Hemisynthesis and absolute configuration of novel 6-pentyl-2H-pyran-2-one derivatives from Trichoderma spp.

Daoubi, Mourad; Pinedo-Rivilla, Cristina; Rubio, M. Belén; Hermosa, Rosa; Monte, Enrique; Aleu, Josefina; Collado, Isidro G.

doi:10.1016/j.tet.2009.04.051

Cited by 25 publications

(16 citation statements)

References 27 publications

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“…Finally, the planar structure of 2 was constructed as shown in Figure 1. Comparing the structure of 2 with that of one known compound, 6-[2 0 -propyloxiran-1-yl]-2H-pyran-2-one isolated from Trichoderma viride UCA 06 [14], we found that both compounds have the same 2-propyloxiran-1-yl moiety attached to C-6 position. Significantly, the absolute configuration of 2-propyloxiran-1-yl moiety in 6-[2 0 -propyloxiran-1-yl]-2H-pyran-2-one has been determined to be 1S, 2R through chemical synthesis of its stereoisomers.…”

Section: Resultsmentioning

confidence: 93%

Two new compounds from the plant endophytic fungus Pestalotiopsis versicolor

Yang

Huang

et al. 2014

Journal of Asian Natural Products Research

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A new coumarin, 4,6-dihydroxy-7-formyl-3-methylcoumarin (1), and an α-pyrone derivative, 6-[(7S,8R)-8-propyloxiran-1-yl]-4-methoxy-pyran-2-one (2), together with four known α-pyrone derivatives (3-6), were isolated from the broth extract of the plant endophytic fungus Pestalotiopsis versicolor. Their structures were elucidated by extensive spectroscopic analysis and by comparison of the chemical shift values with those of related known compounds.

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Section: Resultsmentioning

confidence: 93%

Two new compounds from the plant endophytic fungus Pestalotiopsis versicolor

Yang

Huang

et al. 2014

Journal of Asian Natural Products Research

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“…The transcription factor Thctf1 also regulates the biosynthesis of 6PP in T. harzianum. Chromatographic and spectroscopic analyses showed that Thctf1 null mutants did not produce two secondary metabolites derived from 6PP (6-[(1 R,2 S)dihydroxypentyl]-2H-pyran-2-one and 6-((1 S,2 R)-2propyloxiran-1-yl)-2H-pyran-2-one) and not previously described in the Trichoderma genus, that are present in wildtype culture filtrates [26,27].…”

Section: Pyronesmentioning

confidence: 84%

Trichoderma Secondary Metabolites Active on Plants and Fungal Pathogens

Vinale¹,

Sivasithamparam²,

Ghisalberti³

et al. 2014

TOMYCJ

230

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Beneficial microbes typically produce bioactive molecules that can affect the interactions of plants with their pathogens. Many secondary metabolites may also have antibiotic properties, which enable the producing microbe to inhibit and/or kill other microorganisms i.e. competing for a nutritional niche. Indeed, some of these compounds have been found to play an important role in the biocontrol of plant diseases by various beneficial microbes used worldwide for crop protection and bio-fertilization. In addition to direct toxic activity against plant pathogens, biocontrol-related metabolites may also increase disease resistance by triggering systemic plant defence activity, and/or enhance root and shoot growth. Fungi belonging to the Trichoderma genus are well known producers of secondary metabolites with a direct activity against phytopathogens and compounds that substantially affect the metabolism of the plant. The widescale application of selected metabolites to induce host resistance and/or to promote crop yield may become a reality in the near future and represents a powerful tool for the implementation of IPM strategies.

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“…Among all the compounds recorded in GC-MS Chromatography of hexane extracts of fungal endophytes 2H-pyran-2-one, 5,6-dihydro-6-pentyl, palmitic acid, methyl ester, oleic acid are reported to have antifungal activity [ 44 ], [ 45 ]. Therefore, in order to confirm the contributory effect of these compounds on the antifungal activity of hexane extracts of endophytic fungi, they were procured from commercial sources and their antifungal activity was evaluated against phytopathogens.…”

Section: Resultsmentioning

confidence: 99%

Fungal Endophyte Diversity and Bioactivity in the Indian Medicinal Plant Ocimum sanctum Linn

2015

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Endophytic mycopopulation isolated from India’s Queen of herbs Tulsi (Ocimum sanctum) were explored and investigated for their diversity and antiphytopathogenic activity against widespread plant pathogens Botrytis cinerea, Sclerotinia sclerotiorum, Rhizoctonia solani and Fusarium oxysporum. 90 fungal isolates, representing 17 genera were recovered from 313 disease-free and surface sterilised plant segments (leaf and stem tissues) from three different geographic locations (Delhi, Hyderabad and Mukteshwar) during distinct sampling times in consequent years 2010 and 2011 in India. Fungal endophytes were subjected to molecular identification based on rDNA ITS sequence analysis. Plant pathogens such as F. verticillioides, B. maydis, C. coarctatum, R. bataticola, Hypoxylon sp., Diaporthe phaseolorum, Alternaria tenuissima and A. alternata have occurred as endophyte only during second sampling (second sampling in 2011) in the present study. Bi-plot generated by principal component analysis suggested tissue specificity of certain fungal endophytes. Dendrogram revealed species abundance as a function of mean temperature of the location at the time of sampling. Shannon diversity in the first collection is highest in Hyderabad leaf tissues (H' = 1.907) whereas in second collection it was highest from leaf tissues of Delhi (H' = 1.846). Mukteshwar (altitude: 7500 feet) reported least isolation rate in second collection. Nearly 23% of the total fungal isolates were considered as potent biocontrol agent. Hexane extract of M. phaseolina recovered from Hyderabad in first collection demonstrated highest activity against S. sclerotiorum with IC50 value of 0.38 mg/ml. Additionally, its components 2H-pyran-2-one, 5,6-dihydro-6-pentyl and palmitic acid, methyl ester as reported by GC-MS Chromatogram upon evaluation for their antiphytopathogenic activity exhibited IC50 value of 1.002 and 0.662 against respectively S. sclerotiorum indicating their significant role in antiphytopathogenic activity of hexane extract. The production of 2H-pyran-2-one, 5,6-dihydro-6-pentyl from M. phaseolina, an endophytic fungus is being reported for the first time.

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Hemisynthesis and absolute configuration of novel 6-pentyl-2H-pyran-2-one derivatives from Trichoderma spp.

Cited by 25 publications

References 27 publications

Two new compounds from the plant endophytic fungus Pestalotiopsis versicolor

Two new compounds from the plant endophytic fungus Pestalotiopsis versicolor

Trichoderma Secondary Metabolites Active on Plants and Fungal Pathogens

Fungal Endophyte Diversity and Bioactivity in the Indian Medicinal Plant Ocimum sanctum Linn

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