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

Rheum ribes L. (Rhubarb) is one of the most important edible medicinal plants in the Eastern Anatolia region and is called "Iskin" 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, beta-sitosterol and rutin. The new semi-synthetic anthraquinone derivatives with the N(alpha)Fmoc-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 N(alpha)Fmoc-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 mu g/mL. Further, modification of the aloeemodin with both the ethynyl and the N(alpha)Fmoc-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.