Costatone C-A New Halogenated Monoterpene from the New Zealand Red Alga Plocamium angustum

Mar Drugs. 2019 Jul 19;17(7):418. doi: 10.3390/md17070418.

Abstract

Red algae of the genus Plocamium have been a rich source of halogenated monoterpenes. Herein, a new cyclic monoterpene, costatone C (7), was isolated from the extract of P. angustum collected in New Zealand, along with the previously reported (1E,5Z)-1,6-dichloro-2-methylhepta-1,5-dien-3-ol (8). Elucidation of the planar structure of 7 was achieved through conventional NMR and (-)-HR-APCI-MS techniques, and the absolute configuration by comparison of experimental and DFT-calculated ECD spectra. The absolute configuration of 8 was determined using Mosher's method. Compound 7 showed mild antibacterial activity against Staphylococcus aureus and S. epidermidis. The state of Plocamium taxonomy and its implications upon natural product distributions, especially across samples from specimens collected in different countries, is also discussed.

Keywords: DFT; ECD; Mosher’s analysis; Plocamium angustum; costatone; halogenated monoterpene.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Hydrocarbons, Halogenated / chemistry
  • Hydrocarbons, Halogenated / isolation & purification
  • Hydrocarbons, Halogenated / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Monoterpenes / chemistry
  • Monoterpenes / isolation & purification
  • Monoterpenes / pharmacology*
  • New Zealand
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification
  • Plocamium / chemistry*
  • Staphylococcus aureus / drug effects
  • Staphylococcus epidermidis / drug effects

Substances

  • Anti-Bacterial Agents
  • Hydrocarbons, Halogenated
  • Monoterpenes
  • Plant Extracts