Antimicrobial polyketides from Trichoderma koningiopsis QA-3, an endophytic fungus obtained from the medicinal plant Artemisia argyi

Shi, Xiaoshan; Wang, Dun‐Jia; Li, Xiaoming; Li, Honglei; Meng, Ling‐Hong; Li, Xin; Pi, Yan; Zhou, Xin; Wang, Bin‐Gui

doi:10.1039/c7ra11122c

Cited by 34 publications

(19 citation statements)

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“…Similar to Penicillium, Trichoderma species also produce many bioactive secondary metabolites, such as polyketides, terpenoids, alkaloid, butenolides, etc [20]. As such, some novel compounds were isolated from a few endophytic Trichoderma species associated with the host plants, and demonstrated a wide range of bioactivities including cytotoxic [21], anti-inflammatory [22], antibacterial [23], and antifungal activities [24,25]. Pu et al reported that a T. atroviride strain isolated from Camptotheca acuminate could independently produce camptothecin in the fermentation process, with yields of 197.8 μg/l [26].…”

Section: Discussionmentioning

confidence: 99%

Bioprospecting of Novel and Bioactive Metabolites from Endophytic Fungi Isolated from Rubber Tree Ficus elastica Leaves

Ding¹,

Tao²,

Wang³

et al. 2019

Journal of Microbiology and Biotechnology

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Endophytic fungi are an important component of plant microbiota, and have the excellent capacity for producing a broad variety of bioactive metabolites. These bioactive metabolites not only affect the survival of the host plant, but also provide valuable lead compounds for novel drug discovery. In this study, forty-two endophytic filamentous fungi were isolated from Ficus elastica leaves, and further identified as seven individual taxa by ITS-rDNA sequencing. The antimicrobial activity of these endophytic fungi was evaluated against five pathogenic microorganisms. Two strains, Fes1711 (Penicillium funiculosum) and Fes1712 (Trichoderma harzianum), displayed broad-spectrum bioactivities. Our following study emphasizes the isolation, identification and bioactivity testing of chemical metabolites produced by T. harzianum Fes1712. Two new isocoumarin derivatives (1 and 2), together with three known compounds (3-5) were isolated, and their structures were elucidated using NMR and MS. Compounds 1 and 2 exhibited inhibitory activity against Escherichia coli. Our findings reveal that endophytic fungi from the rubber tree F. elastica leaves exhibit unique characteristics and are potential producers of novel natural bioactive products.

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Section: Discussionmentioning

confidence: 99%

Bioprospecting of Novel and Bioactive Metabolites from Endophytic Fungi Isolated from Rubber Tree Ficus elastica Leaves

Ding¹,

Tao²,

Wang³

et al. 2019

Journal of Microbiology and Biotechnology

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“…In the NOESY experiment, NOEs from H‐4 to H‐9 and H 3 ‐17 and from H‐8 α to H‐2 α and H‐9 indicated the cofacial orientation of these groups ( Figure 4), while correlation from H‐7 to H‐8 β placed these protons on the other side of the molecule. Based on the octant rule for the cyclohexenones, [22–24] the positive Cotton effect (CE) at 310 nm in the ECD spectrum of 2 ( Figure 5) determined the absolute configuration at C‐4 as ( S ), and the positive CEs around 256 and 224 nm assigned the absolute configuration as (7 R ,9 S ,10 S ). Therefore, compound 2 was an epimer at C‐4 of 7‐ O ‐methylkoninginin D and named as 4‐ epi ‐7‐ O ‐methylkoninginin D. Compound 2 could be clearly detected in the HPLC profile ( Figure S38 ) of the initial AcOEt extract of the fungus (without touching of MeOH during extraction procedures) and thus supporting that this compound is not an artifact.…”

Section: Resultsmentioning

confidence: 99%

Polyketides and Terpenoids with Potent Antibacterial Activities from theArtemisia argyi‐Derived FungusTrichoderma koningiopsisQA‐3

Shi¹,

Meng²,

Li³

et al. 2020

Chemistry & Biodiversity

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The AcOEt extract of Artemisia argyi-derived fungus Trichoderma koningiopsis QA-3 showed potent inhibitory activity against pathogenic bacteria. Fractionation of the extract resulted in the isolation of three new polyketides (1-3) and two new terpenoids (4 and 5), together with three known metabolites (6-8). Their chemical structures were analyzed by NMR spectra, ECD, HR-ESI-MS or HR-EI-MS, optical rotation, and X-ray crystallographic data, as well as by comparison with literature reports. In the antibacterial assays, 3hydroxyharziandione (4) showed potent activity against human pathogen Escherichia coli with an MIC value of 0.5 μg/mL, while 6-(3-hydroxypent-1-en-1-yl)-2H-pyran-2-one exhibited strong activity against marine-derived aquatic pathogen Micrococcus luteus with an MIC value of 1.0 μg/mL.

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“…Therefore, it is of paramount importance to accurately identify any mycotoxins that might be produced by a fungal species that is to be used as BCA to ensure they are not capable of producing (types/amounts or both) of harmful mycotoxins during the biocontrol process. Several polyketides have been shown to display antimicrobial activities against agro-pathogenic fungi (Shi et al., 2017). Polyketides have been linked to other roles in fungi, including virulence, abiotic stress resistance and conidia pigmentation (Beltrán-García et al., 2014; Yao et al., 2016).…”

Section: Resultsmentioning

confidence: 99%

Effects of ultraviolet irradiation on the in vitro antagonistic potential of Trichoderma spp. against soil-borne fungal pathogens

Alfiky

2019

Heliyon

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Development of new effective biocontrol agents is largely based on the antagonistic capacity of candidate agents against targeted pathogens in vitro . Different mechanisms contribute to such capacity, including the activity of cell wall-degrading enzymes, secretion of antimicrobial secondary metabolites, growth vigour and resistance to exogenous and endogenous toxins. In this study, a series of laboratory experiments were designed to improve the antagonistic activities of Trichoderma spp. against two plant fungal pathogens, Sclerotium rolfsii and Rhizoctonia solani . A simple but efficient mutagenesis programme was carried out using ultraviolet light to induce modifications in the genetic structure of two Trichoderma biocontrol agents, T. virens and T. asperellum . The obtained mutants were subjected to a) initial screening for media-permeable antifungal metabolites using the cellophane membrane-based method, and b) selected mutants were subjected to a series of antagonistic tests. Results revealed that the antagonistic potential of selected mutants was significantly improved against the two plant pathogens. Genetic stability test results indicated that the UV-derived mutant Tv3, maintained its elevated performance after 12 rounds of sub-culture. Gene expression analysis for five antagonism-associated genes were examined using real-Time PCR. Results revealed that the gene expression of two genes, chitinase 33, a cell wall degrading enzyme and, polyketide synthase, which is responsible for polyketide biosynthesis, a class of secondary metabolites with antimicrobial roles, were significantly upregulated in one of the mutated T. virens strains. Results of our in vitro antagonistic studies along with our molecular analysis indicate that the UV mutagenesis could be an effective strategy to improve Trichoderma antagonistic potential.

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Antimicrobial polyketides from Trichoderma koningiopsis QA-3, an endophytic fungus obtained from the medicinal plant Artemisia argyi

Abstract: Five new and two known antimicrobial polyketides were identified from endophytic Trichoderma koningiopsis QA-3.

Cited by 34 publications

References 30 publications

Bioprospecting of Novel and Bioactive Metabolites from Endophytic Fungi Isolated from Rubber Tree Ficus elastica Leaves

Bioprospecting of Novel and Bioactive Metabolites from Endophytic Fungi Isolated from Rubber Tree Ficus elastica Leaves

Polyketides and Terpenoids with Potent Antibacterial Activities from theArtemisia argyi‐Derived FungusTrichoderma koningiopsisQA‐3

Effects of ultraviolet irradiation on the in vitro antagonistic potential of Trichoderma spp. against soil-borne fungal pathogens

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