scholarly journals Identification and Quantitation of Ursolic and Oleanolic Acids in Ilex aquifolium L. Leaf Extracts Using 13C and 1H-NMR Spectroscopy

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4413
Author(s):  
Doreen Palu ◽  
Ange Bighelli ◽  
Joseph Casanova ◽  
Mathieu Paoli
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
13C Nmr ◽  
1H Nmr Spectroscopy ◽  
Limit Of Detection ◽  
Biologically Active ◽  
Leaf Extracts ◽  
Simple Method ◽  
Ilex Aquifolium ◽  
Limit Of Quantitation

Leaves of Ilex aquifolium L. have been used for their therapeutic properties. In previous studies, components contained in the leaves were first isolated by various chromatographic techniques. Then, quantitation of oleanolic and ursolic acids, which are responsible for the biological and therapeutic activities of the plant, was performed by HPLC, HPTLC, and somewhat by GC-MS. Our objective was to develop a simple method that allows the identification of compounds contained in the leaves of Corsican I. aquifolium and to quantify ursolic and oleanolic acids. Leaves were successively extracted with hexane and dichloromethane. The extracts were chromatographed on silica gel and the fractions of column chromatography submitted to 13C-NMR analysis, following a computerized method developed in the laboratory. 13C-NMR allowed the identification of various triterpenes including ursolic acid and oleanolic acid. Quantitation of both acids was achieved, for the first time, by 1H-NMR after validation of the method (accuracy, precision, linearity, limit of detection and limit of quantitation). Ursolic and oleanolic acids accounted for 55.3% and 20.8% of the dichloromethane extract, respectively. This represents 1.3% and 0.5% of the mass of dried leaves. 1H-NMR spectroscopy appeared as a powerful tool for a rapid quantitation of biologically active compounds from I. aquifolium.

scholarly journals Secondary metabolites of three endemic Centaurea L. species

2014 ◽  
Vol 79 (11) ◽  
pp. 1355-1362 ◽  
Author(s):  
Vele Tesevic ◽  
Ivana Aljancic ◽  
Slobodan Milosavljevic ◽  
Vlatka Vajs ◽  
Iris Djordjevic ◽  
...  
Keyword(s):  
Quantitative Analysis ◽  
Nmr Spectroscopy ◽  
Secondary Metabolites ◽  
Sesquiterpene Lactone ◽  
1H Nmr ◽  
13C Nmr ◽  
1H Nmr Spectroscopy ◽  
13C Nmr Spectroscopy ◽  
Esi Ms ◽  
Aerial Parts

The aerial parts of three endemic Centaurea L. species, namely C. tomorosii Micevski, C. soskae Hayek and C. galicicae Micevski, afforded sesquiterpene lactone cnicin (1) and seven flavonoids: apigenin (2), isokaempferide (3), hispidulin (4), eupatorin (5), cirsimaritin (6), santaflavone (7) and salvigenin (8). The structures of the isolated compounds were determined by UV, 1H NMR and 13C NMR spectroscopy and HR-ESI-MS spectrometry. 1H NMR spectroscopy was used as a method for quantitative analysis of sesquiterpene lactone cnicin.

Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine.

1984 ◽  
Vol 30 (3) ◽  
pp. 426-432 ◽  
Author(s):  
J R Bales ◽  
D P Higham ◽  
I Howe ◽  
J K Nicholson ◽  
P J Sadler
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Nmr Spectroscopy ◽  
Magnetic Resonance ◽  
High Resolution ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Proton Nuclear Magnetic Resonance ◽  
Resonance Spectroscopy ◽  
Simple Method ◽  
Nuclear Magnetic

Abstract Numerous low-Mr metabolites--including creatinine, citrate, hippurate, glucose, ketone bodies, and various amino acids--have been identified in 400- and 500-MHz proton nuclear magnetic resonance (1H NMR) spectra of intact human urine. The presence of many of these was related to the specific condition of the donors: humans in different physiological states (resting, fasting, or post-exercise) and pathological conditions (e.g., diabetes mellitus, cadmium-induced renal dysfunction). We have also monitored the metabolism of simple nonendogenous compounds (methanol and ethanol) and of acetaminophen. The pH-dependencies of the NMR chemical shifts of some urine components are reported. Our studies show that high-resolution 1H NMR spectroscopy provides a fast, simple method for "fingerprint" identification of urinary compounds. In some cases, analytes can be quantified by standard additions or by comparing integrated peak areas for the metabolites with those for creatinine. Determinations of creatinine by 1H NMR spectroscopy compared well with those by an independent chemical assay based on the Jaffé reaction.

scholarly journals The First Application of 1H NMR Spectroscopy for the Assessment of the Authenticity of Perfumes

2019 ◽  
Author(s):  
Grzegorz Ciepielowski ◽  
Barbara Pacholczyk-Sienicka ◽  
Łukasz Albrecht
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Negative Impact ◽  
Poor Quality ◽  
Proton Nuclear Magnetic Resonance ◽  
Resonance Spectroscopy ◽  
Simple Method ◽  
Counterfeit Goods ◽  
Safety Issues

The industry of the counterfeit goods is one of the largest underground business in the world and it is rapidly growing. Counterfeits can lead not only to loss of profit for honest producers but also have a negative impact on consumers who receive poor quality goods at an excessive price and may be exposed to health damages and safety issues. Perfume industry is constantly exposed to the problem of counterfeits with the fast developing parallel market of inspired perfumes being an important issue. It prompts for the identification of methods that classify the quality of this type of products. In this paper the application of proton nuclear magnetic resonance spectroscopy is employed for the authentication of perfumery products for the first time. Molecular composition of several types of authentic brand fragrances for women were compared with their cheaper inspired equivalents and fake products. Our approach offers the prospect of a fast and simple method for discrimination and counterfeit detection of perfumes using 1H NMR spectroscopy.

scholarly journals Quantitative Determination and Validation of Four Ketones in Salvia miltiorrhiza Bunge Using Quantitative Proton Nuclear Magnetic Resonance Spectroscopy

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2043
Author(s):  
Yuanyuan Li ◽  
Zhuoni Hou ◽  
Feng Su ◽  
Jipeng Chen ◽  
Xiaodan Zhang ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Salvia Miltiorrhiza ◽  
Tanshinone Iia ◽  
Proton Nuclear Magnetic Resonance ◽  
Resonance Spectroscopy ◽  
Salvia Miltiorrhiza Bunge ◽  
Simple Method ◽  
Tanshinone I

Salvia mltiorrhiza Bunge (SMB) is native to China, whose dried root has been used as medicine. A few chromatographic- or spectrometric-based methods have already been used to analyze the lipid-soluble components in SMB. However, the methodology of qNMR on the extracts of fresh SMB root has not been verified so far. The purpose of this study was to establish a fast and simple method to quantify the tanshinone I, tanshinone IIA, dihydrotanshinone, and cryptotanshinone in fresh Salvia Miltiorrhiza Bunge root without any pre-purification steps using 1H-NMR spectroscopy. The process is as follows: first, 70% methanol aqueous extracts of fresh Salvia Miltiorrhiza Bunge roots were quantitatively analyzed for tanshinone I, tanshinone IIA, dihydrotanshinone, and cryptotanshinone using 1H-NMR spectroscopy. Different internal standards were tested and the validated method was compared with HPLC. 3,4,5-trichloropyridine was chosen as the internal standard. Twelve samples of Salvia Miltiorrhiza Bunge were quantitatively analyzed by qNMR and HPLC respectively. Then, the results were analyzed by chemometric approaches. This NMR method offers a fast, stable, and accurate analysis of four ketones: tanshinone I, tanshinone IIA, dihydrotanshinone, and cryptotanshinone in fresh roots of Salvia Miltiorrhiza Bunge.

scholarly journals Synthesis and properties of 1-aminocarbonylmethyl-5-aryl- 4-aroyl-3-hydroxy-3-pyrroline-2-ones

2020 ◽  
Vol 64 (10) ◽  
pp. 28-32
Author(s):  
Vladimir L. Gein ◽  
◽  
Evgenia V. Pastukhova ◽  
Keyword(s):  
Acetic Acid ◽  
Nmr Spectroscopy ◽  
Physicochemical Properties ◽  
Hydrazine Hydrate ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Glacial Acetic Acid ◽  
Spectral Characteristics ◽  
Biologically Active ◽  
Three Component Reaction

3-Hydroxy-3-pyrrolin-2-ones are fully hydrogenated heterocyclic compounds, the base of which is included in a number of biologically active substances and drugs. Scientists' interest in 3-Hydroxy-3-pyrrolin-2-ones is due to the fact that, with their availability and high stability, they also have high reactivity due to the active carbonyl group in the third position of the heterocycle and easily interact with moconucleophiles. In addition, the presence of acyl and ethoxycarbonyl groups in the fourth position of the heterocycle makes it possible to obtain various condensed systems in reactions with binucleophiles, thereby making it possible to expand the range of the indicated compounds. We set the task to prepare 5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones containing an amino-carbonylmethyl substituent in the first position of the heterocycle, which were not previously described in the literature. It was also supposed to establish how the obtained compounds react with hydrazine hydrate. A series of 1-aminocarbonylmethyl-5-aryl-4-aroyl-3-hydroxy-3-pyrrolin-2-ones was obtained by setting up a three-component reaction of aroylpyruvic acid methyl ester with aromatic aldehydes and glycinamide hydrochloride in glacial acetic acid. The structure of the obtained compounds was established on the basis of IR and 1H NMR spectroscopy data. Based on the data of 1H NMR spectroscopy and a positive reaction with an alcoholic solution of iron(III) chloride, the predominant existence of the obtained compounds in the enol form was established. The article describes the mechanism of three-component reactions, the structural formulas of the obtained compounds, their physicochemical properties and spectral characteristics, as well as the yields of the reaction products. We have also studied the interaction of 1-substituted 5-aryl-4-acyl-3-hydroxy-3-pyrrolin- 2-ones with such a binucleophilic reagent as hydrazine hydrate. As a result of refluxing 1-amino-carbonylmethyl-3-hydroxy-4-(4-methoxybenzoyl)-5-(2-chlorophenyl)-3-pyrrolin-2-one and hydrazine hydrate in glacial acetic acid, 2-[4-(2-chlorophenyl)-3-(4-methoxyphenyl)-6-oxo-4,6-dihydropyrrolo [3,4-c] pyrazol-5(1H)-yl] acetamide. The article describes the proposed reaction mechanism, product yield, its physicochemical properties and spectral characteristics.

scholarly journals 4,4′-Di-tert-butyl-2,2′-bipyridinium Trifluoromethanesulfonate

Molbank ◽  
10.3390/m1261 ◽  
2021 ◽  
Vol 2021 (3) ◽  
pp. M1261
Author(s):  
Shintaro Kodama ◽  
Kazuki Bunno ◽  
Akihiro Nomoto ◽  
Akiya Ogawa
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
Diethyl Ether ◽  
Elemental Analysis ◽  
1H Nmr Spectroscopy ◽  
Trifluoromethanesulfonic Acid ◽  
Simple Method ◽  
Tert Butyl ◽  
Ft Ir ◽  
Direct Use

4,4′-di-tert-butyl-2,2′-bipyridinium trifluoromethanesulfonate was synthesized by stirring 4,4′-di-tert-butyl-2,2′-bipyridine with scandium(III) trifluoromethanesulfonate in acetonitrile, followed by precipitation with diethyl ether. The structure of the new compound was characterized by FT-IR, 1H, 13C{1H} and 19F{1H} NMR spectroscopy and CHN elemental analysis. This is a safe and simple method to obtain mono-protonated bipyridinium trifluoromethanesulfonate without the direct use of trifluoromethanesulfonic acid.

scholarly journals Synthesis, physic and chemical properties of 2-(4-R-5-(thiophene-2-ylmethyl)-4h-1,2,4-triazole-3-ylthio)acetate acids and their salts

2018 ◽  
pp. 48-54
Author(s):  
O. A. Suhak ◽  
О. I. Panasenko ◽  
Ye. G. Knysh
Keyword(s):  
Biological Activity ◽  
Nmr Spectroscopy ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Chemical Properties ◽  
Biological Action ◽  
Biologically Active ◽  
Physico Chemical ◽  
Methods Of Synthesis ◽  
Medicinal Drugs

Derivatives of 1,2,4-triazole are inherent in various types of biological activity. They can be used as pesticide and medicinal drugs (anticonvulsants, analgetics, antitumor and antibacterial). In this regard the search of new methods of synthesis and investigation of biological activity of 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acids and their salts is relevant nowadays. With the aim of finding the new biologically active compounds 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acids and their salts are synthesized, where R is methyl, ethyl, phenyl. The interaction of 4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-thions with monochloracetate acid in the medium of i-propyl alcohol in the presence of an equivalent amount of alkali the corresponding 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4 triazole-3-ylthio)acetate acids are obtained on the basis of which the corresponding salts of morpholine, dimethylamine, monoethanolamine, pteridine, ZnSO4 , CuSO4, NaOH and KOH are obtained and the structure of the received compounds was confirmed on the basis of the data of elemental, IR-, 1H-NMR-spectroscopy. The synthesis of 2-(4-R-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio) acetate acids and their salts was conducted. With the help of modern physico-chemical methods: elemental analysis, IR, 1H-NMR-spectroscopy the structure of synthesized compounds, and their individuality by HPLC-MS is proved. In the IR spectrum of the compound 2-(4-phenyl-5-(thiophene-2-ylmethyl)-4H-1,2,4-triazole-3-ylthio)acetate acid Ic available band fluctuations groups characteristic for the nucleus of 1,2,4-triazole: NH– in the range of 3 400–3 100 cm-1,–C=N– – 1 690–1 620 cm-1. Also present band fluctuations groups –C–S– at 691 cm-1. Available band fluctuations characteristic of the group –CH2 within 1496.59 cm-1 and group –COO-H– – 1722.70 cm-1. This suggests the possibility to further study the biological action of the synthesized compounds.

scholarly journals Synthesis of 5-aryl-4-acyl-3-hydroxy- 1-carboxymethyl-3-pyrrolin-2-ones

2020 ◽  
Vol 64 (11) ◽  
pp. 9-12
Author(s):  
Vladimir L. Gein ◽  
◽  
Evgenia V. Pastukhova ◽  
Keyword(s):  
Nmr Spectroscopy ◽  
Carbonyl Group ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Spectral Characteristics ◽  
Alcoholic Solution ◽  
Biologically Active ◽  
Acyl Residue ◽  
Reaction Products ◽  
Three Component Reaction

5-Aryl-1,4-disubstituted terahydropyrrole-2,3-diones are five-membered nitrogen heterocycles containing in the first alkyl position or an aryl functionalized substituent and in the fourth position in another state of nature an acyl residue. Trahydropyrrole-2,3-diones constitute a significant class of available and stable substances. Along with this, they easily enter into reactions with various nucleophilic reagents due to the highly reactive carbonyl group in the third position of the heterocycle. The presence of the latter, as well as the carbonyl group of the side chain, makes it possible to form various condensed systems from heterocycles in reactions with binucleophilic reagents. The synthesis of biologically active substances based on 1,4,5-trisubstituted tetrahydropyrrole-2,3-diones is one of the promising ways of using this class of compounds. Previously, it was found that 1,4,5-trisubstituted 3-hydroxy-3-pyrin-2-ones have anti-inflammatory, analgesic, antimicrobial, nootropic, antiplatelet and antiviral activity. We set the task to obtain 5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones, in the first position of the heterocycle there is a carboxymethyl substituent. By setting up a three-component reaction of acylpyruvic acid ether with aromatic aldehydes and glycine in dioxane in dioxane. The structure of the compound was established on the basis of IR and 1H NMR spectroscopy data. Based on the data of 1H NMR spectroscopy and a positive reaction with an alcoholic solution of iron(III) chloride, the predominant presence of compounds in the enol form was established. The article presents the proposed mechanism and schemes of the formula for the synthesis of 5-aryl-4-acyl-3-hydroxy-1-carboxymethyl-3-pyrrolin-2-ones, their physicochemical and spectral characteristics, as well as the yields of the reaction products.

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