Journal Article

Stonikacidin A, an Antimicrobial 4-Bromopyrrole Alkaloid Containing L-Idonic Acid Core from the Northwestern Pacific Marine Sponge Lissodendoryx papillosa

Popov, Roman S., Grebnev, Boris B., Sabutski, Yuri E., Kokoulin, Maxim S., Shubina, Larisa K., Guzii, Alla G., Chingizov, Artur R., Tabakmakher, Kseniya M., Fedorov, Sergey N., Dmitrenok, Pavel S., Ivanchina, Natalia V., Menshov, Alexander S., Yurchenko, Ekaterina A., von Amsberg, Gunhild, Chingizova, Ekaterina A., Dyshlovoy, Sergey A., Makarieva, Tatyana N.

2024

Overview

Stonikacidin A (1), the first representative of a new class of 4-bromopyrrole alkaloids containing an aldonic acid core, was isolated from the marine sponge Lissodendoryx papillosa. The compound is named in honor of Prof. Valentin A. Stonik, who is one of the outstanding investigators in the field of marine natural chemistry. The structure of 1 was determined using NMR, MS analysis, and chemical correlations. The L-idonic acid core was established by the comparison of GC, NMR, MS, and optical rotation data of methyl-pentaacetyl-aldonates obtained from the hydrolysis products of 1 and standard hexoses. The L-form of the idonic acid residue in 1 was confirmed by GC analysis of pentaacetate of (S)-2-butyl ester of the hydrolysis product from 1 and compared with corresponding derivatives of L- and D-idonic acids. The biosynthetic pathway for stonikacidin A (1) was proposed. The alkaloid 1 inhibited the growth of Staphylococcus aureus and Escherichia coli test strains, as well as affected the formation of S. aureus and E. coli biofilms. Compound 1 inhibited the activity of sortase A. Molecular docking data showed that stonikacidin A (1) can bind with sortase A due to the interactions between its bromine atoms and some amino acid residues of the enzyme.

• Publisher: MDPI AG,MDPI
• Subject: Acids / Alkaloids / Alkaloids - chemistry / Alkaloids - isolation & purification / Alkaloids - pharmacology / Amino acids / Aminoacyltransferases / Animals / Anti-Bacterial Agents - chemistry / Anti-Bacterial Agents - isolation & purification / Anti-Bacterial Agents - pharmacology / antimicrobial activity / Antimicrobial agents / Bacterial Proteins / biochemical pathways / biofilm / Biofilms / Biofilms - drug effects / Bromine / Bromine compounds / bromopyrrole alkaloid / class / Cysteine Endopeptidases / E coli / Enzymes / Escherichia coli / Escherichia coli - drug effects / Glucose / Hexoses / Hydrolysis / idonic acid / Lissodendoryx / Lissodendoryx papillosa / Marine chemistry / Marine invertebrates / Metabolites / Microbial Sensitivity Tests / Molecular docking / Molecular Docking Simulation / Neuroblastoma / New class / Nitrogen / NMR / Nuclear magnetic resonance / Optical properties / Optical rotation / Oxidation / Pacific Ocean / Plant metabolites / Porifera / Porifera - chemistry / Pyrroles - chemistry / Pyrroles - isolation & purification / Pyrroles - pharmacology / Residues / Sortase / sortase A / Staphylococcus aureus / Staphylococcus aureus - drug effects