FT-IR and FT-Raman fingerprints of flavonoids – A review

Krysa, Martyna; Szymańska-Chargot, Monika; Zdunek, Artur

doi:10.1016/j.foodchem.2022.133430

Cited by 91 publications

(34 citation statements)

References 56 publications

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“…Vibrational Raman spectra of RUT, OA, and LA have been compared to the spectra of RUT-O and RUT-L esters, respectively. The spectra of the parent compounds are in agreement with the previous data (Krysa et al, 2022). As previously showed, OA possesses the main Raman bands at 602(w), 725(w), 845 (m, sh), 856(m), 866(m), 890(m), 903(m), 971(m), 1,023(m, sh), 1,035(m, sh), 1,065(m), 1,080(m), 1,118(m), 1,265(m), 1,301(s), 1,416(m,sh), 1,440(vs.), and 1,655(s) (De Gelder et al, 2007).…”

Section: Vibrational Spectroscopy Of Bioconjugatessupporting

confidence: 91%

Rutin bioconjugates as potential nutraceutical prodrugs: An in vitro and in ovo toxicological screening

et al. 2022

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Rutin (RUT) is considered one the most attractive flavonoids from a therapeutic perspective due to its multispectral pharmacological activities including antiradical, anti-inflammatory, antiproliferative, and antimetastatic among others. Still, this compound presents a low bioavailability what narrows its clinical applications. To overcome this inconvenience, the current paper was focused on the synthesis, characterization, and toxicological assessment of two RUT bioconjugates obtained by enzymatic esterification with oleic acid (OA) and linoleic acid (LA)—rutin oleate (RUT-O) and rutin linoleate (RUT-L), as flavonoid precursors with improved physicochemical and biological properties. Following the enzymatic synthesis in the presence of Novozyme® 435, the two bioconjugates were obtained, their formation being confirmed by RAMAN and FT-IR spectroscopy. The in vitro and in ovo toxicological assessment of RUT bioconjugates (1–100 µM) was performed using 2D consecrated cell lines (cardiomyoblasts - H9c2(2-1), hepatocytes—HepaRG, and keratinocytes—HaCaT), 3D reconstructed human epidermis tissue (EpiDerm™), and chick chorioallantoic membranes, respectively. The results obtained were test compound, concentration—and cell-type dependent, as follows: RUT-O reduced the viability of H9c2(2-1), HepaRG, and HaCaT cells at 100 µM (to 77.53%, 83.17%, and 78.32%, respectively), and induced cell rounding and floating, as well as apoptotic-like features in the nuclei of all cell lines, whereas RUT-L exerted no signs of cytotoxicity in all cell lines in terms of cell viability, morphology, and nuclear integrity. Both RUT esters impaired the migration of HepaRG cells (at 25 µM) and lack irritative potential (at 100 µM) in vitro (tissue viability >50%) and in ovo (irritation scores of 0.70 for RUT-O, and 0.49 for RUT-L, respectively). Computational predictions revealed an increased lipophilicity, and reduced solubility, drug-likeness and drug score of RUT-O and RUT-L compared to their parent compounds—RUT, OA, and LA. In conclusion, we report a favorable toxicological profile for RUT-L, while RUT-O is dosage-limited since at high concentrations were noticed cytotoxic effects.

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Section: Vibrational Spectroscopy Of Bioconjugatessupporting

confidence: 91%

Rutin bioconjugates as potential nutraceutical prodrugs: An in vitro and in ovo toxicological screening

et al. 2022

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“…The FT-IR spectra between 4000 and 500 cm −1 in E. sagittatum leaves at 10 days, 20 days, and 30 days after spraying with Fe 2+ , Cu 2+ , and Zn 2+ at low concentrations (100 mg·L −1 ), medium concentrations (1000 mg·L −1 ), and high concentrations (2500 mg·L −1 ) are presented in Figure 3 . As shown in the FT-IR spectra between 4000 and 500 cm −1 ( Figure 3 A), some peaks, including peak 3350, peak 2921, peak 2851, peak 1725, peak 1650, peak 1440, peak 1343, peak 1258, and peaks 1069 and 834 cm −1 , emerged [ 24 , 25 , 26 ]. The assignment of functional groups responsible for IR absorption were carried out as follows: (1) absorption peak near 3350 cm −1 , O–H stretching vibration, ν(O–H); (2) absorption peak near 2921 cm −1 , –CH 2 asymmetrical stretching vibration, ν as (–CH 2 ); (3) absorption peak near 2851 cm −1 , –CH 2 symmetrical stretching vibration, ν s (–CH 2 ); (4) absorption peak near 1725 cm −1 , –C=O stretching vibration, ν(–C=O); (5) absorption peak near 1650 cm −1 , –C=C stretching vibration, ν(–C=C); (6) absorption peak near 1440 cm −1 , –CH bending vibration, δ(–CH); (7) absorption peak near 1343 cm −1 , –CH 3 bending vibration, δ(–CH 3 ); (8) absorption peak near 1258 cm −1 , =C–O–C symmetrical stretching vibration, ν s (=C–O–C); (9) absorption peak near 1069 cm −1 , =C–O–C asymmetrical stretching vibration, ν as (=C–O–C); (10) absorption peak near 834 cm −1 , sugar ring stretching vibration, ν(sugar ring).…”

Section: Resultsmentioning

confidence: 99%

A Comprehensive Analysis to Elucidate the Effects of Spraying Mineral Elements on the Accumulation of Flavonoids in Epimedium sagittatum during the Harvesting Period

et al. 2023

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The harvesting period is a critical period for the accumulation of flavonoids in the leaves of the important medicinal plant Epimedium sagittatum. In this study, we conducted an experiment on E. sagittatum leaves sprayed with mineral elements with the aim of improving the quality of the herbal leafage during the harvesting period. We elucidated the changes in flavonoids (icariin, epimedin A, epimedin B, and epimedin C) in E. sagittatum leaves. The sum of main flavonoids content reached a maximum (11.74%) at 20 days after the high-concentration Fe2+ (2500 mg·L−1) treatment. We analyzed the FT-IR spectra characteristics of E. sagittatum leaf samples using the FT-IR technique, and constructed an OPLS-DA model and identified characteristic peaks to achieve differentiated identification of E. sagittatum. Further, widely untargeted metabolomic analysis identified different classes of metabolites. As the most important characteristic flavonoids, the relative contents of icariin, icaritin, icariside I, and icariside II were found to be up-regulated by high-Fe2+ treatment. Our experimental results demonstrate that high-concentration Fe2+ treatment is an effective measure to increase the flavonoids content in E. sagittatum leaves during the harvesting period, which can provide a scientific basis for the improvement of E. sagittatum leaf cultivation agronomic measures.

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“…[ 39 ] Simultaneously, the absorption bands at 2929 and 1416 cm −1 get wider in NAM, and two new weak absorption bands at 2883 and 1364 cm −1 form, representing the CH group and the –OH phenolic group, respectively. [ 42–44 ] Second, several band shifts are observed. Especially, the hydroxyl absorption band in the naringin‐loaded microspheres shifts from 3439 to 3442 cm −1 , and the characteristic absorption bands of the carboxyl group move from 1628 and 1421 cm −1 to 1635 and 1416 cm −1 , respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Especially, the hydroxyl absorption band in the naringin-loaded microspheres shifts from 3439 to 3442 cm À1 , and the characteristic absorption bands of the carboxyl group move from 1628 and 1421 cm À1 to 1635 and 1416 cm À1 , respectively. [43,45] These shifts state that the loading of naringin affects the vibration of groups and changes the bond energy in the material. Third, the characteristic bands of calcium alginate carrier material at 1738, 1266, and 1073 cm À1 become weaker.…”

Section: Microstructurementioning

confidence: 99%

“…-OH [33,37,38] 3439 3442 -OH bonds [40,45] 2919 -CH aliphatic group [37,38] 2929 2929 CH [44] 1644 Carbonyl group [39] 2883 CH [44] 1579 Benzene ring [39] 1738 1733 Carboxylic group [40] 1519 Benzene ring [39] 1628 1635 Carboxylic group [40,45] 1449 Benzene ring [39] 1519 Aromatic OH [63] 1367 -OH phenolic group [42,43] 1421 1416 COOÀ [41] 1296 -OH phenolic group [42,43] 1364 -OH phenolic group [42,43] 1264 Carboxylic group 1266 1267 Carboxylic group [40,45] 1202 -OH phenolic group [42,43] 1073 1074 Alginate ring [41] 1177 -OH phenolic group [42,43] 1030 1030 Alginate ring [41] 1132 -C-O-C [39] 822 822 CH group [41] 1090 Carbonyl group [39] 811 811 CH group [41] 1042 -C-O group [38] 671 671 CH group [41] 900-500 Bending vibration of the ring [43] 556 559 C-O [43] 500-400 500-400 C-C-C [43] immersion in PBS. The spheres release out naringin very fast after soaking.…”

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confidence: 99%

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Synthesis and Characterization of Novel Pyrite/Naringin/Brushite Composite Scaffold for Bone Tissue Engineering

Zhao

Feng²,

et al. 2022

Adv Eng Mater

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Herein, pyrite‐leaching liquid and naringin‐loaded microspheres are incorporated into brushite to prepare composite scaffolds with enhanced osteogenic properties in vitro for bone tissue engineering. The results reveal that the loading of these two medicines has no significant effect on the crystalline phase of the composite, while some changes happen to the chemical groups when the dosage of the microspheres is controlled within 1.5 wt%. After soaking in phosphate buffer for 24 days, the composite containing 0%, 0.38 wt%, 0.75 wt%, and 1.50 wt% naringin‐loaded microspheres show a weight loss rate of 19.28%, 18.81%, 16.92%, and 14.14%, respectively. Simultaneously, the soaking assay reveals that the release of naringin and Fe are both kept within a safe level. A burst release of naringin is avoided since the highest concentration of naringin is detected on day 12 after immersion. The cell experiments show that all the composites have no toxicity to osteoblasts and allow the cells to grow on the surface. Furthermore, adding naringin‐loaded microspheres to the composite (0.75–1.5 wt%) promotes the mineralization ability and the alkaline phosphatase activity of the osteoblasts. Thus, the novel pyrite/naringin/brushite composite scaffold has the potential to be used in bone tissue engineering.

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FT-IR and FT-Raman fingerprints of flavonoids – A review

Cited by 91 publications

References 56 publications

Rutin bioconjugates as potential nutraceutical prodrugs: An in vitro and in ovo toxicological screening

Rutin bioconjugates as potential nutraceutical prodrugs: An in vitro and in ovo toxicological screening

A Comprehensive Analysis to Elucidate the Effects of Spraying Mineral Elements on the Accumulation of Flavonoids in Epimedium sagittatum during the Harvesting Period

Synthesis and Characterization of Novel Pyrite/Naringin/Brushite Composite Scaffold for Bone Tissue Engineering

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