Flavipin production by Epicoccum spp.

Bamford, P.; Norris, Grace; Ward, George E.

doi:10.1016/s0007-1536(61)80028-4

Cited by 61 publications

(30 citation statements)

References 8 publications

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“…Flavipin is produced by several Aspergillus and Epicoccum species as well as by Chaetomium globosum (Raistrick & Rudman, 1956;Bamford et al, 1961;Sekita et al, 1982). The compound is toxic to microorganisms, particularly to fungi (Raistrick & Rudman, 1956;Bamford et al, 1961;Baráthová et al, 1969;Burge et al, 1976;Brown et al, 1987;Mallea et al, 1991;Madrigal & Melgarejo, 1995), and was implicated as the mechanism responsible for the biocontrol of Monilinia laxa, a fungal plant pathogen, by Epicoccum nigrum (Madrigal et al, 1991). The effects against whole organisms other than fungi and bacteria are poorly studied except for a few reported bioassays on plants (Bamford et al, 1961;Burge et al, 1976).…”

Section: Discussionmentioning

confidence: 99%

“…The compound is toxic to microorganisms, particularly to fungi (Raistrick & Rudman, 1956;Bamford et al, 1961;Baráthová et al, 1969;Burge et al, 1976;Brown et al, 1987;Mallea et al, 1991;Madrigal & Melgarejo, 1995), and was implicated as the mechanism responsible for the biocontrol of Monilinia laxa, a fungal plant pathogen, by Epicoccum nigrum (Madrigal et al, 1991). The effects against whole organisms other than fungi and bacteria are poorly studied except for a few reported bioassays on plants (Bamford et al, 1961;Burge et al, 1976). Biochemically, avipin inhibits electron transport, oxidative phosphorylation and protein synthesis, possibly as a result of the aromatic orthodialdehyde functionality cross-linking lysine residues in the proteins of cytochrome C and mitochondrial membranes (White & Elliott, 1972Madrigal & Melgarejo, 1994).…”

Section: Discussionmentioning

confidence: 99%

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Isolation of flavipin, a fungus compound antagonistic to plant-parasitic nematodes

Nitao¹,

Meyer²,

Oliver³

et al. 2002

Nematol

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An isolate of the fungus Chaetomium globosum produced culture broths that inhibited in vitro egg hatch and juvenile mobility of root-knot nematode (Meloidogyne incognita) and hatch of soybean cyst nematode (Heterodera glycines). Extraction and bioassay-directed fractionation of the culture broth ltrate determined that avipin, a low molecular weight compound, was the fungus metabolite responsible for most of the nematode-antagonistic activity. Synthesis of avipin permitted evaluation of the compound as a suppressor of nematode populations on plants in glasshouse studies. Muskmelon (Cucumis melo) plants in steamed and unsteamed soil were inoculated with root-knot nematodes and various concentrations of avipin were applied to the soil. Contrary to expectations from the in vitro studies, the number of galls per g of roots increased with avipin treatment at the 14-day harvest. No effect of avipin on nematode populations was found at the 55-day harvest. In general, plant growth and nematode populations were greater in plants grown in steamed soil.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Isolation of flavipin, a fungus compound antagonistic to plant-parasitic nematodes

Nitao¹,

Meyer²,

Oliver³

et al. 2002

Nematol

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“…[7] Several heterocyclic derivatives of flavipin, such as epicoccine or epicoccone A and B, [8] as well as dimeric congeners, such as epicoccolides A and B or epicocconigrone A, have also been described. [9] Recently, Marsaioli and co-workers isolated epicolactone from Epicoccum nigrum, which dwells as an endophyte in sugarcane.…”

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confidence: 99%

Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin

2014

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Dibefurin is a Ci -symmetric natural product that acts as an inhibitor of calcineurin phosphatase. A six-step synthesis of this compound is reported, which features an oxidative dimerization of the aromatic polyketide epicoccine as the key step. Dibefurin is proposed to be related to epicolactone, a complex yet racemic fungal metabolite that has recently been discovered. Attempts to access epicolactone from epicoccine and epicoccone B resulted in an unusual dimer that is formed through a hetero-Diels-Alder reaction of a para-quinone methide with an ortho-quinone.

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“…3 E. nigrum is distributed worldwide, has been frequently isolated as an endophyte of plants, 4−6 and has been found to live in association with other organisms. 7−9 Previous chemical investigations of E. nigrum have yielded several bioactive secondary metabolites, including flavipin, 10 epicorazines A−C, 11−13 epicocconone, 9 epicolactone, 4 diketopiperazines, 5,7,8 and orevactaene. 6 Herein, we report the isolation, structure elucidation, and biological activities of new polyketide derivatives that show moderate to potent inhibition of protein kinases and histone deacetylases (HDAC) in vitro.…”

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confidence: 99%

Protein Kinase and HDAC Inhibitors from the Endophytic Fungus Epicoccum nigrum

et al. 2013

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A chemical investigation of the endophytic fungus Epicoccum nigrum isolated from leaves of Mentha suaveolens collected in Morocco resulted in the isolation of five new polyketides, epicocconigrones A and B (1 and 2), 3-methoxyepicoccone B (3), 3-methoxyepicoccone (4), and 2,3,4-trihydroxy-6-(methoxymethyl)-5-methylbenzaldehyde (5), together with five known compounds (6-10). The structures of the new compounds were unambiguously determined by extensive analysis of the 1D and 2D NMR and mass spectroscopic data. Compounds 1 and 10 showed potent inhibition of at least 15 protein kinases with IC50 values ranging from 0.07 to 9.00 μM. Moreover, compounds 1 and 10 inhibited histone deacetylase (HDAC) activities with IC50 values of 9.8 and 14.2 μM, respectively. A preliminary structure-activity relationship is discussed. Interestingly, compounds 1 and 10 exert mainly cytostatic effects in human lymphoma RAJI and U-937 cell lines.

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Flavipin production by Epicoccum spp.

Cited by 61 publications

References 8 publications

Isolation of flavipin, a fungus compound antagonistic to plant-parasitic nematodes

Isolation of flavipin, a fungus compound antagonistic to plant-parasitic nematodes

Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin

Protein Kinase and HDAC Inhibitors from the Endophytic Fungus Epicoccum nigrum

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