Chemical Basis for the Phytotoxicity of Indoles in Relation to the Allelopathy of Cereals

Abstract

Phytotoxic activity of an indole series substituted with electron-acceptor and electron-donor groups in the aromatic ring was determined. They are potential decomposition products, of natural indole alkaloids in cereals plants with allelopathic properties. Phytotoxic selectivity was evaluated from antialgal activity against the microalga Chlorella vulgaris, seed germination seeds and biomass weight of seedling of barley, rye, wheat, oat and maize species and the weed Lolium rigidum. Lipophilia character of the compounds was determined by RP-HPLC method. Both, the electronic character of the substituents, evaluated from σ p parameter, and the lipophilia character of the molecules measured from logP HPLC parameter, are involved in the phytotoxic activity. The three bio indicators has shown that the compounds with the higher electron-acceptor groups showed the higher level of phytotoxicity and the molecules with electron-donor groups showed the lowest activity, although, in some cases, this behavior is modified by the lipophilic properties of the molecules. These results are rationalized in terms of polarization of N-H bond of heterocyclic ring. Compounds with the higher logP HPLC values showed the higher phytotoxic activity. Further evidence on the role of lipophilicity was obtained from linear regression between the average inhibitions percentages of biomass and logP HPLC values. The activity increased linearly by increasing the lipophilic character of the compounds. Therefore, quantitative effects in the phytotoxic activity of the electronic properties of the substituents in the aromatic ring and lipophilic character of the indoles can be inferred from σ p and logP HPLC parameters, respectively. The results strongly suggest that the potential decomposition products of the natural indole alkaloids from cereals or other natural sources may be in connection with the allelopathic phenomenon of plants when are released into the soil.

Dynamic of Indole Alkaloids in a Soil and Its Relationships With Allelopathic Properties

“…With the K ' values found for each compound, the LogPHPLC values were calculated, which are shown in the table 5, in addition, the values for Gramine and Indole previously determined are included [45]. The lipophilic values fluctuated between 1.3 and 2.1.…”