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

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 (US)
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 - Apr 1 2011
Externally published	Yes

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

Publisher link

10.1016/j.bmc.2011.02.044

Find It

Find It at U of M Libraries

Cite this

@article{b6eeb6b30e18432faa635dbc59924eae,

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. ",

year = "2011",

month = apr,

day = "1",

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

language = "English (US)",

volume = "19",

pages = "2168--2175",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

number = "7",

}

TY - JOUR

T1 - Synthesis and anti-melanogenic activity of hydroxyphenyl benzyl ether analogues

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

UR - http://www.scopus.com/inward/record.url?scp=79953197167&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79953197167&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2011.02.044

DO - 10.1016/j.bmc.2011.02.044

M3 - Article

C2 - 21429753

AN - SCOPUS:79953197167

SN - 0968-0896

VL - 19

SP - 2168

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

Publisher link

Find It

Other files and links

Fingerprint

Cite this