Studies On The Bioactive Constituents Of Ardisia Gigantifolia Stapf

In this dissertation, the dried rhizome of Ardisia gigantifolia Stapf was extracted with 60% ethanol, and seventeen compounds were isolated using various chromatographic techniques. The structures of the compounds were elucidated on the basis of physical-chemical evidence and spectral analysis. The compounds were established as: gallic acid (1),(2R, 3S, 4S, 4aR, 10bS)-(-)-bergenin (2),(2R, 3S, 4S, 4aR, 10bS)-(+)-3, 4, 10-trihydroxy-2-(hydroxymethyl)-9-methoxy-6-oxo-2,3,4,4a,6,10b-h exahydropyrano[3,2-c]isochromen-8-yl 4-hydroxy-3,5-dimethoxybenzoate (3),(-)-3,4,8,10,10b-pentahydroxy-2-(hydroxymethyl)-9-methoxy-2,3,4,4a-tetrahydropyrano [3,2-c]iso chromen-6(10bH)-one (4), (+)-5-(1,2-dihydroxypentyl)benzene-1,3-diol(5),(-)-5-(1,2-dihydroxypentyl)benzene-1, 3-diol (6), (-)-epicatechin (7),(-)-4'-hydroxy-3', 5'-dimethoxyphenyl-β-D-[6-O-(4"-hydroxy-3", 5"-dimethoxybenzoyl)]-glucopyra noside(8),(-)-4'-hydroxy-3'-methoxyphenyl-β-D-[6-O-(4"-hydroxy-3", 5"-dimethoxybenzoyl)]-glucopyranosi de(9),(-)-4'-hydroxy-2', 6'-dimethoxyphenyl-β-D-[6-O-(4"-hydroxy-3"-methoxybenzoyl)]-glucopyranosi de(10),(-)-3'-hydroxy-4'-methoxyphenyl-β-D-[6-O-(4"-hydroxy-3", 5"-dimethoxybenzoyl)]-glucopyranosi de (11),β-sitosterol (12), 3β-O-{α-L-rhamnopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→2)]-β-D-galactopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside}-16α-hydroxy-13, 28-epoxy-oleanane(13), 3β-O-{α-L-rhamnopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→2)]-β-D-galactopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside}-16α-hydroxy-13, 28-epoxy-oleanane(14), 3β-O-α-L-rhamnopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→2)]-β-D-galactopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside-cyclamiretin A (15), 3β-O-α-L-rhamnopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→2)]-β-D-g alactopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside-cyclamiretin A(16), 3β-O-{α-L-rhamnopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→2)]-β-D-galactopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside}-16α-hydroxy-13, 28-epoxy-30-acetoxyoleane (17), respectively. All the compounds include one phenolic acid compound(1), three coumarins (2-4), two phenolic compounds(5, 6), one flavan(7), four phenolic glycoside compounds(8-11), one sterol(12) and five triterpenoid saponins(13-17). Compounds 3-6, 10, 11 are new compounds, compounds 8 and 9 were isolated from Ardisia for the first time, compounds 1 and 7 were isolated from Ardisia gigantifolia for the first time.The inhibitory effects and their IC₅₀ values of the non-saponin compounds on NO production in murine macrophage activated by LPS and IFN-γwere estimated, and phenolic glycoside compounds 8 and 10 showed strong inhibitory effects. The primary structure-activity relationship was discussed.We also tested the DPPH free radical scavenging activity of the non-saponin compounds. Partial phenolic acid compounds and phenolic glycoside compounds were found to have strong antioxidant activity and primary structure-activity relationship.In our laboratory, eleven triterpenoid saponins, with four kinds of aglycone, were isolated from Ardisia gigantifolia before, and some of them showed potent cytotoxic activity against NCI-H460, SF-268, MCF-7 and HepG2 tumor cell lines in the preliminary tests. In my works, five triterpenoid saponins(13-17) were accumulated.The results indicated that the anti-inflammation components and the potent free radical scavenger are gallic acid, bergenin and their derivates. In summary, the phenolic acid compounds and phenolic glycoside compounds as the potent NO inhibitors, free radical scavengers play the important role in the anti-inflammatory effects of Ardisia gigantifolia, and the anti-cancer components are triterpenoid saponins. Furthermore, the finger printing of the acetic ether part of the Ardisia gigantifolia was tried to established. It provided a reasonable ground for continuous study of this traditional Chinese medicine.