Neolignanamides, lignanamides, and other phenolic compounds from the root bark of Lycium chinense

J Nat Prod. 2013 Jan 25;76(1):51-8. doi: 10.1021/np300655y. Epub 2013 Jan 2.

Abstract

Seven new neolignanamides (1-7), including two pairs of cis- and trans-isomers, and a new lignanamide (8) were isolated from the EtOAc-soluble fraction of an EtOH extract of the root bark of Lycium chinense, together with 22 known phenolic compounds (9-30), four of which were obtained from the genus Lycium for the first time. Compounds 5, 6, and 7 are unusual dimers having a rare connection mode between the two cinnamic acid amide units, while compounds 6, 7, and 8 are the first naturally occurring dimers derived from two dissimilar cinnamic acid amides. The cinnamic acid amides, neolignanamides, and lignanamides possess moderate radical-scavenging activity against the DPPH (2,2-diphenyl-1-picrylhydrazyl) and superoxide radicals.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylamides / chemistry
  • Acrylamides / isolation & purification*
  • Acrylamides / pharmacology
  • Biphenyl Compounds / pharmacology
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / isolation & purification*
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / isolation & purification*
  • Free Radical Scavengers / pharmacology
  • Lycium / chemistry*
  • Molecular Structure
  • Naphthalenes / chemistry
  • Naphthalenes / isolation & purification*
  • Naphthalenes / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular
  • Phenols / chemistry
  • Picrates / pharmacology
  • Plant Bark / chemistry
  • Stereoisomerism

Substances

  • (1,2-trans)-N3-(4-acetamidobutyl)-1-(3,4-dihydroxyphenyl)-7-hydroxy-N2-(4-hydroxyphenethyl)-6,8-dimethoxy-1,2-dihydronaphthalene-2,3-dicarboxamide
  • (E)-3-((2,3-trans)-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-2,3-dihydrobenzo(b)(1,4)dioxin-6-yl)-N-(4-hydroxyphenethyl)acrylamide
  • Acrylamides
  • Biphenyl Compounds
  • Bridged Bicyclo Compounds, Heterocyclic
  • Drugs, Chinese Herbal
  • Free Radical Scavengers
  • Naphthalenes
  • Phenols
  • Picrates
  • 1,1-diphenyl-2-picrylhydrazyl