天然多酚衍生物的合成、结构和酪氨酸酶抑制作用

天然多酚衍生物的合成、结构和酪氨酸酶抑制作用

王艳丽, 黄伟, 陈帅, 陈石泉, 王世范^*

1. 海南大学海洋学院制药工程系, 海南海口 570228
2. 海南大学海洋生物实验教学中心, 海南海口 570228

收稿日期:2010-12-01 修回日期:2011-03-20 出版日期:2011-05-06 发布日期:2011-05-06
通讯作者: 王世范*

Synthesis, structure and tyrosinase inhibition of natural phenols derivatives

Yan-Li Wang, Wei Huang, Shuai Chen, Shi-Quan Chen, Shi-Fan Wang^*

1. Department of Pharmaceutical Engineering, School of Ocean, Hainan University, Haikou 570228, China
2. Experimental Teaching Center of Marine Biology, Hainan University, Haikou 570228, China

Received:2010-12-01 Revised:2011-03-20 Online:2011-05-06 Published:2011-05-06
Contact: Shi-Fan Wang*

摘要/Abstract

摘要：

以香草醛、茴香醛、染料木素和芦荟大黄素为原料合成一系列的衍生物, 测定了衍生物 (E)-1-(5-(4-甲氧基苯基)-3-(4-甲氧基苯乙烯基)-4,5-二氢-1H-吡唑-1-基) 乙酮的晶体结构, 并对这些化合物的酪氨酸酶抑制活性进行了测定。研究结果表明, 香草醛、茴香醛、染料木素和芦荟大黄素的IC50值分别为68 µM, 49 µM, 343 µM 和 160 µM。与标准对照品曲酸 (IC50 = 35 μM) 相比, 香草醛衍生物 (E)-1-(5-(4-甲氧基苯基)-3-(4-甲氧基苯乙烯基)-4,5-二氢-1H-吡唑-1-基) 乙酮和芦荟大黄素衍生物 4,5-二甲氧基-9,10-二氢蒽醌-2-甲酸具有更好的酪氨酸酶抑制活性, 其IC50值分别为18 µM 和 21 µM。

关键词: 天然多酚, 衍生物, 合成, 酪氨酸酶抑制剂

Abstract:

Four series of derivatives of vanillin, anisaldehyde, genistein and aloe emodin were prepared. The single crystal of (E)-1-(5-(4-methoxyphenyl)-3-(4-methoxystyryl)-4,5-dihydro-1H-pyrazol-1-yl) ethanone, which was synthesized from vanillin, was obtained by spontaneous evaporation method. All the compounds were tested for the tyrosinase inhibitory activities. The results demonstrated that the IC50 values of vanillin, anisaldehyde, genistein and aloe emodin against mushroom tyrosinase activity are 68, 49, 343 and 160 µM, respectively. Among the twelve derivatives, (E)-1-(5-(4-methoxyphenyl)-3-(4-methoxystyryl)-4,5-dihydro-1H-pyrazol-1-yl) ethanone from vanillin and 4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid from aloe emodin showed good inhibition against the tyrosinase with IC50 values of 18 µM and 21 µM, respectively.

Key words: Natural phenols, Derivatives, Synthesis, Tyrosinase inhibitor

中图分类号:

R916.2

Supporting:

Foundation item: National Key Technology R&D Program of China (Grant No. 2007BAI27B05).
^*Corresponding author. Tel.: 86-0898-66289567

王艳丽, 黄伟, 陈帅, 陈石泉, 王世范^*. 天然多酚衍生物的合成、结构和酪氨酸酶抑制作用[J]. .

Yan-Li Wang, Wei Huang, Shuai Chen, Shi-Quan Chen, Shi-Fan Wang^*. Synthesis, structure and tyrosinase inhibition of natural phenols derivatives[J]. .

参考文献

[1] Vinson, J.A.; Su, X.; Zubik, L.; Bose, P. J. Agric. Food Chem. 2001, 49, 5315-5321.
[2] Kortenska, V.D.; Yanishlieva, N.V.; Kasaikina, O.T.; Totzeva, I.R.; Boneva, M.I.; Russina, I.F. Eur. J. Lipid Sci. Tech. 2002, 104, 513-519.
[3] Shimizu, K.; Kondo, R.; Sakai, K. Planta Med. 2000, 66, 11-15.
[4] Zhang, X.D.; Hu, X.; Hou, A.J.; Wang, H.Y. Biol. Pharm. Bull. 2009, 32, 86-90.
[5] Yi, W.; Cao, R.H.; Chen, Z.Y.; Yu, L.; Wen, H.; Yan, Q.; Ma, L.; Song, H.C. Chem. Pharm. Bull. 2010, 58, 752-754.
[6] Godbole, D.; Mojamdar, M.; Pal, J.K. Cell Biol. Int. 2006, 30, 895-902.
[7] Cabanes, J.; Chazarra, S.; Garcia-Carmona, F. J. Pharm. Pharmacol. 1994, 46, 982-985.
[8] Kubo, I.; Kinst-Hori, I.; Yokokawa, Y. J. Nat. Prod. 1994, 57, 545-551.
[9] Kubo, I.; Kinst-Hori, I. J. Agric. Food Chem. 1998, 46, 5338-5341.
[10] Gao, H.; Nishida, J.; Saito, S.; Kawabata, J. Molecules. 2007, 12, 86-97.
[11] Moon, Y.H.; Lee, J.H.; Jhon, D.Y.; Jun, W.J.; Kang, S.S.; Sim, J.; Choi, H.; Moon, J.H.; Kim, D. Enzyme Microb. Technol. 2007, 40, 1124-1129.
[12] Tang, L.J.; Zhao, Y.Q.; Xu, R.B.; Liu, W.W. J. Huaqiao Univ (Nat. Sci.). 2009, 30, 289-291.
[13] Liu, Q.R.; Li, X.W.; Zhao, G.Q.; Hao, C.J.; Peng, Q.L. Chem. Res. Appl. 2009, 21, 566-568.
[14] Liu, R.; Cao, S.W.; Deng, Z.Y.; Yu, Y.Y. Chem. Res. Appl. 2008, 20, 1373-1376.
[15] Wang, J.P.; Shang, F.J.; Wang, S.W. Pharm. J. Chin. People's Lib. Army. 2010, 2, 107-109, 153.
16] Yu, Y.Y.; Li, X.H.; Cao, S.W.; Wei, J.Z.; Zeng, W.W. Nat. Prod. Res. Dev. 2009, 21, 194-198.
[17] Chen, X.L.; Yu, Z.Q.; Qu, L.B.; Yuan, J.W.; Lu, J.S.; Zhao, Y.F. Acta Pharm. Sin. 2007, 42, 396-400.
[18] Cui, X.R.; Takahashi, K.; Shimamura, T.; Koyanagi, J.; Komada, F.; Saito, S. Chem. Pharm. Bull. 2008, 56, 497-503.
[19] Wang, S.F.; Jiang, Q.; Ye, Y.H.; Li,Y.; Tan, R.X. Bioorg. Med. Chem. 2005, 13, 4880-4890.
[20] Chang, T.S.; Ding, H.Y.; Lin, H.C. Biosci. Biotechnol. Biochem. 2005, 69, 1999-2001.
[21] Um, S.J.; Park, M.S.; Park, S.H.; Han, H.S.; Kwon, Y.H.; Sin, H.S. Bioorg. Med. Chem. 2003, 11, 5345-5352.
[22] Shaheen, F.; Ahmad, M.; Khan, M.T.H.; Jalil, S.; Ejaz, A.; Sultankhodjaev, M.N.; Arfan, M.; Choudhary, M.; Rahman, A.U. Phytochemistry. 2005, 66, 935-940.