Flavans and diphenylpropanes with PTP1B inhibition from Broussonetia kazinoki

Fitoterapia. 2018 Oct:130:37-42. doi: 10.1016/j.fitote.2018.08.001. Epub 2018 Aug 4.

Abstract

Three new (1a/1b and 2b) and five known flavans (2a, 6a/6b, 7, and 8), one new flavan glycoside (3), and two new (4 and 5) and six known 1,3-diphenylpropanes (9-14) were isolated from the twigs of Broussonetia kazinoki. Compounds 1, 2, and 6 are scalemic mixtures, and were resolved by chiral HPLC to provide 1a/1b, 2a/2b, and 6a/6b. The structures of these compounds were elucidated by extensive spectroscopic methods, including NMR, MS, and ECD analyses. Compounds 1, 2, 5, 8, 9, 11, and 12 showed in vitro inhibition of protein tyrosine phosphatase 1B (PTP1B).

Keywords: 1,3-Diphenylpropanes; Broussonetia kazinoki; Flavans; Moraceae; Protein tyrosine phosphatase 1B.

MeSH terms

  • Broussonetia / chemistry*
  • China
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Molecular Structure
  • Phytochemicals / isolation & purification*
  • Phytochemicals / pharmacology
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Flavonoids
  • Glycosides
  • Phytochemicals
  • PTPN1 protein, human
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1