Solid-phase synthesis of kojic acid-tripeptides and their tyrosinase inhibitory activity, storage stability, and toxicity

Kim, Hanyoung; Choi, Jaehui; Cho, Jin Ku; Kim, Sun Yeou; Lee, Jun Young

doi:10.1016/j.bmcl.2004.03.046

Cited by 81 publications

(49 citation statements)

References 8 publications

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“…The monophenolase activity and the diphenolase activity assays were performed according to a previous report with a slight modification (Kim et al 2004). L-Tyrosine (2 mM) was used as the substrate for the monophenolase activity assay, and L-DOPA (2 mM) was used as the substrate for the diphenolase activity assay.…”

Section: Effects Of Inhibitors On the Mushroom Tyrosinase Activitymentioning

confidence: 99%

A Novel Inhibitor Against Mushroom Tyrosinase with a Double Action Mode and Its Application in Controlling the Browning of Potato

Chen

Zhao

Chen

et al. 2017

Food Bioprocess Technol

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In order to search for a new method for the antibrowning of food products, a novel hydroxypyridinone (HPO) derivative with a formyl group was evaluated for its anti-tyrosinase property. This compound was found to exhibit potent tyrosinase inhibition on the monophenolase activity of mushroom tyrosinase with an IC 50 value of 1.33 μM, indicating that this HPO derivative was 12-fold stronger than kojic acid (IC 50 15.89 μM). This molecule can inhibit tyrosinase via two action modes, namely copper reduction and chelation, and the formation of a Schiff's base with the amino group at the active site of the enzyme. A synergistic effect of these two action modes to enhance the inhibitory activity was observed. This compound was also investigated for the inhibitory effect on diphenolase activity of mushroom; the inhibitory mechanism was found to be reversible and of competitive-uncompetitive mixed-type inhibition. This hydroxypyridinone was demonstrated to effectively control the browning of vegetable products.

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Section: Effects Of Inhibitors On the Mushroom Tyrosinase Activitymentioning

confidence: 99%

A Novel Inhibitor Against Mushroom Tyrosinase with a Double Action Mode and Its Application in Controlling the Browning of Potato

Chen

Zhao

Chen

et al. 2017

Food Bioprocess Technol

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“…C-7 carboxyl group of kojic acid has been converted into esters, hydroxyphenyl ethers, glycosides, and amino-acid derivatives [130]. Kojic acid conjugation to the tripeptide FWY has been investigated and studies have shown that the tripeptide decreases the acid's toxicity, increases its storage stability, and most importantly, increases the inhibitory effect by 100-fold [131].…”

Section: Tyrosinasementioning

confidence: 99%

Peptide‐Based Inhibitors of Enzymes

Knapinska

Amar

Robichaud

et al. 2015

Peptide Chemistry and Drug Design

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“…Besides that, solid-phase synthesis of kojic acid-tripeptides and their tyrosinase inhibitory activity, storage stability, and toxicity, concluded that these derivatives were almost 15 times more stable under ambient stored conditions with a lower toxicity than kojic acid itself. Kojic acid derivatives were relatively higher with tyrosinase inhibitory activities than that of kojic acid [4]. Further evidence claimed kojic acid derivatives are major class of many natural and synthetic compounds that own a high activity profile because of their wide range of biological activities [8].…”

Section: Introductionmentioning

confidence: 99%

“…Latterly, the whitening agent in this acid benefits as an essential ingredient in cosmetic cream to block the formation of pigments by the deep cells on the skin [2]. It was studied intensively by several researches due to its potential as a tyrosinase inhibitor to prevent browning in food production as well as a skin lightening agent for cosmetic preparations [3][4][5]. In Asia, hyroquinone, a well-known whitening agent, was banned for cosmetic usage for its toxicity.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Direct Esterification of Fatty Acid Derivative of Kojic Acid in Co-solvent System: A Statistical Approach

Norddin¹,

Azhar²,

Ashari³

2017

J Chem Eng Process Technol

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The present work deals with direct esterification method to synthesize Kojic acid using immobilized lipase as a biocatalyst in acetonitrile with the addition of dimethylsulfoxide (DMSO) as a solubilizing agent Co-solvent respectively. To increase the esterification yield of KMO, modifications of the process were evaluated, including the use of a cosolvent and the use of Novozyme 435 (Candida antarctica) as a catalyst. The KMO synthesis has been developed and optimized by using Response Surface Methodology (RSM) with Central Composite Rotatable Design (CCRD). The optimized condition of enzyme was 3.35 wt% and 1:3.64 molar ratio of kojic acid and oleic acid at 82.39°C for 255.24 min of reaction. With these condition, the maximum percentage yield was 42.73% with R2 value of 0.866914 and indicated that 86.69% of the variability in the response could be explained by the model. The model was significant and fitted well with the experimental data and the lack of fit was not significant. The efficacy for cosmetic application was successfully tested and showed as non-irritating with a Human Irritancy Equivalent score between 0.55-0.83 which safe to be applied in cosmetic ingredient.

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Solid-phase synthesis of kojic acid-tripeptides and their tyrosinase inhibitory activity, storage stability, and toxicity

Cited by 81 publications

References 8 publications

A Novel Inhibitor Against Mushroom Tyrosinase with a Double Action Mode and Its Application in Controlling the Browning of Potato

A Novel Inhibitor Against Mushroom Tyrosinase with a Double Action Mode and Its Application in Controlling the Browning of Potato

Peptide‐Based Inhibitors of Enzymes

Evaluation of Direct Esterification of Fatty Acid Derivative of Kojic Acid in Co-solvent System: A Statistical Approach

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