Excited states of anthocyanins: the chalcone isomers of malvidin 3,5‐diglucoside

J. C. Lima; Parvin Danesh; Paulo Figueiredo; Fernando S. Pina; António Maçanita

doi:10.1111/j.1751-1097.1994.tb05057.x

Excited states of anthocyanins: the chalcone isomers of malvidin 3,5‐diglucoside

J. C. Lima, Parvin Danesh, Paulo Figueiredo, Fernando S. Pina, António Maçanita

Research output: Contribution to journal › Article › peer-review

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Abstract

Abstract The excited state properties of the chalcone isomers of malvidin 3,5‐diglucoside (malvin) in acidic aqueous solution (0 < pH < 4) were investigated using steady‐state and time‐resolved fluorescence spectroscopy. The two chalcone isomers of malvin were first isolated by high‐performance liquid chromatography and then characterized by UV/visible absorption and fluorescence spectroscopy. The results were supported by molecular orbital calculations. The rate constants for photodeprotonation (k₁= 1 × 10⁹ s^−l) and protonation (k₋₁= 1.3 × 10¹⁰ L mol⁻¹ s^−l) were determined, both from the multiexponential fluorescence decays and the fluorescence intensities measured at the emission wavelengths of the neutral and ionized chalcone forms. The results here obtained are relevant for the understanding of the photoreactivity of anthocyanins in acidic medium.

Original language	English
Pages (from-to)	412-418
Number of pages	7
Journal	Photochemistry And Photobiology
Volume	59
Issue number	4
DOIs	https://doi.org/10.1111/j.1751-1097.1994.tb05057.x
Publication status	Published - 1 Jan 1994

Keywords

Flavylium ion
Hydration
Chemistry
Pigments

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title = "Excited states of anthocyanins: the chalcone isomers of malvidin 3,5‐diglucoside",

abstract = "Abstract The excited state properties of the chalcone isomers of malvidin 3,5‐diglucoside (malvin) in acidic aqueous solution (0 < pH < 4) were investigated using steady‐state and time‐resolved fluorescence spectroscopy. The two chalcone isomers of malvin were first isolated by high‐performance liquid chromatography and then characterized by UV/visible absorption and fluorescence spectroscopy. The results were supported by molecular orbital calculations. The rate constants for photodeprotonation (k1= 1 × 109 s−l) and protonation (k−1= 1.3 × 1010 L mol−1 s−l) were determined, both from the multiexponential fluorescence decays and the fluorescence intensities measured at the emission wavelengths of the neutral and ionized chalcone forms. The results here obtained are relevant for the understanding of the photoreactivity of anthocyanins in acidic medium.",

keywords = "Flavylium ion, Hydration, Chemistry, Pigments",

author = "Lima, {J. C.} and Parvin Danesh and Paulo Figueiredo and Pina, {Fernando S.} and Ant{\'o}nio Ma{\c c}anita",

year = "1994",

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doi = "10.1111/j.1751-1097.1994.tb05057.x",

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T1 - Excited states of anthocyanins: the chalcone isomers of malvidin 3,5‐diglucoside

AU - Lima, J. C.

AU - Danesh, Parvin

AU - Figueiredo, Paulo

AU - Pina, Fernando S.

AU - Maçanita, António

PY - 1994/1/1

Y1 - 1994/1/1

N2 - Abstract The excited state properties of the chalcone isomers of malvidin 3,5‐diglucoside (malvin) in acidic aqueous solution (0 < pH < 4) were investigated using steady‐state and time‐resolved fluorescence spectroscopy. The two chalcone isomers of malvin were first isolated by high‐performance liquid chromatography and then characterized by UV/visible absorption and fluorescence spectroscopy. The results were supported by molecular orbital calculations. The rate constants for photodeprotonation (k1= 1 × 109 s−l) and protonation (k−1= 1.3 × 1010 L mol−1 s−l) were determined, both from the multiexponential fluorescence decays and the fluorescence intensities measured at the emission wavelengths of the neutral and ionized chalcone forms. The results here obtained are relevant for the understanding of the photoreactivity of anthocyanins in acidic medium.

AB - Abstract The excited state properties of the chalcone isomers of malvidin 3,5‐diglucoside (malvin) in acidic aqueous solution (0 < pH < 4) were investigated using steady‐state and time‐resolved fluorescence spectroscopy. The two chalcone isomers of malvin were first isolated by high‐performance liquid chromatography and then characterized by UV/visible absorption and fluorescence spectroscopy. The results were supported by molecular orbital calculations. The rate constants for photodeprotonation (k1= 1 × 109 s−l) and protonation (k−1= 1.3 × 1010 L mol−1 s−l) were determined, both from the multiexponential fluorescence decays and the fluorescence intensities measured at the emission wavelengths of the neutral and ionized chalcone forms. The results here obtained are relevant for the understanding of the photoreactivity of anthocyanins in acidic medium.

KW - Flavylium ion

KW - Hydration

KW - Chemistry

KW - Pigments

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SN - 0031-8655

VL - 59

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IS - 4

ER -

Excited states of anthocyanins: the chalcone isomers of malvidin 3,5‐diglucoside

Abstract

Keywords

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