Facile NMR approach for profiling curcuminoids present in turmeric

Praveen, Aishwarya; Prasad, Durga; Mishra, Soumya; Nagarajan, S.; Chaudhari, Sachin Rama

doi:10.1016/j.foodchem.2020.128646

Cited by 23 publications

(15 citation statements)

References 38 publications

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“…The vinylic hydrogens H7/7’ and H8/8’ are located between 7.62–7.58 ( d , J =15.8 Hz) and 6.73–6.69 ( d , J =15.8 Hz), coupling in trans . In addition, close to the hydrogens H7/H7’ it is observed the hydrogens H2 ( m , 7.58–7.56 ppm) and H2/H2′, between 7.67 ppm and 7.63 ppm ( dtd , J =8.6 Hz), related to the demethoxycurcumin‐coumarin derivative (Figure 3.d) and bisdemethoxycurcumin‐coumarin derivative (Figure 3.e), respectively [44,45] …”

Section: Resultsmentioning

confidence: 73%

“…The signal of carbon 11 is also doubled at 150.9 (sp 2 ) and 93.5 (sp 3 ) ppm. Lastly, it was possible to identify signals of carbons C2 related to three curcuminoids derivatives, which are 142.3 ppm (curcumin‐coumarin derivative), 130.2 ppm (demethoxycurcumin‐coumarin derivative), and 131.2 ppm (bisdemethoxycurcumin‐coumarin derivative) [44,45] . All correlations of 1 H‐ 13 C and 13 C were supported by the HSQC and HMBC spectra (Figures S9, S10, S11, and S12).…”

Section: Resultsmentioning

confidence: 77%

“…Similar results have been reported by other authors. [44,45] Finally, the spectrum shows two singlets. The first singlet at 5.97 ppm is assigned to the hydrogen H16a, while the singlet at 3.92 ppm is related to the hydrogens from methoxy groups.…”

Section: Mass Spectrometrymentioning

confidence: 98%

“…In addition, close to the hydrogens H7/H7' it is observed the hydrogens H2 (m, 7.58-7.56 ppm) and H2/H2', between 7.67 ppm and 7.63 ppm (dtd, J = 8.6 Hz), related to the demethoxycurcumin-coumarin derivative (Figure 3.d) and bisdemethoxycurcumin-coumarin derivative (Figure 3.e), respectively. [44,45] The aryl hydrogens H1/1' occurs in the same region of the hydrogens H18/19/20. Then, it is observed the signal of H5/H5' between 7.20 and 7.17 ppm (dd, J = 8.2 Hz.)…”

Section: Mass Spectrometrymentioning

confidence: 99%

See 3 more Smart Citations

A New Curcuminoids‐Coumarin Derivative: Mechanochemical Synthesis, Characterization and Evaluation of Its In Vitro Cytotoxicity and Antimicrobial Properties

et al. 2021

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Over the years, several drugs have been developed deriving from plants to investigate possible therapeutic roles. Among them, curcuminoids and coumarins, which, display a wide range of biological activity against several strains. Therefore, it was synthesized a curcuminoids-coumarin derivative by a mechanochemical multicomponent reaction. By NMR and HRMS results confirmed the formation of a mixture of three curcuminoids-coumarin derivatives in the same sample. The Influence of time during the milling process was evaluated, resulting in a crystalline product in only 30 min. The LAG milling carried out with different solvents showed that the product is obtained regardless of the solvent polarity. Furthermore, the biological evaluation showed that the curcuminoidscoumarin derivative has better activity against S. aureus than curcumin and 4-hydroxycoumarin. Lastly, the cell viability study exhibited a decrease of cytotoxicity of the derivative, compared to curcumin, against NIH3T3 cells.

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Section: Resultsmentioning

confidence: 73%

Section: Resultsmentioning

confidence: 77%

Section: Mass Spectrometrymentioning

confidence: 98%

Section: Mass Spectrometrymentioning

confidence: 99%

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A New Curcuminoids‐Coumarin Derivative: Mechanochemical Synthesis, Characterization and Evaluation of Its In Vitro Cytotoxicity and Antimicrobial Properties

et al. 2021

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“…These com pounds are natural phenols and they are often employed to color foods and medicines because of the typical yellow color derived from them [51]. They were previously isolated from turmeric and characterized via NMR [52]. The adulterated samples presented a rel atively higher content of curcuminoids (Cur), along with linoleic acid (Lin.…”

Section: Statistical Analysis To Reveal Adulterated Saffron Organic E...mentioning

confidence: 99%

Non-Targeted NMR Method to Assess the Authenticity of Saffron and Trace the Agronomic Practices Applied for Its Production

et al. 2022

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The development of analytical methods aimed at tracing agri-food products and assessing their authenticity is essential to protect food commercial value and human health. An NMR-based non-targeted method is applied here to establish the authenticity of saffron samples. Specifically, 40 authentic saffron samples were compared with 18 samples intentionally adulterated by using turmeric and safflower at three different concentration levels, i.e., 5, 10, and 20 wt%. Statistical processing of NMR data furnished useful information about the main biomarkers contained in aqueous and dimethyl sulfoxide extracts, which are indicative of the presence of adulterants within the analyzed matrix. Furthermore, a discrimination model was developed capable of revealing the type of agronomic practice adopted during the production of this precious spice, distinguishing between organic and conventional cultivation. The main objective of this work was to provide the scientific community involved in the quality control of agri-food products with an analytical methodology able to extract useful information quickly and reliably for traceability and authenticity purposes. The proposed methodology turned out to be sensitive to minor variations in the metabolic composition of saffron that occur in the presence of the two adulterants studied. Both adulterants can be detected in aqueous extracts at a concentration of 5 wt%. A lower limit of detection was observed for safflower contained in organic extracts in which case the lowest detectable concentration was 20%.

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Metabolomics analysis of peony root using NMR spectroscopy and impact of the preprocessing method for NMR data in multivariate analysis

et al. 2023

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Peony root is an important herbal drug used as an antispasmodic analgesic. To evaluate peony roots with different botanical origin, producing areas, and post-harvest processing, 1 H NMR-based metabolomics analysis was employed. Five types of monoterpenoids, including albi orin (4), paeoni orin (6), and sulfonated paeoni orin (25), and six other compounds, including 1,2,3,4,6-penta-O-galloyl-β-d-glucose (18), benzoic acid (21), gallic acid (22), and sucrose (26) were detected in the extracts of peony root samples. Among them, compounds 4, 6, 18, and total monoterpenoids including 21 were quanti ed by quantitative 1 H NMR (qHNMR). Compound 25 was detected in 1 H NMR spectra of sulfurfumigated white peony root (WPR) extracts indicating that 1 H NMR was a fast and effective method for identifying sulfur-fumigated WPR. The content of 26, the main factor affecting extract yield, increased signi cantly in peony root after low-temperature storage for one month, whereas that in WPR did not increase due to the boiling treatment after harvesting. We investigated the impact of preprocessing methods to such analysis for NMR data from commercial samples, resulting that the data matrix transformed from qHNMR spectra and normalized to internal standard were optimum for multivariate analysis. The multivariate analysis demonstrated that among commercial samples derived from P. lacti ora, peony root samples in Japanese market (PR) had high contents of 18 and 22, and red peony root (RPR) samples had high content of monoterpenoids represented by 6; and among RPR samples, those derived from P. veitchii showed higher contents of 18 and 22 than those from P. lacti ora. The 1 H NMR-based metabolomics method coupled with qHNMR was useful for evaluation of peony root and would be applicable for other crude drugs.Both HPLC and LC-MS are targeted analysis methods. To focus on comprehensive constituents of peony root, 1 H nuclear magnetic resonance( 1 H NMR)-based metabolite pro ling method, known as untargeted method, was employed to investigate the component variations caused by multiple factors (differences in origins, producing areas, and post-harvest processing). Previous studies showed that 1 H NMR pro ling offers analytical advantages over HPLC and LC-MS: uncomplicated sample preparation, comprehensive detection of hydrogen-containing compounds, and time savings [14]. However, some points were not clear regarding the preprocessing method of NMR data for multivariate analysis. For the measurement of NMR spectra as the basis of the data matrix in multivariate analysis, both 1 H NMR [15][16][17] and quantitative 1 H NMR (qHNMR) [18][19][20] have been used. Additionally, the transformation from original NMR spectra data to the data matrix used for multivariate analysis needs to be normalized to minimize the in uence of experiment and instrumental variables [21]. There are two normalization methods: 1) normalization to the peak area of the internal standard [15,17,22], 2) normalization to total intensity [16, 18,23]. However, the method m...

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Facile NMR approach for profiling curcuminoids present in turmeric

Cited by 23 publications

References 38 publications

A New Curcuminoids‐Coumarin Derivative: Mechanochemical Synthesis, Characterization and Evaluation of Its In Vitro Cytotoxicity and Antimicrobial Properties

A New Curcuminoids‐Coumarin Derivative: Mechanochemical Synthesis, Characterization and Evaluation of Its In Vitro Cytotoxicity and Antimicrobial Properties

Non-Targeted NMR Method to Assess the Authenticity of Saffron and Trace the Agronomic Practices Applied for Its Production

Metabolomics analysis of peony root using NMR spectroscopy and impact of the preprocessing method for NMR data in multivariate analysis

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