Eight new biflavonoids with lavandulyl units from the roots of Sophora flavescens and their inhibitory effect on PTP1B

Hai-Wei Yan; Hui Zhu; Xiang Yuan; Ya-Nan Yang; Zi-Ming Feng; Jian-Shuang Jiang; Pei-Cheng Zhang

doi:10.1016/j.bioorg.2019.01.058

Eight new biflavonoids with lavandulyl units from the roots of Sophora flavescens and their inhibitory effect on PTP1B

Bioorg Chem. 2019 May:86:679-685. doi: 10.1016/j.bioorg.2019.01.058. Epub 2019 Feb 23.

Authors

Hai-Wei Yan¹, Hui Zhu¹, Xiang Yuan¹, Ya-Nan Yang², Zi-Ming Feng¹, Jian-Shuang Jiang¹, Pei-Cheng Zhang¹

Affiliations

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, PR China.
² State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, PR China; State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guizhou 550025, PR China.

PMID: 30831529
DOI: 10.1016/j.bioorg.2019.01.058

Abstract

In the course of studying the components from the roots of Sophora flavescens, eight new unusual biflavonoids consisting of a flavanone fused with a dihydrochalcone skeleton were isolated. These new chemical structures were elucidated by means of UV, IR, HRESIMS, NMR and ECD spectroscopic data and a comparison of experimental ECD spectra with calculated ECD spectra. Some compounds were subjected to an antidiabetic bioassay on human recombinant PTP1B inhibition, and showed strong inhibitory activity.

Keywords: Biflavonoids; PTP1B inhibitory activity; Sophobiflavonoids A–H; Sophora flavescens.

Publication types

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

MeSH terms

Acyclic Monoterpenes / chemistry
Acyclic Monoterpenes / isolation & purification
Acyclic Monoterpenes / pharmacology*
Biflavonoids / chemistry
Biflavonoids / isolation & purification
Biflavonoids / pharmacology*
Chalcones / chemistry
Chalcones / isolation & purification
Chalcones / pharmacology
Dose-Response Relationship, Drug
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / isolation & purification
Enzyme Inhibitors / pharmacology*
Humans
Molecular Structure
Plant Extracts / chemistry
Plant Extracts / isolation & purification
Plant Extracts / pharmacology*
Plant Roots / chemistry
Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
Protein Tyrosine Phosphatase, Non-Receptor Type 1 / metabolism
Recombinant Proteins / metabolism
Sophora / chemistry*
Structure-Activity Relationship

Substances

Acyclic Monoterpenes
Biflavonoids
Chalcones
Enzyme Inhibitors
Plant Extracts
Recombinant Proteins
PTPN1 protein, human
Protein Tyrosine Phosphatase, Non-Receptor Type 1
dihydrochalcone
lavandulol