Glycopentanolones A-D, four new geranylated quinolone alkaloids from Glycosmis pentaphylla

Bioorg Chem. 2019 Jun:87:714-719. doi: 10.1016/j.bioorg.2019.03.069. Epub 2019 Mar 28.

Abstract

The ethanolic extract obtained from the stems of Glycosmis pentaphylla was found to suppress antigen-mediated degranulation of rat basophilic leukemia (RBL-2H3) cells. Four new geranylated 2-quinolone alkaloids, named glycopentanolones A-D (1-4), and 12 known metabolites (5-16) were isolated from the ethanolic extract from the stems of G. pentaphylla using bioassay-guided fractionation. Their structures were elucidated by a combination of 1D and 2D NMR, and HRESI-MS. The inhibitory effects of the isolated constituents on β-hexosaminidase release from RBL-2H3 cells were examined, and compounds 1, 5, 8 and 11 exhibited potent inhibitory activity with IC50 values between 0.05 and 4.28 μM.

Keywords: 2-Quinolone alkaloid; Glycopentanolone; Glycosmis pentaphylla; β-hexosaminidase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Molecular Structure
  • Quinolones / chemistry
  • Quinolones / isolation & purification
  • Quinolones / pharmacology*
  • Rats
  • Rutaceae / chemistry*
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Quinolones