Cladamide: a new ceramide from the endophytic fungus Cladosporium cladosporioides

Nat Prod Res. 2023 Apr;37(7):1082-1091. doi: 10.1080/14786419.2021.1986709. Epub 2021 Oct 8.

Abstract

A new ceramide, named cladamide (1), in addition to cinnamic acid (2), para-coumaric acid (3), stigmasterol-3-O-β-D-glucoside (4), and uracil (5), was isolated from the white beans culture of Cladosporium cladosporioides, a marine-derived endohpytic fungus isolated from the leaves of the mangrove, Avicennia marina (Forssk.) Vierh. Structure elucidation of compound 1 was established on the basis of extensive 1D and 2D NMR spectroscopic techniques in combination with HR-ESI-MS. The ability of the isolated compounds to inhibit acetylcholine esterase was evaluated. Compound 3 showed the highest acetylcholine esterase inhibitory activity (IC50 = 0.057 ± 0.003 µM), followed by compound 4 (IC50 = 0.068 ± 0.003 µM) and compound 1 (IC50 = 0.099 ± 0.005 µM) compared to donepezil, the positive control, (IC50 = 0.044 ± 0.002 µM). Compounds 2 and 5 showed lower activity (IC50 = 0.182 ± 0.009 and 0.236 ± 0.012 µM, respectively). The results were further validated by molecular docking study.

Keywords: Cladosporium cladosporioides; acetylcholine esterase; ceramide; molecular docking.

MeSH terms

  • Acetylcholine*
  • Cladosporium* / chemistry
  • Esterases
  • Fungi
  • Molecular Docking Simulation
  • Molecular Structure

Substances

  • Acetylcholine
  • Esterases

Supplementary concepts

  • Cladosporium cladosporioides