三种蜂科可食植物——小叶炭疽、西尔山炭疽和球芽毛藻的丙二酰咖啡酰奎宁酸和丙二酰类黄酮苷

IF 4.3 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ACS Omega Pub Date : 2025-09-22 DOI:10.1021/acsomega.5c03770

Adila Nazli, , , Mária Gáborová, , , Tim Ausbüttel, , , Bence Stipsicz, , , Gergő Tóth, , , Szilvia Bősze, , , Szabolcs Béni*, , and , Imre Boldizsár*,

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引用次数: 0

摘要

新的化合物，包括四种异构体单丙二酰二咖啡酰奎宁酸（4-7），一种二丙二酰二咖啡酰奎宁酸(9)，一种类黄酮-二丙二酰葡萄糖苷(8)，以及三种已知的类黄酮-单丙二酰葡萄糖苷（1-3），在密切相关的蜜蜂科可食植物：小叶炭疽，西尔山炭疽和毛竹中发现。通过HPLC-UV-HR-MS/MS和NMR综合分析对它们的结构进行了鉴定，并根据HPLC-MS/MS碎片化特征对异分异构体丙二酰二咖啡酰奎宁酸（4-7）进行了鉴别。该研究证实了器官和植被阶段特异性积累，并利用一步制备高效液相色谱法确定了用于靶向分离的最佳植物组织。丙二酰二咖啡酰奎宁酸4和9对体外非肿瘤Vero E6细胞具有显著的细胞毒性（IC50 < 10 μM）。同时，分离的化合物显示出结构特异性的DPPH自由基清除活性，强调了它们的双重生物学相关性。

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

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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来源期刊

ACS Omega Chemical Engineering-General Chemical Engineering

CiteScore

6.60

自引率

4.90%

发文量

3945

审稿时长

2.4 months

期刊介绍： ACS Omega is an open-access global publication for scientific articles that describe new findings in chemistry and interfacing areas of science, without any perceived evaluation of immediate impact.