Apiol from Parsley Seeds as a Source for the Synthesis of Coenzyme Q 0 Propanoic Acid Conjugates with Amines Featuring Antioxidant Activity

Apiol from Parsley Seeds as a Source for the Synthesis of Coenzyme Q 0 Propanoic Acid Conjugates with Amines Featuring Antioxidant Activity Full article

Journal

ACS Omega
ISSN: 2470-1343

Output data

Year: 2026, DOI: 10.1021/acsomega.5c09328

Authors

Adaeva Olga I. ^1,2 , Demchuk Dmitry V. ^1,2 , Shevchenko Oksana G. ³ , Semenova Marina N. ^1,2 , Semenov Victor V. ^1,2

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry
2	Russian Academy of Sciences
3	Institute of Biology of the Komi Science Center of the Ural Branch of RAS, 28 Kommunisticheskaya Street, 167982 Syktyvkar, Russian Federation

Quinone-containing compounds are known for their freeradical scavenging activity and pronounced antioxidant properties. They could be promising for the alleviation of progressive neuronal damage in neurodegenerative diseases, caused in particular by oxidative stress. In this study, coenzyme Q0 derivatives featuring the fragment of natural quinone propanoic acid conjugated with dopamine, 5-methoxytryptamine, βalanine, and γ-aminobutyric acid were synthesized. Apiol, the main metabolite of parsley seed extract, was used as a starting material. The aim of this study was to explore antioxidant activity of the targeted compounds in vitro using several assays, including determination of free radical scavenging capacity, inhibition of lipid peroxidation in mouse brain homogenate, and evaluation of toxicity and membrane-protective effects in mouse red blood cells (RBCs). All conjugates of the quinone propanoic acid fragment demonstrated significant antioxidant activity. The free radical scavenging capacity of the compounds in DPPH and ABTS tests was associated with the presence and amount of unsubstituted OH groups in the aromatic ring. The dopamine derivative was identified as the most potent inhibitor of both oxidative mouse RBC hemolysis and intracellular generation of reactive oxygen species. The 5-methoxytryptamine quinone derivative considerably suppressed Fe2+/ascorbate-initiated lipid peroxidation in the mouse brain homogenate. All compounds showed no toxicity on a sea urchin embryo model and could be considered potential neuroprotective agents due to the antioxidant properties of the quinone fragment and facile cleavage of the labile amide bond, thereby providing the targeted delivery of biogenic amines into the desired location.

Adaeva O.I. , Demchuk D.V. , Shevchenko O.G. , Semenova M.N. , Semenov V.V.
Apiol from Parsley Seeds as a Source for the Synthesis of Coenzyme Q 0 Propanoic Acid Conjugates with Amines Featuring Antioxidant Activity
ACS Omega. 2026. DOI: 10.1021/acsomega.5c09328

Submitted:	Sep 8, 2025
Accepted:	Apr 22, 2026
Published online:	Apr 28, 2026

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