Application of a computer-assisted structure elucidation program for the structural determination of a new terpenoid aldehyde with an unusual skeleton

Xing-Nuo Li; Clark D Ridge; Eugene P Mazzola; Jianghao Sun; Osvaldo Gutierrez; Arvin Moser; Joseph C DiMartino; Scott A MacDonald; Pei Chen

doi:10.1002/mrc.4466

Application of a computer-assisted structure elucidation program for the structural determination of a new terpenoid aldehyde with an unusual skeleton

Magn Reson Chem. 2017 Mar;55(3):210-213. doi: 10.1002/mrc.4466. Epub 2016 Jul 10.

Authors

Xing-Nuo Li^{1

2}, Clark D Ridge³, Eugene P Mazzola⁴, Jianghao Sun², Osvaldo Gutierrez⁴, Arvin Moser⁵, Joseph C DiMartino⁵, Scott A MacDonald⁵, Pei Chen²

Affiliations

¹ College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China.
² Food Composition and Methods Development Laboratory, Beltsville Human Nutrition Research Center, Agricultural Research Service, US Department of Agriculture, Beltsville, MD 20705, USA.
³ Office of Regulatory Science, Center for Food Safety and Applied Nutrition, US Food and Drug Administration, College Park, MD 20740, USA.
⁴ Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.
⁵ Toronto Department, Advanced Chemistry Development Inc. (ACD/Labs), Toronto, Ontario M5C 1B5, Canada.

Abstract

The structure of a novel compound from Adansonia digitata has been elucidated, and its ¹ H and ¹³ C NMR spectra have been assigned employing a variety of one-dimensional and two-dimensional NMR techniques without degradative chemistry. The Advanced Chemistry Development ACD/Structure Elucidator software was important for determining part of this structure that contained a fused bicyclic system with very few hydrogen atoms, which in turn, exhibited essentially no discriminating HMBC connectivities throughout that portion of the molecule. Copyright © 2016 John Wiley & Sons, Ltd.

Keywords: 13C NMR; 1D NMR; 1H NMR; 2D NMR; Adansonia digitata; NMR; baobab; chemical shift assignments; computer-assisted structure elucidation (CASE); natural products.

Grants and funding

Y01 OD001298-01/OD/NIH HHS/United States