Effectiveness of Volatile Natural Deep Eutectic Solvents (VNADESs) for the Green Extraction of Chelidonium majus Isoquinoline Alkaloids

Molecules. 2022 Apr 28;27(9):2815. doi: 10.3390/molecules27092815.

Abstract

The Chelidonium majus plant is rich in biologically active isoquinoline alkaloids. These alkaline polar compounds are isolated from raw materials with the use of acidified water or methanol; next, after alkalisation of the extract, they are extracted using chloroform or dichloromethane. This procedure requires the use of toxic solvents. The present study assessed the possibility of using volatile natural deep eutectic solvents (VNADESs) for the efficient and environmentally friendly extraction of Chelidonium alkaloids. The roots and herb of the plant were subjected three times to extraction with various menthol, thymol, and camphor mixtures and with water and methanol (acidified and nonacidified). It has been shown that alkaloids can be efficiently isolated using menthol-camphor and menthol-thymol mixtures. In comparison with the extraction with acidified methanol, the use of appropriate VNADESs formulations yielded higher amounts of protopine (by 16%), chelidonine (35%), berberine (76%), chelerythrine (12%), and coptisine (180%). Sanguinarine extraction efficiency was at the same level. Additionally, the values of the contact angles of the raw materials treated with the tested solvents were assessed, and higher wetting dynamics were observed in the case of VNADESs when compared with water. These results suggest that VNADESs can be used for the efficient and environmentally friendly extraction of Chelidonium alkaloids.

Keywords: NADESs; berberine; chelerythrine; chelidonine; coptisine; greater celandine; green chemistry; isoquinoline alkaloids; protopine; sanguinarine.

MeSH terms

  • Alkaloids*
  • Camphor
  • Chelidonium*
  • Deep Eutectic Solvents
  • Isoquinolines
  • Menthol
  • Methanol
  • Plant Extracts
  • Solvents
  • Thymol
  • Water

Substances

  • Alkaloids
  • Deep Eutectic Solvents
  • Isoquinolines
  • Plant Extracts
  • Solvents
  • Water
  • Menthol
  • Thymol
  • Camphor
  • Methanol

Grants and funding

M.W. and P.K. were partially funded by the Ministry of Education and Science of Poland as part of the statutory activities of the Department of Analytical Chemistry, Medical University of Lublin (DS 52), and the Immunology and Genetics Laboratory, Department of Pneumonology, Oncology and Allergology, Medical University of Lublin (DS 392). M.S. is a Scholarship holder of the Polish Minister of Science and Higher Education for Outstanding Young Scientists 2020.