Stagonospora cirsii is a pathogen of Cirsium arvense, causing necrotic lesions on leaves of this noxious weed. The fungus produced toxic metabolites when grown in liquid culture. A new phytotoxin, named stagonolide, was isolated and characterized as (8R,9R)-8-hydroxy-7-oxo-9-propyl-5-nonen-9-olide by spectroscopic methods. Stagonolide was shown to be a nonhost-specific but selective phytotoxin. Leaves of C. arvense were most sensitive and leaves of tomato and pepper (both Solanaceae) were less sensitive to stagonolide, which was assayed at 5 x 10(-3) M, than other plants. Stagonolide assayed at 5 x 10(-6) M was demonstrated to be a strong inhibitor of root growth in seedlings of C. arvense and some other Asteraceae species. Seedlings growth in wheat and radish was much less affected by the toxin, and seedlings of cucumber were insensitive to it.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/jf070742c | DOI Listing |
J Nat Prod
April 2024
All-Russian Institute of Plant Protection, Podbelskogo Street, 3, Pushkin, St. Petersburg 196608, Russian Federation.
Fungal 10-membered lactones (TMLs), such as stagonolide A, herbarumin I, pinolidoxin, and putaminoxin, are promising candidates for the development of nature-derived herbicides. The aim of this study was to analyze the structure-activity relationships (SAR) of C-9-methyl-substituted TMLs with a multitarget bioassay approach to reveal compounds with useful (phytotoxic, entomotoxic, antimicrobial) or undesirable (cytotoxic) bioactivities. A new TML, stagonolide L (), along with five known compounds (stagonolides D () and E (), curvulides A () and B/B (,), and pyrenolide C ()), were purified from cultures of the phytopathogenic fungus , and five semisynthetic derivatives of and (-) were obtained.
View Article and Find Full Text PDFToxins (Basel)
March 2023
Laboratory of Phytotoxicology and Biotechnology, All-Russian Institute of Plant Protection, Pushkin, 196608 Saint-Petersburg, Russia.
Phytotoxic macrolides attract attention as prototypes of new herbicides. However, their mechanisms of action (MOA) on plants have not yet been elucidated. This study addresses the effects of two ten-membered lactones, stagonolide A (STA) and herbarumin I (HBI) produced by the fungus , on , and .
View Article and Find Full Text PDFJ Fungi (Basel)
October 2021
All-Russian Institute of Plant Protection, Saint Petersburg 196608, Russia.
Ten-membered lactones (nonenolides) demonstrate phytotoxic, antimicrobial, and fungicidal activity promising for the development of natural product-derived pesticides. The fungus is able to produce phytotoxic stagonolides A (), J (), K () and herbarumin I () with high yield. The aim of this study was to create a set of structurally related nonenolides and to reveal the structural features that affect their biological activity.
View Article and Find Full Text PDFPlants (Basel)
November 2020
All-Russian Institute of Plant Protection, Podbelskogo St., 3, Pushkin, Saint-Petersburg 196608, Russia.
The use of many fungal phytotoxins as natural herbicides is still limited because they cannot penetrate leaf cuticle without injury and a little is known on their selectivity. In order to assess the herbicidal potential of phytotoxic 10-membered lactones (stagonolide A, stagonolide K, and herbarumin I), the selection of adjuvants, the evaluation of selectivity of the toxins and the efficacy of their formulations were performed. Among four adjuvants tested, Hasten™ (0.
View Article and Find Full Text PDFJ Agric Food Chem
November 2019
All-Russian Institute of Plant Protection, Russian Academy of Agricultural Sciences , Podbelskogo st., 3 , Pushkin , Saint-Petersburg 196608 , Russian Federation.
Two new natural 10-membered macrolides (, ) and one chromene-4,5-dione derivative (), named stagonolides J and K and stagochromene A, respectively, were isolated from the phytopathogenic fungus S-47, together with two known compounds, stagonolide A () and herbarumin I (). Stagonolides J and K and stagochromene A were characterized as (5,7*,8*,9*)-7,8-dihydroxy-9-propyl-5-nonen-9-olide, (5,7,9)-7-hydroxy-9-propyl-5-nonen-9-olide, and (2*,3*)-3-hydroxy-2-propyltetrahydro-2-chromene-4,5(3,4a)-dione, respectively, by spectroscopic (mostly by NMR and ESIMS) data. Compounds - showed different rates of phytotoxic activity on punctured leaf discs of .
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!