(4-methoxy-benzylidene)-(3-methoxy-phenyl)-amine, a nitrogen analog of stilbene as a potent inhibitor of melanin production

被引:20
作者
Choi, SY
Kim, S [1 ]
Kim, H
Suk, K
Hwang, JS
Lee, BG
Kim, AJ
Kim, SY [1 ]
机构
[1] Kyung Hee Univ, Grad Sch EW Med Sci, Seoul 130701, South Korea
[2] Seoul Natl Univ, Coll Pharm, Inst Nat Prod Res, Seoul 110460, South Korea
[3] Hyejeon Coll, Chungnam 350800, South Korea
[4] Pacific R&D Ctr, Skin Res Inst, Yongin, South Korea
关键词
oxyresveratrol; stilbene; whitening agent;
D O I
10.1248/cpb.50.450
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The current study was carried out to investigate in vitro the effects of (4-methoxy-benzylidene)-(3-methoxy phenyl)-amine on melanin biosynthesis which is closely related to hyper-pigmentation (4-Methoxy-benzyllidene)(3-methoxy-phenyl)-amine, nitrogen analog of stilbene, was synthesized by a single step process. This compound inhibited the tyrosinase activity, which converts dopa to dopachrome in the biosynthetic process of melanin, and showed a UV-blocking effect at UV-B band. The compound also exhibited SOD-like activity, which Is involved in the protection against auto-oxidation and inhibited melanin production in melan-a cell line. Our results suggest the possibility that (4-methoxy-benzylidene)-(3-methoxy-phenyl)-amine might be used as a skin whitening agent.
引用
收藏
页码:450 / 452
页数:3
相关论文
共 16 条
[1]   Simple synthesis of 5-substituted resorcinols: A revisited family of interesting bioactive molecules [J].
Alonso, E ;
Ramon, DJ ;
Yus, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :417-421
[2]  
AROCA P, 1993, J BIOL CHEM, V268, P25650
[3]   A LINE OF NONTUMORIGENIC MOUSE MELANOCYTES, SYNGENEIC WITH THE B-16 MELANOMA AND REQUIRING A TUMOR PROMOTER FOR GROWTH [J].
BENNETT, DC ;
COOPER, PJ ;
HART, IR .
INTERNATIONAL JOURNAL OF CANCER, 1987, 39 (03) :414-418
[4]  
CHAKRABORTY AK, 1998, J SCI FOOD AGR, V76, P270
[5]   Inhibitors of mammalian melanocyte tyrosinase:: In vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors [J].
Curto, EV ;
Kwong, C ;
Hermersdörfer, H ;
Glatt, H ;
Santis, C ;
Virador, V ;
Hearing, VJ ;
Dooley, TP .
BIOCHEMICAL PHARMACOLOGY, 1999, 57 (06) :663-672
[6]   ENZYMATIC CONTROL OF PIGMENTATION IN MAMMALS [J].
HEARING, VJ ;
TSUKAMOTO, K .
FASEB JOURNAL, 1991, 5 (14) :2902-2909
[7]  
Ikeda T., 1990, FRAGRANCE J, V6, P59
[8]   ROLE OF TYROSINASE AS THE DETERMINANT OF PIGMENTATION IN CULTURED HUMAN MELANOCYTES [J].
IOZUMI, K ;
HOGANSON, GE ;
PENNELLA, R ;
EVERETT, MA ;
FULLER, BB .
JOURNAL OF INVESTIGATIVE DERMATOLOGY, 1993, 100 (06) :806-811
[9]  
Matsuda H, 1996, BIOL PHARM BULL, V19, P153, DOI 10.1248/bpb.19.153
[10]   Synthesis and cytotoxic activities of a new benzo[c]phenanthridine alkaloid, 7-hydroxynitidine, and some 9-oxygenated benzo[c]phenanthridine derivatives [J].
Nakanishi, T ;
Suzuki, M .
ORGANIC LETTERS, 1999, 1 (07) :985-988