Self-assembly variation of glycyrrhetinic acid epimers: Assembly mechanism and antibacterial efficacy between 18 α-GA and 18 ß-GA.
Colloids Surf B Biointerfaces
; 242: 114120, 2024 Oct.
Article
in En
| MEDLINE
| ID: mdl-39059147
ABSTRACT
Studies have confirmed that the spatial arrangement of chiral molecules has a decisive influence on supramolecular assembly. However, the effect of epimerization caused by the change of a single chiral center on the self-assembly of chiral molecules has not been reported. Herein, we explored a pair of epimers 18 α-glycyrrhetinic acid and 18 ß-glycyrrhetinic acid from Glycyrrhiza uralensis Fisch, which had completely different medicinal activities. In this study, we found that these epimers of glycyrrhetinic acid showed distinct self-assembly properties under the condition of the deionized water and a small amount of DMSO solution. Interestingly, the cis-configured 18 ß-GA could form a 'head-to-tail' interlaced structure and further self-assembled to form nanoparticles, while trans-configured 18 α-GA was connected in a "head-to-head" manner, and due to the excessive steric hindrance that made it difficult to assemble. This work not only clearly demonstrates the impact of epimerization due to changes in a single chiral center on the self-assembly of chiral molecules as well as biological activity, but also provides new insights into the self-assembly of natural organic molecules in the development of nanomedicines and biofunctional materials.
Key words
Full text:
1
Database:
MEDLINE
Main subject:
Glycyrrhetinic Acid
/
Anti-Bacterial Agents
Language:
En
Journal:
Colloids Surf B Biointerfaces
Journal subject:
QUIMICA
Year:
2024
Type:
Article