Depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities

Cho, Jun-Cheol; Rho, Ho Sik; Joo, Yung Hyup; Lee, Chang Seok; Lee, Jaekyoung; Ahn, Soo Mi; Kim, Jung Eun; Shin, Song Seok; Suh, Kyung‐Do; Park, Soo Nam

doi:10.1016/j.bmcl.2012.04.046

Cited by 18 publications

(12 citation statements)

References 20 publications

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“…Among them, kojic acid-phenylalanine amide showed a strong noncompetitive inhibition 417 . Interestingly, some kojic acid derivatives despite their depigmenting activities did not display tyrosinase inhibitory activitiy 419 .…”

Section: Inhibitors From Natural Semisynthetic and Synthetic Sourcesmentioning

confidence: 99%

A comprehensive review on tyrosinase inhibitors

Zolghadri

Bahrami

Khan³

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

740

471

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Tyrosinase is a multi-copper enzyme which is widely distributed in different organisms and plays an important role in the melanogenesis and enzymatic browning. Therefore, its inhibitors can be attractive in cosmetics and medicinal industries as depigmentation agents and also in food and agriculture industries as antibrowning compounds. For this purpose, many natural, semi-synthetic and synthetic inhibitors have been developed by different screening methods to date. This review has focused on the tyrosinase inhibitors discovered from all sources and biochemically characterised in the last four decades.

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Section: Inhibitors From Natural Semisynthetic and Synthetic Sourcesmentioning

confidence: 99%

A comprehensive review on tyrosinase inhibitors

Zolghadri

Bahrami

Khan³

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

740

471

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“…Some articles evaluated kojic acid and/or its derivatives applying both methods (inhibition of tyrosinase and melanin content). 18,29,34,[41][42][43] Benzoate ester derivatives were tested, and, while compounds without adamantane moiety inhibited mushroom tyrosinase but did not inhibit melanin synthesis, the ones with adamantane moiety did otherwise, which is probably related to the differences between the amino acid…”

Section: Moleculementioning

confidence: 99%

Biological activities and safety data of kojic acid and its derivatives: A review

Zilles

Santos

Külkamp‐Guerreiro

et al. 2022

Experimental Dermatology

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Kojic acid (5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) is an organic acid derived from the fermentation of fungi of diverse genus such as Aspergillus and Penicillium, 1 and it was first isolated in 1907. 2,3 Its most common use is as a skin depigmenting agent, attributed mainly to the inhibition of tyrosinase, which is the key enzyme in melanin synthesis. Leucocyte modulation, copper-chelating action and free radical scavenging are also involved in kojic acid depigmenting mechanism. Besides that, antioxidant, antibacterial and anti-inflammatory activities were also reported. 4 There have been reports of antimicrobial and toxicity studies since the forties, 2 but mechanisms of action have not yet been fully elucidated.Among the disadvantages of this molecule, one can mention the possibility of causing contact dermatitis, sensitization, redness and erythema. 5 Kojic acid also has low stability, being sensitive to light

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“…Adamantane is a privileged structure that has earned the reputation of being a “lipophilic bullet” for enhancing pharmacological activity 34 and various methods have been devised for their derivatization, 35 including a Friedel–Crafts strategy that requires trifluoroacetic acid as the solvent. 36 Here, dual FeCl 3 /HCl catalysis allows arylation of 1-adamantanol under mild reaction conditions. Surprisingly, 1-methylcyclopentanol (11e) turned out to be a poor alkylating agent that only gave 23% yield of para -methylcyclopentyl phenol (3ae) even with a higher catalyst loading.…”

Section: Resultsmentioning

confidence: 99%