Two new phenolic compounds from the leaves of Alnus sibirica Fisch. ex Turcz

Nat Prod Res. 2016;30(2):206-13. doi: 10.1080/14786419.2015.1053087. Epub 2015 Jul 27.

Abstract

Two new phenolic compounds, 4-O-glucopyranosyl-5-O-caffeoylshikimic acid (1) and 2,3-digalloyl oregonin (2), were isolated along with eight known phenolic compounds (3-10) from an 80% acetone extract of Alnus sibirica leaves. The chemical structures of these compounds were elucidated using 1D/2D nuclear magnetic resonance and high resolution-MS. The anti-oxidative activities of these compounds were determined by assaying their 1,1-diphenyl-2-picrylhydrazyl radical and nitroblue tetrazolium superoxide anion scavenging activity. All of the isolated phenolic compounds (1-10) exhibited potent anti-oxidative activities. In particular, 2 and 4, which are diarylheptanoids, and 10 which is ellagitannin exhibited excellent anti-oxidative activities with almost the same potency as that of the positive controls L-ascorbic acid and allopurinol.

Keywords: Alnus sibirica; anti-oxidant activity; caffeoylshikimic acid; galloyl-diarylheptanoid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alnus / chemistry*
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology*
  • Ascorbic Acid / pharmacology
  • Biphenyl Compounds / chemistry
  • Diarylheptanoids / chemistry*
  • Diarylheptanoids / pharmacology
  • Drug Evaluation, Preclinical / methods
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology
  • Gallic Acid / analogs & derivatives*
  • Gallic Acid / chemistry
  • Gallic Acid / pharmacology
  • Glucosides / chemistry*
  • Glucosides / pharmacology
  • Hydrolyzable Tannins / pharmacology
  • Magnetic Resonance Spectroscopy
  • Phenols / chemistry
  • Picrates / chemistry
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry*
  • Shikimic Acid / analogs & derivatives*
  • Shikimic Acid / chemistry
  • Shikimic Acid / pharmacology
  • Superoxides / chemistry

Substances

  • 2,3-digalloyl oregonin
  • 4-O-glucopyranosyl-5-O-caffeoylshikimic acid
  • Antioxidants
  • Biphenyl Compounds
  • Diarylheptanoids
  • Free Radical Scavengers
  • Glucosides
  • Hydrolyzable Tannins
  • Phenols
  • Picrates
  • Plant Extracts
  • ellagitannin
  • Superoxides
  • Shikimic Acid
  • Gallic Acid
  • 1,1-diphenyl-2-picrylhydrazyl
  • Ascorbic Acid

Grants and funding

This study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science, and Technology [grant number 2010-0022929].