N-Acyl Dehydrotyrosines, Tyrosinase Inhibitors from the Marine Bacterium Thalassotalea sp. PP2-459

J Nat Prod. 2016 Feb 26;79(2):447-50. doi: 10.1021/acs.jnatprod.5b00972. Epub 2016 Jan 29.

Abstract

Thalassotalic acids A-C and thalassotalamides A and B are new N-acyl dehydrotyrosine derivatives produced by Thalassotalea sp. PP2-459, a Gram-negative bacterium isolated from a marine bivalve aquaculture facility. The structures were elucidated via a combination of spectroscopic analyses emphasizing two-dimensional NMR and high-resolution mass spectrometric data. Thalassotalic acid A (1) displays in vitro inhibition of the enzyme tyrosinase with an IC50 value (130 μM) that compares favorably to the commercially used control compounds kojic acid (46 μM) and arbutin (100 μM). These are the first natural products reported from a bacterium belonging to the genus Thalassotalea.

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

  • Arbutin / pharmacology
  • Gram-Negative Bacteria / chemistry
  • Marine Biology
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Nuclear Magnetic Resonance, Biomolecular
  • Proteobacteria / chemistry*
  • Pyrones / pharmacology
  • Spain
  • Tyrosine* / analogs & derivatives
  • Tyrosine* / chemistry
  • Tyrosine* / isolation & purification
  • Tyrosine* / pharmacology

Substances

  • Pyrones
  • Tyrosine
  • kojic acid
  • Arbutin
  • Monophenol Monooxygenase