Multifunctional Tyrosinase Inhibitor Peptides with Copper Chelating, UV-Absorption and Antioxidant Activities: Kinetic and Docking Studies

Yap, Pei-Gee; Gan, Chee-Yuen

doi:10.3390/foods10030675

Cited by 18 publications

(5 citation statements)

References 50 publications

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“…Therefore, procyanidins, caffeoylquinic acids, and phenolic glycosides contribute significantly to the antioxidant capacity and TYR inhibition activity of P. fortuneana fruits. Furthermore, tryptophan also has a strong contribution, which is consistent with studies that tryptophan has a good antioxidant capacity and can form complexes with TYR, thereby inhibiting its activity (Baenas et al., 2023; Yap & Gan, 2021). Therefore, the seven screened components significantly influence the classification of P. fortuneana fruits at different developmental stages.…”

Section: Resultssupporting

confidence: 84%

Diversity in Pyracantha fortuneana fruits maturity stages enables discrepancy in the phenolic compounds, antioxidant activity, and tyrosinase inhibitory activity

Wang,

Shao,

Yang

et al. 2024

Journal of Food Science

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Pyracantha fortuneana (P. fortuneana) fruit is a wild fruit that is popular because of its delicious taste and numerous nutrients, and phenolic compounds are considered to be the main bioactive components in P. fortuneana fruits. However, the relationship between phenolic compounds and their antioxidant and tyrosinase (TYR) inhibitory activities during the ripening process is still unclear. The study compared the influence of the five developmental stages on the accumulation of phenolic compounds, antioxidant activity, and TYR inhibitory activity in the fruits of P. fortuneana. The compounds were identified by offline two‐dimensional liquid chromatography‐electrochemical detection (2D‐LC‐ECD) combined with liquid chromatography–tandem mass spectrometry, and the main active ingredients were quantified. The results showed that stage II had higher total phenolic and flavonoid content, as well as higher antioxidant and TYR inhibitory activity, but the total anthocyanin content was lowest at this stage. A total of 30 compounds were identified by 2D‐LC‐ECD. Orthogonal partial least squares discriminant analysis screened out six major potential markers, including phenolic acids, procyanidins, and flavonoids. In addition, it was found that caffeoylquinic acids, procyanidins, and flavonoids were higher in stage II than in stages I, III, IV, and V, whereas anthocyanins accumulated gradually from stages III to V. Therefore, this study suggests that the changes in antioxidant and TYR inhibitory activities of P. fortuneana during the five developmental stages may be due to the transformation of procyanidins, caffeoylquinic acids, and phenolic glycosides into other forms during the fruit maturation process.Practical Application: Differences in chemical constituents, antioxidant, and tyrosinase inhibitory activities in fruit maturity stages of P. fortuneana were elucidated to provide reference for rational harvesting and utilization of the fruits and their bioactive components. These findings are expected to provide a comprehensive assessment of the bioactive profile and guide the food industrial production.

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Section: Resultssupporting

confidence: 84%

Diversity in Pyracantha fortuneana fruits maturity stages enables discrepancy in the phenolic compounds, antioxidant activity, and tyrosinase inhibitory activity

Wang,

Shao,

Yang

et al. 2024

Journal of Food Science

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“…It has been reported that tyrosinase inhibitory peptides should be composed with arginine and/or phenylalanine for strong binding with tyrosinase and inhibitory activity. Additionally, hydrophobic amino acids such as valine, alanine, and leucine, as well as aromatic residual of threonine and tyrosine, are also essential for the activity of tyrosinase inhibitory peptides [ 37 , 38 ]. The anti-melanogenic potential of sericin was discovered through its activity as a mushroom tyrosinase inhibitor [ 21 , 22 ].…”

Section: Discussionmentioning

confidence: 99%

Recycled Sericin Hydrolysates Modified by Alcalase® Suppress Melanogenesis in Human Melanin-Producing Cells via Modulating MITF

Joyjamras

Netcharoensirisuk

Roytrakul

et al. 2022

IJMS

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Because available depigmenting agents exhibit short efficacy and serious side effects, sericin, a waste protein from the silk industry, was hydrolyzed using Alcalase® to evaluate its anti-melanogenic activity in human melanin-producing cells. Sericin hydrolysates consisted of sericin-related peptides in differing amounts and smaller sizes compared with unhydrolyzed sericin, as respectively demonstrated by peptidomic and SDS-PAGE analysis. The lower half-maximum inhibitory concentration (9.05 ± 0.66 mg/mL) compared with unhydrolyzed sericin indicated a potent effect of sericin hydrolysates on the diminution of melanin content in human melanoma MNT1 cells. Not only inhibiting enzymatic activity but also a downregulated expression level of tyrosinase was evident in MNT1 cells incubated with 20 mg/mL sericin hydrolysates. Quantitative RT-PCR revealed the decreased mRNA level of microphthalmia-associated transcription factor (MITF), a tyrosinase transcription factor, which correlated with the reduction of pCREB/CREB, an upstream cascade, as assessed by Western blot analysis in MNT1 cells cultured with 20 mg/mL sericin hydrolysates for 12 h. Interestingly, treatment with sericin hydrolysates for 6–24 h also upregulated pERK, a molecule that triggers MITF degradation, in human melanin-producing cells. These results warrant the recycling of wastewater from the silk industry for further development as a safe and effective treatment of hyperpigmentation disorders.

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“…For peptides, diphenolase inhibitory peptides interact with aromatic amino acid residues and chelate copper ions within the active site adjacent to the substrate-binding pocket. The GYSLGNWVCAAK peptide acts as a competitive inhibitor with copper chelating activity [133]. Recently, from rice-bran albumin, the SSEYYGGEGSSSEQGYYGEG peptide has been shown to have effective tyrosinase inhibitory and copper-chelating activities.…”

Section: Copper Chelating Tyrosinase Inhibitorsmentioning

confidence: 99%

Naturally-Occurring Tyrosinase Inhibitors Classified by Enzyme Kinetics and Copper Chelation

Kim

Choi

Abekura

et al. 2023

IJMS

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Currently, there are three major assaying methods used to validate in vitro whitening activity from natural products: methods using mushroom tyrosinase, human tyrosinase, and dopachrome tautomerase (or tyrosinase-related protein-2, TRP-2). Whitening agent development consists of two ways, melanin synthesis inhibition in melanocytes and downregulation of melanocyte stimulation. For melanin levels, the melanocyte cell line has been used to examine melanin synthesis with the expression levels of TRP-1 and TRP-2. The proliferation of epidermal surfaced cells and melanocytes is stimulated by cellular signaling receptors, factors, or mediators including endothelin-1, α-melanocyte-stimulating hormone, nitric oxide, histamine, paired box 3, microphthalmia-associated transcription factor, pyrimidine dimer, ceramide, stem cell factors, melanocortin-1 receptor, and cAMP. In addition, the promoter region of melanin synthetic genes including tyrosinase is upregulated by melanocyte-specific transcription factors. Thus, the inhibition of growth and melanin synthesis in gene expression levels represents a whitening research method that serves as an alternative to tyrosinase inhibition. Many researchers have recently presented the bioactivity-guided fractionation, discovery, purification, and identification of whitening agents. Melanogenesis inhibition can be obtained using three different methods: tyrosinase inhibition, copper chelation, and melanin-related protein downregulation. There are currently four different types of inhibitors characterized based on their enzyme inhibition mechanisms: competitive, uncompetitive, competitive/uncompetitive mixed-type, and noncompetitive inhibitors. Reversible inhibitor types act as suicide substrates, where traditional inhibitors are classified as inactivators and reversible inhibitors based on the molecule-recognizing properties of the enzyme. In a minor role, transcription factors can also be downregulated by inhibitors. Currently, the active site copper iron-binding inhibitors such as kojic acid and chalcone exhibit tyrosinase inhibitory activity. Because the tyrosinase catalysis site structure is important for the mechanism determination of tyrosinase inhibitors, understanding the enzyme recognition and inhibitory mechanism of inhibitors is essential for the new development of tyrosinase inhibitors. The present review intends to classify current natural products identified by means of enzyme kinetics and copper chelation to exhibit tyrosinase enzyme inhibition.

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Multifunctional Tyrosinase Inhibitor Peptides with Copper Chelating, UV-Absorption and Antioxidant Activities: Kinetic and Docking Studies

Cited by 18 publications

References 50 publications

Diversity in Pyracantha fortuneana fruits maturity stages enables discrepancy in the phenolic compounds, antioxidant activity, and tyrosinase inhibitory activity

Diversity in Pyracantha fortuneana fruits maturity stages enables discrepancy in the phenolic compounds, antioxidant activity, and tyrosinase inhibitory activity

Recycled Sericin Hydrolysates Modified by Alcalase® Suppress Melanogenesis in Human Melanin-Producing Cells via Modulating MITF

Naturally-Occurring Tyrosinase Inhibitors Classified by Enzyme Kinetics and Copper Chelation

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