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.
All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Molecular Medicine
- Pharmaceutical Science
- Drug Discovery
- Complementary and alternative medicine
- Organic Chemistry