Design and synthesis of a new bioactive compound for marine antifouling inspired by natural products

Nat Prod Res. 2024 May;38(9):1624-1628. doi: 10.1080/14786419.2022.2152020. Epub 2022 Dec 5.

Abstract

A marine antifouling compound, N-octyl-2-hydroxybenzamide (OHBA), inspired by ceramide and paeonol molecules, was created. First, methyl salicylate was synthesized with salicylic acid and methanol, followed by n-octylamine through an ester-amine condensation reaction. Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry confirmed the characteristic structure of the OHBA compound. Bioassays showed that OHBA inhibits the growth of typical marine fouling organisms, such as Vibrio azureus, Navicula subminuscula, Ulva pertusa, Mytilus edulis, and Amphibalanus amphitrite, indicating its broad-spectrum antifouling ability. A one-year marine real-sea test further demonstrated the excellent antifouling properties of OHBA. OHBA is also extremely biodegradable, with a half-life of 6.3 days, making it a less environmentally harmful replacement for widely-used heavy metal-containing antifoulants.

Keywords: Natural products; biodegradability; chemical synthesis; marine antifouling.

MeSH terms

  • Animals
  • Aquatic Organisms
  • Biofouling* / prevention & control
  • Biological Products* / pharmacology
  • Salicylic Acid
  • Thoracica*

Substances

  • Biological Products
  • Salicylic Acid