Planta Med 2013; 79 - PN52
DOI: 10.1055/s-0033-1348733

Configurational Assignments of Conformationally Restricted Bis-Monoterpene Hydroquinones: Utility in Exploration of Endangered Plants

J Oh 1, JJ Bowling 1, Y Zou 1, AG Chittiboyina 2, RJ Doerksen 3, D Ferreira 1, TD Leininger 4, MT Hamann 1
  • 1Department of Pharmacognosy and Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA
  • 2National Center for Natural Products Research, The University of Mississippi, Thad Cochran Research Center, University, MS 38677, USA
  • 3Department of Medicinal Chemistry and Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA
  • 4Center for Bottomland Hardwoods Research, USDA Forest Service, 432 Stoneville Road, Stoneville, MS 38776, USA

Endangered plant species are a prominent resource for new chemistry. Lindera melissifolia is native to the Southeastern U.S. and scarcely populates the edges of lakes and ponds. Two meroterpenoids, melissifolianes A (1) and B (2) were purified and the 2-D structures elucidated using NMR and HRESIMS. The relative configuration of 1 was established employing the combination of NOE-based distance restraints and the comparisons of experimental and calculated coupling constants. The comparison of calculated and experimental ECD established the absolute configuration of 1. The relative configuration of a racemic mixture, melissifoliane B (2) was assigned utilizing J-based analysis combined with quantum mechanics and NMR techniques.