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

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 extra...

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Bibliographic Details
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
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Summary: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.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.202100867