Keikipukalides, Furanocembrane Diterpenes from the Antarctic Deep Sea Octocoral Plumarella delicatissima

J Nat Prod. 2018 Jan 26;81(1):117-123. doi: 10.1021/acs.jnatprod.7b00732. Epub 2017 Dec 20.

Abstract

During a 2013 cruise in the Southern Ocean we collected specimens of the octocoral Plumarella delicatissima between 800 and 950 m depth. Five new furanocembranoid diterpenes, keikipukalides A-E (1-5), the known diterpene pukalide aldehyde (6), and the known norditerpenoid ineleganolide (7) were isolated from the coral. These Plumarella terpenes lack mammalian cytotoxicity, while 2-7 display activity against Leishmania donovani between 1.9 and 12 μM. Structure elucidation was facilitated by one- and two-dimensional NMR spectroscopy and mass spectrometry, and keikipukalides A and E were confirmed by X-ray crystallography.

Publication types

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

MeSH terms

  • Animals
  • Antarctic Regions
  • Anthozoa / chemistry*
  • Crystallography, X-Ray / methods
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology
  • Leishmania donovani / drug effects
  • Macrocyclic Compounds / chemistry*
  • Macrocyclic Compounds / isolation & purification
  • Macrocyclic Compounds / pharmacology
  • Mass Spectrometry / methods
  • Nuclear Magnetic Resonance, Biomolecular / methods

Substances

  • Diterpenes
  • Macrocyclic Compounds