Two new stereoisomers of tetrahydrofuranoid lignans from the flower buds of Magnolia fargesii

Jun Lee, Dongho Lee, Dae Sik Jang, Joo Won Nam, Jong Pyung Kim, Ki Hun Park, Min Suk Yang, Eun Kyoung Seo

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Two new stereoisomers of tetrahydrofuranoid lignans, 7S,8R,7′S, 8′R- (1) and 7R,8S,7′S,8′R-3,4,3′,4′-tetramethoxy- 9,7′-dihydroxy-8.8′,7.O.9′-lignan (2) along with nine known lignans including tetrahydrofuranoids (3, 4) and tetrahydrofurofuranoids (5-11) were isolated from a CHCl3-soluble fraction of the flower buds of Magnolia fargesii. Two tetrahydrofuranoids, magnostellin A (3) and lariciresinol dimethyl ether (4) were isolated from this species for the first time. The structures of these compounds (1-11) were identified by spectroscopic methods as well as by comparison with published values. Absolute configurations of new stereoisomers (1, 2) were determined by the Mosher's esterification method and Circular Dichroism (CD) studies. All the isolates (1-11) were evaluated for their antioxidant activities using modified superoxide radical-scavenging assay. Compounds 5-8 showed the potent superoxide radical-scavenging activities with the ED50 values of 19.2, 19.2, 16.5, and 27.7 μM, respectively, as compared with standard antioxidants (BHA: 22.8 μM; Trolox: 940 μM).

Original languageEnglish
Pages (from-to)137-139
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume55
Issue number1
DOIs
Publication statusPublished - 2007 Jan 1

Fingerprint

Magnolia
Lignans
Stereoisomerism
Scavenging
Superoxides
Antioxidants
Butylated Hydroxyanisole
Esterification
Circular Dichroism
Assays

Keywords

  • Antioxidant activity
  • Lignan
  • Magnolia fargesii
  • Magnoliaceae
  • Superoxide radical
  • Tetrahydrofuranoid
  • Xinyi

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

Cite this

Two new stereoisomers of tetrahydrofuranoid lignans from the flower buds of Magnolia fargesii. / Lee, Jun; Lee, Dongho; Jang, Dae Sik; Nam, Joo Won; Kim, Jong Pyung; Park, Ki Hun; Yang, Min Suk; Seo, Eun Kyoung.

In: Chemical and Pharmaceutical Bulletin, Vol. 55, No. 1, 01.01.2007, p. 137-139.

Research output: Contribution to journalArticle

Lee, Jun ; Lee, Dongho ; Jang, Dae Sik ; Nam, Joo Won ; Kim, Jong Pyung ; Park, Ki Hun ; Yang, Min Suk ; Seo, Eun Kyoung. / Two new stereoisomers of tetrahydrofuranoid lignans from the flower buds of Magnolia fargesii. In: Chemical and Pharmaceutical Bulletin. 2007 ; Vol. 55, No. 1. pp. 137-139.
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