Absolute configuration of podophyllotoxone and its inhibitory activity against human prostate cancer cells.
10.1016/S1875-5364(15)60007-3
- Author:
Juan LI
1
,
2
;
Juan FENG
3
;
Cheng LUO
4
;
Ho-Yung Sung HERMAN
5
;
Ren-Wang JIANG
1
,
6
Author Information
1. Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, Guilin 541006, China
2. Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, China.
3. Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, China.
4. State Key Laboratory of New Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, China.
5. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong.
6. Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, China. Electronic address: trwjiang@jnu.edu.cn.
- Publication Type:Journal Article
- Keywords:
Absolute configuration;
Molecular docking;
Podophyllotoxone;
Prostate cancer;
Tubulin
- MeSH:
Antineoplastic Agents;
chemistry;
pharmacology;
Berberidaceae;
chemistry;
Cell Line, Tumor;
Dose-Response Relationship, Drug;
G2 Phase;
drug effects;
Humans;
Hydrogen Bonding;
drug effects;
Male;
Molecular Conformation;
Molecular Docking Simulation;
Phytotherapy;
Plant Extracts;
chemistry;
pharmacology;
Plant Roots;
chemistry;
Podophyllotoxin;
chemistry;
pharmacology;
Polymerization;
Prostatic Neoplasms;
drug therapy;
Tubulin;
drug effects;
Tubulin Modulators;
pharmacology
- From:
Chinese Journal of Natural Medicines (English Ed.)
2015;13(1):59-64
- CountryChina
- Language:English
-
Abstract:
Podophyllotoxone (1) was isolated from the roots of Dysosma versipellis. The structure was determined by spectroscopic analysis in combination with single-crystal X-ray analysis. The absolute configuration of compound 1 was assigned based on the Flack parameter. It showed significant inhibitory activities against human prostate cancer cells PC3 and DU145 with IC50 values being 14.7 and 20.6 μmol·L(-1), respectively. It also arrested the cells at G2/M phase. Tubulin polymerization assay showed that it inhibited the tubulin polymerization in a dose-dependent manner, and molecular docking analysis revealed a different binding mode with tubulin as compared with those known tubulin inhibitors.
