Synthesis and cytotoxic activity of 3, 4, 11-trihydroxyl modified derivatives of bergenin.
10.1016/S1875-5364(14)60136-9
- Author:
De-Biao YAN
1
;
Dong-Ping ZHANG
1
;
Ming LI
1
;
Wen-Yuan LIU
2
,
3
;
Feng FENG
4
,
5
;
Bin DI
6
;
Qing-Long GUO
7
;
Ning XIE
8
Author Information
1. Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
2. Department of Pharmaceutical Analysis, China Pharmaceutical University, Nanjing 210009, China
3. Key Laboratory of Drug Quality Control and Pharmacovigilance, Ministry of Education, China Pharmaceutical University, Nanjing 210009, China. Electronic address: liuwenyuan8506@163.com.
4. Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China
5. Jiangsu Key Laboratory of Carcinogenesis and Intervention, China Pharmaceutical University, Nanjing 210009, China. Electronic address: fengfeng@cpu.edu.cn.
6. Department of Pharmaceutical Analysis, China Pharmaceutical University, Nanjing 210009, China.
7. Jiangsu Key Laboratory of Carcinogenesis and Intervention, China Pharmaceutical University, Nanjing 210009, China.
8. Jiangxi Qingfeng Pharmaceutical Ltd., Ganzhou 341008, China.
- Publication Type:Journal Article
- Keywords:
3-, 4-, and/or 11-trihydroxyl modified derivatives;
Bergenin;
Cytotoxic activity;
Structure-activity relationships
- MeSH:
Antineoplastic Agents, Phytogenic;
chemical synthesis;
pharmacology;
therapeutic use;
Benzopyrans;
pharmacology;
therapeutic use;
Cell Line, Tumor;
Dipterocarpaceae;
chemistry;
Humans;
Male;
Molecular Structure;
Phytotherapy;
Plant Extracts;
pharmacology;
therapeutic use;
Prostatic Neoplasms;
drug therapy;
Stomach Neoplasms;
drug therapy;
Structure-Activity Relationship
- From:
Chinese Journal of Natural Medicines (English Ed.)
2014;12(12):929-936
- CountryChina
- Language:English
-
Abstract:
To synthesize a series of 3-, 4-, and/or 11-trihydroxy modified bergenin derivatives and evaluated their cytotoxic activity in vitro. The phenolic hydroxyl groups of bergenin were protected by benzyl groups with benzyl bromide. Treatment of dibenzyl bergenin with the corresponding acid in the presence of EDC·HCl and DMAP in CH2Cl2, followed by hydrogenation over Pd/C catalysts, afforded derivatives of bergenin esters. All of the target compounds were identified by IR, MS, and (1)H NMR. Twenty-six novel and three known derivatives of bergenin esters were synthesized. Their cytotoxicity values were evaluated by the MTT assay on the inhibition of DU-145 and BGC-823 cells in vitro. Several triply-substituted (3a, 4a, 5a, 6a, 7a) and doubly-substituted (8b, 9b) bergenin derivatives exhibited higher cytotoxic activity than bergenin. The result showed that the size of substituents and the lipophilicity of the bergenin esters displayed an important role on their cytotoxic activity.
