Malonyl-Caffeoylquinic Acids and Malonyl-Flavonoid-Glucosides
from Three Edible Apiaceae Plants Anthriscus Cerefolium,
Anthriscus Sylvestris, and Chaerophyllum Bulbosum

J 2025

Malonyl-Caffeoylquinic Acids and Malonyl-Flavonoid-Glucosides from Three Edible Apiaceae Plants Anthriscus Cerefolium, Anthriscus Sylvestris, and Chaerophyllum Bulbosum

NAZLI, Adila; Mária GÁBOROVÁ; Tim AUSBUTTEL; Bence STIPSICZ; Gergo TOTH et al.

Základní údaje

Originální název

Malonyl-Caffeoylquinic Acids and Malonyl-Flavonoid-Glucosides from Three Edible Apiaceae Plants Anthriscus Cerefolium, Anthriscus Sylvestris, and Chaerophyllum Bulbosum

Autoři

NAZLI, Adila; Mária GÁBOROVÁ; Tim AUSBUTTEL; Bence STIPSICZ; Gergo TOTH; Szilvia BOSZE; Szabolcs BENI a Imre BOLDIZSAR

Vydání

ACS Omega, WASHINGTON, ACS, 2025, 2470-1343

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.300 v roce 2024

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14160/25:00143915

Organizační jednotka

Farmaceutická fakulta

Klíčová slova anglicky

ANTIOXIDANT ACTIVITY; DICAFFEOYLQUINIC ACIDS; PHENOLIC-COMPOUNDS; QUINIC ACID; L. HOFFM.; IDENTIFICATION; GLYCOSIDES; PETALS

Štítky

rivok, ÚPL

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 9. 3. 2026 18:12, Mgr. Irena Doubková

Anotace

V originále

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 mu M). At the same time, the isolated compounds displayed structure-specific DPPH radical scavenging activity, underscoring their dual biological relevance.

Citovat

NAZLI, Adila; Mária GÁBOROVÁ; Tim AUSBUTTEL; Bence STIPSICZ; Gergo TOTH; Szilvia BOSZE; Szabolcs BENI a Imre BOLDIZSAR. Malonyl-Caffeoylquinic Acids and Malonyl-Flavonoid-Glucosides from Three Edible Apiaceae Plants Anthriscus Cerefolium, Anthriscus Sylvestris, and Chaerophyllum Bulbosum. ACS Omega. WASHINGTON: ACS, 2025, roč. 10, č. 38, s. 43656-43668. ISSN 2470-1343. Dostupné z: https://doi.org/10.1021/acsomega.5c03770.

@article{2559357,
   author = {Nazli, Adila and Gáborová, Mária and Ausbuttel, Tim and Stipsicz, Bence and Toth, Gergo and Bosze, Szilvia and Beni, Szabolcs and Boldizsar, Imre},
   article_location = {WASHINGTON},
   article_number = {38},
   doi = {https://doi.org/10.1021/acsomega.5c03770},
   keywords = {ANTIOXIDANT ACTIVITY; DICAFFEOYLQUINIC ACIDS; PHENOLIC-COMPOUNDS; QUINIC ACID; L. HOFFM.; IDENTIFICATION; GLYCOSIDES; PETALS},
   language = {eng},
   issn = {2470-1343},
   journal = {ACS Omega},
   title = {Malonyl-Caffeoylquinic Acids and Malonyl-Flavonoid-Glucosides from Three Edible Apiaceae Plants Anthriscus Cerefolium, Anthriscus Sylvestris, and Chaerophyllum Bulbosum},
   url = {https://pubs.acs.org/doi/pdf/10.1021/acsomega.5c03770?utm_source=clarivate&getft_integrator=clarivate},
   volume = {10},
   year = {2025}
}

TY  - JOUR
ID  - 2559357
AU  - Nazli, Adila - Gáborová, Mária - Ausbuttel, Tim - Stipsicz, Bence - Toth, Gergo - Bosze, Szilvia - Beni, Szabolcs - Boldizsar, Imre
PY  - 2025
TI  - Malonyl-Caffeoylquinic Acids and Malonyl-Flavonoid-Glucosides from Three Edible Apiaceae Plants Anthriscus Cerefolium, Anthriscus Sylvestris, and Chaerophyllum Bulbosum
JF  - ACS Omega
VL  - 10
IS  - 38
SP  - 43656-43668
EP  - 43656-43668
PB  - ACS
SN  - 24701343
KW  - ANTIOXIDANT ACTIVITY
KW  - DICAFFEOYLQUINIC ACIDS
KW  - PHENOLIC-COMPOUNDS
KW  - QUINIC ACID
KW  - L. HOFFM.
KW  - IDENTIFICATION
KW  - GLYCOSIDES
KW  - PETALS
UR  - https://pubs.acs.org/doi/pdf/10.1021/acsomega.5c03770?utm_source=clarivate&getft_integrator=clarivate
N2  - 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 mu M). At the same time, the isolated compounds displayed structure-specific DPPH radical scavenging activity, underscoring their dual biological relevance.
ER  -

NAZLI, Adila; Mária GÁBOROVÁ; Tim AUSBUTTEL; Bence STIPSICZ; Gergo TOTH; Szilvia BOSZE; Szabolcs BENI a Imre BOLDIZSAR. Malonyl-Caffeoylquinic Acids and Malonyl-Flavonoid-Glucosides from Three Edible Apiaceae Plants Anthriscus Cerefolium, Anthriscus Sylvestris, and Chaerophyllum Bulbosum. \textit{ACS Omega}. WASHINGTON: ACS, 2025, roč.~10, č.~38, s.~43656-43668. ISSN~2470-1343. Dostupné z: https://doi.org/10.1021/acsomega.5c03770.

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