Polyacetylenes and sterols from the aerial parts of Chrysanthemum coronarium L.(Garland)

Abstract

The aerial parts of Chrysanthemum coronarium were extracted in MeOH, and the extract was partitioned using EtOAc, n-BuOH and H2O. The repeated column chromatography of EtOAc fraction gave four sterols, whose chemical structures were identified as stigmast-4-en-6-o1-3-one (1), stigmast-4- en-6-ol-3-one (2), which have been so far reported only in the aquatic plants and were isolated for the first time from the land plants, -sitosterol (3) and daucosterol (4) based on several spectral data including gCOSY, gHSQC, gHMBC and comparison of the data with those of literature. And the repeated column chromatography of EtOAc and n-BuOH fractions gave nine polyacetylens, which were identified as 2-[(lZ,4Z)-5-methylsulfinyl-2-pentyn-4-enyliden]-1,6- dioxaspiro[4,4]non-3-ene (5), 2-[(IE,4Z)-5-methylsulfinyl-2-pentyn-4-enyliden]- 1,6-dioxaspiro[4,4]non-3-ene (6), 2-[lZ-2,4-dipentyn-6-methyliden]-1,6-dioxaspiro [4,4]non-3-ene (7), 2-[lE-2,4-dipentyn-6-methyliden]-1,6-ioxaspiro[4,4]non-3- ene (8), 2-[lE-2,4-dipentyn-6-methyliden]-1,6-dioxaspiro[4,5]non-3-ene (9), 2-[lZ- 2,4-dipentyn-6-methylidene]-1,6-dioxaspiro[4,4]non-3,7-dien-9-ol (10), 2-[lE-2, 4-dipentyn-6-methyliden]-1,6-dioxaspiro[4,4]non-3,7-dien-9-ol (11), 2-[lE-2,4- dipentyn-6-methyliden]-1,6-dioxaspiro[4,4] non-3,7-dien-9-ol (12) and 2-[1Z- 2,4-dipentyn-6-methyliden ]-1,6-dioxaspiro[4,4]non-3,7-dien-9-o1 (13). Some of them showed the inhibitory effect on the activity of ACAT (Acyl-CoA: cholesterol acyltransferase), the catalyzing enzymes of the intracellular esterification of cholesterol, and FPTase (Farnesyl-protein transferase), the farnesylation enzymes for Ras protein in charge of cancer promotion, PLT aggregation, and the growth of HUVEC (Human umbilical vascular endothelial cell) or A549 cells.