Polyphenol oxidase inhibited by 4-hydroxycinnamic acid and naringenin: Multi-spectroscopic analyses and molecular docking simulation at different pH

Jiang, Hong; Zhou, Lei; Sun, Yuefang; Yu, Kaibo; Yu, Wenzhi; Tian, Yuqing; Liu, Junping; Zou, Liqiang; Liu, Wei

doi:10.1016/j.foodchem.2022.133662

Cited by 17 publications

(3 citation statements)

References 34 publications

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“…The result suggested a stronger bonding between enzyme and CHOS-PPN conjugates [ 23 ]. The biomolecular quenching constant ( kq ) of PPO by CHOS or CHOS-PPN conjugates was in the order of 10 13 L/mol/s ( Table 2 and Figure 3 E–H), which was higher than the dynamic quenching rate constant (2 × 10 10 L/mol/s), regardless of the temperature used [ 24 ]. Therefore, static quenching was suggested for all samples, which was in line with K SV .…”

Section: Resultsmentioning

confidence: 99%

Inhibition Mechanism of Chitooligosaccharide-Polyphenol Conjugates toward Polyphenoloxidase from Shrimp Cephalothorax

et al. 2023

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Crustaceans are perishable with a short shelf-life. They are prone to deterioration after capture, particularly during handling, processing, and storage due to melanosis caused by polyphenoloxidase (PPO). Therefore, inhibitory effects of chitooligosaccharide (CHOS) in comparison with CHOS-catechin (CHOS-CAT), CHOS-epigallocatechin gallate (CHOS-EGCG), and CHOS-gallic acid (CHOS-GAL) conjugates on Pacific white shrimp cephalothorax PPO were studied. IC50 of CHOS-CAT (0.32 mg/mL) toward PPO was less than those of all conjugates tested (p < 0.05). CHOS-CAT exhibited the mixed-type inhibition. Kic (0.58 mg/mL) and Kiu (0.02 mg/mL) of CHOS-CAT were lower than those of other conjugates (p < 0.05). CHOS-CAT showed static fluorescence-quenching, suggesting a change in micro-environment around the active site of PPO. Moreover, CHOS-CAT was linked with various amino acid residues, including Tyr208 or Tyr209 of proPPO via van der Waals, hydrophobic interaction, and hydrogen bonding as elucidated by the molecular docking of proPPO. Although CHOS-CAT had the highest PPO inhibitory activity, it showed a lower binding energy (−8.5 kcal/mol) than other samples, except for CHOS-EGCG (−10.2 kcal/mol). Therefore, CHOS-CAT could act as an anti-melanosis agent in shrimp and other crustaceans to prevent undesirable discoloration associated with quality losses.

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Section: Resultsmentioning

confidence: 99%

Inhibition Mechanism of Chitooligosaccharide-Polyphenol Conjugates toward Polyphenoloxidase from Shrimp Cephalothorax

et al. 2023

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“…PPO is inactive at pH values below 3 (Moon et al, 2020). Jiang et al (2022) suggested that acidic pH markedly strengthened the inhibitory effect of phenolic acids on PPO. For the nonenzymatic oxidation of catechin, the reaction was highly dependent on pH, and it had a higher oxidation rate at neutral pH (Janeiro & Oliveira Brett, 2004).…”

Section: Phmentioning

confidence: 99%

From polyphenol to o‐quinone: Occurrence, significance, and intervention strategies in foods and health implications

Geng

Liu

et al. 2023

Comp Rev Food Sci Food Safe

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Polyphenol oxidation is a chemical process impairing food freshness and other desirable qualities, which has become a serious problem in fruit and vegetable processing industry. It is crucial to understand the mechanisms involved in these detrimental alterations. o-Quinones are primarily generated by polyphenols with di/tri-phenolic groups through enzymatic oxidation and/or auto-oxidation. They are highly reactive species, which not only readily suffer the attack by nucleophiles but also powerfully oxidize other molecules presenting lower redox potentials via electron transfer reactions. These reactions and subsequent complicated reactions are capable of initiating quality losses in foods, such as browning, aroma loss, and nutritional decline. To attenuate these adverse influences, a variety of technologies have emerged to restrain polyphenol oxidation via governing different factors, especially polyphenol oxidases and oxygen. Despite tremendous efforts devoted, to date, the loss of food quality caused by quinones has remained a great challenge in the food processing industry. Furthermore, o-quinones are responsible for the chemopreventive effects and/or toxicity of the parent catechols on human health, the mechanisms by which are quite complex. Herein, this review focuses on the generation and reactivity of oquinones, attempting to clarify mechanisms involved in the quality deterioration of foods and health implications for humans. Potential innovative inhibitors and technologies are also presented to intervene in o-quinone formation and subsequent reactions. In future, the feasibility of these inhibitory strategies should be evaluated, and further exploration on biological targets of o-quinones is of great necessity.

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“…Among these compounds, 3-hydroxybenzoic acid was found to be the most effective inhibitor. Moreover, Jiang et al (2022) studied the PPO inhibition by 4-hydroxycinnamic acid and naringenin and showed that both compounds exhibited an inhibitory effect, with 4-hydroxycinnamic acid being the most competitive inhibitor. Furthermore, different studies suggested that epigallocatechin-3-gallate (Tian et al, 2022), quercetin (Aksoy, 2020), and cyanidin-3-sophoroside (Hemachandran et al, 2017) may inhibit PPO.…”

Section: Inhibitory Effectmentioning

confidence: 99%

Advanced interactional characterization of the inhibitory effect of anthocyanin extract from Hibiscus sabdariffa L. on apple polyphenol oxidase

(Boldea),

Aprodu,

Enachi

et al. 2023

Journal of Food Science

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In this study, a comprehensive approach to advance the inhibitory effect of Hibiscus sabdariffa extract on apple polyphenol oxidase (PPO) was performed. PPO was extracted, purified, and characterized for optimal activity, whereas response surface methodology generated a quadratic polynomial model to fit the experimental results for hibiscus extraction. The optimum conditions allowed to predict a maximum recovery of anthocyanins (256.11 mg delphinidin‐3‐O‐glucoside/g), with a validated value of 272.87 mg delphinidin‐3‐O‐glucoside/g dry weight (DW). The chromatographic methods highlighted the presence of gallic acid (36,812.90 µg/g DW extract), myricetin (141,933.84 µg/g DW extract), caffeic acid (101,394.07 µg/g DW extract), sinapic acid (1157.46 µg/g DW extract), kaempferol (2136.76 µg/g DW extract), and delphinidin 3‐O‐β‐d‐glucoside (226,367.08 µg/g DW extract). The inactivation of PPO followed a first‐order kinetic model. A temperature‐mediated flexible fit between PPO and anthocyanins was suggested, whereas the molecular docking tests indicated that PPO is a good receptor for cafestol, gallic acid, and catechin, involving hydrophobic and hydrogen bond interactions.Practical ApplicationIt is well known that enzymatic browning is one of the most important challenges in the industrial minimal processing of selected fruit and vegetable products. Novel inhibitors for polyphenol oxidase are proposed in this study by using an anthocyanin‐enriched extract from Hibiscus sabdariffa L. Based on our results, combining the chemical effect of phytochemicals from hibiscus extract with different functional groups with minimal heating could be an interesting approach for the development of a new strategy to inhibit apple polyphenol oxidase.

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Polyphenol oxidase inhibited by 4-hydroxycinnamic acid and naringenin: Multi-spectroscopic analyses and molecular docking simulation at different pH

Cited by 17 publications

References 34 publications

Inhibition Mechanism of Chitooligosaccharide-Polyphenol Conjugates toward Polyphenoloxidase from Shrimp Cephalothorax

Inhibition Mechanism of Chitooligosaccharide-Polyphenol Conjugates toward Polyphenoloxidase from Shrimp Cephalothorax

From polyphenol to o‐quinone: Occurrence, significance, and intervention strategies in foods and health implications

Advanced interactional characterization of the inhibitory effect of anthocyanin extract from Hibiscus sabdariffa L. on apple polyphenol oxidase

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