Benzyl benzoates: New phlorizin analogs as mushroom tyrosinase inhibitors

被引：18

作者：

Fang, Yuntai ^{[1
]}

Chen, Yaozong ^{[1
]}

Feng, Guanfeng ^{[1
]}

Ma, Lin ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Inst Organ Chem, Sch Chem & Chem Engn, Guangzhou, Guangdong, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2011年 / 19卷 / 03期

关键词：

Phlorizin analogs; Benzyl benzoates; Mushroom tyrosinase; Inhibition;

D O I：

10.1016/j.bmc.2010.12.051

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In our research, 14 benzyl benzoates with hydroxyl(s) (3-16) were synthesized and their inhibitory activity on mushroom tyrosinase was tested. Results indicated that among these compounds, 4-hydroxybenzyl 3,5-dihydroxybenzoate (3), 4-hydroxybenzyl 2,4-dihydroxybenzoate (5), 4-hydroxybenzyl 2,4,6-dihydroxybenzoate (7), 3-hydroxybenzyl 3,5-dihydroxybenzoate (8), 3-hydroxybenzyl 2,4-dihydroxybenzoate (10) exhibited inhibitory activity with their IC50 less than 10 mu M. Further studies showed these five compounds were competitive inhibitors of tyrosinase and their structure-activity relationships were investigated in this article. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1167 / 1171

页数：5

共 16 条

[1]

[边延江 Bian Yanjiang], 2006, [精细石油化工, Speciality Petrochemicals], V23, P17

[2] An Updated Review of Tyrosinase Inhibitors [J].

Chang, Te-Sheng .

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2009, 10 (06) :2440-2475

[3] N-benzylbenzamides: A new class of potent tyrosinase inhibitors [J].

Cho, SJ ;

Roh, JS ;

Sun, WS ;

Kim, SH ;

Park, KD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (10) :2682-2684

[4] Bacterial tyrosinases [J].

Claus, H ;

Decker, H .

SYSTEMATIC AND APPLIED MICROBIOLOGY, 2006, 29 (01) :3-14

[5] Synthesis and evaluation of 2,4',6'-trihydroxychalcones as a new class of tyrosinase inhibitors [J].

Jun, Nishida ;

Hong, Gao ;

Jun, Kawabata .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (06) :2396-2402

[6] Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future [J].

Kim, YJ ;

Uyama, H .

CELLULAR AND MOLECULAR LIFE SCIENCES, 2005, 62 (15) :1707-1723

[7] Synthetic tyrosyl gallate derivatives as potent melanin formation inhibitors [J].

Lee, Chan Woo ;

Son, Eun-Mi ;

Kim, Han Sung ;

Xu, Pan ;

Batmunkh, Tuyagerel ;

Lee, Burm-Jong ;

Koo, Kyung Ah .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (19) :5462-5464

[8] Inhibitory effect of p-hydroxybenzyl alcohol on tyrosinase activity and melanogenesis [J].

Liu, Szu-Hsiu ;

Pan, I-Horng ;

Chu, I-Ming .

BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2007, 30 (06) :1135-1139

[9]

Martin G. M. C, 2007, EUR J MED CHEM, V42, P1370

[10] 2-Hydroxy-4-isopropylbenzaldehyde, a potent partial tyrosinase inhibitor [J].

Nihei, K ;

Yamagiwa, Y ;

Kamikawa, T ;

Kubo, I .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (03) :681-683

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