scholarly journals Elucidation and Identification of an Antifungal Compound from Pseudomonas aeruginosa DA3.1 Isolated from Soil in Vietnam

2020 ◽  
Vol 13 (10) ◽  
Author(s):  
Nguyen Thi Trung ◽  
Nguyen Tien Cuong ◽  
Nguyen Thi Thao ◽  
Dao Thi Mai Anh ◽  
Do Thi Tuyen
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Pseudomonas Aeruginosa ◽  
Antifungal Activity ◽  
Carboxylic Acid ◽  
Magnetic Resonance ◽  
13C Nmr ◽  
Bacterial Strain ◽  
Antifungal Compound ◽  
Fusarium Sp ◽  
High Antifungal Activity

Background: Fusarium sp. and Rhizoctonia sp. fungi have been always threats to short-term crops. In Vietnam, corn and soybean suffer serious losses annually. Therefore, it is necessary to utilize an environmentally friendly antifungal compound that is highly effective against phytopathogenic fungi. Pseudomonas sp. is a popular soil bacterial strain and well known for its high antifungal activity. Objectives: This study was carried out to evaluate and assess the antifungal activity of a local bacterial strain namely DA3.1 that was later identified as Pseudomonas aeruginosa. This would be strong scientific evidence to develop an environmentally friendly biocide from a local microorganism strain for commercial use. Methods: The antifungal compound was purified from ethyl acetate extraction of deproteinized cell culture broth by a silica gel column (CH2Cl2/MeOH (0% - 10% MeOH)). The purity of the isolated compound was determined by HPLC, and its molecular structure was elucidated using spectroscopic experiments including one-dimensional (1D) (1H NMR, 13C NMR, DEPT) and two-dimensional (2D) (HMBC and HSQC) spectra. The activity of the purified compound against Fusarium sp. and Rhizoctonia sp. fungi was measured using the PDA-disk diffusion method, and its growth-promoting ability was evaluated using the seed germination test of corn and soybean. Results: The results showed that the antifungal compound produced by Pseudomonas aeruginosa DA3.1 had a retention factor (Rf) of 0.86 on thin layer chromatography (TLC). Based on the evidence of spectral data including proton nuclear magnetic resonance (1H NMR), carbon nuclear magnetic resonance (13C NMR), distortionless enhancement by polarization transfer (DEPT), heteronuclear multiple bond correlation (HMBC), and heteronuclear single quantum coherence (HSQC), the chemical structure was elucidated as phenazine-1-carboxylic. The purified compound showed inhibitory activity against F. oxysporum and R. solani and exhibited the ability of the germination of corn and soybean seeds. The results revealed the benefit of native P. aeruginosa DA3.1 and phenazine-1-carboxylic acid for use as a biocontrol agent, as well as a plant growth promoter. Conclusions: The antifungal compound isolated from local Pseudomonas DA3.1 was identified as phenazine-1-carboxylic acid that posed high antifungal activity and was a plant germination booster.

scholarly journals The N’-Substituted Derivatives of 5-Chloro-3-Methylisothiazole-4-Carboxylic Acid Hydrazide with Antiproliferative Activity

Molecules ◽  
2019 ◽  
Vol 25 (1) ◽  
pp. 88
Author(s):  
Izabela Jęśkowiak ◽  
Stanisław Ryng ◽  
Marta Świtalska ◽  
Joanna Wietrzyk ◽  
Iwona Bryndal ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Carboxylic Acid ◽  
Magnetic Resonance ◽  
Magnetic Resonance Spectroscopy ◽  
13C Nmr ◽  
Antiproliferative Activity ◽  
Acid Hydrazide ◽  
Resonance Spectroscopy ◽  
Carboxylic Acid Hydrazide ◽  
Anti Cancer

Thanks to the progress in oncology, pharmacological treatment of cancer is gaining in importance and in the near future anti-cancer chemotherapeutics are expected to be the main method of treatment for cancer diseases. What is more, the search for new anti-cancer compounds with the desired application properties is constantly underway. As a result of designed syntheses, we obtained some new N’-substituted 5-chloro-3-methylisothiazole-4-carboxylic acid hydrazide derivatives with anticancer activity. The structure of new compounds was determined by mass spectrometry (MS), elemental analysis, proton nuclear magnetic resonance spectroscopy (1H-NMR), carbon nuclear magnetic resonance spectroscopy (13C-NMR), 1H-13C NMR correlations and infrared spectroscopy (IR). Moreover, the structures of the compounds were confirmed by crystallographic examination. The antiproliferative MTT tests for 11 prepared compounds was conducted towards human biphenotypic B cell myelomonocytic leukemia MV4-11. SRB test was used to examine their potential anticancer activity towards human colon adenocarcinoma cell lines sensitive LoVo, resistant to doxorubicin LoVo/DX, breast adenocarcinoma MCF-7 and normal non-tumorigenic epithelial cell line derived from mammary gland MCF-10A. The most active compound was 5-chloro-3-methyl-N′-[(1E,2E)-(3-phenyloprop-2-en-1-ylidene]isothiazole-4-carbohydrazide, which showed the highest antiproliferative activity against all tested cell lines.

scholarly journals Study of the biologically active acyclic ureas by nuclear magnetic resonance

2020 ◽  
Vol 100 (4) ◽  
pp. 60-74
Author(s):  
А.А. Bakibaev ◽  
◽  
М.Zh. Sadvakassova ◽  
V.S. Malkov ◽  
R.Sh. Еrkasov ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Functional Groups ◽  
13C Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Biologically Active ◽  
Resonance Spectroscopy ◽  
13C Nmr Spectra ◽  
Nuclear Magnetic

A wide variety of acyclic ureas comprising alkyl, arylalkyl, acyl, and aryl functional groups are investigated by nuclear magnetic resonance spectroscopy. In general, spectral characteristics of more than 130 substances based on acyclic ureas dissolved in deuterated dimethyl sulfoxide at room temperature are studied. The re-sults obtained based on the studies of 1H and 13C NMR spectra of urea and its N-alkyl-, N-arylalkyl-, N-aryl- and 1,3-diaryl derivatives are presented, and the effect of these functional groups on the chemical shifts in carbonyl and amide moieties in acyclic urea derivatives is discussed. An introduction of any type of substitu-ent (electron-withdrawing or electron-donating) into urea molecule is stated to result in a strong upfield shift in 13C NMR spectra relatively to unsubstituted urea. A strong sensitivity of NH protons to the presence of acyl and aryl groups in nuclear magnetic resonance spectra is pointed out. In some cases, qualitative depend-encies between the chemical shifts in the NMR spectra and the structure of the studied acyclic ureas are re-vealed. A summary of the results on chemical shifts in the NMR spectra of the investigated substances allows determining the ranges of chemical shift variations of the key protons and carbon atoms in acyclic ureas. The literature describing the synthesis procedures are provided. The results obtained significantly expand the methods of reliable identification of biologically active acyclic ureas and their metabolites that makes it promising to use NMR spectroscopy both in biochemistry and in clinical practice.

scholarly journals GALLIC ACID FROM PODS OF JIRINGA (ARCHIDENDRON JIRINGA [JACK] I.C. NIELSEN) AND ITS ANTIOXIDANT

2018 ◽  
Vol 11 (13) ◽  
pp. 114 ◽  
Author(s):  
Misri Yanty Lubis ◽  
Lamek Marpaung ◽  
Muhammad Pandapotan Nasution ◽  
Partomuan Simanjuntak
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Antioxidant Activity ◽  
Phenolic Compounds ◽  
Magnetic Resonance ◽  
Gallic Acid ◽  
13C Nmr ◽  
Pure Compound ◽  
Infra Red ◽  
High Antioxidant Activity

 Objective: This study was aimed to isolate and investigate antioxidant activity of gallic acid in pods of jiringa (Archidendron jiringa [Jack] I.C. Nielsen).Methods: Pods of jiringa were extracted by maceration. Phenolic compounds were tested using FeCl3. Identification of pure compound was obtained from spectra data from nuclear magnetic resonance of proton H (1H NMR), NMR of carbon (13C NMR), infra-red, and mass spectrometry. Antioxidant activity was investigated using 1,1-diphenyl-2-picrylhydrazyl method.Results: The IC50 of gallic acid from jiringa’s pods (A. jiringa [Jack] I.C. Nielsen) was 3.65 μg/ml. This value showed that gallic acid from jiringa’s pods (A. jiringa [Jack] I.C. Nielsen) had high antioxidant activity.Conclusions: Gallic acid presents in pods of jiringa (A. jiringa [Jack] I.C. Nielsen) and has high antioxidant activity.

scholarly journals Dereplication of Natural Extracts Diluted in Glycerin: Physical Suppression of Glycerin by Centrifugal Partition Chromatography Combined with Presaturation of Solvent Signals in 13C-Nuclear Magnetic Resonance Spectroscopy

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 5061
Author(s):  
Marine Canton ◽  
Jane Hubert ◽  
Stéphane Poigny ◽  
Richard Roe ◽  
Yves Brunel ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
13C Nmr ◽  
Model Mixture ◽  
Partition Chromatography ◽  
Centrifugal Partition Chromatography ◽  
Chemical Profiling ◽  
Natural Extracts ◽  
13C Nuclear Magnetic Resonance ◽  
Nuclear Magnetic

For scientific, regulatory, and safety reasons, the chemical profile knowledge of natural extracts incorporated in commercial cosmetic formulations is of primary importance. Many extracts are produced or stabilized in glycerin, a practice which hampers their characterization. This article proposes a new methodology for the quick identification of metabolites present in natural extracts when diluted in glycerin. As an extension of a 13C nuclear magnetic resonance (NMR) based dereplication process, two complementary approaches are presented for the chemical profiling of natural extracts diluted in glycerin: A physical suppression by centrifugal partition chromatography (CPC) with the appropriate biphasic solvent system EtOAc/CH3CN/water 3:3:4 (v/v/v) for the crude extract fractionation, and a spectroscopic suppression by presaturation of 13C-NMR signals of glycerin applied to glycerin containing fractions. This innovative workflow was applied to a model mixture containing 23 natural metabolites. Dereplication by 13C-NMR was applied either on the dry model mixture or after dilution at 5% in glycerin, for comparison, resulting in the detection of 20 out of 23 compounds in the two model mixtures. Subsequently, a natural extract of Cedrus atlantica diluted in glycerin was characterized and resulted in the identification of 12 metabolites. The first annotations by 13C-NMR were confirmed by two-dimensional NMR and completed by LC-MS analyses for the annotation of five additional minor compounds. These results demonstrate that the application of physical suppression by CPC and presaturation of 13C-NMR solvent signals highly facilitates the quick chemical profiling of natural extracts diluted in glycerin.

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