Antifungal Substances Against Pathogenic Fungi, Talaroconvolutins, from Talaromyces convolutus

Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan.
Journal of Natural Products (Impact Factor: 3.8). 07/2000; 63(6):768-72. DOI: 10.1021/np990371x
Source: PubMed


The dichloromethane extract of Talaromyces convolutus cultivated on barley exhibited antifungal activity against Candida albicans. In the course of a search for the active compounds, four new tetramic acid derivatives, talaroconvolutins A (1), B (2), C (3), and D (4), were isolated along with ZG-1494alpha (5), and mitorubrin derivatives. The structures of talaroconvolutins A-D (1-4) were established on the basis of spectroscopic and chemical investigations and chemical correlations. The antifungal activity of the talaroconvolutins against the pathogenic fungi Aspergillus fumigates, Aspergillus niger, C. albicans, and Cryptococcus neoformans was determined.

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    • "Several studies showed that Talaromyces species can be used in biological control against to plant pathogenic fungi because of their antagonist activity (Suzuki et al. 2000; Inglis and Kawchuk 2002; Duo-Chuan et al. 2005; Naraghi et al. 2010). Manoch and Dethoup (2011) showed that T. thailandensis provided the most effective inhibition against to Fusarium oxysporum, Colletotrichum capsici, Phytophthora palmivora and Lasiodiplodia theobromae. "
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    ABSTRACT: Two new Talaromyces species, T. thailandensis and T. tratensis, isolated from forest soil in Trat in Thailand are described. ITS barcodes were used to show the relationships between the newly described species and other Talaromyces taxa. b-tubulin and RPB1 sequences were used for the detailed analysis and the phylogenetic data showed that Talaromyces tratensis resolved in a clade closely related to T. rotundus, T. phialosporus and T. tardifaciens, which contain species that typically display restricted growth. Talaromyces thailandensis was resolved in different clades for each gene in a position closely related to T. macrosporus and T. flavus where they can be distinguished by length of stipe and shape of conidia.
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    • "The pyrrocidines were first reported from the fermentation broth of an unidentified species of Cylindrocarpon LL- Cyan426, isolated from a mixed douglas dir hardwood forest on Crane Island Preserve, Washington, in 1993 (He et al. 2002, Bigelis et al. 2003). The pyrrolidinone function has been reported in another antifungal compound , talaroconvolutin A produced by Talaromyces convolutus (Suzuki et al. 2000) along with four tetramic acid derivatives including ZG-1494, a compound first isolated from Penicillium rubrum (West et al. 1996). P. rubrum also produces rubratoxin B which interferes with cell wall synthesis and leads to hyphal deformation in many fungi (Reiss 1972). "
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    ABSTRACT: The maize endophyte Acremonium zeae is antagonistic to kernel rotting and mycotoxin producing fungi Aspergillus flavus and Fusarium verticillioides in cultural tests for antagonism, and interferes with A. flavus infection and aflatoxin contamination of preharvest maize kernels. Chemical studies of an organic extract from maize kernel fermentations of Acremonium zeae (NRRL 13540), which displayed significant antifungal activity against Aspergillus flavus and F. verticillioides, revealed that the metabolites accounting for this activity were two newly reported antibiotics pyrrocidines A and B. Pyrrocidines were detected in fermentation extracts for 12 NRRL cultures of Acremonium zeae isolated from maize kernels harvested in Illinois (4/4 cultures), North Carolina (5/5), Georgia (1/2) and unrecorded locations within the USA (2/2). Pyrrocidine B was detected by LCMSMS in whole symptomatic maize kernels removed at harvest from ears of a commercial hybrid that were wound-inoculated in the milk stage with A. zeae (NRRL 13540) or (NRRL 13541). The pyrrocidines were first reported from the fermentation broth of an unidentified filamentous fungus LL-Cyan426, isolated from a mixed Douglas Fir hardwood forest on Crane Island Preserve, Washington, in 1993. Pyrrocidine A exhibited potent activity against most Gram-positive bacteria, including drug-resistant strains, and was also active against the yeast Candida albicans. In an evaluation of cultural antagonism between 13 isolates of A. zeae in pairings with A. flavus (NRRL 6541) and F. verticillioides (NRRL 25457), A. zeae (NRRL 6415) and (NRRL 34556) produced the strongest reaction, inhibiting both organisms at a distance while continuing to grow through the resulting clear zone at an unchanged rate. Maximum colony diameters for A. zeae (NRRL 6415) and (NRRL 13540), on potato dextrose agar after 14 d, were attained within the range of 25-30 degrees C, with less growth recorded at 15 degrees and 37.5 degrees and no growth at 5 degrees. Potential interactions between A. zeae and other maize endophytes are considered and the significance of these interactions relative to the aflatoxin and fumonisin contamination of preharvest maize is presented. This is the first report of natural products from Acremonium zeae.
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    ABSTRACT: Pyrrocidines A (1) and B (2), two new antibiotics, containing rare 13-membered macrocycles, were isolated from the fermentation broth of a fungus, LL-Cyan426. Pyrrocidine A (1) exhibited potent activity against Gram-positive bacteria, including drug-resistant strains. The structures of these compounds were established using spectroscopic methods.
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