2. Academic Validation
  3. Kojic acid-natural product conjugates as mushroom tyrosinase inhibitors

Kojic acid-natural product conjugates as mushroom tyrosinase inhibitors

  • Eur J Med Chem. 2020 Sep 1;201:112480. doi: 10.1016/j.ejmech.2020.112480.
Morteza Ashooriha 1,  Mehdi Khoshneviszadeh 2,  Mahsima Khoshneviszadeh 3,  Alireza Rafiei 4,  Mostafa Kardan 4,  Rezvan Yazdian-Robati 5,  Saeed Emami 6
Affiliations

Affiliations

  • 1 Department of Medicinal Chemistry, Student Research Committee, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran.
  • 2 Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran; Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran.
  • 3 Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran.
  • 4 Department of Immunology and Molecular and Cell Biology Research Center, Faculty of Medicine, Mazandaran University of Medical Sciences, Sari, Iran.
  • 5 Molecular and Cell Biology Research Center, Faculty of Medicine, Mazandaran University of Medical Sciences, Sari, Iran.
  • 6 Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran. Electronic address: [email protected].
PMID: 32652434 DOI: 10.1016/j.ejmech.2020.112480
Abstract

As part of our effort to develop potential Tyrosinase inhibitors, we have conjugated the well-known Tyrosinase Inhibitor kojic acid (KA) with several phenolic Natural Products such as umbelliferone, sesamol, thymol, carvacrol, eugenol, isoeugenol, vanillin, isovanillin, and apocynin that some reports have shown their activity on Tyrosinase enzyme. The designed compounds were synthesized using click reaction and 1,2,3-triazole formation. All compound showed potent anti-tyrosinase activity significantly higher than KA. The best activities were observed with apocynin and 4-coumarinol analogs (10c and 16c) displaying IC50 values of 0.03 and 0.02 μM, respectively. The potency of 16c was >460-times more than that of KA. Cell-based assays against B16F10 and HFF cells revealed that the representative compounds can efficiently suppress the melanogenesis without significant toxicity on cells.

Keywords

Hyperpigmentation; Kojic acid; Natural products; Tyrosinase inhibitor.

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