Polyacetylenes from Chrysanthemum leucanthemum

Fifteen acetylenic compounds have been isolated and characterized from the flower heads of Chrysanthemum leucanthemum L. Five of these acetylenes have not previously been published as naturally occurring compounds. These are: 1,7(c)-hexadecadien-10,12,14-triyne; 1,8(c)-heptadecadien-11,13,15-triyne; 4(c)-tridecen-7,9,11-triyn-l-ol; 1,8(t)-hexadecadien-10,12,14-triyn-(6·7)-oxirane; and [3(t),5(t)-tridecadien-7,9,11-triyn-l-yl]-3-methyl-2-butenoate. The first three compounds are interesting since they are important intermediates in previously postulated biogenetic pathways. Ten acetylenes have been identified from the roots of the same plant, all of these having different structures from those of the flower heads. One of the acetylenes, [3(t), 5(t)-tridecadien-7,9,11-triyn-l-yl]-3-methylbutyrate, from the roots has never been reported as a naturally occurring compound.