PhD Scientific Days 2025

Pharmaceutical Sciences and Health Technologies IV.

Bioactive Metabolites from Chaerophyllum and Anthriscus Species

Name of the presenter

Nazli Adila

Institute/workplace of the presenter

Department of Pharmacognosy, Semmelweis University

Authors

Adila Nazli¹, Mária Gáborová², Tim Ausbüttel^3,4, Bence Stipsicz^5,6, Gergő Tóth^7,8, Szilvia Bősze^6,9, Szabolcs Béni¹⁰, Imre Boldizsár^3,4,8

1: Department of Pharmacognosy, Semmelweis University
2: Department of Natural Drugs, Faculty of Pharmacy, Masaryk University, 612 00 Brno, Czechia
3: Department of Pharmacognosy, Semmelweis University, 1085 Budapest, Hungary
4: Department of Plant Anatomy, Institute of Biology, Eötvös Loránd University, Pázmány Péter sétány 1/C, 1117 Budapest, Hungary
5: Institute of Biology, Doctoral School of Biology, ELTE Eötvös Loránd University, Pázmány Péter sétány 1/C, 1117 Budapest, Hungary
6: HUN-REN-ELTE Research Group of Peptide Chemistry, Hungarian Research Network, ELTE Eötvös Loránd University, Pázmány Péter sétány 1/A, 1117 Budapest, Hungary
7: Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre u. 9, 1092 Budapest, Hungary
8: Center for Pharmacology and Drug Research & Development, Semmelweis University, 1085 Budapest, Hungary
9: Department of Genetics, Cell- and Immunobiology, Semmelweis University, 1089 Budapest, Nagyvárad tér 4, Hungary
10: Integrative Health and Environmental Analysis Research Laboratory, Department of Analytical Chemistry, Institute of Chemistry, Eötvös Loránd University, 1117 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 HPLC-HR-MS/MS, 2) define optimum tissues and vegetation phases, allowing for the isolation of compounds 3) structural characterization of compounds by 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:
This project was supported by the 2024-2.1.1-EKÖP-2024-00004 University Research Scholarship Program of the Ministry for Culture and Innovation from the source of the National Research, Development and Innovation Fund (EKÖP-2024-78); the SE 250 + Excellence PhD Scholarship.