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

Mana Sampei, Midori A. Arai, Masami Ishibashi

研究成果: Article査読

2 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)651-654
ページ数4
ジャーナルJournal of Natural Medicines
72
3
DOI
出版ステータスPublished - 2018 6 1
外部発表はい

ASJC Scopus subject areas

  • 薬科学
  • 創薬
  • 補完代替医療
  • 有機化学

フィンガープリント

「Total syntheses of schizandriside, saracoside and (±)-isolariciresinol with antioxidant activities」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル