Total syntheses of schizandriside, saracoside and (±)-isolariciresinol with antioxidant activities

Mana Sampei, Midori A. Arai, Masami Ishibashi

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Lignans are widely distributed in plants and exhibit significant pharmacological effects, including anti-tumor and antioxidative activities. Here, we describe the total synthesis of schizandriside (1), a compound we previously isolated from Saraca asoca by monitoring antioxidative activity using the 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Starting from a tandem Michael-aldol reaction, the lignan skeleton was synthesized in 6 steps, including a cyclization step. To determine the stereochemistry of 1, we synthesized the natural product (±)-isolariciresinol (18) from alcohol 17. Comparison of the spectral data showed good agreement. Glycosylation was investigated using four different glycosyl donors. Only the Koenigs–Knorr condition using silver trifluoromethanesulfonate with 1,1,3,3-tetramethylurea provided the glycosylated product. Deprotection and purification using reverse-phase high-performance liquid chromatography gave schizandriside (1) and its diastereomer saracoside (2). Synthesized 1, 2 and 18 showed antioxidant activity with IC50 = 34.4, 28.8, 53.0 μM, respectively.

Original languageEnglish
Pages (from-to)651-654
Number of pages4
JournalJournal of Natural Medicines
Volume72
Issue number3
DOIs
Publication statusPublished - 2018 Jun 1
Externally publishedYes

Keywords

  • Antioxidant activity
  • Lignan glycoside
  • Natural product
  • Total synthesis

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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