Synthesis and anti-melanogenic activity of hydroxyphenyl benzyl ether analogues

Kiran Sapkota, Eunmiri Roh, Eunyoung Lee, Eun Mi Ha, Jae Ho Yang, Eung Seok Lee, Youngjoo Kwon, Youngsoo Kim, Younghwa Na

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

In order to develop potent skin whitening agents, we have synthesized 17 hydroxyphenyl benzyl ether compounds and tested their melanin synthesis inhibitory activity, DPPH free radical scavenging activity and tyrosinase inhibitory activity. Compounds 32, 35 and 36 possessing 4-hydroxyphenyl benzyl ether structure showed excellent inhibitory capacity with almost 50-fold than arbutin used as a reference in the inhibition test of α-MSH stimulated melanin synthesis in B-16 cells. 4-Hydroxyphenyl benzyl ether compounds also showed good antioxidant activity in the DPPH free radical scavenging test. The tyrosinase function was effectively inhibited by 3,5-dihydroxyphenyl benzyl ether analogues, especially compounds 18, 22, and 24.

Original languageEnglish (US)
Pages (from-to)2168-2175
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume19
Issue number7
DOIs
StatePublished - Apr 1 2011
Externally publishedYes

Keywords

  • 3,5-Dihydroxyphenyl benzyl ether
  • 4-Hydroxyphenyl benzyl ether
  • DPPH free radical scavenging
  • Tyrosinase
  • α-MSH induced melanin synthesis

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