Details

Autor(en) / Beteiligte

• Ashooriha, Morteza
• Khoshneviszadeh, Mehdi
• Khoshneviszadeh, Mahsima
• Rafiei, Alireza
• Kardan, Mostafa
• Yazdian-Robati, Rezvan
• Emami, Saeed

Titel

Kojic acid–natural product conjugates as mushroom tyrosinase inhibitors

Ist Teil von

• European journal of medicinal chemistry, 2020-09, Vol.201, p.112480, Article 112480

Ort / Verlag

France: Elsevier Masson SAS

Erscheinungsjahr

2020

Quelle

MEDLINE

Beschreibungen/Notizen

• 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. [Display omitted] •A series of kojic acid (KA)–natural product conjugates were prepared via click reaction.•All compounds 2c-16c were highly potent tyrosinase inhibitors (IC50s ≤ 3.75 μM).•Apocynin and 4-coumarinol derivatives (10c and 16c) were the most potent compounds.•The 4-coumarinol analog (16c) was >460-fold more potent than KA.•Certainly, 16c can suppress melanogenesis without significant toxicity on B16F10 cells.