The epimerization of sesamin and asarinin

Chia Ying Li, Tahsin J. Chow, Tian Shung Wu

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Sesamin (1) and asarinin (2) are two C-7′ epimeric lignans. Molecular modeling by semiempirical methods indicated that 1 is more stable than 2 by about 2.5 kcal/mol. However, epimerization under acidic conditions led to a 44.8/55.2 equilibrium ratio of 1 and 2. Single-crystal X-ray diffraction analyses indicated that 1 was monoclinic with a = 10.0435(19) Å, b = 6.9151(8) Å, c = 11.8460(13) Å, and 2 was triclinic with a= 5.595(5) Å, b = 9.5910(18) Å, c = 15.620(4) A. The unexpected equilibrium ratio of 1 and 2 indicated that structural changes are dependent on the conditions of the extraction processes.

Original languageEnglish
Pages (from-to)1622-1624
Number of pages3
JournalJournal of Natural Products
Volume68
Issue number11
DOIs
Publication statusPublished - 2005 Nov 1

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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