Kojyl thioether derivatives having both tyrosinase inhibitory and anti-inflammatory properties

被引:78
作者
Rho, Ho Sik [1 ]
Ahn, Soo Mi [1 ]
Yoo, Dae Sung [3 ]
Kim, Myung Kyoo [2 ]
Cho, Dong Ha [3 ]
Cho, Jae Youl [3 ]
机构
[1] AmorePacific Corp, R&D Ctr, Yongin 446729, South Korea
[2] Samkyung Costech Co Ltd, Suwon 443734, South Korea
[3] Kangwon Natl Univ, Coll Biomed Sci, Chunchon 200701, South Korea
关键词
Kojyl thioether; Derivatives; Tyrosinase; Anti-inflammatory property; KOJIC ACID-DERIVATIVES; AMINO-ACID;
D O I
10.1016/j.bmcl.2010.09.042
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
This study was conducted to examine the tyrosinase inhibitory and anti-inflammatory activities of kojic acid derivatives. A series of kojic acid derivatives containing thioether, sulfoxide, and sulfone linkages were synthesized. In the tyrosinase assay, kojyl thioether derivatives containing appropriate lipophilic alkyl chains (pentane, hexane, and cyclohexane) showed potent inhibitory activity. However, sulfoxides and sulfones exhibited decreased activity. Similar experimental results were obtained with inhibitory activities of NO production being induced by LPS. The presence of thioether linkage and appropriated lipophilic acid moiety was critical for the tyrosinase inhibitory and anti-inflammatory activities. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6569 / 6571
页数:3
相关论文
共 15 条
[1]   ANTILEUKEMIC ACTIVITY OF 4-PYRANONE DERIVATIVES [J].
BRANSOVA, J ;
BRTKO, J ;
UHER, M ;
NOVOTNY, L .
INTERNATIONAL JOURNAL OF BIOCHEMISTRY & CELL BIOLOGY, 1995, 27 (07) :701-706
[2]   INHIBITORY EFFECT OF KOJIC ACID ON SOME PLANT AND CRUSTACEAN POLYPHENOL OXIDASES [J].
CHEN, JS ;
WEI, CI ;
ROLLE, RS ;
OTWELL, WS ;
BALABAN, MO ;
MARSHALL, MR .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1991, 39 (08) :1396-1401
[3]   6-DESMETHOXYHORMOTHAMNIONE, A NEW CYTO-TOXIC STYRYLCHROMONE FROM THE MARINE CRYPTOPHYTE CHRYSOPHAEUM-TAYLORI [J].
GERWICK, WH .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (02) :252-256
[4]   Synthesis of kojic acid derivatives containing phenolic hydroxy groups [J].
Kadokawa, J ;
Nishikura, T ;
Muraoka, R ;
Tagaya, H ;
Fukuoka, N .
SYNTHETIC COMMUNICATIONS, 2003, 33 (07) :1081-1086
[5]   SYNTHESIS OF AMINO-ACID DERIVATIVES OF KOJIC ACID AND THEIR TYROSINASE INHIBITORY ACTIVITY [J].
KOBAYASHI, Y ;
KAYAHARA, H ;
TADASA, K ;
NAKAMURA, T ;
TANAKA, H .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1995, 59 (09) :1745-1746
[6]   Synthesis of N-kojic-amino acid and N-kojic-amino acid-kojiate and their tyrosinase inhibitory activity [J].
Kobayashi, Y ;
Kayahara, H ;
Tadasa, K ;
Tanaka, H .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (12) :1303-1308
[7]   Synthesis of tyrosinase inhibitory kojic acid derivative [J].
Lee, YS ;
Park, JH ;
Kim, MH ;
Seo, SH ;
Kim, HJ .
ARCHIV DER PHARMAZIE, 2006, 339 (03) :111-114
[8]   Prevention of the photodamage in the hairless mouse dorsal skin by kojic acid as an iron chelator [J].
Mitani, H ;
Koshiishi, I ;
Sumita, T ;
Imanari, T .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2001, 411 (1-2) :169-174
[9]  
Ohyama Y., 1990, Flavour fragr J, V6, P53
[10]  
Rho HS, 2008, B KOREAN CHEM SOC, V29, P1569