Acylphloroglucinolated Catechin and Phenylethyl Isocoumarin Derivatives from Agrimonia pilosa

J Nat Prod. 2016 Sep 23;79(9):2376-83. doi: 10.1021/acs.jnatprod.6b00566. Epub 2016 Sep 2.

Abstract

Eight new compounds (1-8), including five acylphloroglucinolated catechins (1-5) and three phenylethyl isocoumarin glycosides (6-8), were isolated from Agrimonia pilosa along with six other known compounds (9-14). The new compounds were characterized structurally by NMR, MS, and ECD analyses. Compounds 4 and 5 were assigned as acylphloroglucinolated procyanidin derivatives, which are described for the first time from Nature. The absolute configuration of compound 8 was elucidated by computational analysis of its ECD spectrum. The isolated compounds were evaluated for their inhibitory activity against lipopolysaccharide-induced NO production in BV2 microglial cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agrimonia / chemistry*
  • Animals
  • Biflavonoids
  • Catechin / chemistry
  • Catechin / isolation & purification*
  • Catechin / pharmacology
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology
  • Isocoumarins / chemistry
  • Isocoumarins / isolation & purification*
  • Isocoumarins / pharmacology
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Phloroglucinol / analogs & derivatives*
  • Phloroglucinol / chemistry
  • Phloroglucinol / isolation & purification
  • Proanthocyanidins
  • Republic of Korea

Substances

  • Biflavonoids
  • Drugs, Chinese Herbal
  • Glycosides
  • Isocoumarins
  • Lipopolysaccharides
  • Proanthocyanidins
  • Nitric Oxide
  • procyanidin
  • Catechin
  • Phloroglucinol