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Christian Hertweck - One of the best experts on this subject based on the ideXlab platform.

  • Epicoccalone, a Coumarin‐Type Chymotrypsin Inhibitor, and Isobenzofuran Congeners from an Epicoccum sp. Associated with a Tree Fungus
    European Journal of Organic Chemistry, 2008
    Co-Authors: Hilaire V. Kemami Wangun, Keishi Ishida, Christian Hertweck
    Abstract:

    The bioactivity-guided fractionation of metabolites from an Epicoccum sp. isolated from the fruiting body of the tree fungus Pholiota squarrosa led to the discovery of a new inhibitor of the serine protease α-chymotrypsin. The structure of the active compound, epicoccalone (1), was fully elucidated by spectrometric and spectroscopic methods, revealing a coumarin ring system with an unprecedented substitution pattern. Two isobenzofuran-derived co-metabolites were identified that are remarkably similar to the epicoccalone coumarin core, strongly suggesting that these metabolites share the same orsellinic acid like polyketide pathway.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  • epicoccalone a coumarin type chymotrypsin inhibitor and isobenzofuran congeners from an Epicoccum sp associated with a tree fungus
    European Journal of Organic Chemistry, 2008
    Co-Authors: Hilaire Kemami V Wangun, Christian Hertweck, Keishi Ishida
    Abstract:

    The bioactivity-guided fractionation of metabolites from an Epicoccum sp. isolated from the fruiting body of the tree fungus Pholiota squarrosa led to the discovery of a new inhibitor of the serine protease α-chymotrypsin. The structure of the active compound, epicoccalone (1), was fully elucidated by spectrometric and spectroscopic methods, revealing a coumarin ring system with an unprecedented substitution pattern. Two isobenzofuran-derived co-metabolites were identified that are remarkably similar to the epicoccalone coumarin core, strongly suggesting that these metabolites share the same orsellinic acid like polyketide pathway.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  • epicoccamides b d glycosylated tetramic acid derivatives from an Epicoccum sp associated with the tree fungus pholiota squarrosa
    Journal of Natural Products, 2007
    Co-Authors: Hilaire Kemami V Wangun, Hansmartin Dahse, Christian Hertweck
    Abstract:

    Three new tetramic acid derivatives, epicoccamides B–D, together with the known epicoccamide, were isolated from an Epicoccum sp. associated with the tree fungus Pholiota squarrosa. The structures of the new compounds were elucidated on the basis of their physical data and chemical degradation. The epicoccamides differ in substitution pattern and in the size of the central carbon chain. The derivative with the longest chain, epicoccamide D, induces morphogenesis and pigment formation in surface cultures of the fungus Phoma destructiva at a concentration of 1.7 mM. Moreover, it exhibits weak to moderate cytotoxicity to HeLa cell lines (CC50 17.0 µM) and antiproliferative effects toward mouse fibroplast (L-929) and human leukemia cell lines (K-562) with growth inhibition (GI50) of 50.5 and 33.3 µM, respectively.

  • epicoccarines a b and epipyridone tetramic acids and pyridone alkaloids from an Epicoccum sp associated with the tree fungus pholiota squarrosa
    Organic and Biomolecular Chemistry, 2007
    Co-Authors: Hilaire Kemami V Wangun, Christian Hertweck
    Abstract:

    Investigation of the metabolic profile of a fungus (Epicoccum sp.) isolated from the fruiting body of the tree fungus Pholiota squarrosa led to the discovery of two novel tetramic acid derivatives, epicoccarine A (2) and B (3), as well as a new pyridone alkaloid, epipyridone (1), with an unusually cyclized side chain. It appears that 1 is biogenetically derived from the ring expansion of 2 followed by a proposed hetero-Diels–Alder reaction. 2 shows selective antibacterial activity against Gram positive bacteria, in particular Mycobacterium vaccae.

Dehai Li - One of the best experts on this subject based on the ideXlab platform.

Welington Luiz Araujo - One of the best experts on this subject based on the ideXlab platform.

  • the biotechnological potential of Epicoccum spp diversity of secondary metabolites
    Critical Reviews in Microbiology, 2018
    Co-Authors: Raissa Mesquita Braga, Gabriel Padilla, Welington Luiz Araujo
    Abstract:

    AbstractEpicoccum is a genus of ubiquitous fungi typically found in air, in soil, and on decaying vegetation. They also commonly display an endophytic lifestyle and are isolated from diverse plant ...

  • epicolactone natural product isolated from the sugarcane endophytic fungus Epicoccum nigrum
    European Journal of Organic Chemistry, 2012
    Co-Authors: Francisca Diana Da Silva Araujo, Leia Cecilia De Lima Favaro, Welington Luiz Araujo, Fabio L De Oliveira, Ricardo Aparicio, Anita J Marsaioli
    Abstract:

    The endophytic fungus Epicoccum nigrum was isolated from sugarcane and the bioguided fractionation of the ethyl acetate extract led to the isolation of epicolactone, mellein, and 4,5-dimethylresorcinol. Characterization of epicolactone by MS, NMR and X-ray crystallography revealed a new natural

  • Epicolactone – Natural Product Isolated from the Sugarcane Endophytic Fungus Epicoccum nigrum
    European Journal of Organic Chemistry, 2012
    Co-Authors: Francisca Diana Da Silva Araujo, Leia Cecilia De Lima Favaro, Welington Luiz Araujo, Fabio L De Oliveira, Ricardo Aparicio, Anita J Marsaioli
    Abstract:

    The endophytic fungus Epicoccum nigrum was isolated from sugarcane and the bioguided fractionation of the ethyl acetate extract led to the isolation of epicolactone, mellein, and 4,5-dimethylresorcinol. Characterization of epicolactone by MS, NMR and X-ray crystallography revealed a new natural

  • Epicoccum nigrum p16 a sugarcane endophyte produces antifungal compounds and induces root growth
    PLOS ONE, 2012
    Co-Authors: Leia Cecilia De Lima Favaro, Fernanda Luiza De Souza Sebastianes, Welington Luiz Araujo
    Abstract:

    Background Sugarcane is one of the most important crops in Brazil, mainly because of its use in biofuel production. Recent studies have sought to determine the role of sugarcane endophytic microbial diversity in microorganism-plant interactions, and their biotechnological potential. Epicoccum nigrum is an important sugarcane endophytic fungus that has been associated with the biological control of phytopathogens, and the production of secondary metabolites. In spite of several studies carried out to define the better conditions to use E. nigrum in different crops, little is known about the establishment of an endophytic interaction, and its potential effects on plant physiology.

  • polyphasic analysis of intraspecific diversity in Epicoccum nigrum warrants reclassification into separate species
    PLOS ONE, 2011
    Co-Authors: Leia Cecilia De Lima Favaro, Fernando L Melo, Carlos I Aguilarvildoso, Welington Luiz Araujo
    Abstract:

    Background Epicoccum nigrum Link (syn. E. purpurascens Ehrenb. ex Schlecht) is a saprophytic ascomycete distributed worldwide which colonizes a myriad of substrates. This fungus has been known as a biological control agent for plant pathogens and produces a variety of secondary metabolites with important biological activities as well as biotechnological application. E. nigrum produces darkly pigmented muriform conidia on short conidiophores on sporodochia and is a genotypically and phenotypically highly variable species. Since different isolates identified as E. nigrum have been evaluated as biological control agents and used for biocompound production, it is highly desirable that this species name refers to only one lineage. However, according to morphological and genetic variation, E. nigrum present two genotypes that may comprise more than one species. Methodology/Principal Findings We report the application of combined molecular (ITS and β-tubulin gene sequence analysis, PCR-RFLP and AFLP techniques), morphometric, physiological, genetic compatibility and recombination analysis to study the taxonomic relationships within an endophytic population that has been identified as E. nigrum. This combined analysis established two genotypes showing morphological, physiological and genetic divergence as well as genetic incompatibility characterized by colony inhibition, strongly indicating that these genotypes correspond to different species. Genotype 1 corresponds to E. nigrum while genotype 2 represents a new species, referred to in this study as Epicoccum sp. Conclusions/Significance This research contributes to the knowledge of the Epicoccum genus and asserts that the classification of E. nigrum as a single variable species should be reassessed. In fact, based on the polyphasic approach we suggest the occurrence of cryptic species within E. nigrum and also that many of the sequences deposited as E. nigrum in GenBank and culture collection of microbial strains should be reclassified, including the reference strain CBS 161.73 sequenced in this work. In addition, this study provides valuable tools for differentiation of Epicoccum species.

Wei Wang - One of the best experts on this subject based on the ideXlab platform.

Qianqun Gu - One of the best experts on this subject based on the ideXlab platform.