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Biotransformation of the trichoderma metabolite 6-n-pentyl-2H-pyran-2-one (6PAP) by selected fungal isolates
1The Horticultural and Food Research Institute Ltd., Ruakura Research Centre, Private Bag 3123, Hamilton, New Zealand.
Abstract:
A variety of fungi were tested for their ability to transform the antifungal Trichoderma metabolite 6-n-pentyl-2H-pyran-2-one (6PAP) (1). Three Penicillium isolates, a Sclerotinia isolate, and a Fusarium isolate were all able to rapidly metabolize 1 and gave mixtures of isomers of monohydroxylated 1 and, in some cases, products resulting from further oxidation to carboxylic acids. Among these products were four previously unidentified metabolites (6, 7, 8, and 9) which were isolated and characterized by NMR spectroscopy. Sphaeropsis sapinea, Ophiostoma quercus, Ophiostoma piceae, a Verticillium sp., and two additional Fusarium isolates were unable to metabolize 1 efficiently.
Insights
Certain fungi can transform the antifungal compound 6-n-pentyl-2H-pyran-2-one (6PAP). Some Penicillium, Sclerotinia, and Fusarium isolates rapidly metabolized 6PAP, producing new hydroxylated and oxidized compounds, including four novel metabolites.
Area of Science:
- Mycology
- Natural Product Chemistry
- Biochemistry
Background:
- The antifungal metabolite 6-n-pentyl-2H-pyran-2-one (6PAP) is produced by Trichoderma fungi.
- Understanding the microbial transformation of natural products is crucial for discovering new bioactive compounds and biosynthetic pathways.
Purpose of the Study:
- To investigate the metabolic fate of 6PAP when exposed to various fungal species.
- To identify and characterize any new metabolites produced from 6PAP transformation.
Main Methods:
- Incubation of 6PAP with different fungal isolates.
- Isolation and purification of transformation products.
- Structure elucidation of novel metabolites using Nuclear Magnetic Resonance (NMR) spectroscopy.
Main Results:
- Three Penicillium, one Sclerotinia, and one Fusarium isolate efficiently metabolized 6PAP.
- Metabolism resulted in monohydroxylated isomers and further oxidized carboxylic acid derivatives.
- Four previously unidentified metabolites (compounds 6, 7, 8, and 9) were isolated and characterized.
- Other fungal isolates, including Sphaeropsis sapinea and Ophiostoma species, showed limited ability to metabolize 6PAP.
Conclusions:
- Specific fungal species possess enzymatic machinery capable of transforming 6PAP.
- The transformation pathways involve hydroxylation and oxidation, leading to novel chemical structures.
- This study expands the known metabolic diversity of 6PAP and highlights potential for discovering new bioactive fungal metabolites.