Ingol Esters, Cytotoxic Agents of the Macrocyclic Type

A Tri-Ester of Ingol From the Latex of Euphorbia kamerunica

“…Extraction.-Latex samples, in batches of 500 ml, were dried by evaporation and extracted with acetone and an ether soluble fraction was prepared (6). A gradient of hexane-benzene-ethylacetate was used to separate this resin by column chromatography (6). Compound 1 was eluted with benzene-ethylacetate (1:1).…”

“…The following data resulted: ms (electron-impact, 70 e.v. 200°), m/z 532 (M+-, 0.7%), 472 (4%), 432 (0.3%), 390 (1%), 372 (0.5%), 330 (4%), 312 (2%), 294 (2%), 211 (8%), 109 (13%), 105 (22%), 85 (83%), 83 (100%); ir (KBr disc) v max, cm-1, 3420, 2910, 1730, 1705, 1650, 1365, 1230; 'H-nmr (250 MHz, CDC1,) 6.876 (q, 7=6.99 Hz, 1H, tigliate), 5.540 (s, 1H-5), 5.263 hydrolysis.-Compound 1 was hydrolyzed with 0.5M KOH in methanol. The reaction mixture was separated into two fractions by tic on silica gel G with hexane-ether-ethyl acetate (1:1:1) as solvent.…”

Euphorbiane: A Novel Triterpenoid with an Unprecedented Skeleton from Euphorbia tirucalli

“…3,4 In previous literature reports, Ingol esters (macrocyclic diterpenes) have been isolated from species of Euphorbia and showed to possess cytotoxic activity. 5,6 As a part of our continuing interest in bioactive constituents, 7,8 we examined the 95% EtOH extract of the fresh stems of E. tirucalli L. Herein, we wish to report the isolation and identification of one novel triterpenoid (euphorbiane, 1) with an unprecedented skeleton from this plant. In addition, seven known compounds were also isolated from this plant including b-amyrone (2), 9 glutinone (3), 10 taraxerone (4), 11,12 friedelin (5), 13 glutinol (6), 14 euphol (7), 15 and b-sitosterol (8).…”