Matrix metalloproteinase inhibitor and sunscreen effective compounds from Rumex crispus L.: isolation, identification, bioactivity and molecular docking study

• Published in: Phytochemical analysis Vol. 31; no. 6; pp. 818 - 834
• Main Authors: Uzun, Mine, Guvenalp, Zuhal, Kazaz, Cavit, Demirezer, L. Omur
• Format: Journal Article
• Language: English
• Published: England Wiley Subscription Services, Inc 01.11.2020
• Subjects: Aging; Anthraquinones; anti‐ageing; Biological activity; Chromatography; Emodin; Enzymes; Extracellular matrix; Flavonoids; Introduced species; Mass spectrometry; Mass spectroscopy; Matrix metalloproteinase; matrix metalloproteinase inhibitor; Matrix Metalloproteinase Inhibitors - pharmacology; Matrix metalloproteinases; Metalloproteinase; Molecular docking; Molecular Docking Simulation; Naphthalene; NMR; Nuclear magnetic resonance; Rumex; Rumex crispus; Rumex crispus L; Sun; sun protection factor; Sun screens; Sunscreening Agents; Tannins; Ultraviolet radiation; matrix metalloproteinase inhibitor; anti-ageing; molecular docking; Rumex crispus L; sun protection factor
• ISSN: 0958-0344; 1099-1565
• DOI: 10.1002/pca.2948

Introduction Rumex (Polygonaceae) species are widely grown worldwide and their main compounds are anthranoids, tannins, naphthalenes and flavonoids. Matrix metalloproteinase (MMP) enzymes that cause the breakdown of the extracellular matrix and harmful ultraviolet (UV) rays are two important causes of skin ageing. Although there have been many studies on anthraquinones, there are not many studies on their anti‐ageing effects. Objective The aim of this study was to determine the anti‐ageing effects of pure compounds isolated from Rumex crispus L. by measuring their MMP inhibitory and sunscreen activities. Methodology Molecular docking studies on anthranoid, flavonoid, tannin and naphthalene skeletons with MMP enzymes were applied for the first time. Various chromatographic methods were used for isolation studies. The structure elucidation was performed by spectroscopic [UV, infrared (IR), electrospray ionisation mass spectrometry (ESI‐MS), nuclear magnetic resonance (NMR)] methods. To determine the anti‐ageing capacity of compounds, MMP‐1, MMP‐8, MMP‐13 enzyme inhibitory effects and sun protection factors (SPFs) were investigated for the first time. Results Molecular docking results showed that skeletons had low binding energy to the target and were likely to inhibit MMP enzymes. Then, eight anthraquinones and a naphthalene glycoside were isolated from the underground parts of Rumex crispus L. According to the results, MMP inhibitory effects of compounds were found to be high. In vitro and molecular docking study results confirmed each other. All anthraquinones showed high sun protection and emodin showed highest UV capability with SPF of 30.59. Conclusion This study shows that anthraquinones may be evaluated as new potential MMP inhibitors, sun protective and anti‐ageing agents. The aim of this study was to determine the anti‐ageing effects of pure compounds isolated from Rumex crispus L. In this study molecular docking studies on anthranoid, flavonoid, tannin and naphthalene skeletons with matrix metalloproteinase (MMP) enzymes were applied for the first time. Also, in vitro MMP‐1, MMP‐8, and MMP‐13 enzyme inhibitory effects and sun protection factors (SPFs) were investigated for the first time. This study shows that anthraquinones may be evaluated as new potential MMP inhibitor, sunscreen and anti‐ageing agents.