The peculiarity of malvidin 3-O-(6-O-p-coumaroyl) glucoside aggregation. Intra and intermolecular interactions

Johan Mendoza; Joana Oliveira; Paula Araújo; Nuno Basílio; Natércia Teixeira; Natércia F. Brás; Fernando Pina; Kumi Yoshida; Victor de Freitas

doi:10.1016/j.dyepig.2020.108382

The peculiarity of malvidin 3-O-(6-O-p-coumaroyl) glucoside aggregation. Intra and intermolecular interactions

Johan Mendoza, Joana Oliveira, Paula Araújo, Nuno Basílio, Natércia Teixeira, Natércia F. Brás, Fernando Pina, Kumi Yoshida, Victor de Freitas

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Abstract

The aggregation of malvidin 3-O-(6-O-p-coumaroyl) glucoside flavylium cation (OeninCoum) in water is reported. Intra and intermolecular interactions of OeninCoum were characterized by UV–vis absorption, ¹H NMR and circular dichroism (CD). Theoretical calculations were also performed to describe the intramolecular interactions. At higher temperature (>60 °C) the intermolecular aggregates are disrupted but CD signal attributed to an intramolecular interaction remains. Moreover, the kinetic and thermodynamic data for Oenin and OeninCoum at 50 °C and 25 °C shows that the increase of temperature stabilizes the quinoidal base of this later.

Original language	English
Article number	108382
Journal	Dyes and Pigments
Volume	180
DOIs	https://doi.org/10.1016/j.dyepig.2020.108382
Publication status	Published - Sep 2020

Keywords

CD
Coumaroyl derivatives
Intramolecular and intermolecular interactions
NMR
Oenin
Temperature

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10.1016/j.dyepig.2020.108382Licence: CC BY-NC-ND

Mendoza et al.revisedAccepted author manuscript, 1.53 MBLicence: CC BY-NC-ND

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title = "The peculiarity of malvidin 3-O-(6-O-p-coumaroyl) glucoside aggregation. Intra and intermolecular interactions",

abstract = "The aggregation of malvidin 3-O-(6-O-p-coumaroyl) glucoside flavylium cation (OeninCoum) in water is reported. Intra and intermolecular interactions of OeninCoum were characterized by UV–vis absorption, 1H NMR and circular dichroism (CD). Theoretical calculations were also performed to describe the intramolecular interactions. At higher temperature (>60 °C) the intermolecular aggregates are disrupted but CD signal attributed to an intramolecular interaction remains. Moreover, the kinetic and thermodynamic data for Oenin and OeninCoum at 50 °C and 25 °C shows that the increase of temperature stabilizes the quinoidal base of this later.",

keywords = "CD, Coumaroyl derivatives, Intramolecular and intermolecular interactions, NMR, Oenin, Temperature",

author = "Johan Mendoza and Joana Oliveira and Paula Ara{\'u}jo and Nuno Bas{\'i}lio and Nat{\'e}rcia Teixeira and Br{\'a}s, {Nat{\'e}rcia F.} and Fernando Pina and Kumi Yoshida and {de Freitas}, Victor",

note = "UIDB/50006/2020 PTDC/QUI-OUT/29013/2017 MEX/Ref. 288188 SFRH/BD/143309/2019 IF/00225/2015 IF/01355/2014 CEECIND/00466/2017 REQUIMTE/EEC2018/PTDC/QUI-OUT/29925/2017 ",

year = "2020",

month = sep,

doi = "10.1016/j.dyepig.2020.108382",

language = "English",

volume = "180",

journal = "Dyes and Pigments",

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TY - JOUR

T1 - The peculiarity of malvidin 3-O-(6-O-p-coumaroyl) glucoside aggregation. Intra and intermolecular interactions

AU - Mendoza, Johan

AU - Oliveira, Joana

AU - Araújo, Paula

AU - Basílio, Nuno

AU - Teixeira, Natércia

AU - Brás, Natércia F.

AU - Pina, Fernando

AU - Yoshida, Kumi

AU - de Freitas, Victor

N1 - UIDB/50006/2020 PTDC/QUI-OUT/29013/2017 MEX/Ref. 288188 SFRH/BD/143309/2019 IF/00225/2015 IF/01355/2014 CEECIND/00466/2017 REQUIMTE/EEC2018/PTDC/QUI-OUT/29925/2017

PY - 2020/9

Y1 - 2020/9

N2 - The aggregation of malvidin 3-O-(6-O-p-coumaroyl) glucoside flavylium cation (OeninCoum) in water is reported. Intra and intermolecular interactions of OeninCoum were characterized by UV–vis absorption, 1H NMR and circular dichroism (CD). Theoretical calculations were also performed to describe the intramolecular interactions. At higher temperature (>60 °C) the intermolecular aggregates are disrupted but CD signal attributed to an intramolecular interaction remains. Moreover, the kinetic and thermodynamic data for Oenin and OeninCoum at 50 °C and 25 °C shows that the increase of temperature stabilizes the quinoidal base of this later.

AB - The aggregation of malvidin 3-O-(6-O-p-coumaroyl) glucoside flavylium cation (OeninCoum) in water is reported. Intra and intermolecular interactions of OeninCoum were characterized by UV–vis absorption, 1H NMR and circular dichroism (CD). Theoretical calculations were also performed to describe the intramolecular interactions. At higher temperature (>60 °C) the intermolecular aggregates are disrupted but CD signal attributed to an intramolecular interaction remains. Moreover, the kinetic and thermodynamic data for Oenin and OeninCoum at 50 °C and 25 °C shows that the increase of temperature stabilizes the quinoidal base of this later.

KW - CD

KW - Coumaroyl derivatives

KW - Intramolecular and intermolecular interactions

KW - NMR

KW - Oenin

KW - Temperature

UR - http://www.scopus.com/inward/record.url?scp=85083346858&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2020.108382

DO - 10.1016/j.dyepig.2020.108382

M3 - Article

AN - SCOPUS:85083346858

VL - 180

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

M1 - 108382

ER -

The peculiarity of malvidin 3-O-(6-O-p-coumaroyl) glucoside aggregation. Intra and intermolecular interactions

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Keywords

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