Structural Revisions of Two Highly Aromatic Naphthoquinone-Derived Dimers Based on NMR Analysis, Computer-Assisted Structure Elucidation Methods, and Computations
Tian‐Ming Lv, De‐Li Chen, Jingjing Liang, Ming Bai, Bin Lin, Xiao‐Xiao Huang, Guoxu Ma, Shao‐Jiang Song
Abstract
Eleucanainones A and B are two structurally complex naphthoquinone-derived dimers whose structure identification is difficult. Large yellow fragments of the preliminary CASE (computer-assisted structure elucidation) analysis revealed that the original structures might be questionable. Structural revisions of the two compounds were proposed on the basis of NMR analysis, CASE methods, conformation analysis, and DFT (density functional theory) NMR calculations with a custom DP4+ analysis. In addition, a polyketide-folded biosynthetic pathway of the two revised structures was proposed.
Topics & Concepts
ChemistryNaphthoquinoneComputational chemistryDensity functional theoryProton NMRMoleculeCombinatorial chemistryStereochemistryOrganic chemistryBioactive Compounds and Antitumor AgentsMorinda citrifolia extract usesNatural product bioactivities and synthesis