A new methylene bisflavan-3-ol from the branches and leaves of Potentilla fruticosa

Nat Prod Res. 2020 May;34(9):1238-1245. doi: 10.1080/14786419.2018.1557169. Epub 2019 Jan 19.

Abstract

Dasiphora fruticosa L. (Rosaceae), also known as Potentilla fruticosa L. (syn.), is a hardy deciduous shrub widely distributed in the north temperate regions of the world. Three methylene bisflavan-3-ols (1-3), together with a procyanidin dimer, (-)-afzelechin-(4α→8)-(-)-afzelechin (4) were isolated for the first time from the branches and leaves of the titled plant, in addition to 11 known compounds (5-15). Their structures were elucidated by means of extensive spectroscopic analysis and by comparison with data reported in the literatures. Methylene 6,8-bis(7-O-glucosyl) catechin (1) was determined to be a new dimeric flavan-3-ol glycoside through a methylene linkage between C-8 and C-8 of two units. At a concentration of 128 μg/mL, the known compounds 9 - 13 exhibited antibacterial activities on Escherichia coli, Staphylococcus aureus subsp. aureus, Salmonella enterica subsp. enterica, and Pseudomonas aeruginosa. Compound 12 also showed certain glucose uptake stimulating activity.

Keywords: Dasiphora fruticosa; Potentilla fruticosa (syn.); Rosaceae; anti-bacterial; flavan-3-ol dimers; methylene 6,8-bis(7-O-glucosyl)catechin.

MeSH terms

  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Bacteria / drug effects
  • Biflavonoids / isolation & purification
  • Catechin / isolation & purification
  • Flavonoids / isolation & purification*
  • Glucose / pharmacokinetics
  • Glycosides / analysis
  • Glycosides / isolation & purification
  • Phenols / isolation & purification
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Plant Leaves / chemistry
  • Potentilla / chemistry*
  • Proanthocyanidins / isolation & purification
  • Rosaceae / chemistry*

Substances

  • Anti-Bacterial Agents
  • Biflavonoids
  • Flavonoids
  • Glycosides
  • Phenols
  • Plant Extracts
  • Proanthocyanidins
  • flavan-3-ol
  • procyanidin
  • Catechin
  • Glucose
  • afzelechin