Thesis (Ph.D.)--Chulalongkorn University, 2010

The investigation for chemical constituents and their biological activities from CH₂Cl₂, EtOAc and n-BuOH crude extracts of the roots of Morinda pandurifolia Kuntze led to the isolation of one synthetically known anthraquinone; flavopurpurin (77), along with ten known anthraquinones; nordamnacanthal (16), damnacanthal (17), lucidin-ѡ-ethyl ether (18), phomarin (73), lucidin(74), lucidin-ѡ-ethyl ether (75), anthragallol-2,3-dimethyl ether (76), 1-methoxy-2-methyl anthraquinone (78), 3-hydroxy-1-methoxy-2-methoxymethyl anthraquinone (79), anthragallol (80) and two known iridoid glycosides; asperulosidic acid (43), deacetyl asperulosidic acid (44). This is the first report on phytochemical investigation and biological activities of this plant. Chromatographic separation of CH₂Cl₂ and MeOH crude extracts of the roots of Morinda coreia Ham led to the isolation of two synthetically known anthraquinones; 1,3,8-trihydroxy-2-methoxy-7-methyl anthraquinone (81) and 1-hydroxy-5,6-dimethoxy-2-methyl anthraquinone (82), a known anthraquinone glycoside; 1,3-dihydroxy-2-hydroxymethyl anthraquinone 3-O-β-glucopyranoside (lucidin-3-O-β-glucoside, 83), and five known anthraquinones; nordamnacanthal (16), damnacanthal (17), phomarin (73), 1-methoxy-2-methyl anthraquinone (78) and anthragallol (80). The structures of all isolated compounds were elucidated by physical properties and spectroscopic methods as well as comparison with previous literature data. All of isolated compounds (16-18, 43-44 and 73-83) were also evaluated for their cytotoxicity against KB and HeLa cell lines. Compounds 16, 17 and 73 showed moderate cytotoxicity against KB cells with IC₅₀ values in the range of 5.99-7.67 μg/mL, and compounds 75, 77, 78 and 80 showed weak cytotoxicity against KB cells with IC₅₀ values in the range of 12.06-21.05 μg/mL. Compounds 16, 17, 73 and 77 showed weak cytotoxicity against HeLa cells with IC₅₀ values in the range of 12.26-16.65 μg/mL. In addition, compounds 18, 43, 44, 74, 76, 79 and 81-83 were inactive to both cell lines.This is also the first report giving a complete structural assignment for two synthetically known compounds 77 and 81.