Conjugation of antifungal benzoic acid derivatives as a path for detoxification in Penicillium brasilianum, an endophyte from Melia azedarach

Fill, Taícia Pacheco; Pallini, Heloisa Fassina; Din, Zia Ud; Jurberg, Igor D.; Silva, José Vinicius da; Rodrigues‐Filho, Edson

doi:10.1016/j.bioorg.2018.08.038

Cited by 9 publications

(4 citation statements)

References 21 publications

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“…[13] P. brasilianum is an endophytic fungus commonly found in plants such as Melia azedarach and rice. [16,17] Furthermore, several studies suggested that the endophyte P. brasilianum likens an enzyme factory, comprising polygalacturonases, cellulases, β-glucosidases and xylanolytic enzymes with biotechnological application potential. [18 -21] In this study, we found that the endophyte P. brasilianum can biotransform iridoid glycosides into other compounds.…”

Section: Resultsmentioning

confidence: 99%

Microbial Biotransformation of Iridoid Glycosides from Gentiana Rigescens by Penicillium Brasilianum

Liu

Han

et al. 2020

Chemistry & Biodiversity

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This study aimed to investigate the metabolic effects of endophytic fungi in Gentiana rigescens. From the 100 selected morphospecies, strain 7-2 (Penicillium brasilianum) showed a remarkable biocatalytic activity for gentiopicroside and swertiamarin, yielding seven products, including one new compound, 5-ethylidene-8hydroxy-4,5,6,8-tetrahydropyrano[3,4-c]pyran-1-one (M04), alongside six known compounds. Gentianine (M01) was the only metabolite of swertiamarin in this study, while the remaining ones were all gentiopicroside metabolites. Among these, five compounds: gentianine (M01), (5S,6S)-5-(hydroxymethyl)-6-methyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one (M02), (5R,6S)-5-(hydroxymethyl)-6-methyl-5,6-dihydro-1H,3H-pyrano[3,4-c] pyran-1-one (M03), 2-(3-formyl-2-oxo-3,6-dihydro-2H-pyran-4-yl)but-3-enoic acid (M06), and 2-oxo-4-(1-oxobut-3-en-2-yl)-3,6-dihydro-2H-pyran-3-carboxylic acid (M07) were similar to gentiopicroside metabolites in humans. Screening the metabolic potential of endophytic fungi in Gentiana rigescens provides an outstanding source for assessing the bioactive metabolites of iridoid glycosides. The above findings suggested that the endophytic fungi of G. rigescens possess multi-enzyme systems that mimic metabolic reactions in mammalian organisms.

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Section: Resultsmentioning

confidence: 99%

Microbial Biotransformation of Iridoid Glycosides from Gentiana Rigescens by Penicillium Brasilianum

Liu

Han

et al. 2020

Chemistry & Biodiversity

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“…nicotianae , especially HWJ3 with high inhibition efficiency, which was identified as Penicillium janthinellum . Previous studies showed that some endophytic Penicilllium species can produce various secondary metabolites, including taxol and benzoic acid derivatives, some of which have antibiotic, anticancer and/or cytotoxic activities (Jin et al 2013; El‐Batal et al, 2021; Fill et al, 2018; Mishra et al, 2012). Similarly, Chaetomium has a potential role in the biocontrol of many plant pathogens (Ramirez et al, 2018), and Aspergillus flavipes has been reported as a novel and efficient biocontrol agent of P. parasitica (El‐Sayed & Ali, 2020).…”

Section: Discussionmentioning

confidence: 99%

Diversity and importance of culturable endophytic fungi of tobacco (Nicotinana tabacum) cultivated in southwestern China

Wang

Sun

Ya-li

et al. 2022

Journal of Phytopathology

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Tobacco (Nicotiana tabacum) is one of the most important economic crops in China; however, black shank caused by Phytophthora parasitica is major threat to its cultivation. So far, little is known regarding potential antagonistic effects of endophytes on plant pathogens. A total of 109 culturable endophytic fungal strains were recovered from various tissues of six tobacco cultivars that are commonly cultivated in southwestern China. Morphological and molecular identification showed that these isolates belonged to 18 different genera, including Aspergillus, Chaetomium, Gibellulopsis and Penicillium as predominant genera, which were frequently observed in stem, leaf and root tissues. Among them, only 17 endophytic fungal strains exerted antagonistic effects on P. parasitica in the dual-culture test, and the highest inhibition rate of 73% was produced by a Penicillium janthinellum strain isolated from stem tissue of a cultivar HD. Nevertheless, a field trial revealed that Shannon-Wiener indices were negatively correlated with the disease index and with the incidence of tobacco blank shank in cultivars K326, YUN85, D101 and GUI1, which was further supported by the evaluation of endophytic community similarity. Our results contribute to the understanding of functions and diversity of endophytic fungi, and culturable endophytic fungal strains may be considered potential libraries for screening novel bioactive and effective metabolites to control P. parasitica in crops which requires further research.

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“…In addition, endophytic fungi can catalyze the synthesis of N -glycoside and amide bonds with high selectivity. For example, F. verticillioides from Zea mays catalyzed the formation of the N -glycosidic bond of carbamate to produce N -(2-hydroxyphenyl)-malonic acid with anticancer and antioxidant activity, and P. brasiliensis from Zea mays promoted the formation of an amide bond between halogenated benzoic acid and amino acid (Fill et al 2018 ; Schulz et al 2016 ). The most commercial potential of endophyte is highly regioselective oxidation to hydroxyl, carbonyl, and epoxy groups.…”

Section: Research Progress On the Biosynthesis Of Natural Products By Endophytic Fungimentioning

confidence: 99%

Biotransformation ability of endophytic fungi: from species evolution to industrial applications

Liu

Zhou

Cui

et al. 2021

Appl Microbiol Biotechnol

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Increased understanding of the interactions between endophytic fungi and plants has led to the discovery of a new generation of chemical compounds and processes between endophytic fungi and plants. Due to the long-term co-evolution between fungal endophytes and host plants, endophytes have evolved special biotransformation abilities, which can have critical consequences on plant metabolic processes and their composition. Biotransformation or bioconversion can impact the synthesis and decomposition of hormones, sugars, amino acids, vitamins, lipids, proteins, and various secondary metabolites, including flavonoids, polysaccharides, and terpenes. Endophytic fungi produce enzymes and various bioactive secondary metabolites with industrial value and can degrade or sequester inorganic and organic small molecules and macromolecules (e.g., toxins, pollutants, heavy metals). These fungi also have the ability to cause highly selective catalytic conversion of high-value compounds in an environmentally friendly manner, which can be important for the production/innovation of bioactive molecules, food and nutrition, agriculture, and environment. This work mainly summarized recent research progress in this field, providing a reference for further research and application of fungal endophytes. Key points •The industrial value of degradation of endophytes was summarized. • The commercial value for the pharmaceutical industry is reviewed. Graphical abstract

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Conjugation of antifungal benzoic acid derivatives as a path for detoxification in Penicillium brasilianum, an endophyte from Melia azedarach

Cited by 9 publications

References 21 publications

Microbial Biotransformation of Iridoid Glycosides from Gentiana Rigescens by Penicillium Brasilianum

Microbial Biotransformation of Iridoid Glycosides from Gentiana Rigescens by Penicillium Brasilianum

Diversity and importance of culturable endophytic fungi of tobacco (Nicotinana tabacum) cultivated in southwestern China

Biotransformation ability of endophytic fungi: from species evolution to industrial applications

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