Thesis (Ph.D.)--Chulalongkorn University, 2007

Investigation of the chemical constituents of the leaves of Aglaia forbesii King. (Meliaceae) led to the isolation of three new cyclopenta[bc]benzopyran type flavaglines, desacetylpyramidaglains A, C and D, and a new cycloartane type triterpenoid, (23R, 24S)-23,24,25-trihydroxycycloartan-3-one, together with the bisamide pyramidatine, the sesquiterpene spathulenol, two pregnane steroids, 2β,3β-dihydroxy-5α-pregn-17(20)-(Z)-en-16-one and 2β,3β-dihydroxy-5α-pregn-17(20)-(E)-en-16-one, two stigmastane steroids, a mixture of β-sitosterol and stigmasterol and two common triterpenoids, lupeol and lupenone. Similar study on the leaves of A. oligophylla Miq. yielded eleven of its constituents including the cyclopenta[b]benzofuran flavagline, rocaglaol, eight dammarane type triterpenoids, including dipterocarpol, a mixture of ocotillone and cabraleone, ocotillol-II, 20S,24S-dihydroxydammar-25-en-3-one, 20X,25-epoxy-24R-hydroxy-3-dammaranone, and a mixture of 20S,25-epoxy-24R-hydroxydammar-3α-ol and 20S,25-epoxy-24R-hydroxydammar-3β-ol, and a mixture of the bisamides odorine and 2'-epi-odorine. The structures of these isolates were determined by extensive spectroscopic studies, including comparison of their UV, IR, MS and NMR properties with previously reported data. Each isolated compounds from the two plants was evaluated for anti-tuberculosis activity against Mycobacterium tuberculosis H₃₇Ra, anti-herpes simplex activity, and cytotoxic activity against NCI-H187 small cell lung cancer cell line. All of the compounds from Aglaia forbesii except desacetylpyramidaglains A and C exhibited anti-TB activity, of which desacetylpyramidaglain D and pyramidatine showed the highest activity. Furthermore, some of the compounds isolated from this plant, including 23,24,25-trihydroxycycloartan-3-one, desacetylpyramidaglain D, and 2β,3β-dihydroxy-5α-pregn-17(20)-(E)-en-16-one, also exhibited anti-HSV-1 activity, while lupeol showed moderately cytotoxic activity against NCI-H187 cancer cell line. In addition, four compounds from Aglaia oligophylla, a mixture of 20S,25-epoxy-24R-hydroxydammar-3α-ol and 20S,25-epoxy-24R-hydroxydammar-3β-ol, and a mixture of the bisamides odorine and 2'-epi-odorine exhibited anti-TB activity