Chemical investigation of the stems of Salacia verrucosa Wight (family Celastraceae) led to the isolation of one new (21α-hydroxyfriedelane-1,3-dione) and three known 1,3-diketofriedelane triterpenes (friedelane-1,3-dione, 26-hydroxyfriedelane-1,3-dione and 30-hydroxyfriedelane-1,3-dione), three friedelane-type triterpenes (friedelin, kokoonol and 21α-hydroxyfriedelan-3-one), and one oleanane-type triterpene (3β,22α-dihydroxyolean-12-en-29-oic acid). From the stems of Ficus foveolata (Wall. ex Miq.) Miq. (family Moraceae), two new (foveolide A and foveoeudesmenone) and two known eudesmane-type sesquiterpenes [4(15)-eudesmene-1β,6α-diol and 4(15)-eudesmene-1β,5α-diol], a new sesquiterpenoid dimer (foveolide B), one new (foveospirolide) and one known phenolic compound (ethyl rosmarinate), together with three known triterpenes (friedelin, taraxerol and betulin) were isolated. The chemical structures of these plant constituents were determined by spectroscopic analyses, including UV, IR, MS and NMR, and comparison with previously reported data. Friedelane-1,3-dione was strongly cytotoxic against human colon cancer cell line (SW620) with an IC [subscript 50] value of 2.02 µM, whereas 26-hydroxyfriedelane-1,3-dione and 21α-hydroxyfriedelan-3-one were moderately cytotoxic against colon, liver (HepG2) and gastric (KATO-III) cancer cell lines. 26-Hydroxyfriedelane-1,3-dione also exhibited moderate cytotoxicity against lung (CHAGO) and breast (BT474) cancer cell lines. Foveolide A was moderately cytotoxic against colon, liver, breast and gastric cancer cell lines, while foveolide B was specifically cytotoxic toward colon cancer cell line. In addition, foveolide A exhibited anti-tuberculosis activity against Mycobacterium tuberculosis with a minimum inhibitory concentration of 200 µM.

Thesis (Ph.D.)--Chulalongkorn University, 2012