Structural and vibrational study of 3-hydroxyflavone and 3-methoxyflavone

Cornard, Jean-Paul; Vrielynck, L.; Merlin, J.; Wallet, Jean‐Claude

doi:10.1016/0584-8539(94)01425-g

Cited by 46 publications

(20 citation statements)

References 10 publications

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“…The Raman bands of the flavonol references shown in Fig. 2 are related between 1550 and 1700 cm −1 to the ν(CO), ν(C2C3) stretching vibrations and 8b(A), 8b(B) benzenic ring vibrations61, 62 (the nomenclature of normal modes used in this paper is as given by Varsany for the atomic displacements in ‘mono‐light’ substituted benzenes63). Flavonols have a more intensive band at 1570 cm −1 than anthocyanins (Fig.…”

Section: Discussionmentioning

confidence: 99%

Discrimination of carotenoid and flavonoid content in petals of pansy cultivars (Viola x wittrockiana) by FT‐Raman spectroscopy

Gamsjaeger

Barańska

Schulz

et al. 2011

J Raman Spectroscopy

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Fourier Transform Raman spectroscopy (FT-Raman) has been applied for the non-destructive in-situ analysis of pigments on differently colored flower petals of pansy cultivars (Viola x wittrockiana). The main target of the present study was to investigate how far the Raman mapping technique through FT-Raman spectroscopy and cluster analysis of the Raman spectra is a potential method for the direct, in-situ discrimination of flavonoids (flavonols against anthocyanins) and of carotenoids occurring in flowers, using intact and differently colored flower petal of Viola x wittrockiana for this case study. In order to get more information about the reliability of the direct in-situ flavonoid detection by the Raman method, pigments extracts of the petals were separated by thin-layer chromatography (TLC) and investigated by Raman spectroscopy. Hierarchical cluster analysis (HCA) of the Raman spectra from reference pigments (carotenoids, anthocyanins and flavonols), from areas of the flower petals, and from the TLC extracts allowed discriminating the various pigments, in particular flavonoids (flavonols against anthocyanins) and carotenoids. With a two-dimensional Raman mapping technique, which provides a chemical image of the sample under investigation, we determined by cluster analysis the distribution of carotenoids, anthocyanins and flavonols from the outer layer of the petals, and by integrating through suitable spectral regions selected as characteristic markers for particular pigments their relative concentration could approximately be determined. We found a satisfactory correlation between the patterns seen on the visible images and the patterns on the chemical images obtained by Raman mapping.

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Section: Discussionmentioning

confidence: 99%

Discrimination of carotenoid and flavonoid content in petals of pansy cultivars (Viola x wittrockiana) by FT‐Raman spectroscopy

Gamsjaeger

Barańska

Schulz

et al. 2011

J Raman Spectroscopy

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“…Given that the OH stretching region has not been explored experimentally, these DFT results will be only commented in relation to the behavior of the band mainly reflecting 5-OH bending (see below). It should be noticed that, due to the very strong intramolecular H-bond between the 5-OH and the C_O of luteolin, the 5-OH moiety interacts with the alcoholic solvent molecules However, intermolecular interactions (and notably H-bonds) are known to have much stronger effects on the vibrational bands of flavonoids, especially on the C_O stretching of flavonoids devoid of the 5-OH group ( [37]; see also [20,31]). We suggest that the presence of the strong intramolecular H-bond between the 5-OH group (donor) and the C_O moiety (acceptor), creating a 6-membered ring system, plays a key role in determining the vibrational properties of luteolin.…”

Section: Experimental Vibrational Spectra and Dft Calculationsmentioning

confidence: 97%

Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations

Marrassini

Idrissi

Waele

et al. 2015

Journal of Molecular Liquids

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“…Despite the considerable amount of work reported for these systems both by Raman and SERS techniques [51][52][53][54], a complete and accurate assignment has not yet been achieved. Furthermore, FTIR has a huge potential for the study of this kind of polyhydroxylated compounds [47,[55][56][57]. The present work intends to attain a thorough vibrational analysis (Raman and FTIR) of these chromone derivatives, concomitantly studied by theoretical methods.…”

Section: Spectral Assignmentmentioning

confidence: 99%

A conformational study of hydroxyflavones by vibrational spectroscopy coupled to DFT calculations

Machado

Carvalho

Otero

et al. 2013

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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This article appeared in a journal published by Elsevier. The attached copy is furnished to the author for internal non-commercial research and education use, including for instruction at the authors institution and sharing with colleagues.Other uses, including reproduction and distribution, or selling or licensing copies, or posting to personal, institutional or third party websites are prohibited. The conformational preferences of a series of hydroxyflavones were studied by Raman and FTIR spectroscopies, coupled to Density Functional Theory calculations. Special attention was paid to the effect of hydroxyl substitution, due to its importance on the biological activity of these compounds. Their conformational preferences were found to be determined mainly by the orientation of the hydroxylic groups at C 7 and within the catechol moiety, leading to the occurrence of distinct conformers in the solid state. A complete assignment of the experimental spectra was carried out for these molecules, in the light of their most stable conformers and the corresponding predicted vibrational pattern.

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Structural and vibrational study of 3-hydroxyflavone and 3-methoxyflavone

Cited by 46 publications

References 10 publications

Discrimination of carotenoid and flavonoid content in petals of pansy cultivars (Viola x wittrockiana) by FT‐Raman spectroscopy

Discrimination of carotenoid and flavonoid content in petals of pansy cultivars (Viola x wittrockiana) by FT‐Raman spectroscopy

Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations

A conformational study of hydroxyflavones by vibrational spectroscopy coupled to DFT calculations

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