Neopetromin, a Cyclic Tripeptide with a C–N Cross-Link, from the Marine Sponge <i>Neopetrosia</i> sp., That Causes Vacuole Fragmentation in Tobacco BY-2 Cells
Yuki Hitora, Ahmed H. El‐Desoky, Yusaku Sadahiro, Ai Sejiyama, A. Kinoshita, Yuji Ise, Esther D. Angkouw, Remy E. P. Mangindaan, Takumi Higaki, Sachiko Tsukamoto
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.
Topics & Concepts
TripeptideFragmentation (computing)SpongeStereochemistryOzonolysisChemistryVacuoleCyclic peptidePeptideTyrosineHydrolysisBiochemistryBiologyOrganic chemistryBotanyCytoplasmEcologyMicrobial Natural Products and BiosynthesisMarine Sponges and Natural ProductsChemical Synthesis and Analysis