Isolation and characterisation of secondary metabolites from Trifolium vesiculosum Savi and their antiproliferative activities

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ÇEVİK D., Aru B., Karagoz S., Gurizi N., DEMİRKIRAN Ö.

Natural Product Research, cilt.38, sa.19, ss.3344-3352, 2024 (SCI-Expanded, Scopus) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 38 Sayı: 19
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1080/14786419.2023.2246632
  • Dergi Adı: Natural Product Research
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, CINAHL, Food Science & Technology Abstracts, MEDLINE, Veterinary Science Database
  • Sayfa Sayıları: ss.3344-3352
  • Anahtar Kelimeler: antiproliferative activity, apoptosis, cell cycle, phytochemical isolation, secondary metabolites, Trifolium vesiculosum Savi
  • Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
  • Trakya Üniversitesi Adresli: Evet

Özet

One unreported flavonol namely morin-7-O-methyl ether (1) along with seven known compounds were isolated from the aerial parts of Trifolium vesiculosum Savi which were elucidated by using extensive spectroscopic methods such as 1D and 2D NMR and HR-MS. According to the cell viability assay (MTS) on the purified compounds (1-8), quercetin-3-O-(6’’-trans-p-coumaroyl)-β-galactoside (4) revealed remarkable antiproliferative activity most particularly against breast cancer cells (IC50 = 2.90 ± 0.25 µM in HCC1937 and 7.98 ± 0.57 µM in MCF7) while moderate inhibitory activity (IC50 = 17.96 ± 0.51-51.70 ± 2.69 µM) on prostate, colorectal and liver cancer cell viability was observed. Further mechanistic examinations (Annexin V/PI staining, DNA content and detection of reactive oxygen species analyses) showed that compound 4 significantly induced apoptosis, enhanced mitochondrial reactive oxygen species (ROS) accumulation, and caused cell cycle arrest in cancer cells by increasing accumulation of cells at G0/G1 and/or G2/M phases of the cell cycle.