Dihydroisocoumarins and Phenylglycosides from Scorzonera longiana, Their Antimicrobial Activities and Molecular Docking Studies


KORKMAZ B., RENDA G., BOZDAL G., ÇOŞKUNÇELEBİ K., Bozdeveci A., UZUNER U., ...More

CHEMISTRY & BIODIVERSITY, vol.20, no.4, 2023 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 4
  • Publication Date: 2023
  • Doi Number: 10.1002/cbdv.202201052
  • Journal Name: CHEMISTRY & 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: Scorzonera longiana, dihydroisocoumarin glycoside, phenyl glycoside, antimicrobial activity, docking study, RADICAL-SCAVENGING ACTIVITY, PHENOLIC-COMPOUNDS, ACID-DERIVATIVES, LATIFOLIA FISCH, ANTIOXIDANT, HYDRANGENOL, GLYCOSIDES, TRITERPENOIDS, CONSTITUENTS, ROOTS
  • Recep Tayyip Erdoğan University Affiliated: Yes

Abstract

Five new phenyl dihydroisocoumarin glycosides (1-5) and two known compounds (6-7) were identified from the butanol fraction of Scorzonera longiana. The structures of 1-7 were elucidated based on spectroscopic methods. Antimicrobial, antitubercular, and antifungal evaluation of compounds 1-7 were carried out using the microdilution method against nine microorganisms. Compound 1 was active only against Mycobacterium smegmatis (Ms) with a MIC value of 14.84 mu g/mL. All tested compounds (1-7) were active against Ms but only compounds 3-7 were active against fungi (C. albicans, S. cerevisiae) with MIC values of 25.0-125 mu g/mL. In addition, molecular docking studies were conducted against Ms DprE1 (PDB ID: 4F4Q), Mycobacterium tuberculosis (Mbt) DprE1 (PDB ID: 6HEZ), and arabinosyltransferase C (EmbC, PDB ID: 7BVE) enzymes. Compounds 2, 5, and 7 are the most effective Ms 4F4Q inhibitors. Compound 4 was the most promising inhibitory activity on Mbt DprE with the lowest binding energy of -9,9 kcal/mol.