Studies On The Chemical Constituents Of Twigs And Leaves Of Illicium Henryi

Illicium is a major genus of Illiciaceae family, consisting of about 50 different species in northern hemisphere. Most of the green herbal medicinal plant, about 28 species, distributed in southern part of China. They have shown many kinds of activities, including antibacterial, central excitation, set up leucocyte and analgesia, and so on. Thus, recently decades, more and more attentions have been paid to Illicium genus and their chemical constituents. Investigations on Illicium genus have led to the identification of many compounds, such as sesquiterpene, phenylpropanoid, lignan, diterpene, monoterpene and triterpene.In this dissertation, we investigated the EtOH extract of twigs and leaves of Illicium henryi collected from JiangXi province. As a result,37 compounds were isolated by silica gel, Sephadex LH-20, ODS, HPLC, PTLC and HPLC chromatography, furthermore,32 compounds among of them were identified by spectral analysis as follows:5-allyl-1-(4-allyl-2-methoxyphenoxy)-2,3-dimethoxybenzene (1), difengpin-A (2),5’-demethoxy-dihydrobuddlenol B (3), 1β-isopropyl-4β-methyl-9β-hydroxy spiro [4.5] dec-6-en-8-one (4),10-hydroxyacoronene (5), 15-hydroxycalamenene (6), (-)-1-hydroxyl-1,3,5-bisabolatrien-10-one (7), acoradiepoxide (8), trans-3-methoxy-4,5-methylene-dioxycinnamal-dehyde (9),2,3-dimethoxy-4,5-methylenedioxy-allylbenzene (10),3-methoxy-4, 5-methylenediox-allylbenzene (11), difengpin (12),4,4’-dihydroxy-3,3’-dimethoxy-9,9’-epoxylignan (13), pinoresinol (14), secoisolariciresinol (15), 1-O-caffeoylglcerol (16), methyl caffeate (17), kaempferol (18), quercetin (19), quercetin-3-O-α-L-rhamnoside (20),3’,4’,7-trihydroxyflavone (21), 3’-methoxy-4’,7-dihydroxyflavone (22),p-menthane-1,2,8-triol (23), bis(2-ethylhexyl)ester (24),4-hydroxy-4,6-dimethyl-l-tetralone (25),2-(4-hydroxyphenyl) ethyl acetate (26), ethyl p-hydroxybenzoate (27), senkyunolide (28),3,4-dihydroxybenzoic acid (29), benzoic acid (30),β-sitosterol (31),β-daucosterol (32).In those compounds, compounds 1-5 were determined as new compounds,25 was a new natural product,6-8,13-14,24 and 28 were isolated from the genus Illicium for the first time, and compounds 9-12,15-23, 26-27 and 29-32 were isolated from this plant for the first time.The anti-inflammatory activities of crude extract, four extractive fractions and eight compounds from this plant were tested. High-dosed of crude extract (100 ug/ml, inhibition ratio 43%) and compounds 5 (100 ug/ml, inhibition ratio 49%),8 (100 ug/ml, inhibition ratio 36%) exhibited slight inhibitory effect on NO production at high dosage in LPS-stimulated RAW 264.7 cells.Further cells injury investigation of crude extract, four extractive fractions on PC 12 cell lines induced by L-glutamat and H2O2 were performed, the result exhibited that the tested all samples don’t prossess protective effect.All compounds were test for toxicity by MTT assay at the same time. The result showed that petroleum fraction, H2O fraction and compounds 5-allyl-l-(4-allyl-2-methoxyphenoxy)-2,3-dimethoxybenzene (1), difengpin-A (2),trans-3-methoxy-4,5-methylene-dioxycinnamal-dehyde (9),2,3-dimethoxy-4,5-methylenedioxy-allylbenzene (10) exihibited toxic to PC 12 and RAW 264.7 cells lines. Conclusion:Thirty-seven compounds were obtained from Illicium henryi, including five new compounds, one new natural product, seven compounds isolated from this genus, and nineteen compounds from this plant for the first time. On the basis of bioassay, it was found that high-dosed crude extract, compounds 10-hydroxyacoronene (5) and acoradiepoxide (8) displayed anti-inflammatory activity in vivo and petroleum ether fraction, and H2O fraction, compounds 5-allyl-l-(4-allyl-2-methoxyphenoxy)-2,3-dimethoxy-benzene (1), difengpin-A (2),trans-3-methoxy-4,5-methylene-dioxy-cinnamal-dehyde (9),2,3-dimethoxy-4,5-methylenedioxy-allylbenzene (10) possess toxicity to PC 12 and RAW 264.7 cells.