Formation of Samin Diastereomers by Acid-Catalyzed Transformation of Sesamolin with Hydrogen Peroxide

Hsin Ya Tsai, Wei Ju Lee, I. Hsuan Chu, Wei Ching Hung, Nan Wei Su

Research output: Contribution to journalArticle

Abstract

The conversion of sesame lignans is of interest because the derived products may have potential applications. Here, in investigating the transformation of sesamin and sesamolin, main endogenous sesame lignans in sesame seeds, in both acidic aqueous and anhydrous systems, 7R,7'S-samin was identified as one of the major products of sesamolin in both systems catalyzed with common inorganic acids, but sesaminol was not generated. In investigating the effect of different oxidizing agents on the acid-catalyzed conversion of sesame lignans, 7R,7'S-samin was still the major product of sesamolin, whereas sesamolin as well as 7R,7'S-samin stereoselectively rendered 7R,7'R-samin in the presence of hydrogen peroxide. Hydrogen peroxide may play a role in stabilizing the transitional oxonium ions, derived from acid hydrolysis of sesamolin or 7R,7'S-samin by forming a seven-membered ring intermediate through hydrogen bonding, to consequently produce 7R,7'R-samin as the final product.

Original languageEnglish
Pages (from-to)6430-6438
Number of pages9
JournalJournal of Agricultural and Food Chemistry
Volume68
Issue number23
DOIs
Publication statusPublished - Jun 10 2020

Keywords

  • acid-catalyzed transformation
  • furofuran lignans
  • hydrogen peroxide
  • samin diastereomers
  • sesame oil
  • sesamolin-derivative

ASJC Scopus subject areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

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