3-ol (34), 3-methoxyl-4-hydroxyl-phenpro-panol-O-β-D-glucopyranoside (35), shikimic acid (36), shikimic acid methyl ester (37),4-O-β-D-glucopyranosyloxy-benzoic acid methyl ester (38), 3-methoxyl-4-O-β-D-glucopyranosyloxy-benzoic acid methyl ester (39), 4-hydroxy-phenethyl alcohol-O-β-D-glucopyranoside (40), 2,3-dehydroillifunone (41), illioliganone A (42^*),methylene-di-2,3-dehydroillifunone (43^*), methylene-di-illifunone D (44^*), illifun-pyranone (45^*), illifunone C (46), illifunone D (47), neomajucin (48) illioliganone B(49^*), illioliganone C (50^*) oligandriortholactone (51^*).Part of lignans (27, 28, 29, 31, 32, 34) showed significant anti-inflammatoryactivity and some prenylated C₆-C₃ compounds (41, 43, 46, 47, 49) and asesquiterpene lactone (48) exhibited potential activity of inhibiting potassium (K⁺)channel. The antitumor test in vitro against human tumor cell lines with MTT methodindicated that these compounds of sesquiterpene lactones and prenylated C₆-C₃compounds presented weak activities on the growth control activities against severalcancer cell lines.