Study of micelles and surface properties of triterpene saponins with improved isolation method from Hedera helix

• Published in: Chemical papers Vol. 78; no. 3; pp. 1875 - 1885
• Main Authors: Bajcura, Martin, Lukáč, Miloš, Pisárčik, Martin, Horváth, Branislav
• Format: Journal Article
• Language: English
• Published: Cham Springer International Publishing 01-02-2024
• Subjects: Biochemistry; Biotechnology; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Industrial Chemistry/Chemical Engineering; Materials Science; Medicinal Chemistry; Original Paper; Critical micelle concentration; Triterpene saponins; Zeta potential; Surface activity; Micelle size
• ISSN: 0366-6352; 1336-9075; 2585-7290
• DOI: 10.1007/s11696-023-03212-5

Triterpene saponin fractions were extracted from
Hedera helix
, and in-depth analysis of their physicochemical properties was conducted. Hederasaponin B and hederacoside C were extracted from
Hedera helix
leaves, and their purification was carried out using reverse phase column chromatography with a modified method, providing an affordable alternative to HPLC. Structurally, hederacoside C differs from hederasaponin B only by the presence of a hydroxyl group at the carbon 23 of the aglycon. The critical micelle concentration (cmc) measurement confirmed hydrophilic nature of hederacoside C that led to a higher cmc value compared to hederasaponin B and alpha-hederin. Therefore, the cmc value of hederasaponin B is nearly an order of magnitude lower compared to hederacoside C. Additionally, the study of the surface tension revealed that the more lipophilic alpha-hederin displayed a greater surface tension value (γ
cmc
 = 39.8 mN·m
−1
) compared to hederasaponin B and hederacoside C. Measurements of the surface tension dependence on the concentration in water were enabled to determine the area corresponding to a single saponin molecule at the water/air phase interface (A
cmc
). Notably, structural changes had negligible effects, as Acmc values remained practically identical. Particle size determination further indicated that hederacoside C forms only micelles compared to the remaining substances that showed signs of vesicles formation. Alpha-hederin, as the only measured molecule capable of ionization, showed a negative zeta potential.