Hyperpatulols A-I, spirocyclic acylphloroglucinol derivatives with anti-migration activities from the flowers of Hypericum patulum

Yang-Yang Liu; Zhen Ao; Qi-Qi Xu; Dong-Rong Zhu; Chen Chen; Xiao-Bing Wang; Jian-Guang Luo; Ling-Yi Kong

doi:10.1016/j.bioorg.2019.03.025

Hyperpatulols A-I, spirocyclic acylphloroglucinol derivatives with anti-migration activities from the flowers of Hypericum patulum

Bioorg Chem. 2019 Jun:87:409-416. doi: 10.1016/j.bioorg.2019.03.025. Epub 2019 Mar 20.

Authors

Yang-Yang Liu¹, Zhen Ao¹, Qi-Qi Xu¹, Dong-Rong Zhu¹, Chen Chen¹, Xiao-Bing Wang¹, Jian-Guang Luo², Ling-Yi Kong³

Affiliations

¹ Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China.
² Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China. Electronic address: luojg@cpu.edu.cn.
³ Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China. Electronic address: cpu_lykong@126.com.

PMID: 30921742
DOI: 10.1016/j.bioorg.2019.03.025

Abstract

Nine new spirocyclic acylphloroglucinol derivatives, hyperpatulols A-I (1-9), were characterized from the flowers of Hypericum patulum. Their structures were elucidated by the basic analysis of the obtained spectroscopic data, and their absolute configurations were assigned by both the electronic circular dichroism (ECD) exciton chirality method and ECD calculation. The evaluation of their anti-migration effects on U2-OS human osteosarcoma cells showed that compound 4 exhibited moderate inhibitory activity in a dose-dependent manner. Further pharmacological studies revealed that 4 could regulate the expression of the proteins Vimentin and E-cadherin.

Keywords: Anti-migration activity; ECD calculation; ECD exciton chirality method; Hypericum patulum; Spirocyclic acylphloroglucinol derivatives.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antigens, CD / genetics
Antigens, CD / metabolism
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Cadherins / genetics
Cadherins / metabolism
Cell Line, Tumor
Cell Movement / drug effects
Cell Proliferation / drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Flowers / chemistry*
Humans
Hypericum / chemistry*
Molecular Structure
Phloroglucinol / analogs & derivatives
Phloroglucinol / chemistry
Phloroglucinol / pharmacology*
Spiro Compounds / chemistry
Spiro Compounds / isolation & purification
Spiro Compounds / pharmacology*
Structure-Activity Relationship
Vimentin / genetics
Vimentin / metabolism

Substances

Antigens, CD
Antineoplastic Agents, Phytogenic
CDH1 protein, human
Cadherins
Spiro Compounds
VIM protein, human
Vimentin
Phloroglucinol