Tyrosinase inhibitors from Rhododendron collettianum and their structure-activity relationship (SAR) studies

被引：46

作者：

Ahmad, VU ^{[1
]}

Ullah, F ^{[1
]}

Hussain, J ^{[1
]}

Farooq, U ^{[1
]}

Zubair, M ^{[1
]}

Khan, MTH ^{[1
]}

Choudhary, MI ^{[1
]}

机构：

[1] Univ Karachi, HEJ Res Inst Chem, Karachi 75270, Pakistan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2004年 / 52卷 / 12期

关键词：

coumarinolignoid; methylchromone; Rhododendron collettianum; tyrosinase inhibition; structure-activity relationship;

D O I：

10.1248/cpb.52.1458

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new coumarinolignoid 8'-epi-cleomiscosin A (1) together with the new glycoside 8-O-beta-D-glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one (2) have been isolated from the aerial parts of Rhododendron collettianum and their structures determined on the basis of spectroscopic evidences. Tyrosinase inhibition study of these compounds and their structure-activity relationship (SAR) were also investigated. The compounds exhibited potent to mild inhibition activity against the enzyme. Especially, the compound I showed strong inhibition (IC50 = 1.33,mu(M)) against the enzyme tyrosinase, as compared to the standard tyrosinase inhibitors kojic acid (IC50 = 16.67 mu(M)) and L-mimosine (IC50 = 3.68 mu(M)), indicating its potential used for the treatment of hyperpigmentation associated with the high production of melanocytes.

引用

页码：1458 / 1461

页数：4

共 13 条

[1]

ANIL BR, 1982, HETEROCYCLES, V19, P19

[2] AQUILLOCHIN, A COUMARINOLIGNAN FROM AQUILARIA-AGALLOCHA [J].

BHANDARI, P ;

PANT, P ;

RASTOGI, RP .

PHYTOCHEMISTRY, 1982, 21 (08) :2147-2149

[3]

GHOSAL S, 1982, PHYTOCHEMISTRY, V21, P2943, DOI 10.1016/0031-9422(80)85074-6

[4]

HEARING VJ, 1987, METHOD ENZYMOL, V142, P154

[5]

JIANGSA, 1977, CHINESE MATERIA MED, P2506

[6] Isolation of rhododaurichromanic acid B and the anti-HIV principles rhododaurichromanic acid A and rhododaurichromenic acid from Rhododendron dauricum [J].

Kashiwada, Y ;

Yamazaki, K ;

Ikeshiro, Y ;

Yamagishi, T ;

Fujioka, T ;

Mihashi, K ;

Mizuki, K ;

Cosentino, LM ;

Fowke, K ;

Morris-Natschke, SL ;

Lee, KH .

TETRAHEDRON, 2001, 57 (08) :1559-1563

[7] Diterpenoids from the fruits of Rhododendron molle [J].

Li, CJ ;

Wang, LQ ;

Chen, SN ;

Qin, GW .

JOURNAL OF NATURAL PRODUCTS, 2000, 63 (09) :1214-1217

[8]

Mabry T.J., 2012, SYSTEMATIC IDENTIFIC

[9] DETERMINATION OF ABSOLUTE-CONFIGURATION OF A SECONDARY HYDROXY GROUP IN A CHIRAL SECONDARY ALCOHOL USING GLYCOSIDATION SHIFTS IN C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].

SEO, S ;

TOMITA, Y ;

TORI, K ;

YOSHIMURA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (11) :3331-3339

[10]

SHARMA SC, 1986, THESIS U DELHI

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