Study On The Chemical Constituents Of The Roots Of Macrothelypteris Torresiana

Ferns are widely distributed in humid and warm places. Fern is a very ancient family of plants, which was thriving on earth for two hundred million years. The fern plant has more than 12000 species and 2600 species distributes in China. The recent pharmacological studies showed that fern plants have multiple bioactivities, especially the activities of antibacterial, antivirus and anti-tumor. So we study the chemical constituents of Macrothelypteris torresiana in this thesis.Macrothelypteris torresiana (Gaud.) Ching (Thelypteridaceae) is widely distributed in south of China and was found in Myanmar, Nepal, Bhutan, India, Vietnam, Japan, the Philippines, Indonesia, Australia, America in tropical and subtropical regions. Although this plant is not recorded as a medicine in the Compendium of Materia Medica and not used as a medicine in folk, it is found that the protoapigenin isolated from the M. torresiana showed good cytotoxicity. Further more, some unusual flavonoids were isolated from the species M. torresiana and showed significant antitumor activities. For the purpose of anti-tumor agent from the M. torresiana, we investigated the compounds from the roots of M. torresiana. Eleven compounds were isolated from MeOH extract of the roots of M.torresiana by silica gel, sephadex LH-20 and ODS-C18 .These compounds have been identified on the basis of spectroscopic data (IR, UV, MS, 1H-NMR, 13C-NMR, HSQC, HMBC), X-ray and chemical method, and their structures were elucidated as 1:β-sitosterol; 2:β-sitosterol-3-O-β-D-glucoside-6′-eicosanate; 3: 5, 7-dihydroxy-2- (1, 2-isopropyldioxy-4-oxocyclohex-5-enyl)-chromen-4-one; 4: protoapigenone; 5: 2-(cis-1, 2-dihydroxy-4-oxo-cyclohex-5-enyl)-5, 7-dihydroxy-chromone; 6: 5, 7- dihydroxy-2-(1-hydroxy-2, 6-dimethoxy-4-oxo-cyclohex)-chromen-4-one; 7:β-sitosterol glucoside; 8: 2-(trans-1,4-dihydroxy-cyclohexyl)-5, 7-dihydroxy- chromone; 9: protoapigenin; 10: apigenin-4′-O-β-D-glucoside; 11: protoapigenin-4′-O-β-D-glucoside. Among them, two compounds (3, 6) are new compounds.Cytotoxicity activity of flavanoids compounds from the roots of M. torresiana assayed by MTT in vitro. The cytotoxicity activity assay indicated that compound 3 and 6 have cytotoxicity for test human tumor cell. Compound 3 and 6 exhibited anti-tumor activities toward Hep G2 with IC50 values of 48.65μg/mL and 66.53μg/mL, respectively. Activity of 3 and 6 is weaker than activity of protoapigenone.