Anthraquinone and stilbene derivatives from the cultivated Korean Rhubarb Rhizomes

Ko, Sung Kwon; Whang, Wan Kyunn; Kim, Il Hyuk

doi:10.1007/bf02976414

Cited by 20 publications

(6 citation statements)

References 14 publications

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“…Furthermore, recent studies have reported that rhubarb possesses anticoagulant and antiplatelet activities (9) and have determined that these are primarily associated with stilbene derivatives such as resveratrol, rhaponticin, and piceatannol (9,10). Although anthraquinone derivatives are principal components of rhubarb (11,12), the effects of anthraquinone derivatives on platelet activity are not thoroughly understood.…”

Section: Introductionmentioning

confidence: 99%

Chrysophanol-8-O-glucoside, an Anthraquinone Derivative in Rhubarb, Has Antiplatelet and Anticoagulant Activities

et al. 2012

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Abstract. Rhubarb is a widely used traditional medicine and has been reported to elicit a number of biological effects including anti-inflammatory and antiplatelet effects. In the present study, we investigated the effects of anthraquinone derivatives isolated from rhubarb on platelet activity. Of four anthraquinone derivatives isolated from rhubarb examined, chrysophanol-8-O-glucoside (CP-8-O-glc) was found to have the most potent inhibitory effect on collagen-and thrombin-induced platelet aggregation. CP-8-O-glc-treated mice showed significantly prolonged bleeding times. Furthermore, CP-8-O-glc was found to have a significant inhibitory effect on rat platelet aggregation ex vivo and on thromboxane A 2 formation in vitro. In coagulation tests, CP-8-O-glc did not alter prothrombin time, and it prolonged the activated partial thromboplastin time. However, CP-8-O-glc only inhibited platelet phosphatidylserine exposure, but not exert direct inhibition on intrinsic factors. This study demonstrates the antiplatelet and anticoagulant effects of CP-8-O-glc and suggests that this compound might be of therapeutic benefit for the prevention of plateletrelated cardiovascular diseases.

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Section: Introductionmentioning

confidence: 99%

Chrysophanol-8-O-glucoside, an Anthraquinone Derivative in Rhubarb, Has Antiplatelet and Anticoagulant Activities

et al. 2012

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“…Structure determinations were accomplished via NMR and MS data by comparison with literature 26–32 data and the nine compounds are shown in Tables 1 and 2.…”

Section: Resultsmentioning

confidence: 99%

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

Uzun

Güvenalp

Kazaz

et al. 2020

Phytochemical Analysis

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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 antiageing 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.

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“…Rhapontigenin is a stilbene derivative and is a major component in Rheum undulatum (Kashiwada et al, 1984;Ko et al, 1995;Ko, 2000). Several reports suggest that rhapontigenin exhibits various pharmacological effects (Matsuda et al, 2001a(Matsuda et al, , 2001bKim et al, 2000Kim et al, , 2002Oshino et al, 1978;Ko et al, 1999;Park et al, 2002;Oh et al, 1998;Choi et al, 2006), yet there are no reports on the antioxdant activity of rhapontigenin isolated from Rheum undulatum and its cytoprotection effect against oxidative stress.…”

Section: Discussionmentioning

confidence: 96%

Rhapontigenin fromRheum undulatumProtects Against Oxidative-Stress-Induced Cell Damage Through Antioxidant Activity

Zhang

Kang

Piao

et al. 2007

Journal of Toxicology and Environmental Health, Part A

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The antioxidant properties of rhapontigenin and rhaponticin isolated from Rheum undulatum were investigated. Rhapontigenin was found to scavenge intracellular reactive oxygen species (ROS), the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, and hydrogen peroxide (H2O2). The radical scavenging effect of rhapontigenin was more effective than rhaponticin. Rhapontigenin protected against H2O2-induced membrane lipid peroxidation and cellular DNA damage, which are the main targets of oxidative stress-induced cellular damage. The radical scavenging activity of rhapontigenin protected Chinese hamster lung fibroblast (V79-4) cells exposed to H2O2 by inhibiting apoptosis. Rhapontigenin inhibited cell damage induced by serum starvation and was also found to increase the activity of catalase and its protein expression. Further, rhapontigenin increased phosphorylation of extracellular signal-regulated kinase (ERK) and inhibited the activity of activator protein 1 (AP-1), a redox-sensitive transcription factor. In summary, these results suggest that rhapontigenin protects V79-4 cells against oxidative damage by enhancing the cellular antioxidant activity and modulating cellular signal pathways.

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Anthraquinone and stilbene derivatives from the cultivated Korean Rhubarb Rhizomes

Cited by 20 publications

References 14 publications

Chrysophanol-8-O-glucoside, an Anthraquinone Derivative in Rhubarb, Has Antiplatelet and Anticoagulant Activities

Chrysophanol-8-O-glucoside, an Anthraquinone Derivative in Rhubarb, Has Antiplatelet and Anticoagulant Activities

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

Rhapontigenin fromRheum undulatumProtects Against Oxidative-Stress-Induced Cell Damage Through Antioxidant Activity

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