Annunziata Golino

Potential allelopathic interference of Melilotus neapolitana metabolites on three coexisting species of Mediterranean herbaceous plant community

Abstract This study is focused on the allelopathic interference of Melilotus neapolitana, an annual stenomediterranean species frequently occurring in the herbaceous plant community of the Mediterranean macchia, on three coexisting species of the Mediterranean herbaceous plant community. The ethereal and methanol extracts of the plant led to the isolation of 11 allelochemicals: coumarin, cis- and trans-melilotoside, the dihydromelilotoside, seven flavone glycosides, as well as the inactive β-sitosterol, a C13-norterpene glucoside and a polyphenol. All the structures have been elucidated on the basis of their spectroscopic features. The organic extracts and all the pure compounds have been assayed for their allelopathic activity on three coexisting species, Petrorhagia velutina, Dactylis hispanica, and Phleum subulatum. The cluster analysis has shown a clear structure-activity relationship, by evidencing four main groups of compounds with a specific effect patterns. Coumarin, the most abundant compound both in the plant extracts and soil, is found to be highly phytotoxic on all the tested species. As for the flavone glycosides, it is shown that aglycones play an important role due to their bioactivity.

Kaempferol glycosides from Lobularia maritima and their potential role in plant interactions.

Six kaempferol glycosides, four of them characterized for the first time, were isolated from the leaf extract of Lobularia maritima. The structural elucidation was performed by a combined approach using Electrospray-Ionization Triple-Quadrupole Mass-Spectrometric (ESI/TQ/MS) techniques, and 1D- and 2D-NMR experiments (1H, 13C, DEPT, DQ-COSY, TOCSY, ROESY, NOESY, HSQC, HMBC, and HSQC-TOCSY). The isolated kaempferol derivatives have different disaccharide substituents at C(3) and four of them have a rhamnose unit at C(7). To evaluate their potential allelopathic role within the herbaceous plant community, the compounds, as well as the aglycone obtained from enzymatic hydrolysis, have been tested in vitro on three coexisting plant species, Dactylis hispanica, Petrorhagia velutina, and Phleum subulatum. The results obtained allow us to hypothesize that the type of the sugar modulates the biological response. The bioassay data, analyzed by a multivariate approach, and grouping the compounds on the basis of the number of sugar units and the nature of carbohydrates present in the disaccharide moiety, indicate a structure-activity relationship.