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Goondapyrones A-J: Polyketide α and γ Pyrone Anthelmintics from an Australian Soil-Derived Streptomyces sp.
- Source :
-
Antibiotics (Basel, Switzerland) [Antibiotics (Basel)] 2024 Oct 18; Vol. 13 (10). Date of Electronic Publication: 2024 Oct 18. - Publication Year :
- 2024
-
Abstract
- An investigation of ×19 soil samples collected under the auspices of the Australian citizen science initiative, Soils for Science, returned ×559 chemically dereplicated microbial isolates, of which ×54 exhibited noteworthy anthelmintic activity against either the heartworm Dirofilaria immitis microfilaria and/or the gastrointestinal parasite Haemonchus contortus L1-L3 larvae. Chemical (GNPS and UPLC-DAD) and cultivation (MATRIX) profiling prompted a detailed chemical investigation of Streptomyces sp. S4S-00196A10, which yielded new anthelmintic polyketide goondapyrones A-J ( 1 - 10 ), together with the known actinopyrones A ( 11 ) and C ( 12 ). Structures for 1 - 12 were assigned on the basis of detailed spectroscopic and chemical analysis, with preliminary structure activity relationship analysis revealing selected γ-pyrones >50-fold and >13-fold more potent than isomeric α-pyrones against D. immitis mf motility (e.g., EC <subscript>50</subscript> 0.05 μM for 1 ; EC <subscript>50</subscript> 2.7 μM for 5 ) and H. contortus L1-L3 larvae development (e.g., EC <subscript>50</subscript> 0.58 μM for 1 ; EC <subscript>50</subscript> 8.2 μM for 5 ), respectively.
Details
- Language :
- English
- ISSN :
- 2079-6382
- Volume :
- 13
- Issue :
- 10
- Database :
- MEDLINE
- Journal :
- Antibiotics (Basel, Switzerland)
- Publication Type :
- Academic Journal
- Accession number :
- 39452255
- Full Text :
- https://doi.org/10.3390/antibiotics13100989