Structural Revision of Macropodumine A and Structure of 2-Deoxymacropodumine A, Daphniphyllum Alkaloids with 11-Membered Macrolactone Rings

J Nat Prod. 2019 Mar 22;82(3):427-430. doi: 10.1021/acs.jnatprod.8b00232. Epub 2018 Dec 12.

Abstract

An unusual Daphniphyllum alkaloid, 2-deoxymacropodumine A (1), possessing an 11-membered macrolactone ring, was obtained from an extract of the stems of Daphniphyllum angustifolium. The structure of 1 was elucidated by 1D and 2D NMR spectroscopic methods and chemical calculations. Based on a comparison of the experimental and calculated NMR data, the structure of macropodumine A (2'), an analogue of 1, was also revised.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Daphniphyllum / chemistry*
  • Lactones / chemistry*
  • Molecular Structure
  • Polycyclic Compounds / chemistry*
  • Proton Magnetic Resonance Spectroscopy

Substances

  • Alkaloids
  • Lactones
  • Polycyclic Compounds
  • macropodumine A