Neopetrocyclamines A and B, polycyclic diamine alkaloids from the sponge Neopetrosia cf exigua

J Nat Prod. 2015 Mar 27;78(3):543-7. doi: 10.1021/np500759r. Epub 2015 Jan 13.

Abstract

Two new polycyclic alkaloids, neopetrocyclamines A and B (1 and 2), along with the known metabolites papuamine (3) and haliclonadiamine (4), were isolated from the Indonesian sponge Neopetrosia cf exigua. Neopetrocyclamine A contains a formamidinium moiety, a rare functional group. While these compounds share the same basic biosynthetic building blocks, the size of the ring system differs in 1 and 2 because of the formamidinium moiety. Biological evaluations of 1-4 revealed that papuamine is cytotoxic against glioblastoma SF-295 cells (GI50 = 0.8 μM).

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Diamines / chemistry
  • Diamines / isolation & purification*
  • Diamines / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Indonesia
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Polycyclic Compounds / chemistry
  • Polycyclic Compounds / isolation & purification*
  • Polycyclic Compounds / pharmacology
  • Porifera / chemistry*

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Diamines
  • Polycyclic Compounds
  • haliclonadiamine
  • neopetrocyclamine A
  • neopetrocyclamine B
  • papuamine