The Equilibria of Triterpene Sapogenins-Phosphatidylcholine in Monolayers at the Air/Water Interface

Int J Mol Sci. 2023 Nov 9;24(22):16144. doi: 10.3390/ijms242216144.

Abstract

Sapogenins are the non-sugar parts of saponins (aglycones), high-molecular-weight glycosides linked to one or more sugar side chains. This group of compounds presents many properties, e.g., the potent properties of reducing surface tension and foaming properties, as evidenced by the amphipathic nature of these substances. They are used in the cosmetics industry, the washing and detergent industry, and the food industry. In addition, they have many healing properties. They lower blood cholesterol but are also used to synthesize steroid drugs or hormones. As reported in the literature, saponins also show antitumor activity, leading to cell cycle inhibition and apoptosis of various neoplastic cells. In this study, the influence of two sapogenins: asiatic acid (AA) and oleanolic acid (OA), on the properties of monolayers made of phosphatidylcholine (DPPC) was investigated. The method used in these studies was the Langmuir method with Brewster angle microscopy. The interactions between the tested compounds in mixed monolayers were described. Using mathematical equations, we established that oleanolic acid and asiatic acid formed complexes with DPPC at 1:1 ratios, characterized by high stability constants. We derived the parameters characterizing the formed complexes and described the phase transitions that occur during the formation of pure and mixed monolayers.

Keywords: 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine (DPPC); BAM method; Langmuir method; asiatic acid; complex formation; monolayer; oleanolic acid.

MeSH terms

  • 1,2-Dipalmitoylphosphatidylcholine / chemistry
  • Lecithins
  • Oleanolic Acid*
  • Sapogenins*
  • Saponins*
  • Surface Properties
  • Triterpenes*
  • Water / chemistry

Substances

  • asiatic acid
  • Sapogenins
  • Oleanolic Acid
  • Triterpenes
  • Water
  • Lecithins
  • Saponins
  • 1,2-Dipalmitoylphosphatidylcholine

Grants and funding

The KSV NIMA BAM apparatus was funded by the European Funds for Regional Development and the National Funds of the Ministry of Science and Higher Education as part of the Operational Program Development of Eastern Poland 2007–2013 (POPW.01.03.00-20-044/11).