Biologically Active Acetylenic Amino Alcohol and N-Hydroxylated 1,2,3,4-Tetrahydro-β-carboline Constituents of the New Zealand Ascidian Pseudodistoma opacum

J Nat Prod. 2016 Mar 25;79(3):607-10. doi: 10.1021/acs.jnatprod.5b00770. Epub 2015 Dec 15.

Abstract

The first occurrence of an acetylenic 1-amino-2-alcohol, distaminolyne A (1), isolated from the New Zealand ascidian Pseudodistoma opacum, is reported. The isolation and structure elucidation of 1 and assignment of absolute configuration using the exciton coupled circular dichroism technique are described. In addition, a new N-9 hydroxy analogue (2) of the known P. opacum metabolite 7-bromohomotrypargine is also reported. Antimicrobial screening identified modest activity of 1 toward Escherichia coli, Staphylococcus aureus, and Mycobacterim tuberculosis, while 2 exhibited a moderate antimalarial activity (IC50 3.82 μM) toward a chloroquine-resistant strain (FcB1) of Plasmodium falciparum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Alkynes / isolation & purification*
  • Alkynes / pharmacology*
  • Animals
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification*
  • Antimalarials / pharmacology*
  • Carbolines / chemistry
  • Carbolines / isolation & purification*
  • Carbolines / pharmacology*
  • Chloroquine / pharmacology
  • Drug Resistance, Bacterial / drug effects
  • Escherichia coli / drug effects
  • Inhibitory Concentration 50
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects
  • New Zealand
  • Plasmodium falciparum / drug effects
  • Staphylococcus aureus / drug effects
  • Urochordata / chemistry*

Substances

  • Alkynes
  • Antimalarials
  • Carbolines
  • tryptoline
  • Chloroquine