Two new malyngamides from a Madagascan Lyngbya majuscula

J Nat Prod. 2000 Jul;63(7):965-8. doi: 10.1021/np000038p.

Abstract

The lipid extract of a Madagascan Lyngbya majuscula has yielded malyngamides Q and R, both amides of 7-methoxytetradec-4-enoic acid. The isolation of these metabolites was accomplished using preparative liquid chromatography, with final purification through repetitive reversed-phase HPLC. Structure elucidation was accomplished utilizing 1D and 2D NMR spectroscopic characterization of the natural products and comparisons with malyngamides A and B. DPFGSE 1D NOE data suggested a different geometrical stereochemistry at C-6 in malyngamides Q and R from that observed for malyngamide A, as well as the other known malyngamides. The Z stereochemistry was confirmed for malyngamide R by measurement of key diagnostic (3)J(CH) couplings utilizing the HSQMBC pulse sequence. The absolute stereochemistry of C-4' ' of the pyrrolidone ring was defined by chiral GCMS analysis of serine released by ozonolysis and acid hydrolysis.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amides / chemistry
  • Amides / isolation & purification*
  • Cyanobacteria / chemistry*
  • Molecular Structure
  • Pyrroles / chemistry
  • Pyrroles / isolation & purification*
  • Spectrum Analysis

Substances

  • Amides
  • Pyrroles
  • malyngamide Q
  • malyngamide R