qNMR for profiling the production of fungal secondary metabolites

Brooks, Wilson C.; Paguigan, Noemi D.; Raja, Huzefa A.; Moy, Fred; Cech, Nadja B.; Pearce, Cedric J.; Oberlies, Nicholas H.

doi:10.1002/mrc.4571

Cited by 7 publications

(7 citation statements)

References 53 publications

(64 reference statements)

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“…NMR is an appealing platform for conducting quantification studies on complex systems [1][2][3][4][5]. To ensure robustness and precision of the method, several practical guides for spectra acquisition and accurate processing were developed [10].…”

Section: Resultsmentioning

confidence: 99%

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A Step Towards Optimization of the qNMR Workflow: Proficiency Testing Exercise at an GxP-Accredited Laboratory

Monakhova

Diehl²

2021

Appl Magn Reson

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Quantitative nuclear magnetic resonance (qNMR) is considered as a powerful tool for multicomponent mixture analysis as well as for the purity determination of single compounds. Special attention is currently paid to the training of operators and study directors involved in qNMR testing. To assure that only qualified personnel are used for sample preparation at our GxP-accredited laboratory, weighing test was proposed. Sixteen participants performed six-fold weighing of the binary mixture of dibutylated hydroxytoluene (BHT) and 1,2,4,5-tetrachloro-3-nitrobenzene (TCNB). To evaluate the quality of data analysis, all spectra were evaluated manually by a qNMR expert and using in-house developed automated routine. The results revealed that mean values are comparable and both evaluation approaches are free of systematic error. However, automated evaluation resulted in an approximately 20% increase in precision. The same findings were revealed for qNMR analysis of 32 compounds used in pharmaceutical industry. Weighing test by six-fold determination in binary mixtures and automated qNMR methodology can be recommended as efficient tools for evaluating staff proficiency. The automated qNMR method significantly increases throughput and precision of qNMR for routine measurements and extends application scope of qNMR.

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Section: Resultsmentioning

confidence: 99%

“…Quantitative nuclear magnetic resonance (qNMR) is an important method to assess the purity of organic compounds as well as to perform multicomponent analysis of complex mixtures. The application range of qNMR nowadays varies from small organic molecules to large proteins [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

A Step Towards Optimization of the qNMR Workflow: Proficiency Testing Exercise at an GxP-Accredited Laboratory

Monakhova

Diehl²

2021

Appl Magn Reson

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“…The reproducibility of the measurements was established through three replicate analyses of the sample of unknown amount of isolated fomentariol [ 11 , 12 ]. The integration region for the signal of fomentariol was 4.28–4.36 ppm, while for the signal of toluene, used as internal standard, it was 2.29–2.35 ppm ( Figure 7 ).…”

Section: Resultsmentioning

confidence: 99%

Isolation and Determination of Fomentariol: Novel Potential Antidiabetic Drug from Fungal Material

Maljurić

Golubović

Ravnikar

et al. 2018

Journal of Analytical Methods in Chemistry

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Diabetes mellitus is one of the leading world's public health problems. Therefore, it is of a huge interest to develop new antidiabetic drugs. Apart from traditional therapy of diabetes, nowadays, importance is given to natural substances with antidiabetic potential. Fomes fomentarius is a mushroom widely used for different purposes, due to its range of already confirmed activities. Fomentariol is a constituent of Fomes fomentarius, responsible for its antidiabetic potential. In that respect, it is important to develop a method for isolation and quantification of fomentariol from fungal material, which will be simple and efficient. Multistep, complex extraction applied in the previously reported studies was avoided with ethanol, providing rapid single-step extraction. The presence of fomentariol in ethanolic extract was confirmed by high-resolution mass spectrometry. Semipreparative HPLC method was developed and applied for isolation from ethanol extract and purification of the active compound fomentariol. It was a gradient reversed-phase method with a mobile phase consisting of acetonitrile and 0.1% formic acid in water and total run time of 15 minutes. The amount of 6.5 mg of high-purity fomentariol was determined by quantitative NMR with toluene as internal standard. The isolated and determined amount of substance can be further used for the quantitative estimation of activity of fomentariol.

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“…31 Based on morphological characterization and molecular phylogenetic analysis, strain MSX48662 was identified as Xylaria cubensis (Sordariomycetes, Ascomycota). The sequence data for the strain utilized in the study was deposited in GenBank under accession number KX229783.…”

Section: Methodsmentioning

confidence: 99%

“…An isolate of the filamentous fungus Xylaria cubensis (strain MSX48662) was found to be a prolific producer of 1 , biosynthesizing over 100 mg per a single rice-based fermentation culture grown in a 2.8 L Fernbach flask, 31 and thus, it was used for resupply purposes. Hence, the fungal extract was subjected to further studies and afforded six compounds, including 1 and structurally related analogues, four of which were known ( 2 , 3 , 5 , and 6 ) and one of which ( 4 ) was new to the literature.…”

Section: Introductionmentioning

confidence: 99%

Chemoselective fluorination and chemoinformatic analysis of griseofulvin: Natural vs fluorinated fungal metabolites

Paguigan

Al‐Huniti

Raja

et al. 2017

Bioorganic & Medicinal Chemistry

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Griseofulvin is a fungal metabolite and antifungal drug used for the treatment of dermatophytosis in both humans and animals. Recently, griseofulvin and its analogues have attracted renewed attention due to reports of their potential anticancer effects. In this study griseofulvin (1) and related analogues (2–6, with 4 being new to literature) were isolated from Xylaria cubensis. Six fluorinated analogues (7–12) were synthesized, each in a single step using the isolated natural products and Selectflour, so as to examine the effects of fluorine incorporation on the bioactivities of this structural class. The isolated and synthesized compounds were screened for activity against a panel of cancer cell lines (MDA-MB-435, MDA-MB-231, OVCAR3, and Huh7.5.1) and for antifungal activity against Microsporum gypseum. A comparison of the chemical space occupied by the natural and fluorinated analogues was carried out by using principal component analysis, documenting that the isolated and fluorinated analogues occupy complementary regions of chemical space. However, the most active compounds, including two fluorinated derivatives, were centered around the chemical space that was occupied by the parent compound, griseofulvin, suggesting that modifications must preserve certain attributes of griseofulvin to conserve its activity.

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qNMR for profiling the production of fungal secondary metabolites

Cited by 7 publications

References 53 publications

A Step Towards Optimization of the qNMR Workflow: Proficiency Testing Exercise at an GxP-Accredited Laboratory

A Step Towards Optimization of the qNMR Workflow: Proficiency Testing Exercise at an GxP-Accredited Laboratory

Isolation and Determination of Fomentariol: Novel Potential Antidiabetic Drug from Fungal Material

Chemoselective fluorination and chemoinformatic analysis of griseofulvin: Natural vs fluorinated fungal metabolites

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