Neocomplanines A and B, a complanine family isolated from the marine fireworm

J Nat Prod. 2010 Mar 26;73(3):303-5. doi: 10.1021/np900694j.

Abstract

Two new members of the complanine family, neocomplanines A (2) and B (3), were isolated as minor components of the methanolic extract of the "marine fireworm" Eurythoe complanata. The structures of the neocomplanines were revealed spectroscopically to be a trimethylammonium unit with a saturated carbon chain. The planar structures of neocomplanines A and B were confirmed successfully through total syntheses that used epichlorohydrin as a starting material. The neocomplanines show inflammatory activity and also enhanced PKC activity in combination with TPA in the presence of Ca(2+) in vitro; both are similar to the effects of complanine (1). The molecular mechanism of the effects of complanine-related compounds is discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Animals
  • Marine Biology
  • Molecular Structure
  • Polychaeta / chemistry*
  • Protein Kinase C / drug effects*
  • Protein Kinase C / metabolism
  • Quaternary Ammonium Compounds / chemistry
  • Quaternary Ammonium Compounds / isolation & purification*

Substances

  • Alkenes
  • Quaternary Ammonium Compounds
  • complanine
  • neocomplanine A
  • neocomplanine B
  • Protein Kinase C