Stagonolides J and K and Stagochromene A, Two New Natural Substituted Nonenolides and a New Disubstituted Chromene-4,5-dione Isolated from Stagonospora cirsiiS-47 Proposed for the Biocontrol of Sonchus arvensis

Autor: Dalinova, Anna, Dubovik, Vsevolod, Chisty, Leonid, Kochura, Dmitriy, Ivanov, Alexander, Smirnov, Sergey, Petrova, Maria, Zolotarev, Andrey, Evidente, Antonio, Berestetskiy, Alexander
Zdroj: Journal of Agricultural and Food Chemistry; November 2019, Vol. 67 Issue: 47 p13040-13050, 11p
Abstrakt: Two new natural 10-membered macrolides (1, 2) and one chromene-4,5-dione derivative (3), named stagonolides J and K and stagochromene A, respectively, were isolated from the phytopathogenic fungus Stagonospora cirsiiS-47, together with two known compounds, stagonolide A (4) and herbarumin I (5). Stagonolides J and K and stagochromene A were characterized as (5E,7R*,8S*,9R*)-7,8-dihydroxy-9-propyl-5-nonen-9-olide, (5E,7R,9S)-7-hydroxy-9-propyl-5-nonen-9-olide, and (2R*,3R*)-3-hydroxy-2-propyltetrahydro-2H-chromene-4,5(3H,4aH)-dione, respectively, by spectroscopic (mostly by NMR and ESIMS) data. Compounds 1–5showed different rates of phytotoxic activity on punctured leaf discs of Sonchus arvensis. The antimicrobial, cytotoxic, and antiprotozoal activity of isolated compounds was also evaluated. Based on our data, stagonolide K and herbarumin I can be proposed as a potential scaffold for the development of a new natural herbicide and estimated as possible selection/quality markers of a bioherbicide based on S. cirsii, while stagonolide A can be considered as a mycotoxin.
Databáze: Supplemental Index