Phloroglucinol Derivatives with Protein Tyrosine Phosphatase 1B Inhibitory Activities from Eugenia jambolana Seeds

J Nat Prod. 2017 Feb 24;80(2):544-550. doi: 10.1021/acs.jnatprod.6b01073. Epub 2017 Jan 30.

Authors

Feifei Liu¹, Tao Yuan², Wei Liu¹, Hang Ma³, Navindra P Seeram³, Yuanyuan Li¹, Li Xu¹, Yu Mu¹, Xueshi Huang¹, Liya Li¹

Affiliations

¹ Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University , Shenyang 110819, People's Republic of China.
² Key Laboratory of Plant Resources and Chemistry of Arid Zone and State Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences , Urumqi 830011, People's Republic of China.
³ Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island , Kingston, Rhode Island 02881, United States.

PMID: 28134521
DOI: 10.1021/acs.jnatprod.6b01073

Abstract

Fifteen new phloroglucinol derivatives, jamunones A-O (1-8 and 10-16, respectively), along with one known analogue spiralisone C (9), were isolated from Eugenia jambolana seeds. Their structures were elucidated by detailed nuclear magnetic resonance and mass spectrometry spectroscopic data interpretation. Compounds 1-9, 11, 12, and 14-16 inhibited protein tyrosine phosphatase 1B activity with IC₅₀ values ranging from 0.42 to 3.2 μM.

Publication types

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

MeSH terms

India
Inhibitory Concentration 50
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Phloroglucinol* / analogs & derivatives
Phloroglucinol* / isolation & purification
Phloroglucinol* / pharmacology
Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
Seeds / chemistry*
Syzygium / chemistry*

Substances

Phloroglucinol
PTPN1 protein, human
Protein Tyrosine Phosphatase, Non-Receptor Type 1