Kojic acid–amino acid conjugates as tyrosinase inhibitors

Noh, Jihyun; Kwak, Seon‐Yeong; Seo, Hyosuk; Seo, Joo‐Hyun; Kim, Byung‐Gee; Lee, Jun Young

doi:10.1016/j.bmcl.2009.08.041

Cited by 120 publications

(65 citation statements)

References 26 publications

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“…Therefore, several attempts have successfully been made to synthesize conjugates to improve their properties. For example, Kojic acid has been conjugated by converting the C-7 hydroxyl group into an ester, hydroxyphenyl ether, glycoside, amino acid derivate or tripeptide derivates [107]. In addition to increased stability, the effect can also be modified.…”

Section: Antioxidantsmentioning

confidence: 99%

“…In addition to increased stability, the effect can also be modified. One example of successful conjugation is kojic acid-amino acid amides leading to superior effect with 90% increased tyrosinase inhibitory activity [107]. Another derivate commonly used is magnesium ascorbyl phosphate, which is a stable derivate of ascorbic acid (vitamin C), leading to reduced skin pigmentation [108].…”

Section: Antioxidantsmentioning

confidence: 99%

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The melanogenesis and mechanisms of skin‐lightening agents – existing and new approaches

Gillbro¹,

Olsson²

2011

Intern J of Cosmetic Sci

305

251

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SynopsisSkin-lightening products are commercially available for cosmetic purposes to obtain lighter skin complexion. Clinically, they are also used for treatment of hyperpigmentary disorders such as melasma, café au lait spot and solar lentigo. All of these target naturally melanin production, and many of the commonly used agents are known as competitive inhibitors of tyrosinase, one of the key enzymes in melanogenesis. In this review, we present an overview of commonly used skin-whitening ingredients that are commercialized, but we also hypothesize on other mechanisms that could be important targets to control skin pigmentation such as for example regulation of the adrenergic and glutaminergic signalling and also control of tetrahydrobiopterins in the human skin. Ré suméLes produits éclaircissants sont disponibles dans le commerce pour des buts cosmétiques afin d'obtenir un tient plus clair. Ils sont égale-ment utilisés en clinique, pour le traitement de troubles hyper pigmentaires comme le melasma, les taches café au lait et le lentigo solaire. Tous ces produits ont pour cible la production naturelle de mélanine et beaucoup de ceux généralement utilisés sont reconnus comme des inhibiteurs compétitifs de la tyrosinase, une des enzymes clés de la mélanogénèse. Dans cette revue, nous présentons une vue d'ensemble des ingrédients généralement utilisés et commercialisés comme blanchissant cutanés mais nous formulons aussi l'hypothèse que d'autres mécanismes pourraient être des cibles importantes pour contrôler la pigmentation de la peau comme par exemple la régula-tion du signal adrénergique et glutaminergique ou le contrôle des tetrahydrobiopterines dans la peau humaine.

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Section: Antioxidantsmentioning

confidence: 99%

Section: Antioxidantsmentioning

confidence: 99%

The melanogenesis and mechanisms of skin‐lightening agents – existing and new approaches

Gillbro¹,

Olsson²

2011

Intern J of Cosmetic Sci

305

251

View full text Add to dashboard Cite

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“…Some potent anti-tyrosinase agents, such as kojic acid, arbutin and deoxyarbutin, are unstable in aqueous environments [25][26][27]. Thus, we compared the stability of SJ-FC with the stabilities of two well-known and frequently used tyrosinase inhibitors, ascorbic acid and arbutin, using a tyrosinase inhibitory activity-based method in PG and H 2 …”

Section: Discussionmentioning

confidence: 99%

Tyrosinase Inhibitory Activity and Thermostability of the Flavonoid Complex from <i>Sophora japonica</i> L (Fabaceae)

Lai¹,

Lin²,

Chiang³

2014

Trop. J. Pharm Res

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“…The kojic acid is a competitive tyrosinase inhibitor and exhibited a mixed inhibitory effect on diphenolase activity of mushroom tyrosinase 31 . Therefore, we used kojic acid as the standard inhibitor of tyrosinase for comparison purposes.…”

Section: Bioassay For Inhibition Of Tyrosinase Activitymentioning

confidence: 99%

Design, synthesis and bioevaluation of novel umbelliferone analogues as potential mushroom tyrosinase inhibitors

Ashraf

Rafiq

Seo

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of umbelliferone analogues were synthesized and their inhibitory effects on the DPPH and mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant mushroom tyrosinase inhibitory activities. Especially, 2-oxo-2-[(2-oxo-2H-chromen-7-yl)oxy]ethyl-2,4-dihydroxybenzoate (4e) bearing 2,4-dihydroxy substituted phenyl ring exhibited the most potent tyrosinase inhibitory activity with IC 50 value 8.96 mM and IC 50 value of kojic acid is 16.69. The inhibition mechanism analyzed by LineweaverBurk plots revealed that the type of inhibition of compound 4e on tyrosinase was noncompetitive. The docking study against tyrosinase enzyme was also performed to determine the binding affinity of the compounds. The compounds 4c and 4e showed the highest binding affinity with active binding site of tyrosinase. The initial structure activity relationships (SARs) analysis suggested that further development of such compounds might be of interest. The statistics of our results endorses that compounds 4c and 4e may serve as a structural template for the design and development of novel tyrosinase inhibitors.

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Kojic acid–amino acid conjugates as tyrosinase inhibitors

Cited by 120 publications

References 26 publications

The melanogenesis and mechanisms of skin‐lightening agents – existing and new approaches

The melanogenesis and mechanisms of skin‐lightening agents – existing and new approaches

Tyrosinase Inhibitory Activity and Thermostability of the Flavonoid Complex from <i>Sophora japonica</i> L (Fabaceae)

Design, synthesis and bioevaluation of novel umbelliferone analogues as potential mushroom tyrosinase inhibitors

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