Structure determination of two new trichothecenes from a halotolerant fungus <i>Myrothecium</i> sp. GS‐17 by NMR spectroscopy

Zhang, Songya; Li, Zhan‐Lin; Guan, Liping; Wu, Xin; Pan, Huaqi; Bai, Jiao; Hua, Hui‐Ming

doi:10.1002/mrc.3845

Cited by 15 publications

(10 citation statements)

References 29 publications

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“…The EtOAc extract was separated on silica gel and ODS open-column chromatography, and then subjected to semi-preparative HPLC to yield compound 1 . As shown in Figure 1, the structure of compound 1 was confirmed as verrucarin A ( 1 ) through NMR and MS spectra analyses, and comparison with published literature data [12,13].…”

Section: Resultssupporting

confidence: 58%

Inhibitory Effects of Verrucarin A on Tunicamycin-Induced ER Stress in FaO Rat Liver Cells

et al. 2015

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Endoplasmic reticulum (ER) stress is linked with development and maintenance of cancer, and serves as a therapeutic target for treatment of cancer. Verrucarin A, isolated from the broth of Fusarium sp. F060190, showed potential inhibitory activity on tunicamycin-induced ER stress in FaO rat liver cells. In addition, the compound decreased tunicamycin-induced GRP78 promoter activity in a dose dependent manner without inducing significant inhibition of luciferase activity and cell growth for 6 and 12 h. Moreover, the compound decreased the expression of GRP78, CHOP, XBP-1, and suppressed XBP-1, and reduced phosphorylation of IRE1α in FaO rat liver cells. This evidence suggests for the first time that verrucarin A inhibited tunicamycin-induced ER stress in FaO rat liver cells.

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Section: Resultssupporting

confidence: 58%

Inhibitory Effects of Verrucarin A on Tunicamycin-Induced ER Stress in FaO Rat Liver Cells

et al. 2015

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“…The crude extract of this fungus was shown to exhibit strong growth inhibitory activity against human leukemia (HL‐60) cell line. Many different bioactive secondary metabolites such as trichothecenes, amides, polyketides, sterols, and lactones, those compounds were isolated from this strain . During the following research, we found a new glycosylated polyketide, named myrothecoside.…”

Section: Introductionmentioning

confidence: 85%

Myrothecoside, a Novel Glycosylated Polyketide from the Terrestrial FungusMyrotheciumsp. GS-17

et al. 2016

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Based on the chemical analysis and targeted bioactivity screening, a new polyketide glycoside, myrothecoside, was isolated from a terrestrial halotolerant fungus, Myrothecium sp. GS‐17. The structure of myrothecoside was elucidated on the basis of extensive spectroscopic analysis including 1D‐ and 2D‐NMR (1H,1H‐COSY, HSQC, HMBC, and NOESY) experiments, combined with mass spectroscopic data and physicochemical properties. This compound exhibited weak cytotoxicity against human leukemia (HL‐60) cancer cell with an IG50 value of 63.61 μm, and also antifungal activities against plant pathogenic fungi Rhizoctonia solani and Fusarium oxysporum using standard agar diffusion tests at 20 μg/disk.

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“…Verrucarin Z ( 2 ) showed a similar activity against Mucor miehei at a concentration of 50 μg/disk when compared with the positive drug nystatin [ 42 ]. The 8a-hydroxyroridin H ( 4 ) and myrothecin A ( 19 ) exhibited bioactivities against plant pathogenic fungi Rhizoctonia solani and Fusarium oxysporum [ 49 ]. Manami et al suggested that the C-12-epoxide of trichothecene was essential for the antifungal activity against Cochliobolus miyabeanus [ 61 ].…”

Section: Biological Activities Of Macrocyclic Trichothecenesmentioning

confidence: 99%

Recent Advances on Macrocyclic Trichothecenes, Their Bioactivities and Biosynthetic Pathway

Zhu

Cen

et al. 2020

Toxins

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Macrocyclic trichothecenes are an important group of trichothecenes bearing a large ring. Despite the fact that many of trichothecenes are of concern in agriculture, food contamination, health care and building protection, the macrocyclic ones are becoming the research hotspot because of their diversity in structure and biologic activity. Several researchers have declared that macrocyclic trichothecenes have great potential to be developed as antitumor agents, due to the plenty of their compounds and bioactivities. In this review we summarize the newly discovered macrocyclic trichothecenes and their bioactivities over the last decade, as well as identifications of genes tri17 and tri18 involved in the trichothecene biosynthesis and putative biosynthetic pathway. According to the search results in database and phylogenetic trees generated in the review, the species of the genera Podostroma and Monosporascus would probably be great sources for producing macrocyclic trichothecenes. Moreover, we propose that the macrocyclic trichothecene roridin E could be formed via acylation or esterification of the long side chain linked with C-4 to the hydroxyl group at C-15, and vice versa. More assays and evidences are needed to support this hypothesis, which would promote the verification of the proposed pathway.

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Structure determination of two new trichothecenes from a halotolerant fungus Myrothecium sp. GS‐17 by NMR spectroscopy

Cited by 15 publications

References 29 publications

Inhibitory Effects of Verrucarin A on Tunicamycin-Induced ER Stress in FaO Rat Liver Cells

Inhibitory Effects of Verrucarin A on Tunicamycin-Induced ER Stress in FaO Rat Liver Cells

Myrothecoside, a Novel Glycosylated Polyketide from the Terrestrial FungusMyrotheciumsp. GS-17

Recent Advances on Macrocyclic Trichothecenes, Their Bioactivities and Biosynthetic Pathway

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