Planta Med 2013; 79 - PN67
DOI: 10.1055/s-0033-1348748

Michael Addition Artifacts of Major Withanolides in Physalis longifolia

CM Cao 1, H Zhang 1, RJ Gallagher 1, BN Timmermann 1
  • 1Department of Medicinal Chemistry, University of Kansas, Lawrence, KS 66045, United States

Five artificial withanolides 1-5, including three new compounds 1 – 3, were isolated and identified as derivatives of the three major withanolides 6-8 naturally present in Physalis longifolia. These artifacts formed in the presence of methanol through intra/inter-molecular Michael additions at the β-carbon of α, β-unsaturated carbonyl moiety in ring A. The mechanism was further confirmed by using deuterated methanol. As methanol is extensively used in withanolide isolation and purification, a comprehensive literature investigation was also conducted to identify potential withanolide artifacts reported to date.