Isolation, Characterization and in Silico Studies of Secondary Metabolites from Jurinea macrocephala DC. with Antiproliferative Activity

• Published in: Chemistry & biodiversity 2022-04, Vol.19 (4), p.e202100867-n/a
• Main Authors: Gürbüz, Perihan, Doğan, Şengül Dilem, Gündüz, Miyase Gözde, Uzun, Kübra, Uzunhisarcıklı, Ebru, Yerer, Mükerrem Betül
• Format: Article
• Language: English
• Subjects: Antineoplastic Agents, Phytogenic - chemistry; Aromatase; Asteraceae; Asteraceae - chemistry; Binding sites; Breast cancer; Breast Neoplasms - drug therapy; Cell Line, Tumor; Chromatography; Cytotoxicity; Drug development; Female; Flavonoids; Flavonoids - chemistry; Humans; Jurinea; Lung cancer; lupan; Metabolites; Molecular docking; Molecular Docking Simulation; molecular modeling; Molecular Structure; NMR; Nuclear magnetic resonance; Oral administration; Plant Extracts - chemistry; Secondary metabolites; Toxicity; Triterpenes; Tumor cell lines
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.202100867

In the present work, cytotoxic potential of Jurinea macrocephala DC. (Asteraceae) was evaluated on A549 lung cancer and MCF‐7 breast cancer cell lines. Isolation studies were carried out using various and repetitive chromatographic methods in order to determine the phytochemical profile of the extracts. These studies led to the identification of twelve compounds; four triterpenes (1–4) and eight flavonoids (5–12). Spectroscopic examination (1D and 2D NMR, ESI‐MS) and comparison with relevant literature data were used to deduce the structures of all isolated molecules. To rationalize the obtained cytotoxicity data against breast cancer cell lines, the isolated compounds were docked into the binding site of aromatase, an important target enzyme for the treatment of breast cancer. Molecular docking studies revealed that flavonoids without sugar moieties (5–8) showed the best binding affinities. Overall, these mentioned compounds turned out to be also the most appropriate oral drug candidates after the calculation of their Lipinski parameters.