Lahorenoic acids A-C, ortho-dialkyl-substituted aromatic acids from the biocontrol strain Pseudomonas aurantiaca PB-St2

J Nat Prod. 2013 Feb 22;76(2):135-41. doi: 10.1021/np3005166. Epub 2013 Feb 12.

Abstract

Three new aromatic acids, named lahorenoic acids A (1), B (2), and C (3), have been isolated along with the known compounds phenazine-1-carboxylic acid (4), 2-hydroxyphenazine-1-carboxylic acid (5), 2-hydroxyphenazine (6), 2,8-dihydroxyphenazine (7), cyclo-Pro-Tyr (8), cyclo-Pro-Val (9), cyclo-Pro-Met (10), and WLIP (11) and characterized from the biocontrol strain Pseudomonas aurantiaca PB-St2. The structures of these compounds were deduced by 1D and 2D NMR spectroscopic and mass spectral data interpretation. Compounds 2, 4, and 7 showed moderate antibacterial activity against mycobacteria and other Gram-positive bacteria, while 4 was also found to exhibit cytotoxic and antifungal properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / isolation & purification*
  • Carboxylic Acids / pharmacology
  • Gram-Positive Bacteria / drug effects
  • Molecular Structure
  • Mycobacteriaceae / drug effects
  • Nuclear Magnetic Resonance, Biomolecular
  • Phenazines / chemistry
  • Phenazines / isolation & purification
  • Phenazines / pharmacology
  • Pseudomonas / chemistry*

Substances

  • Antifungal Agents
  • Carboxylic Acids
  • Phenazines
  • lahorenoic acid A
  • lahorenoic acid B
  • lahorenoic acid C
  • 1-phenazinecarboxylic acid