Secoiridoid glucosides and related compounds from Syringa reticulata and their antioxidant activities.

Bioorg Med Chem Lett

Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan.

Published: November 2011

AI Article Synopsis

  • A 70% ethanol extract from Syringareticulata bark demonstrates strong antioxidant properties and led to the discovery of 17 compounds, including a new glucoside called reticuloside.
  • The isolated compounds jaspolyoside, oleuropein, and 2-(3,4-dihydroxy)-phenylethyl-β-d-glucopyranoside showed significant ability to scavenge superoxide anions with low EC(50) values.
  • The study revealed that the 2-(3,4-dihydroxyphenyl)-ethoxy group is crucial for enhancing antioxidant activity among the compounds.

Article Abstract

A 70% EtOH extract from the bark of Syringareticulata has shown significant antioxidant activity. Chemical study on the extract resulted in the isolation of seventeen compounds (1-17), including a novel oleoside-type secoiridoid glucoside, reticuloside (1), and the structures were elucidated on the basis of extensive spectroscopic analyses. Among the isolated compounds, jaspolyoside (2), oleuropein (4) and 2-(3,4-dihydroxy)-phenylethyl-β-d-glucopyranoside (17), showed the most potent superoxide anion scavenging activity with the EC(50) values of 4.97, 2.57 and 4.97μM, respectively. The structure-activity relationship indicated that the presence of 2-(3,4-dihydroxyphenyl)-ethoxy group is important for exhibiting the activity.

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http://dx.doi.org/10.1016/j.bmcl.2011.08.089DOI Listing

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