Trichothioneic acid, a new antioxidant compound produced by the fungal strain Trichoderma virens FKI-7573

Miyano, Rei; Matsuo, Hirotaka; Mokudai, Takayuki; Noguchi, Yoshihiko; Higo, Mayuka; Nonaka, Kenichi; Niwano, Yoshimi; Sunazuka, Toshiaki; Shiomi, Kazuro; Takahashi, Yōko; Ōmura, Satoshi; Nakashima, Takuji

doi:10.1016/j.jbiosc.2019.11.007

Cited by 13 publications

(12 citation statements)

References 26 publications

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“…Chemical survey of T. virens FKI-7573 generated an undescribed N-containing compound, i.e., trichothioneic acid (134) (Figure 7) (Miyano et al, 2020). 134 contained a heptelidic acid and an L-ergothioneine substructure.…”

Section: Alkaloids and Other Nitrogen-containing Compoundsmentioning

confidence: 99%

“…Harzianoic acids 80 and 81 exerted potency to decrease the HCV RNA with EC 50 s of 24.5 and 20.4 µM, respectively (Li et al, 2019). Trichothioneic acid (134) showed OH radical-scavenging and singlet oxygen-quenching ability in a dose-dependent manner, which was equivalent to those of positive controls (Miyano et al, 2020). The activity of harzianic acid (140) as a plant growth promoter was evaluated (Vinale et al, 2013).…”

Section: Other Activitiesmentioning

confidence: 99%

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Trichoderma: A Treasure House of Structurally Diverse Secondary Metabolites With Medicinal Importance

Zhang

Tang²,

Huang

et al. 2021

Front. Microbiol.

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Fungi play an irreplaceable role in drug discovery in the course of human history, as they possess unique abilities to synthesize diverse specialized metabolites with significant medicinal potential. Trichoderma are well-studied filamentous fungi generally observed in nature, which are widely marketed as biocontrol agents. The secondary metabolites produced by Trichoderma have gained extensive attention since they possess attractive chemical structures with remarkable biological activities. A large number of metabolites have been isolated from Trichoderma species in recent years. A previous review by Reino et al. summarized 186 compounds isolated from Trichoderma as well as their biological activities up to 2008. To update the relevant list of reviews of secondary metabolites produced from Trichoderma sp., we provide a comprehensive overview in regard to the newly described metabolites of Trichoderma from the beginning of 2009 to the end of 2020, with emphasis on their chemistry and various bioactivities. A total of 203 compounds with considerable bioactivities are included in this review, which is worth expecting for the discovery of new drug leads and agrochemicals in the foreseeable future. Moreover, new strategies for discovering secondary metabolites of Trichoderma in recent years are also discussed herein.

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Section: Alkaloids and Other Nitrogen-containing Compoundsmentioning

confidence: 99%

Section: Other Activitiesmentioning

confidence: 99%

Trichoderma: A Treasure House of Structurally Diverse Secondary Metabolites With Medicinal Importance

Zhang

Tang²,

Huang

et al. 2021

Front. Microbiol.

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“…Fungi from this genus can produce a variety of structurally intriguing compounds, including terpenoids, polyphenols, pyrones, cyclopeptides, and polyketides ( Tchameni et al, 2020 ). Many of them showed various biological activities, including antimicrobial ( Shi et al, 2020 ), antimicroalgal ( Zou et al, 2021a ), antioxidant ( Miyano et al, 2020 ), antifouling ( Yu et al, 2021 ), anti-hepatitis C virus (HCV) ( Li B. et al, 2019 ), and cytotoxic activities ( Liu et al, 2020 ), implying the potential of Trichoderma species as a source of drugs for agricultural and/or human uses. Some Trichoderma species have been commercialized as agents to control phytopathogenic fungi or stimulate plant growth ( Morán-Diez et al, 2021 ; Zou et al, 2021b ).…”

Section: Introductionmentioning

confidence: 99%

β-Carboline Alkaloids From the Deep-Sea Fungus Trichoderma sp. MCCC 3A01244 as a New Type of Anti-pulmonary Fibrosis Agent That Inhibits TGF-β/Smad Signaling Pathway

Hao

Chen

et al. 2022

Front. Microbiol.

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Pulmonary fibrosis is a scarring disease of lung tissue, which seriously threatens human health. Treatment options are currently limited, and effective strategies are still lacking. In the present study, 25 compounds were isolated from the deep-sea fungus Trichoderma sp. MCCC 3A01244. Among them, two β-carboline alkaloids, trichocarbolines A (1) and C (4) are new compounds. The chemical structures of these compounds were elucidated based on their HRESIMS, 1D and 2D NMR spectra, optical rotation calculation, and comparisons with data reported in the literature. Trichocarboline B [(+)- and (–)-enantiomers] had previously been synthesized, and this is its first report as a natural product. Their anti-pulmonary fibrosis (PF) activity and cytotoxicity were investigated. Compounds 1, 11, and 13 strongly inhibited TGF-β1-induced total collagen accumulation and showed low cytotoxicity against the HFL1 cell line. Further studies revealed compound 1 inhibited extracellular matrix (ECM) deposition by downregulating the expression of protein fibronectin (FN), proliferating cell nuclear antigen (PCNA), and α-smooth muscle actin (α-SMA). Mechanistic study revealed that compound 1 decreased pulmonary fibrosis by inhibiting the TGF-β/Smad signaling pathway. As a newly identified β-carboline alkaloid, compound 1 may be used as a lead compound for developing more efficient anti-pulmonary fibrosis agents.

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“…For example, staurosporine, neoxaline, and pyrindicin were discovered using Dragendorff's reagent, which can be used to detect tertiary or quaternary amines [1][2][3][4][5]9,10]. Trichothioneic acid, which contains an ergothioneine moiety, was discovered by nitrogen rule screening [11]. By contrast, with the exception of ultrahigh resolution mass spectrometry [12,13], screening methods for sulfur compounds have not been reported.…”

Section: Introductionmentioning

confidence: 99%

Screening for Sulfur Compounds by Molybdenum-Catalyzed Oxidation Combined with Liquid Chromatography-Mass Spectrometry

et al. 2020

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The molybdenum (Mo)-catalyzed oxidation of sulfide under neutral conditions yields sulfone. This reaction proceeds more smoothly than olefin epoxidation and primary or secondary alcohol oxidation. In this study, Mo-catalyzed oxidation was used to screen for sulfur compounds (named “MoS-screening”) in microbial broths by liquid chromatography-mass spectrometry (LC/MS). To demonstrate proof-of-concept, known sulfur microbial compounds were successfully identified from a mixture of non-sulfur microbial compounds as sulfinyl or sulfonyl products of Mo-catalyzed oxidation. Then our MoS-screening method was used to screen 300 samples of microbial broth for sulfur compounds. One of the identified compounds was a kitasetaline-containing N-acetyl cysteine moiety produced by an actinomycete strain. These results demonstrate the potential of MoS-screening in the search for new sulfur compounds from microbial sources.

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Trichothioneic acid, a new antioxidant compound produced by the fungal strain Trichoderma virens FKI-7573

Cited by 13 publications

References 26 publications

Trichoderma: A Treasure House of Structurally Diverse Secondary Metabolites With Medicinal Importance

Trichoderma: A Treasure House of Structurally Diverse Secondary Metabolites With Medicinal Importance

β-Carboline Alkaloids From the Deep-Sea Fungus Trichoderma sp. MCCC 3A01244 as a New Type of Anti-pulmonary Fibrosis Agent That Inhibits TGF-β/Smad Signaling Pathway

Screening for Sulfur Compounds by Molybdenum-Catalyzed Oxidation Combined with Liquid Chromatography-Mass Spectrometry

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