PhD Scientific Days 2024

Budapest, 9-10 July 2024

Pharmaceutical Sciences and Health Technologies I.

Isolation and Characterization of Malonyl-Caffeoylquinic Acids and Malonyl-Flavonoid Glucosides from Three Closely Related Edible Apiaceae Plants

Author(s)

Adila Nazli1, Mária Gáborová2, Tim Ausbüttel1,3, Bence Stipsicz4,5, Szilvia Bősze5, Imre Boldizsár1,3, Szabolcs Béni6
1: Department of Pharmacognosy, Semmelweis University, Budapest, Hungary
2: Department of Natural Drugs, Masaryk University, Brno, Czech Republic
3: Department of Plant Anatomy, Institute of Biology, Eötvös Loránd University, Budapest, Hungary
4: Doctoral School of Biology, Institute of Biology, Eötvös Loránd University, Faculty of Science, Budapest, Hungary
5: HUN-REN-ELTE Research Group of Peptide Chemistry, Hungarian Research network, Eötvös Loránd University, Budapest, Hungary4
6: Department of Analytical Chemistry, Institute of Chemistry, Eötvös Loránd University,Budapest, Hungary

Text of the abstract

Introduction: Anthriscus cerefolium, Anthriscus sylvestris, and Chaerophyllum bulbosum are closely related Apiaceae plants with medicinal and culinary importance. However, their phytochemical composition is poorly investigated and scientific validation for the safety of these herbs is still lacking.
Aims and Methods: Current study was designed to 1) depict the accumulation of the compounds in various organs of selected plants during a complete vegetation cycle of one year by high-performance liquid chromatography coupled with high-resolution tandem mass spectrometry (HPLC-HR-MS/MS), 2) define optimum tissues and vegetation phases, allowing for the isolation of compounds 3) structural characterization of compounds by nuclear magnetic resonance spectroscopy (NMR), 4) evaluate the antioxidant and cytostatic potential of the isolated compounds
Results: 1,5-dicaffeoyl-3-malonylquinic acid (1) was the main compound in all samples of A. cerefolium, A. sylvestris and C. bulbosum. Subsequently, 1,5-dicaffeoyl-4-malonylquinic acid (2) was isolated from early spring leaves of A. cerefolium and C. bulbosum. Moreover, 1,5-dicaffeoyl-3,4-dimalonylquinic acid (3) was isolated from early spring leaves of A. cerefolium and from the flowers of C. bulbosum collected in June. Furthermore, 3,5-dicaffeoyl-1-malonylquinic acid (4) and 3,5-dicaffeoyl-4-malonyl-epi-quinic acid (5) were isolated from leaves of A. sylvestris collected in January. Quercetin-3-O-(6''-O-malonyl)-β-D-glucoside (6) and kaempferol-3-O-(6''-O-malonyl)-β-D-glucoside (7) were isloted from C. bulbosum flowers collected in June. Luteolin-7-O-(6''-O-malonyl)-β-D-glucoside (8) and luteolin-7-O-(2'',6''-di-O-malonyl)-β-D-glucoside (9) were isolated from early spring leaves of C. bulbosum. All malonyl-caffeoylquinic acid derivativatives (1, 2, 3, 4, 5) and a flavonoid (9) were considered novel compounds. Isolated compounds showed promising DPPH inhibitory activity except compound 7. Malonyl-caffeoylquinic acids (1, 3) reduced the viability of the non-cancerous Vero cells (IC50 < 10 µM).
Conclusion: Our results confirmed the structure-specific antioxidant and cytostatic activity of malonyl-caffeoylquinic acids and malonyl-flavonoids.
Funding: National Research, Development and Innovation Office, Hungary (grants: OTKA NKFIH K-135712, K-142904), Tempus Public Foundation, Doctoral School of Biology, ELTE. (BS).