Phomachalasins A–D, 26-oxa[16] and [15]cytochalasans produced by Phoma exigua var. exigua, a potential mycoherbicide for Cirsium arvense biocontrol

Phoma exigua var. exigua, a fungal pathogen isolated from Cirsium arvense and Sonchus arvensis, proposed as a biocontrol agent of this noxious perennial weeds, produces in liquid and solid cultures different phytotoxic metabolites with potential herbicidal activity. The phytotoxic cytochalasins B, F, Z2, and Z3 and deoxaphomin were previously identified together with p-hydroxybenzaldehyde. Using spectroscopic methods, four new cytochalasins, termed phomachalasins A–D, were isolated and characterized as three new closely related 26-oxa[16] and one new [15]cytochalasans. They belong to a new subgroup of cytochalasans bearing a 1,2,3,4,6,7-hexasubstituted bicycle[3.2.0]heptene joined to the macrocyclic ring. None of the four new metabolites showed phytotoxic or antimicrobial activity. The lack of both phytotoxic and antimicrobial activities showed by all phomachalasins A–D was probably due to the strong modification of both functionalities and conformational freedom of the macrocyclic ring caused by its junction with the bulky and quite rigid new bicycle, namely bicycle[3.2.0]heptene