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Perylenequinones act as broad-spectrum fungicides by generating reactive oxygen species both in the dark and in the light.

Natural perylenequinonoid pigments (PQPs) have long been known as excellent photosensitizers. Here it is reported that PQPs, when dispersed into a micellar system, are unexpectedly very effective in inhibiting the growth of various fungi in the dark and that light can enhance the activity further. In both cases, reactive oxygen species (ROS) play a crucial role. The unique ROS-based antifungal mechanism and the excellent physicochemical properties of PQPs promise the advent of a new generation of wide-spectrum agrofungicides.

Agrochemicals↗

Screening study of lead compounds for natural product-based fungicides: antifungal activity and biotransformation of 6alpha,7alpha-dihydroxy-beta-himachalene by Botrytis cinerea.

Eleven beta-himachalene derivatives were tested, using the poisoning food technique, for their potential antifungal activity against the phytopathogen Botrytis cinerea. Compounds 1-11 displayed moderate activity, whereas the 6,7-diol derivative (12) produced an inhibition of 91% after 6 days. The microbial transformation of 12 was investigated and yielded four new compounds hydroxylated at positions C-5 (13), C-2 (14), C-4 (15), and C-12 (16). The structures were established on the basis of their spectroscopic data including two-dimensional NMR analysis (HMQC, HMBC, nOesy) and nOes. The results obtained from biotransformation experiments shed further light on the detoxification mechanism of the phytopathogenic fungus against this compound and give an indication of the structural modifications that may be necessary if substrates of this type are to be further developed as selective fungal control agents for B. cinerea.

Benzoates↗