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Cirsium vulgare (Savi) Ten. is a plant from the Asteraceae family that is commonly used in traditional medicine. The purpose of this work was to investigate the antioxidant and antimicrobial characteristics of phenolic compounds found in ethanol and dry extracts of C. vulgare leaves, inflorescence, and roots during various phenological stages. Apigenin-7-O-glucoside and chlorogenic acid were identified in practically all C. vulgare extracts. Extracts from leaves collected at the end of the phenological dormancy period and in the first growing year had the highest antioxidant (cupric ion-reducing antioxidant capacity of 12,938 Trolox equivalents/g dry weight) and antimicrobial activity (against Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa, Proteus vulgaris, and Candida albicans) with MIC values of ethanol extract from 16.7 mg/mL to 8.35 mg/mL. These extracts included a high concentration of chlorogenic acid and apigenin-7-O-glucoside. Also, dry extracts from C. vulgare roots and inflorescences showed a higher antimicrobial effect compared to ethanolic extracts with MIC values from 5.57 mg/mL to 3 mg/mL. The study emphasizes the critical role of phenological stages and raw material composition in the accumulation of phenolic compounds and their biological activity in C. vulgare. The findings suggest that extracts from C. vulgare leaves, especially those collected at the end of the phonological dormancy period, are promising candidates for further research into bioactive compounds with potential medicinal applications. The strong antioxidant and antibacterial properties of these extracts highlight their potential for development into natural pharmaceutical products. [ABSTRACT FROM AUTHOR]