Neopetromin, a Cyclic Tripeptide with a C-N Cross-Link, from the Marine Sponge Neopetrosia sp., That Causes Vacuole Fragmentation in Tobacco BY-2 Cells

J Nat Prod. 2024 Apr 26;87(4):1197-1202. doi: 10.1021/acs.jnatprod.4c00158. Epub 2024 Mar 19.

Abstract

HPLC-MS analysis revealed the presence of an unreported peptide in the extract of the marine sponge Neopetrosia sp. Its structure was determined as a tripeptide, named neopetromin (1), composed of two tyrosine and one tryptophan residues with a heteroaromatic C-N cross-link between side chains. The absolute configuration of amino acids was determined using Marfey's method after ozonolysis and hydrolysis of 1. Compound 1 promoted vacuole fragmentation in an actin-independent manner in tobacco BY-2 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Marine Biology
  • Molecular Structure
  • Nicotiana* / chemistry
  • Oligopeptides / chemistry
  • Oligopeptides / isolation & purification
  • Oligopeptides / pharmacology
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / pharmacology
  • Porifera* / chemistry
  • Tryptophan / chemistry
  • Tryptophan / pharmacology
  • Vacuoles* / drug effects

Substances

  • Peptides, Cyclic
  • Oligopeptides
  • Tryptophan