Bioactive new bitter-tasting p-hydroxystyrene glycoside and other constituents from the fern Elaphoglossum spathulatum

Abstract

Two bitter-tasting compounds were isolated from an Argentine collection of Elaphoglossum spathulatum, a new p-hydroxystyrene glycoside that we named elaphoside-A, and naringin. Structure elucidation of the new compound was carried out on the basis of extensive twodimensional 600 MHz NMR analyses, as well as high resolution-mass spectrometry and chemical degradation and derivatization. Moreover, we report herein the isolation of the hopanoid diploptene, stigmasterol, -sitosterol, ergost-5-en-3-ol, phytol, aspidinol, desaspidinol, vitamin E, neophytadiene, 1-(2,4,6-trihydroxyphenyl)-2-pentanone, and 6,10,14-trimethyl-2pentadecanone. In addition, we evaluated the alimentary and ovipositional response of Ceratitis capitata to the extracts and pure compounds of E. spathulatum. The new styrene glycoside produced severe disturbance in the ovipositional behavior of this pest insect.