Testacosides A-D, glycoglycerolipids produced by Microbacterium testaceum isolated from Tedania brasiliensis

Appl Microbiol Biotechnol. 2024 Dec;108(1):112. doi: 10.1007/s00253-023-12870-0. Epub 2024 Jan 12.

Abstract

Marine bacteria living in association with marine sponges have proven to be a reliable source of biologically active secondary metabolites. However, no studies have yet reported natural products from Microbacterium testaceum spp. We herein report the isolation of a M. testaceum strain from the sponge Tedania brasiliensis. Molecular networking analysis of bioactive pre-fractionated extracts from culture media of M. testaceum enabled the discovery of testacosides A-D. Analysis of spectroscopic data and chemical derivatizations allowed the identification of testacosides A-D as glycoglycerolipids bearing a 1-[α-glucopyranosyl-(1 → 3)-(α-mannopyranosyl)]-glycerol moiety connected to 12-methyltetradecanoic acid for testacoside A (1), 14-methylpentadecanoic acid for testacoside B (2), and 14-methylhexadecanoic acid for testacosides C (3) and D (4). The absolute configuration of the monosaccharide residues was determined by 1H-NMR analysis of the respective diastereomeric thiazolidine derivatives. This is the first report of natural products isolated from cultures of M. testaceum. KEY POINTS: • The first report of metabolites produced by Microbacterium testaceum. • 1-[α-Glucopyranosyl-(1 → 3)-(α-mannopyranosyl)]-glycerol lipids isolated and identified. • Microbacterium testaceum strain isolated from the sponge Tedania brasiliensis.

Keywords: Glycoglycerolipids; Marine bacteria; Molecular networking.

MeSH terms

  • Actinomycetales* / metabolism
  • Animals
  • Biological Products* / metabolism
  • Glycerol / metabolism
  • Glycolipids*
  • Magnetic Resonance Spectroscopy
  • Microbacterium
  • Porifera* / chemistry

Substances

  • glycerolglycolipids
  • Glycerol
  • Biological Products
  • Glycolipids

Supplementary concepts

  • Microbacterium testaceum