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

doi:10.1016/j.bmc.2011.02.044

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

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

20 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 language	English
Pages (from-to)	2168-2175
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	19
Issue number	7
DOIs	https://doi.org/10.1016/j.bmc.2011.02.044
State	Published - 1 Apr 2011

Bibliographical note

Funding Information:
This work was supported by the RIC program of MKE (Ministry of Knowledge Economy), Korea.

Keywords

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

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10.1016/j.bmc.2011.02.044

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title = "Synthesis and anti-melanogenic activity of hydroxyphenyl benzyl ether analogues",

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.",

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

author = "Kiran Sapkota and Eunmiri Roh and Eunyoung Lee and Ha, {Eun Mi} and Yang, {Jae Ho} and Lee, {Eung Seok} and Youngjoo Kwon and Youngsoo Kim and Younghwa Na",

note = "Funding Information: This work was supported by the RIC program of MKE (Ministry of Knowledge Economy), Korea. ",

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doi = "10.1016/j.bmc.2011.02.044",

language = "English",

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AU - Sapkota, Kiran

AU - Roh, Eunmiri

AU - Lee, Eunyoung

AU - Ha, Eun Mi

AU - Yang, Jae Ho

AU - Lee, Eung Seok

AU - Kwon, Youngjoo

AU - Kim, Youngsoo

AU - Na, Younghwa

N1 - Funding Information: This work was supported by the RIC program of MKE (Ministry of Knowledge Economy), Korea.

PY - 2011/4/1

Y1 - 2011/4/1

N2 - 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.

AB - 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.

KW - 3,5-Dihydroxyphenyl benzyl ether

KW - 4-Hydroxyphenyl benzyl ether

KW - DPPH free radical scavenging

KW - Tyrosinase

KW - α-MSH induced melanin synthesis

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EP - 2175

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 7

ER -

Synthesis and anti-melanogenic activity of hydroxyphenyl benzyl ether analogues

Abstract

Bibliographical note

Keywords

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