Isolation of a phytotoxic isocoumarin from Diaporthe eres‐infected Hedera helix (English ivy) and synthesis of its phytotoxic analogs

BACKGROUND

The fungus Diaporthe eres was isolated from a fungal pathogen‐infected leaf of Hedera helix (English ivy) exhibiting necrosis. It is hypothesized that the causative fungus produces phytotoxins as evidenced by necrotic lesions on the leaves.

RESULTS

The fungus was isolated and grown in Czapek Dox broth culture medium and potato dextrose broth culture medium and identified as Diaporthe eres. The ethyl acetate extracts of the culture broths were phytotoxic to lettuce (Lactuca sativa) and bentgrass (Agrostis stolonifera). 3,4‐Dihydro‐8‐hydroxy‐3,5‐dimethylisocoumarin ( 1 ) and tyrosol ( 2 ) were isolated and identified as the phytotoxic constituents. Six analogs of 3,4‐dihydro‐isocoumarin were synthesized and shown to be phytotoxic. The synthesized 3,4‐dihydro‐8‐hydroxy‐3,7‐dimethylisocoumarin and 3,4‐dihydro‐8‐hydroxy‐3,3,7‐trimethylisocoumarin were two‐ to three‐fold more phytotoxic than the naturally occurring 1 in a Lemna paucicostata growth bioassay.

CONCLUSION

Synthesis and herbicidal activities of the several new analogs of 1 are reported for the first time. These promising molecules should be used as templates for synthesis and testing of more analogs. © 2017 Society of Chemical Industry     

Pollen-style compatibility relations in natural populations of the wild diploid potato species Solanum spegazzinii Bitt.

Solanum spegazzinii Bitt., a wild diploid potato species endemic to Argentina, possesses resistance to adverse biotic and abiotic agents. Northwestern Argentinean populations grouped according to their morphological variability (G1 = localities East of the Calchaquí Valley, G2 = Calchaquí Valley and G3 = locality Belén) presented problems in seed set following controlled crosses. Thus, to evaluate if the morphological variability previously reported was sustained on a genetic basis, three introductions per group and five plants per introduction were used in controlled crosses (genotypic combinations). These were classified according to the number of seeds produced per fruit. Pollen-style compatibility relations were studied in those crosses that did not set seeds or that produced less than 30 seeds each. Within groups, G1 produced seeds normally, whereas hybridization barriers were found in 71.4% and 50.0% of the combinations within G2 and G3, respectively; on the other hand, from 46.7% to 73.3% of the combinations among groups exhibited similar barriers. Variability in the expression of the sites of pollen tube inhibition in the style was observed both within and among groups. Speculations are made on the possible hybrid origin of the populations. This revised version was published online in July 2006 with corrections to the Cover Date.