Trichoderma koningii produces a pyrone compound with antibiotic properties

Simón, A.; Dunlop, Robert W.; Ghisalberti, Emilio L.; Sivasithamparam, Krishnapillai

doi:10.1016/0038-0717(88)90050-8

Cited by 98 publications

(49 citation statements)

References 4 publications

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“…6-PAP was detected in the headspace of all T. atroviride and T. viridescens isolates, as well as in individual cultures of T. citrinoviride (4 isolates), T. hamatum (8 isolates), and T. viride (3 isolates). Previously, these compounds had been described as being produced by T. viride (Collins and Halim 1972;Bonnarme et al 1997), T. harzianum (Claydon et al 1987;Serrano-Carreon et al 1992;Scarselletti and Faull 1994;Bonnarme et al 1997;Whitaker et al 1998;El-Hasan et al 2007, Souza Ramos et al 2008Vinale et al 2008;Siddiquee et al 2012), T. koningii (Cutler et al 1986;Simon et al 1988), and T. atroviride (Reithner et al 2005(Reithner et al , 2007Stoppacher et al 2010;Polizzi et al 2011).…”

Section: Discussionmentioning

confidence: 99%

“…6-PAP and other α-pyrone analogs have been detected in cultures of several Trichoderma strains, such as T. viride (Collins and Halim 1972), T. harzianum (Claydon et al 1987;Bonnarme et al 1997), T. koningii (Simon et al 1988), and T. atroviride (Reithner et al 2005(Reithner et al , 2007. However, it should be noted that the identification of most of these strains was based only on morphological characters, which are known to be prone to misidentification.…”

Section: Introductionmentioning

confidence: 99%

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Formation of 6-n-pentyl-2H-pyran-2-one (6-PAP) and other volatiles by different Trichoderma species

et al. 2013

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Formation of 6-n-pentyl-2H-pyran-2-one (6-PAP) and other volatiles by different Trichoderma species

et al. 2013

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“…Compound 14 was first identified by Collins and Halim (1972) in the culture broth of T. viride. Since then, it has been obtained from T. harzianum (Claydon et al 1987) and T. koningii (Simon et al 1988 growth reduction in R. solani and a 31.7% reduction in F. oxysporum after 2 days. When used in spore germination tests, 0.45 mg/ml was found to completely inhibit the germination of Fusarium spores.…”

Section: Simple Pyronesmentioning

confidence: 99%

Secondary metabolites from species of the biocontrol agent Trichoderma

et al. 2007

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Trichoderma species are free-living fungi that are highly interactive in root, soil and foliar environments and have been used successfully in field trials to control many crop pathogens. Structural and biological studies of the metabolites isolated from Trichoderma species are reviewed. This review, encompassing all the literature in this field up to the present and in which 269 references are cited, also includes a detailed study of the biological activity of the metabolites, especially the role of these metabolites in biological control mechanisms. Some aspects of the biosynthesis of these metabolites and related compounds are likewise discussed.

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“…The anti-tyrosinase active component of two strains (MFA581 and 898) was purified by assay-guided isolation to yield the known kojic acid. 5,6) In a continuing study on the anti-tyrosinase active fungal strain (MFA58), we found 6-n-pentyl-a-pyrone (1), 7) trichodenone A (2), 8) cyclonerodiol (3), 9) and cyclopentenones designated as myrothenones A (4) and B (5) produced by the marine-derived fungus Myrothecium sp. In this paper, the structure determination of 4 and 5 and tyrosinase inhibitory activity of 1 and 4 are reported.…”

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confidence: 99%

Myrothenones A and B, Cyclopentenone Derivatives with Tyrosinase Inhibitory Activity from the Marine-Derived Fungus Myrothecium sp.

Kim

Lee

et al. 2005

Chem. Pharm. Bull.

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New 3-amino-5-ethenylcyclopentenones, myrothenones A (4) and B (5), were isolated together with known 6-n-pentyl-a a-pyrone (1), trichodenone A (2), and cyclonerodiol (3) from the marine algicolous fungus of genus of Myrothecium. The structure and absolute stereochemistry of the new compounds were established by spectral interpretation and X-ray analysis. Compounds 1 and 4 exhibited a tyrosinase inhibitory activity with IC 50 value of 0.8 and 6.6 m mM, respectively, which are more active than kojic acid (IC 50 , 7.7 m mM) currently being used as a functional personal-care compound.Key words marine-derived fungus; Myrothecium sp.; myrothenone; 6-npentyl-a-pyrone; trichodenone A; tyrosinase inhibitory activity Marine microorganisms such as bacteria and fungi inhabit virtually any environment in the sea, and they are the source of greatest diversity in the sea.1,2) The source of increasing interests, these microbes have been shown to produce novel substances with utilities in fine chemicals, drugs and cosmetics, and functional personal-care products. 3)Tyrosinase is known as a key enzyme implicated in the metabolism of melanin in melanocytes, and it is involved in skin-coloring and local hyperpigmentation such as melasma, ephelis, and lentigo. 4)Therefore, the anti-tyrosinase active compounds have been of great concern as functional personal-care products for skin-whitening effects and for preventive and therapeutic effects on the local hyperpigmentation diseases.In our screening aimed at identifying tyrosinase inhibitors of microbial origin, we investigated tyrosinase inhibiting activity from the fungal extracts, and a significant activity was observed in three strains (MFA58, 581 and 898). The anti-tyrosinase active component of two strains (MFA581 and 898) was purified by assay-guided isolation to yield the known kojic acid. 5,6) In a continuing study on the anti-tyrosinase active fungal strain (MFA58), we found 6-n-pentyl-a-pyrone (1), 7) trichodenone A (2), 8) cyclonerodiol (3), 9) and cyclopentenones designated as myrothenones A (4) and B (5) produced by the marine-derived fungus Myrothecium sp. In this paper, the structure determination of 4 and 5 and tyrosinase inhibitory activity of 1 and 4 are reported.The fungal strain (stock #, MFA58) was isolated from the surface of the marine green alga Enteromorpha compressa collected at Baegunpo, Busan in 2002. The fungus, identified to be an Myrothecium sp. by fatty acid methyl ester analysis, 10) was cultured (10 l) in a seawater-based medium.11) The filtered broth was extracted with EtOAc to afford crude extracts (0.8 g). The extract revealed a significant anti-tyrosinase activity, and it was separated by assay-guided fractionation using repeated silica gel flash chromatography (n-hexane in ethyl acetate) and HPLC (ODS-A, MeOH-H 2 Oϭ5 : 1) to yield compounds 1 (150 mg), 2 (3.5 mg), 3 (17.0 mg), 4 (8.0 mg), and 5 (8.5 mg).Myrothenone B (5) 12) was isolated as a colorless oil, which was analyzed for C 7 H 9 NO 2 (4 unsaturations) by HR-FAB-MS and 13 C-NMR methods. ...

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Trichoderma koningii produces a pyrone compound with antibiotic properties

Cited by 98 publications

References 4 publications

Formation of 6-n-pentyl-2H-pyran-2-one (6-PAP) and other volatiles by different Trichoderma species

Formation of 6-n-pentyl-2H-pyran-2-one (6-PAP) and other volatiles by different Trichoderma species

Secondary metabolites from species of the biocontrol agent Trichoderma

Myrothenones A and B, Cyclopentenone Derivatives with Tyrosinase Inhibitory Activity from the Marine-Derived Fungus Myrothecium sp.

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