Mass spectrometry detection of minor new meridianins from the Antarctic colonial ascidians Aplidium falklandicum and Aplidium meridianum

J Mass Spectrom. 2015 Jan;50(1):103-11. doi: 10.1002/jms.3502.

Abstract

Taking into account the broad biological activities found in the meridianin indole alkaloids isolated to date, we have re-examined the organic extracts of an Antarctic collection of the tunicates Aplidium meridianum and A. falklandicum (Chordata: Ascidiacea) by HPLC in conjunction with a high-resolution mass spectrometer (HPLC-MS). A new set of analogs of meridianins A-G has been detected, and their structures are proposed on the basis of the molecular formulae identified by LC-HRMS analysis using a C18 column with a gradient of water/acetonitrile and an LTQ-FT-MS Orbitrap detector. Remarkably, dimers derived from meridianin A and from meridianin B or E were also detected. Our findings provide further evidence of the broad variability within the meridianin-like derivatives of this highly bioactive alkaloid family.

Keywords: A. falklandicum; Aplidium meridianum; FTMS-Orbitrap; LC-MS; indole alkaloids; marine natural products; meridianin-dimers; meridianins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antarctic Regions
  • Chromatography, High Pressure Liquid / methods
  • Dimerization
  • Indole Alkaloids / analysis
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / isolation & purification
  • Molecular Structure
  • Pyrimidines / chemistry
  • Pyrimidines / isolation & purification
  • Spectrometry, Mass, Electrospray Ionization / methods*
  • Urochordata / chemistry*

Substances

  • Indole Alkaloids
  • Pyrimidines
  • meridianin A
  • meridianin G