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Structure-Activity Relationships of Natural C-9-Methyl-Substituted 10-Membered Lactones and Their Semisynthetic Derivatives.
- Source :
-
Journal of natural products [J Nat Prod] 2024 Apr 26; Vol. 87 (4), pp. 914-923. Date of Electronic Publication: 2024 Apr 08. - Publication Year :
- 2024
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Abstract
- 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 ( 1 ), along with five known compounds (stagonolides D ( 2 ) and E ( 3 ), curvulides A ( 4 ) and B <subscript>1</subscript> /B <subscript>2</subscript> ( 5a , b ), and pyrenolide C ( 6 )), were purified from cultures of the phytopathogenic fungus Stagonospora cirsii , and five semisynthetic derivatives of 3 and 4 ( 7 - 11 ) were obtained. The absolute configuration of 4 was revised to 2 Z , 4 S , 5 S , 6 R , and 9 R. The identity of 5a , b and stagonolide H is discussed. The phytotoxicity of compound 4 , the entomotoxicity of 5a , b , and nonselective toxicity of compound 6 are demonstrated. The latter confirms the hypothesis that the α,β-unsaturated carbonyl group is associated with the high general toxicity of TML, regardless of its position in the ring and other substituents. The epoxide in compound 4 is important for phytotoxicity. The revealed SAR patterns will be useful for further rational design of TML-based herbicides including curvulide A analogs with a 4,5-epoxy group.
Details
- Language :
- English
- ISSN :
- 1520-6025
- Volume :
- 87
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 38587866
- Full Text :
- https://doi.org/10.1021/acs.jnatprod.3c01216