Variabines A and B: new β-carboline alkaloids from the marine sponge Luffariella variabilis

J Nat Med. 2014 Jan;68(1):215-9. doi: 10.1007/s11418-013-0778-8. Epub 2013 May 18.

Abstract

Two new β-carboline alkaloids, variabines A (1) and B (2), were isolated from the Indonesian marine sponge Luffariella variabilis. Their structures were elucidated from spectral data, and 1 was found to be a sulfonated derivative of 2. Although numerous β-carboline alkaloids have been isolated from natural sources to date, 1 is the first β-carboline derivative containing a sulfate group. Compound 2 inhibited chymotrypsin-like activity of the proteasome and Ubc13 (E2)-Uev1A interaction with IC50 values of 4 and 5 μg/mL, respectively, whereas 1 had little effect on the activity or interaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Carbolines / isolation & purification*
  • Carbolines / pharmacology
  • Humans
  • Liver / drug effects
  • Liver / enzymology
  • Molecular Structure
  • Porifera / chemistry*
  • Proteasome Inhibitors / isolation & purification
  • Proteasome Inhibitors / pharmacology*
  • Rats
  • Transcription Factors / antagonists & inhibitors
  • Transcription Factors / metabolism
  • Ubiquitin-Conjugating Enzymes / antagonists & inhibitors
  • Ubiquitin-Conjugating Enzymes / metabolism

Substances

  • Alkaloids
  • Carbolines
  • Proteasome Inhibitors
  • Transcription Factors
  • variabine A
  • variabine B
  • UBE2N protein, human
  • UBE2V1 protein, human
  • Ubiquitin-Conjugating Enzymes