Formation of Samin Diastereomers by Acid-Catalyzed Transformation of Sesamolin with Hydrogen Peroxide
Journal
Journal of agricultural and food chemistry
Journal Volume
68
Journal Volume
68
Journal Issue
23
Journal Issue
23
Pages
6430-6438
Start Page
6430
End Page
6438
ISSN
00218561
Date Issued
2020-06-10
Author(s)
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.
Subjects
acid-catalyzed transformation
furofuran lignans
hydrogen peroxide
samin diastereomers
sesame oil
sesamolin-derivative
Publisher
American Chemical Society
Type
journal article