The fate of acylated anthocyanins in mildly heated neutral solution

Fenger, Julie-Anne; Robbins, Rebecca J.; Collins, Thomas M.; Dangles, Olivier

doi:10.1016/j.dyepig.2020.108326

Cited by 31 publications

(27 citation statements)

References 27 publications

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“…can also conduct to other compounds, e.g., 3,5,7-trihydroxycoumarin and 2,4,6-trihydroxyphenylacetic acid as reported in Fenger et al [21]. Recently, some researchers showed that gallic acid and phloroglucinaldehyde resulting from eggplant anthocyanin degradation are further oxidized into pyrogallol and phloroglucinol, respectively [22].…”

Section: Kinetics and Thermal Degradation Route Of Anthocyaninsmentioning

confidence: 95%

A Review of the Current Knowledge of Thermal Stability of Anthocyanins and Approaches to Their Stabilization to Heat

Oancea

2021

Antioxidants

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Anthocyanins are colored valuable biocompounds, of which extraction increases globally, although functional applications are restrained by their limited environmental stability. Temperature is a critical parameter of food industrial processing that impacts on the food matrix, particularly affecting heat-sensitive compounds such as anthocyanins. Due to the notable scientific progress in the field of thermal stability of anthocyanins, an analytical and synthetic integration of published data is required. This review focuses on the molecular mechanisms and the kinetic parameters of anthocyanin degradation during heating, both in extracts and real food matrices. Several kinetic models (Arrhenius, Eyring, Ball) of anthocyanin degradation were studied. Crude extracts deliver more thermally stable anthocyanins than purified ones. A different anthocyanin behavior pattern within real food products subjected to thermal processing has been observed due to interactions with some nutrients (proteins, polysaccharides). The most recent studies on the stabilization of anthocyanins by linkages to other molecules using classical and innovative methods are summarized. Ensuring appropriate thermal conditions for processing anthocyanin-rich food will allow a rational design for the future development of stable functional products, which retain these bioactive molecules and their functionalities to a great extent.

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Section: Kinetics and Thermal Degradation Route Of Anthocyaninsmentioning

confidence: 95%

A Review of the Current Knowledge of Thermal Stability of Anthocyanins and Approaches to Their Stabilization to Heat

Oancea

2021

Antioxidants

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“…However, after Fe 2+ addition, autoxidation was strongly accelerated for PA because the corresponding iron complex was not stable enough, and the protection offered by iron binding was significant for P4 and PB only. In our recent work, adding Fe 2+ also was shown to increase the yield in some major degradation products of PA and P1 [ 18 ]. In summary, strong π-stacking interactions within the complexes ensured an efficient iron sequestration, thus preventing the pro-oxidant activity of loosely bound iron ions [ 16 ].…”

Section: Resultsmentioning

confidence: 99%

“…In summary, strong π-stacking interactions within the complexes ensured an efficient iron sequestration, thus preventing the pro-oxidant activity of loosely bound iron ions [ 16 ]. The tight metal binding also explained the total inhibition of intramolecular acyl transfer, normally occurring when solutions of P4 or PB are heated [ 18 ].…”

Section: Resultsmentioning

confidence: 99%

Acylated Anthocyanins from Red Cabbage and Purple Sweet Potato Can Bind Metal Ions and Produce Stable Blue Colors

Fenger

Sigurdson

Robbins³

et al. 2021

IJMS

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Red cabbage (RC) and purple sweet potato (PSP) are naturally rich in acylated cyanidin glycosides that can bind metal ions and develop intramolecular π-stacking interactions between the cyanidin chromophore and the phenolic acyl residues. In this work, a large set of RC and PSP anthocyanins was investigated for its coloring properties in the presence of iron and aluminum ions. Although relatively modest, the structural differences between RC and PSP anthocyanins, i.e., the acylation site at the external glucose of the sophorosyl moiety (C2-OH for RC vs. C6-OH for PSP) and the presence of coordinating acyl groups (caffeoyl) in PSP anthocyanins only, made a large difference in the color expressed by their metal complexes. For instance, the Al3+-induced bathochromic shifts for RC anthocyanins reached ca. 50 nm at pH 6 and pH 7, vs. at best ca. 20 nm for PSP anthocyanins. With Fe2+ (quickly oxidized to Fe3+ in the complexes), the bathochromic shifts for RC anthocyanins were higher, i.e., up to ca. 90 nm at pH 7 and 110 nm at pH 5.7. A kinetic analysis at different metal/ligand molar ratios combined with an investigation by high-resolution mass spectrometry suggested the formation of metal–anthocyanin complexes of 1:1, 1:2, and 1:3 stoichiometries. Contrary to predictions based on steric hindrance, acylation by noncoordinating acyl residues favored metal binding and resulted in complexes having much higher molar absorption coefficients. Moreover, the competition between metal binding and water addition to the free ligands (leading to colorless forms) was less severe, although very dependent on the acylation site(s). Overall, anthocyanins from purple sweet potato, and even more from red cabbage, have a strong potential for development as food colorants expressing red to blue hues depending on pH and metal ion.

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“…A similar behaviour was observed also for INZEA_7ATM1 (a* = 9.62 ± 0.22). As it has been discussed in Section 3.2, ACNs at acid pH values were stabilized as the flavylium cation form and so intense reds were expected thanks to the extended conjugation between the two aromatic fragments that allows the absorption of visible light with a variable wavelength ranging from 480-550 cm −1 , depending on the substituents of the rings [23,57,58].…”

Section: Colour Propertiesmentioning

confidence: 95%

“…The lower a* value was obtained for INZEA_7ATM10 (1.41 ± 0.01) which showed the clearest and most similar colour to that of neat INZEA (light biscuit colour) and the lowest ∆E* value. This behaviour was related to the pH value applied during the nanofiller synthesis without the presence of any modifier (nanopigment ATM10 in Table 1), being ACNs a mixture of neutral and anionic bases slowly evolving into a mixture of hemiketal and chalcones [58].…”

Section: Colour Propertiesmentioning

confidence: 99%

Anthocyanin Hybrid Nanopigments from Pomegranate Waste: Colour, Thermomechanical Stability and Environmental Impact of Polyester-Based Bionanocomposites

et al. 2021

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In the present work, anthocyanin (ACN) hybrid nanopigments were synthetized by using a natural pomegranate dye (PD) and calcined hydrotalcite (HT) and montmorillonite (MMT) nanoclays. A wide colour gamut was obtained with MMT-based nanopigments ranging from reddish to bluish hues caused by structural transformations of ACNs at different pH values. However, a buffer effect was observed with HT obtaining samples a similar final colour regardless of the synthesis conditions. Nanopigments added with a biomordant extracted from pomegranate peels showed a different colour compared to the incorporation of a commercial mordant due to the intrinsic colouring properties of the pomegranate bioadditive. The developed nanopigments were incorporated at 7 wt% loading to produce novel polyester-based bionanocomposites which were characterized in terms of thermal, mechanical and colour properties. The encapsulation of PD into the nanoclays improved its thermal stability, in particular for MMT-based nanopigments. The pH changes observed during the nanofillers synthesis affected the final colour of the MMT-based nanocomposites, inducing a general increase in ∆E* and a decrease in gloss values. Slight improvements were obtained in terms of elastic modulus for MMT-based polymer samples confirming the applicability of the developed bionanocomposites as colouring and reinforcement materials. A very similar environmental profile was obtained for MMT and HT-based nanofillers showing MMT-based nanopigments a slightly better general behaviour. The results of the LCA study evidenced the suitability of the processes used in this work to the circular bioeconomy approach through sustainable food waste management and the production of bioplastics using waste substrates.

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The fate of acylated anthocyanins in mildly heated neutral solution

Cited by 31 publications

References 27 publications

A Review of the Current Knowledge of Thermal Stability of Anthocyanins and Approaches to Their Stabilization to Heat

A Review of the Current Knowledge of Thermal Stability of Anthocyanins and Approaches to Their Stabilization to Heat

Acylated Anthocyanins from Red Cabbage and Purple Sweet Potato Can Bind Metal Ions and Produce Stable Blue Colors

Anthocyanin Hybrid Nanopigments from Pomegranate Waste: Colour, Thermomechanical Stability and Environmental Impact of Polyester-Based Bionanocomposites

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