title: Absolute configuration of podophyllotoxone and its inhibitory activity against human prostate cancer cells.
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.
authors: 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; Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, China.
authors: Juan
authors: J
authors: Li
authors: Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, China.
authors: Juan
authors: J
authors: Feng
authors: State Key Laboratory of New Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, China.
authors: Cheng
authors: C
authors: Luo
authors: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong.
authors: Ho-Yung Sung
authors: HY
authors: Herman
authors: 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; 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.
authors: Ren-Wang
authors: RW
authors: Jiang
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D028141:Berberidaceae / Q000737:chemistry*; D045744:Cell Line, Tumor; D004305:Dose-Response Relationship, Drug; D016195:G2 Phase / Q000187:drug effects; D006801:Humans; D006860:Hydrogen Bonding / Q000187:drug effects; D008297:Male; D008968:Molecular Conformation; D062105:Molecular Docking Simulation; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D018517:Plant Roots / Q000737:chemistry*; D011034:Podophyllotoxin / Q000737:chemistry / Q000494:pharmacology*; D058105:Polymerization; D011471:Prostatic Neoplasms / Q000188:drug therapy*; D014404:Tubulin / Q000187:drug effects; D050257:Tubulin Modulators / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D010936:Plant Extracts; D014404:Tubulin; D050257:Tubulin Modulators; D011034:Podophyllotoxin
keywords: Absolute configuration; Molecular docking; Podophyllotoxone; Prostate cancer; Tubulin