Antioxidation and tyrosinase inhibition of polyphenolic curcumin analogs

Zhi Yun Du; Yong Fu Jiang; Zhi Kai Tang; Rong Qing Mo; Gui Hua Xue; Yu Jing Lu; Xi Zheng; Chang Zhi Dong; Kun Zhang

doi:10.1271/bbb.110547

Antioxidation and tyrosinase inhibition of polyphenolic curcumin analogs

Zhi Yun Du, Yong Fu Jiang, Zhi Kai Tang, Rong Qing Mo, Gui Hua Xue, Yu Jing Lu, Xi Zheng, Chang Zhi Dong, Kun Zhang

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

A series of polyphenolic curcumin analogs were synthesized and their inhibitory effects on mushroom tyrosinase and the inhibition of 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical formation were evaluated. The results indictated that the analogs possessing m-diphenols and o-diphenols exhibited more potent inhibitory activity on tyrosinase than reference compound rojic acid, and that the analogs with o-diphenols exhibited more potent inhibitory activity of DPPH free-radical formation than reference compound vitamin C. The inhibition kinetics, analyzed by Lineweaver-Burk plots, revealed that compounds B ₂ and C ₂ bearing o-diphenols were non-competitive inhibitors, while compounds B ₁₁ and C ₁₁ bearing m-diphenols were competitive inhibitors. In particular, representative compounds C ₂ and B ₁₁ showed no side effects at a dose of 2,000 mg/kg in a preliminary evaluation of acute toxicity in mice. These results suggest that such polyphenolic curcumin analogs might serve as lead compounds for further design of new potential tyrosinase inhibitors.

Original language	English (US)
Pages (from-to)	2351-2358
Number of pages	8
Journal	Bioscience, Biotechnology and Biochemistry
Volume	75
Issue number	12
DOIs	https://doi.org/10.1271/bbb.110547
State	Published - 2011
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

Keywords

Antioxidation
Inhibition kinetics
Polyphenolic curcumin analogs
Tyrosinase inhibition

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10.1271/bbb.110547

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title = "Antioxidation and tyrosinase inhibition of polyphenolic curcumin analogs",

abstract = "A series of polyphenolic curcumin analogs were synthesized and their inhibitory effects on mushroom tyrosinase and the inhibition of 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical formation were evaluated. The results indictated that the analogs possessing m-diphenols and o-diphenols exhibited more potent inhibitory activity on tyrosinase than reference compound rojic acid, and that the analogs with o-diphenols exhibited more potent inhibitory activity of DPPH free-radical formation than reference compound vitamin C. The inhibition kinetics, analyzed by Lineweaver-Burk plots, revealed that compounds B 2 and C 2 bearing o-diphenols were non-competitive inhibitors, while compounds B 11 and C 11 bearing m-diphenols were competitive inhibitors. In particular, representative compounds C 2 and B 11 showed no side effects at a dose of 2,000 mg/kg in a preliminary evaluation of acute toxicity in mice. These results suggest that such polyphenolic curcumin analogs might serve as lead compounds for further design of new potential tyrosinase inhibitors.",

keywords = "Antioxidation, Inhibition kinetics, Polyphenolic curcumin analogs, Tyrosinase inhibition",

author = "Du, {Zhi Yun} and Jiang, {Yong Fu} and Tang, {Zhi Kai} and Mo, {Rong Qing} and Xue, {Gui Hua} and Lu, {Yu Jing} and Xi Zheng and Dong, {Chang Zhi} and Kun Zhang",

note = "Funding Information: This work was supported financially by National Natural Science Foundation of China (no. 21042003), the Science and Technology Planning Project of Guangdong Province (2007A020300007-10), the Natural Science Foundation of Guangdong Province (S2011010004967), and the Guangdong Provincial Higher Education 211 Project (Batch 3) Foundation.",

year = "2011",

doi = "10.1271/bbb.110547",

language = "English (US)",

volume = "75",

pages = "2351--2358",

journal = "Bioscience, Biotechnology and Biochemistry",

issn = "0916-8451",

publisher = "Japan Society for Bioscience Biotechnology and Agrochemistry",

number = "12",

}

TY - JOUR

T1 - Antioxidation and tyrosinase inhibition of polyphenolic curcumin analogs

AU - Du, Zhi Yun

AU - Jiang, Yong Fu

AU - Tang, Zhi Kai

AU - Mo, Rong Qing

AU - Xue, Gui Hua

AU - Lu, Yu Jing

AU - Zheng, Xi

AU - Dong, Chang Zhi

AU - Zhang, Kun

N1 - Funding Information: This work was supported financially by National Natural Science Foundation of China (no. 21042003), the Science and Technology Planning Project of Guangdong Province (2007A020300007-10), the Natural Science Foundation of Guangdong Province (S2011010004967), and the Guangdong Provincial Higher Education 211 Project (Batch 3) Foundation.

PY - 2011

Y1 - 2011

N2 - A series of polyphenolic curcumin analogs were synthesized and their inhibitory effects on mushroom tyrosinase and the inhibition of 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical formation were evaluated. The results indictated that the analogs possessing m-diphenols and o-diphenols exhibited more potent inhibitory activity on tyrosinase than reference compound rojic acid, and that the analogs with o-diphenols exhibited more potent inhibitory activity of DPPH free-radical formation than reference compound vitamin C. The inhibition kinetics, analyzed by Lineweaver-Burk plots, revealed that compounds B 2 and C 2 bearing o-diphenols were non-competitive inhibitors, while compounds B 11 and C 11 bearing m-diphenols were competitive inhibitors. In particular, representative compounds C 2 and B 11 showed no side effects at a dose of 2,000 mg/kg in a preliminary evaluation of acute toxicity in mice. These results suggest that such polyphenolic curcumin analogs might serve as lead compounds for further design of new potential tyrosinase inhibitors.

AB - A series of polyphenolic curcumin analogs were synthesized and their inhibitory effects on mushroom tyrosinase and the inhibition of 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical formation were evaluated. The results indictated that the analogs possessing m-diphenols and o-diphenols exhibited more potent inhibitory activity on tyrosinase than reference compound rojic acid, and that the analogs with o-diphenols exhibited more potent inhibitory activity of DPPH free-radical formation than reference compound vitamin C. The inhibition kinetics, analyzed by Lineweaver-Burk plots, revealed that compounds B 2 and C 2 bearing o-diphenols were non-competitive inhibitors, while compounds B 11 and C 11 bearing m-diphenols were competitive inhibitors. In particular, representative compounds C 2 and B 11 showed no side effects at a dose of 2,000 mg/kg in a preliminary evaluation of acute toxicity in mice. These results suggest that such polyphenolic curcumin analogs might serve as lead compounds for further design of new potential tyrosinase inhibitors.

KW - Antioxidation

KW - Inhibition kinetics

KW - Polyphenolic curcumin analogs

KW - Tyrosinase inhibition

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ER -

Antioxidation and tyrosinase inhibition of polyphenolic curcumin analogs

Abstract

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