Synthetic Ellagic Acid Glycosides Inhibit Early Stage Adhesion of Streptococcus agalactiae Biofilms as Observed by Scanning Electron Microscopy

• Published in: Chemistry : a European journal Vol. 26; no. 44; pp. 9923 - 9928
• Main Authors: Chambers, Schuyler A., Gaddy, Jennifer A., Townsend, Steven D.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 06.08.2020; Wiley Subscription Services, Inc
• Subjects: Acids; Adhesion; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; antibiofilm activity; Antiinfectives and antibacterials; Bacterial Adhesion - drug effects; Biofilms; Biofilms - drug effects; Biofilms - growth & development; Cell adhesion; Chemistry; Chemistry, Multidisciplinary; Ellagic acid; Ellagic Acid - chemical synthesis; Ellagic Acid - pharmacology; ellagic acid glycosides; ESKAPE pathogens; Evaluation; Glycoconjugates; Glycosides; Glycosides - chemical synthesis; Glycosides - pharmacology; Microbial Sensitivity Tests; Microorganisms; Microscopy, Electron, Scanning; Pathogens; Physical Sciences; Scanning electron microscopy; Science & Technology; Streptococcus agalactiae; Streptococcus agalactiae - drug effects; Streptococcus agalactiae - growth & development; Streptococcus agalactiae - ultrastructure; Streptococcus infections; Synthesis; scanning electron microscopy; WOMEN; ESKAPE pathogens; ANTIBIOTIC-RESISTANCE; GROUP-B STREPTOCOCCUS; STAPHYLOCOCCUS-AUREUS; MECHANISMS; GLYCOSYLATION; ellagic acid glycosides; Streptococcus agalactiae; HUMAN-MILK OLIGOSACCHARIDES; antibiofilm activity
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202000354

Ellagic acid derivatives possess antimicrobial and antibiofilm properties across a wide‐range of microbial pathogens. Due to their poor solubility and ambident reactivity it is challenging to synthesize, purify, and characterize the activity of ellagic acid glycosides. In this study, we have synthesized three ellagic acid glycoconjugates and evaluated their antimicrobial and antibiofilm activity in Streptococcus agalactiae (Group B Streptococcus, GBS). Their significant impacts on biofilm formation were examined via SEM to reveal early‐stage inhibition of cellular adhesion. Additionally, the synthetic glycosides were evaluated against five of the six ESKAPE pathogens and two fungal pathogens. These studies reveal that the ellagic acid glycosides possess inhibitory effects on the growth of gram‐negative pathogens. Synthetic ellagic acid glycosides possess carbohydrate‐specific antibiofilm activity against Streptococcus agalactiae. SEM has revealed that these compounds likely inhibit early stage bacterial adhesion mechanisms. Additionally, these compounds possess antimicrobial activity against gram‐negative ESKAPE pathogens, further broadening the antibiotic profile of synthetic ellagic acid glycosides (see figure).