The isolation of secondary metabolites from Rheum ribes L. and the synthesis of new semi-synthetic anthraquinones: Isolation, synthesis and biological activity

Gecibesler I. H., Disli F., Bayindir S., Toprak M., Tufekci A. R., Sahin Yaglıoglu A., ...More

Food Chemistry, vol.342, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 342
  • Publication Date: 2021
  • Doi Number: 10.1016/j.foodchem.2020.128378
  • Journal Name: Food Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, PASCAL, Aerospace Database, Aquatic Science & Fisheries Abstracts (ASFA), BIOSIS, CAB Abstracts, Chemical Abstracts Core, Chimica, Communication Abstracts, Compendex, EMBASE, Food Science & Technology Abstracts, MEDLINE, Metadex, Veterinary Science Database, Civil Engineering Abstracts
  • Keywords: Anthraquinone, Antioxidant, Bioactivity, Food, Human serum albumin, In silico, Rheum ribes, Rhubarb
  • Ondokuz Mayıs University Affiliated: No

Abstract

Rheum ribes L. (Rhubarb) is one of the most important edible medicinal plants in the Eastern Anatolia region and is called “Işkın” by local people. Resveratrol and 6-O-methylalaternin were isolated from the Rhubarb for the first time in addition to well-known secondary metabolites including emodin, aloe-emodin, β-sitosterol and rutin. The new semi-synthetic anthraquinone derivatives with the NαFmoc-L-Lys and ethynyl group were synthesized from the isolated anthraquinones emodin and aloe-emodin of Rhubarb to increase the bioactivities. Aloe-emodin derivative with NαFmoc-L-Lys shows the highest inhibition values by 94.11 ± 0.12 and 82.38 ± 0.00% against HT-29 and HeLa cell lines, respectively, at 25 µg/mL. Further, modification of the aloe-emodin with both the ethynyl and the NαFmoc-L-Lys groups showed an antioxidant activity-enhancing effect. From molecular docking studies, the relative binding energies of the emodin and aloe-emodin derivatives to human serum albumin ranged from −7.30 and −10.62 kcal/mol.