Novel Cytotoxic Sesquiterpene Ester Derivatives from the Roots of Ferula mervynii

YAZICI BEKTAŞ N., ALTIPARMAK ÜLBEGİ G., AKSOY SAĞIRLI P., MİSKİ M.

Chemistry and Biodiversity, vol.20, no.3, 2023 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 3
  • Publication Date: 2023
  • Doi Number: 10.1002/cbdv.202201058
  • Journal Name: Chemistry and Biodiversity
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), CAB Abstracts, Chemical Abstracts Core, EMBASE, MEDLINE, Veterinary Science Database
  • Keywords: Apiaceae, cytotoxicity, Ferula mervynii, nor-ketoelemane type sesquiterpene, putative biosynthetic pathway, quantum chemistry calculation, sesquiterpene, ANTITUMOR-ACTIVITY, DAUCANE ESTERS, ARYL ESTERS, ANTIOXIDANT, COMMUNIS, APIACEAE, CELLS, RESIN
  • Karadeniz Technical University Affiliated: No

Abstract

This study is the first chemical investigation of Ferula mervynii M. Sağıroğlu & H. Duman, an endemic species to Eastern Anatolia. The isolations of nine compounds including six previously undescribed sesquiterpene esters, 8-trans-cinnamoyltovarol (1), 8-trans-cinnamoylantakyatriol (3), 6-acetyl-8-trans-cinnamoyl-3-epi-antakyatriol (5), 6-acetyl-8-trans-cinnamoylshiromodiol (6), 6-acetyl-8-trans-cinnamoylfermedurone (7), and 6-acetyl-8-trans-cinnamoyl-(1S),2-epoxyfermedurone (8), were described along with three known sesquiterpene esters, 6-acetyl-8-benzoyltovarol (2), 6-acetyl-8-trans-cinnamoylantakyatriol (4), and ferutinin (9). The structures of novel compounds were elucidated through extensive spectroscopic analyses and quantum chemistry calculations. The putative biosynthetic pathways for compounds 7 and 8 were discussed. The extracts and isolated compounds were tested for cytotoxic activity against the COLO 205, K-562, MCF-7 cancer cell lines, and Human Umbilical Vein Endothelial Cell (HUVEC) lines using MTT assay. Compound 4 showed the highest activity against the MCF-7 cell lines with an IC50 value of 16.74±0.21 μM.