Malonyl-Caffeoylquinic Acids and Malonyl-Flavonoid-Glucosides from Three Edible Apiaceae Plants Anthriscus cerefolium, Anthriscus sylvestris, and Chaerophyllum bulbosum

Nazli, Adila and Gáborová, Mária and Ausbüttel, Tim and Stipsicz, Bence and Tóth, Gergő and Bősze, Szilvia and Béni, Szabolcs and Boldizsár, Imre (2025) Malonyl-Caffeoylquinic Acids and Malonyl-Flavonoid-Glucosides from Three Edible Apiaceae Plants Anthriscus cerefolium, Anthriscus sylvestris, and Chaerophyllum bulbosum. ACS OMEGA, 10. pp. 43656-43668. ISSN 2470-1343

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Abstract

Novel compounds, including four isomeric monomalonyl-dicaffeoylquinic acids (4–7), one dimalonyl-dicaffeoylquinic acid (9), and one flavonoid-dimalonyl-glucoside (8), along with three known flavonoid-monomalonyl-glucosides (1–3), were discovered in closely related edible Apiaceae plants: Anthriscus cerefolium, Anthriscus sylvestris, and Chaerophyllum bulbosum. Their structures were elucidated through comprehensive HPLC-UV-HR-MS/MS and NMR analyses, and isomeric malonyl-dicaffeoylquinic acids (4–7) were differentiated based on HPLC-MS/MS fragmentation characteristics. The study confirmed organ- and vegetation phase-specific accumulation, identifying optimal plant tissues for targeted isolation using a one-step preparative HPLC method. Malonyl-dicaffeoylquinic acids 4 and 9 exhibited significant cytotoxicity to nontumorous Vero E6 cells in vitro (IC50 < 10 μM). At the same time, the isolated compounds displayed structure-specific DPPH radical scavenging activity, underscoring their dual biological relevance.

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