Cytotoxic Guanidine Alkaloids from a French Polynesian Monanchora n. sp. Sponge

J Nat Prod. 2016 Aug 26;79(8):1929-37. doi: 10.1021/acs.jnatprod.6b00168. Epub 2016 Jul 15.

Abstract

Four bicyclic and three pentacyclic guanidine alkaloids (1-7) were isolated from a French Polynesian Monanchora n. sp. sponge, along with the known alkaloids monalidine A (8), enantiomers 9-11 of known natural product crambescins, and the known crambescidins 12-15. Structures were assigned by spectroscopic data interpretation. The relative and absolute configurations of the alkaloids were established by analysis of (1)H NMR and NOESY spectra and by circular dichroism analysis. The new norcrambescidic acid (7) corresponds to interesting biosynthetic variation within the pentacyclic core. All compounds exhibited antiproliferative and cytotoxic efficacy against KB, HCT116, HL60, MRC5, and B16F10 cancer cells, with IC50 values ranging from 4 nM to 10 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Axinella / chemistry*
  • Drug Screening Assays, Antitumor
  • Guanidines / chemistry
  • Guanidines / isolation & purification*
  • Guanidines / pharmacology*
  • HCT116 Cells
  • HL-60 Cells
  • Humans
  • Inhibitory Concentration 50
  • KB Cells
  • Marine Biology
  • Nuclear Magnetic Resonance, Biomolecular
  • Polynesia

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Guanidines