Synthesis, characterization, antioxidant and tyrosinase inhibitory activities of hesperetin derivatives

Abstract

A series of hesperetin derivatives were synthesized by Williamson etherification, Steglich esterification and ring-opening by modifying the 7 hydroxyl group, 3’ hydroxyl group and C ring of hesperetin. All compounds were confirmed by IR, ¹H NMR, ¹³C NMR and HR-MS. The antioxidant activity of hesperetin derivatives was tested by ABTS method. Hp-1, Hp-2(b,d), Hp-3, Hp-5, Hp-6(a-d) and Hp-7(a-c) had antioxidant effects, and Hp-7a had the strongest antioxidant effect, which was better than the positive control quercetin, and the TEAC value was 4.62 mM. Hp-2b, Hp-3, Hp-7b and Hp-7c hesperetin derivatives had inhibitory effects on tyrosinase, and were superior to α-arbutin positive control. Hp-2b had the best inhibitory effect on tyrosinase, and the IC₅₀ value was 0.657 ± 0.093 mmol·L⁻¹.

GRAPHICAL ABSTRACT

Keywords:

• Antioxidant activity
• chalcone
• hesperetin
• tyrosinase inhibitory activity
• Williamson etherification

Correction Statement

This article has been corrected with minor changes. These changes do not impact the academic content of the article.

Additional information

Funding

This work was financially supported by the Key Laboratory of Natural Medicines of the Changbai Mountain, Ministry of Education, Yanbian University.