Essential oils and a novel polyacetylene from Eryngium yuccifolium Michaux. (Apiaceae)

The essential oils of Eryngium yuccifolium Michaux. (Apiaceae) were isolated from the leaves, stalks and roots by hydrodistillation. Analysis of the oils by GC and GC-MS revealed that the leaves oil contained 49 compounds, of which germacrene D (18.3%), terpinolene (17.8%), bicyclogermacrene (8.8%), alpha-pinene (7.6%), beta-caryophyllene (6.2%) and falcarinol (9.6%) were found to be the major constituents. In addition, 40 compounds were identified from the stalk oil, among which, germacrene D (38.4%), gamma-amorphene (12.2%), bicyclogermacrene (10.1%), bicyclosesquiphellandrene (3.4%) and falcarinol (3.2%) were the major components. The roots oil was found to contain 25 compounds, of which, terpinolene (25.8%), trans-beta-bergamotene (18.6%) and the benzaidehyde 2,3,6-trimethylbenzaldehyde (13.9%), were the major constituents. Yuccifolol (nonadeca-1,11-diene-4,6,8-triyne-3,10-diol), a novel polyacetylene, was isolated and identified from the hexane:ether extract of the aerial parts, together with the known polyacetylenes, falcarinone [heptadeca-1,9-(Z)-dien-4,6-diyn-3-one], falcarinol (heptadeca-1,9-dien-4,6-diyn-3-ol) and heptadeca-1,8-diene-4,6-diyne-3,9-diol. The chemical structures of these constituents were established by NMR (DEPT, COSY, HMQC and HMBC) as well as HRESI-MS analysis. Copyright (c) 2006 John Wiley. & Sons, Ltd.