| Literature DB >> 21044810 |
Shu Fu Lin1, Yu-Hsiang Lin, Mengju Lin, Yi-Feng Kao, Ru-Wen Wang, Li-Wei Teng, Shih-Hsien Chuang, Jia-Ming Chang, Ta-Tung Yuan, Kuo Chu Fu, Kuan Pin Huang, Ying-Shuen Lee, Chao-Cheng Chiang, Sheng-Chuan Yang, Chun-Liang Lai, Chu-Bin Liao, Paonien Chen, Young-Sun Lin, Kuei-Tai Lai, Hung-Jyun Huang, Ju-Ying Yang, Chia-Wei Liu, Win-Yin Wei, Chi-Kuan Chen, Richard A Hiipakka, Shutsung Liao, Jiann-Jyh Huang.
Abstract
A series of 3-O-acylated (-)-epigallocatechins were synthesized and their inhibition of steroid 5α-reductase was studied. They were prepared from the reaction of EGCG with tert-butyldimethylsilyl chloride followed by reductive cleavage of the ester bond. The resultant (-)-epigallocatechins penta-O-tert-butyldimethylsilyl ether was esterified with different fatty acids then desilylated to provide the corresponding products. The activity of 3-O-acylated (-)-epigallocatechins increased with the increasing carbon numbers of the fatty acid moiety, reaching maximum for 16 carbon atoms (compound 4h) with an IC50 of 0.53 μM, which was ∼12-fold more potent than EGCG (IC50=6.29 μM). Introduction of monounsaturated fatty acid provided the most potent compound 6 (IC50=0.48 μM), which showed moderate anti-tumor activity in vivo.Entities:
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Year: 2010 PMID： 21044810 DOI： 10.1016/j.ejmech.2010.10.011
Source DB: PubMed Journal: Eur J Med Chem ISSN： 0223-5234 Impact factor: 6.514