Rational synthesis and characterization of a novel pH-responsive pyranoflavylium-starch conjugate from potato sidestreams

被引：0
作者：
Cunha, Mariana [1 ]
Pires, Ana Sofia [1 ]
Sampaio-Dias, Ivo E. [1 ]
Goncalves, Idalina [2 ]
de Freitas, Victor [1 ]
Cruz, Luis [1 ]
机构：
[1] Univ Porto, Fac Ciencias, Dept Quim & Bioquim, REQUIMTE LAQV, Rua Campo Alegre 687, P-4169007 Porto, Portugal
[2] Univ Aveiro, CICECO Aveiro Inst Mat, Dept Mat & Ceram Engn, P-3810193 Aveiro, Portugal
来源：
FOOD CHEMISTRY | 2025年 / 489卷
关键词：
Pyranoflavylium dye; Starch conjugation; LC-DAD/ESI-MS; FTIR spectroscopy; Chemical equilibria; pH-responsive biomaterials;
D O I：
10.1016/j.foodchem.2025.145048
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A pH-responsive 4 '-hydroxy-10-aminoethylcarbamoylpyranoflavylium dye (PyFlav) inspired by natural compounds was synthesized and conjugated to chemically functionalized starch derived from potato industry side-streams. The PyFlav dye was characterized through LC-DAD/ESI-MS, 1D and 2D NMR, and UV-VIS spectroscopy, with acidic constant values determined as pKa1 = 5.19 +/- 0.03; pKa2= 9.27 +/- 0.22. Potato-derived native starch was oxidized and then covalently bound to the amine-containing PyFlav dye, yielding a starch-PyFlav conjugate through a Schiff base reaction. The structural and chemical properties of the oxidized starch and starch-PyFlav conjugate were studied by FTIR-ATR spectroscopy, which confirmed successful functionalization by the emergence of an imine bond in the conjugate. This conjugation will permit the formation of pH-responsive membranes/films to exploit their application as smart colorimetric labels for food spoilage monitoring.
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页数：7
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