Two new stereoisomers of neolignan and lignan from the flower buds of magnolia fargesii

Jun Lee, Eun Kyoung Seo, Dae Sik Jang, Tae Joung Ha, K. I.M. Jong-Pyung, Joo Won Nam, Green Bae, Yun Mi Lee, Min Suk Yang, Jin Sook Kim

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33 Scopus citations

Abstract

A new stereoisomer of 8-O-4′ system neolignan, (7R,8S)-1-(3,4- dimethoxyphenyl)-2-[4-(3-hydroxy-1-propenyl)-2-methoxyphenoxy]-propane-1,3-diol (1) and a new stereoisomer of tetrahydrofuranoid lignan, (7R,8S,7'S,8'R)-(3,4,5, 3′,4′)-pentamethoxy-9,7′-dihydroxy-8.8′,7.0. 9′-lignan (2) along with seven known lignans and neolignans (3-9) were isolated from the methanol extracts of the flower buds of Magnolia fargesii. The structures of these compounds (1-9) were elucidated by spectroscopic methods including 1D- and 2D-NMR as well as by comparison with reported values. Absolute configurations of new stereoisomers 1 and 2 were determined by circular dichroism (CD) spectra. The absolute configuration of (S,8S,10S)-[tetrahydro-4- hydroxy-2-(3,4,5-tri-methoxyphenyl)furan-3-yl]methyl 3,4-dimethoxy benzoate (3) was determined by Mosher's esterification method for the first time in this study. Three lignans, tanegool (4), (+)-dehydrodiconiferyl alcohol (5), and epieudes-min (6), were isolated from this plant for the first time. Superoxide radical scavenging activities of the isolates (1-9) were measured by irradiated riboflavin/ethylenediaminetetraacetic acid (EDTA)/Nitroblue tetrazolium (NBT) system, and their in vitro rat lens aldose reductase (RLAR) inhibitory activities were also evaluated.

Original languageEnglish
Pages (from-to)298-301
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume57
Issue number3
DOIs
StatePublished - Mar 2009

Keywords

  • Aldose reductase
  • Diabetic complication
  • Lignan
  • Magnolia fargesii
  • Superoxide radical

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