Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 67, Issue 47, Pages 13040-13050Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.9b04573
Keywords
macrolides; mycotoxin; bioherbicide; stagonolide; stagochromene
Funding
- Russian Science Foundation [16-16-00085]
- Department of Chemical Sciences, University of Naples Federicoo II, Naples, Italy
- Russian Science Foundation [19-16-11008] Funding Source: Russian Science Foundation
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Two new natural 10-membered macrolides (1, 2) and one chromene-4,S-dione derivative (3), named stagonolides J and K and stagochromene A, respectively, were isolated from the phytopathogenic fungus Stagonospora cirsii S-47, together with two known compounds, stagonolide A (4) and herbarumin I (5). Stagonolides J and K and stagochromene A were characterized as (SE,7R*,85*,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 1-5 showed 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.
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