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Inhibitory constituents of LPS-induced nitric oxide production from Arctium lappa
Abstract
The methanolic extract from the seeds of Arctium lappa was found to inhibit the LPS-induced nitric oxide (NO) production in murine macrophage RAW264.7 cells. Bioassay-guided fractionation of a methylene chloride soluble fraction led to the isolation of three lignan compounds, arctiin (1), arctigenin (2), and lappaol B (3). Their structures were elucidated by UV, IR, MS, and NMR data, as well as by comparison with those of the literatures. Arctigenin (2) and lappaol B (3) had an iNOS inhibitory activity with IC50 values of 12.5 and 25.9 μM, respectively.
... With the advancement of different state-of-the-art analytical techniques, more active ingredients of burdock have been identified over the last decade (Park et al., 2007). The major active ingredients isolated from this herb are: tannin, arctigenin, arctin, beta-eudesmol, caffeic acid, chlorogenic acid, inulin, trachelogenin 4, sitosterol-beta-D-glucopyranoside, lappaol and diarctigenin (Table 1). ...
... Therefore, inhibition of NO production by iNOS in macrophages are potential treatments for certain inflammatory diseases (Wang et al., 2007). Lappol F and diarctignin strongly inhibited NO production in lipopolysccachride (LPS)-stimulated murine macrophage RAW264.7 cells with IC 50 values of 9.5 and 9.6 µM, respectively (Park et al., 2007). Further study elucidated that diarctigenin could directly target NF-κB-activating signaling cascade by direct inhibition of the DNA binding ability of NF-κB and inhibition of NF-κB-regulated iNOS expression (Kim et al., 2008). ...
Arctium lappa, commonly known as burdock, is being promoted/recommended as a healthy and nutritive food in Chinese societies. Burdock has been used therapeutically in Europe, North America and Asia for hundreds of years. The roots, seeds and leaves of burdock have been investigated in view of its popular uses in traditional Chinese medicine (TCM). In this review, the reported therapeutic effects of the active compounds present in the different botanical parts of burdock are summarized. In the root, the active ingredients have been found to "detoxify" blood in terms of TCM and promote blood circulation to the skin surface, improving the skin quality/texture and curing skin diseases like eczema. Antioxidants and antidiabetic compounds have also been found in the root. In the seeds, some active compounds possess anti-inflammatory effects and potent inhibitory effects on the growth of tumors such as pancreatic carcinoma. In the leaf extract, the active compounds isolated can inhibit the growth of micro-organisms in the oral cavity. The medicinal uses of burdock in treating chronic diseases such as cancers, diabetes and AIDS have been reported. However, it is also essential to be aware of the side effects of burdock including contact dermatitis and other allergic/inflammatory responses that might be evoked by burdock.
... Extracts from Terminalia chebula and Embelia ribes showed lipase inhibition, chebulagic acid being the responsible component for antilipase activity, with MIC of 12.5 í µí¼g/mL against P. acnes [117]. Among various compounds isolated from the methanolic extract of the seeds of Arctium lappa, namely,isolappaol C, lappaol C, lappaol D, lappaol F, and diarctigenin, the latter two strongly inhibited NO production in the LPS-stimulated RAW264.7 cells [118]. Geraniin, isolated from Phyllanthus embelica, showed strong activity in DPPH and lipid peroxidation assays as well as NO scavenging activity [72, 119]. ...
Acne is a common but serious skin disease, which affects approximately 80% adolescents and young adults in 11-30 age group. 42.5% of men and 50.9% of women continue to suffer from this disease into their twenties. Bacterial resistance is now at the alarming stage due to the irrational use of antibiotics. Hence, search for new lead molecule/bioactive and rational delivery of the existing drug (for better therapeutic effect) to the site of action is the need of the hour. Plants and plant-derived products have been an integral part of health care system since time immemorial. Therefore, plants that are currently used for the treatment of acne and those with a high potential are summarized in the present review. Most active plant extracts, namely, P. granatum, M. alba, A. anomala, and M. aquifolium exhibit minimum inhibitory concentration (MIC) in the range of 4-50 µg/mL against P. acnes, while aromatic oils of C. obovoides, C. natsudaidai, C. japonica, and C. nardus possess MICs 0.005-0.6 μL/mL and phytomolecules such as rhodomyrtone, pulsaquinone, hydropulsaquinone, honokiol, magnolol, xanthohumol lupulones, chebulagic acid and rhinacanthin-C show MIC in the range of 0.5-12.5 μg/mL. Novel drug delivery strategies of important plant leads in the treatment of acne have also been discussed.
... The dominant active constituents of the herb are the lignan compounds which have been shown to have antioxidant, anti-inflammatory, and antimicrobial effects (Cho et al. 2002;Ayres and Loike 1990). Arctigenin, a representative dibenzylbutyrolactone lignan from Fructus Arctii was found to have an inducible nitric oxide synthase inhibitory activity (Park et al. 2005). On the other hand, arctiin, another important lignan, showed anticancer properties in animals models (Matsuzaki et al. 2008). ...
Dactylogyrus intermedius is a significant monogenean parasite on the gills of cyprinid fishes and can cause serious problem in fish aquaculture. In the present study, bioassay-guided fractionation was employed to identify the active compounds from Fructus Arctii against D. intermedius. Five solvents (petroleum ether, chloroform, ethyl acetate, ethanol, and water) were applied for the extraction of Fructus Arctii. Among them, only the chloroform extract exhibited promising anthelmintic efficacy and therefore, subjected to the further isolation and purification using various chromatographic techniques. Two compounds showing potent activity were obtained and identified by spectral data (infrared, nuclear magnetic resonance, and mass spectrometry) as: arctigenin (1) and arctiin (2). They were found to be significantly effective against D. intermedius with median effective concentration (EC(50)) values of 0.62 and 3.55 mg L(-1), respectively. Arctigenin exhibited higher activity as compared with the positive control mebendazole with an EC(50) value of 1.25 mg L(-1). The 48-h acute toxicity tests (LC(50)) of arctigenin and arctiin were found to be 8.47 and 14.14 mg L(-1) for goldfish, respectively. These results provided evidence that the studied plant extract, as well as the isolated compounds, might be potential sources of new antiparasitic drug for the control of Dactylogyrus.
Arctium species are known for a variety of pharmacological effects due to their diverse volatile and non-volatile secondary metabolites. Representatives of Arctium species contain non-volatile compounds including lignans, fatty acids, acetylenic compounds, phytosterols, polysaccharides, caffeoylquinic acid derivatives, flavonoids, terpenes/terpenoids and volatile compounds such as hydrocarbons, aldehydes, methoxypyrazines, carboxylic and fatty acids, monoterpenes and sesquiterpenes. Arctium species also possess bioactive properties such as anti-cancer, anti-diabetic, anti-oxidant, hepatoprotective, gastroprotective, antibacterial, antiviral, antimicrobial, anti-allergic, and anti-inflammatory effects. This review aims to provide a complete overview of the chemistry and biological activities of the secondary metabolites found in therapeutically used Arctium species. Summary of pharmacopeias and monographs contents indicating the relevant phytochemicals and therapeutic effects are also discussed, along with possible safety considerations.
The roots of Rosa multiflora Thunberg have been used in traditional oriental medicine as remedies for rheumatic arthralgia and scabies. In this study, the anti-fungal, anti-oxidant, and anti-inflammatory activities of a supercritical extract of Rosa multiflora root were investigated in vitro. To investigate the anti-oxidant and anti-inflammatory effects of the supercritical extract, 2, 2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS) radical scavenging activity, and the inhibition of nitric oxide production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells were examined, respectively. In addition, the anti-fungal activities of the extract were assessed. The results showed a concentration-dependent, increase in ABTS radical scavenging activity. The supercritical fluid extracts of Rosa multiflora root exhibited low toxicity to RAW 264.7 cells at 100 ?g/mL the highest concentration tested. Cells stimulated with LPS produced more nitric oxide than normal control cells; however, cells treated with the supercritical fluid extract decreased this production in a concentration-dependent manner. Finally, the supercritical fluid extracts showed significant anti-fungal activity. These results suggest that extracts of the roots of Rosa multiflora might be used to develop potent anti-fungal, anti-oxidant, and anti-inflammatory agents, and may be useful as ingredients for related new functional cosmetic materials. Copyright © The Korean Society of Food Preservation. All rights reserved.
Two flavan 3-ols i.e., (+)-catechin (1), (-)-epicatechin (2)], three flavanonols i.e., [taxifolin (3), taxifolin 3-O-β-D-glucopyranoside (4) and taxifolin 4′-O-β-D-glucopyranoside (5), one proanthocyanidin i.e., procyanidin B-3 (6) and one i.e., neolignan (+)-lyoniresinol 3α-O-β- D-xylopyranoside (7) have been isolated from the stems of Quercus acuta Thunberg (QAS) by anti-oxidative activity-guided isolation. Although these compounds have been reported previously. To our best of knowledge, this is the first study to report their isolation from Q. acuta Thunberg. Anti-oxidative activity was measured using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical and superoxide dismutase (SOD)-like superoxide anion (generated by xanthine oxidase/hypoxanthine) scavenging assays. Anti-inflammatory activity was assessed by quantifying the nitric oxide in the supernatant of lipopolysaccharide (LPS)-stimulated mouse Raw 264.7 macrophage cells.
Phytochemical examination of the fruits of Actinidia arguta has led to the isolation three organic acids, one coumarin, and three flavonoids. Structures of these compounds were elucidated as protocatechuic acid (1), caffeic acid (2), caffeoyl-β-D-glucopyranoside (3), esculetin (4), quercetin (5), quercetin 3-O-β-D-galactopyranoside (6), and quercetin 3-O-α-L-rhamnopyranosyl (1 → 6)-O-β-D-glucopyranoside (7) by comparisons with previously reported spectral data. To investigate the anti-inflammatory and anti-oxidative effects of these compounds, nitric oxide production inhibitory activity in LPS-stimulated RAW 264.7 cells and DPPH radical scavenging activities were examined. Nitric oxide productions were reduced significantly by the addition of compounds [1 (IC50 = 59.27 μg/ml), 2 (IC50 = 27.95 μg/ml), 3 (IC50 = 73.09 μg/ml), 4 (IC50 =67.44 μg/ml), 5 (IC50 = 17.40 μg/ml), 6 (IC50 = 41.99 μg/ml), 7 (IC50 = 54.46 μg/ml)], and extracts (IC50 = 56.21 μg/ml) compared with positive control, L-NMMA (IC50 = 14.48 μg/ml). The phenolic compounds also showed anti-oxidative activities. Especially, Compounds 1 (IC50 = 8.87 μg/ml), 4 (IC50 = 3.41 μg/ml), and 5 (IC50 = 6.06 μg/ml) showed potent anti-oxidative activities similar to L-ascorbic acid (IC50 = 5.89 μg/ml).
To investigate anti-thrombosis and anti-oxidation activities of the root of Arctium lappa L (RALL), which has been used as foodstuff and oriental medicine in Korea, the ethanol extract and its subsequent organic solvent fractions of the RALL were prepared. The yield of ethanol extraction was 10.94%, and the content of total polyphenol and total sugar of ethanol extract were 5.01 and 694.53 mg/g, respectively. The fraction yields of n-hexane, ethylacetate (EA), butanol and water residue were 1.62, 0.42, 5.98 and 85.38%, respectively. In anticoagulation activity assay, the ethanol extract of RALL did not show significant changes in thrombin time (TT), prothrombin time (PT) and activated partial thromboplastin time (aPTT), whereas the EA fractions showed 13 folds extended TT, PT, and aPTT respectively. Interestingly, the water residue showed strong activation effect against blood clotting factors with shortened aPTT, which might provide the evidence of coagulation agent of RALL in folk remedy. In anti-platelet aggregation assay, the activity of the ethanol extract and its fractions were comparable to that of aspirin. Especially the EA fraction showed 2-folds higher inhibitory activity than aspirin. In anti-oxidation activity assay, the EA fraction also showed strong in DPPH, ABTS and nitrite scavenging activity, and reducing power activity. The extract and fractions of RALL have ignorable hemolytic activity against human RBC up to 0.5 mg/mL concentration. Our results suggest that the EA fraction of RALL have potentials as safe and novel anti-thrombosis agent.
AimThis study was designed to examine the effect of Burdock root tea on inflammatory markers and oxidative stress indicators in patients with knee osteoarthritis (OA).Methods
Thirty-six patients (10 men and 26 women) aged 50–70 years old with knee osteoarthritis referred to the Physical Medicine and Rehabilitation Department of the Tabriz University of Medical Sciences Hospitals, were selected for the study and randomly divided into two groups. Anthropometric measurements, including height, weight and body mass index (BMI) were measured. For all individuals along the 42 days of study period, the same drug treatments, including two lots of 500 mg acetaminophen twice a day and one glucosamine 500 mg once a day,were considered. The intervention group received daily three cups of Burdock root tea (each cup containing 2 g/150 mL boiled water) half-hour after the meal. The control group received three cups containing 150 cc boiled water daily. We assessed inflammatory markers such as high sensitivity C-reactive protein (hs-CRP) and interleukin-6 (IL-6) and oxidative stress indicators such as total antioxidants capacity (TAC), glutathione peroxidase (GPX), superoxide dismutase (SOD) and thiobarbituric acid reactive substances before and after the intervention.ResultsThe results showed that burdock root tea significantly decreased the levels of serum IL-6 (P = 0.002), hs-CRP (P = 0.003) and malondialdehyde (P < 0.001), while the levels of serum TAC (P < 0.001) and activities of SOD (P = 0.009) were significantly increased. GPX activities increased but not significantly.Conclusions
The results suggested that Arctium lappa L. root tea improves inflammatory status and oxidative stress in patients with knee osteoarthritis.
In spite of billions of dollars spent on cancer research each year, overall cancer incidence and cancer survival has not changed significantly in the last half century. Instead, the recent projection from the World Health Organization suggests that global cancer incidence and death is expected to double within the next decade. This requires an "out of the box" thinking approach. While traditional medicine used for thousands of years is safe and affordable, its efficacy and mechanism of action are not fully reported. Demonstrating that traditional medicine is efficacious and how it works can provide a "bed to bench" and "bench to bed" back approach toward prevention and treatment of cancer. This current review is an attempt to describe the contributions of traditional Korean medicine (TKM) to modern medicine and, in particular, cancer treatment. TKM suggests that cancer is an outcome of an imbalance of body, mind, and spirit; thus, it requires a multimodal treatment approach that involves lifestyle modification, herbal prescription, acupuncture, moxibustion, traditional exercise, and meditation to restore the balance. Old wisdoms in combination with modern science can find a new way to deal with the "emperor of all maladies."
The roots of Rhododendron mucronulatum Turzaninov have been used in Oriental traditional medicine for the treatment of dysuria, fever, increase of digestive activity and tonics in China and Korea. Activity guided isolation of the roots of Rhododendron mucronulatum Turzaninov has led to the isolation of three flavonoids, one flavan 3-ol and one proanthocyanidin. Chemical investigation of the 80% Me2CO extract from the roots of Rhododendron mucronulatum led to the isolation and identification of five compounds: taxifolin (1), taxifolin 3-O-β-d-glucopyranoside (2), quercetin 3-O-α-l-arabinofuranoside (3), (-)-epicatechin (4), procyanidin B-3 (5). To investigate the antioxidative and antiinflammatory effects of these compounds, their 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities and the protein levels of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in LPS-stimulated HaCaT cells were also quantified by western blotting and their end products, nitric oxide (NO) and prostaglandin E2 (PGE2), respectively. Compounds (1–5) showed potent DPPH radical scavenging compared with positive controls (l-ascorbic acid). Also, compounds 1 and 2 dose-dependently inhibited the expressions of inflammatory mediators, NO and PGE2, suggesting they are promising candidates as antiinflammatory agents. Copyright © 2011 John Wiley & Sons, Ltd.
The roots of Ulmus macrocarpa Hance (Ulmaceae) have been used as an oriental traditional medicine for the treatment of inflammation, ulcers, cancers, and parasites. Activity guided isolation from the roots of U. macrocarpa yielded three flavonoids [catechin 7-O-β-D-apiofuranoside (1), (+)-catechin (2), taxifolin 6-C-glucopyranoside (3)], and one coumarin [fraxin (4)]. To investigate the antioxidative and anti-inflammatory effects of these compounds, DPPH radical scavenging activity and inhibitory activity against nitric oxide (NO) production in LPS-stimulated RAW 264.7 cells were examined and the expression of inducible NO synthase (iNOS) and cyclooxidase-2 (COX-2) were measured by RT-PCR and Western Blotting in HaCaT cells. Compounds 1, 2, and 3 showed moderate antioxidative activities compared with L-ascorbic acid as a positive control. NO production was reduced and the expressions of iNOS and COX-2 and their mRNA were inhibited by the addition of samples (1-4). These results suggest that the phenolic compounds from the roots of U. macrocarpa might be developed as antioxidant and anti-inflammatory agents.
A new butyrolactone sesquilignan, isolappaol C (1), together with four known lignans, lappaol C (2), lappaol D (3), lappaol F (4), and diarctigenin (5), were isolated from the methanolic extract of the seeds from the Arctium lappa plant. The structure of isolappaol C (1) was determined by spectral analysis including 1D- and 2D-NMR. All the isolates were evaluated for their inhibitory effects on the LPS-induced nitric oxide production using murine macrophage RAW264.7 cells. Lappaol F (4) and diarctigenin (5) strongly inhibited NO production in the LPS-stimulated RAW264.7 cells with IC(50) values of 9.5 and 9.6 microM, respectively.
The absolute configuration of lappaol A and F was determined by the correlation of the ozonolysis products with 2R,3R-(−)-dicarbomethoxymethyl-γ-butyrolactone and S-(−)-methyl paraconate.
A novel lignan, diarctigenin, together with the known butyrolactone derivatives, arctigenin and arctiin, has been isolated from the seeds of Arctium lappa. Its structure was elucidated as bis-5′,5′-arctigenin by spectral analyses and chemical modification.
In the previous paper, we reported the differentiation inducing activities of lignoids from Arctium Fructus (the fruits of Arctium lappa L., Compositae) against mouse myeloid leukemia cells (M1). We reinvestigated the active components of this extract and isolated three new dilignans. Furthermore, structure modifications were carried out using the most active lignan (arctigenin, 1) and its structure-activity relationship was investigated. Its aliphatic esters were more effective in inducing the differentiation of M1 cells than its aromatic esters. Especially, n-decanoate, which was the most active derivative, induced more than half of the M1 cells into phagocytic cells at a concentration of 2 microM.
The isolation of (-)-arctiin (1), arctigenin (2), onopordopicrin (3), kaempferide, eriodictyol, luteolin and stigmasterol from the aerial parts of Carduus micropterus ssp. perspinosus, is reported.
Arctigenin and demethyltraxillagenin, dibenzylbutyrolactone lignans, are phenylpropanoid metabolites with antioxidant and anti-inflammatory activities. The effects of arctigenin and demethyltraxillagenin on the nuclear factor-kappaB (NF-kappaB)-mediated inducible nitric oxide synthase (iNOS, EC1.14.13.39) gene expression were studied in Raw264.7 cells.
Activation of NF-kappaB was determined by gel mobility shift assay, immunocytochemistry and immunoblot analysis of I-kappaBalpha. Expression of the iNOS gene was assessed by Northern and Western blot analyses. NO production was monitored by chemiluminescent detection using a nitric oxide analyzer.
Arctigenin (1 microM) inhibited lipopolysaccharide (LPS)-inducible nuclear NF-kappaB activation and nuclear translocation of p65, which was accompanied by inhibition of I-kappaBalpha phosphorylation, whereas demethyltraxillagenin was less active. LPS-inducible increase in the iNOS mRNA was 80-90% inhibited by 0.01-1 microM arctigenin, whereas similar extents of inhibition were noted by 50-100 microM demethyltraxillagenin. Immunoblot analysis revealed that arctigenin potently inhibited the induction of iNOS by LPS (IC50 < 0.01 microM). The IC50 value of demethyltraxillagenin was approximately 50 microM. Production of nitrite and nitrate by LPS in culture medium was also comparably suppressed by the lignans.
These results demonstrated that arctigenin potently inhibited LPS-inducible iNOS expression in murine macrophages through suppression of I-kappaBalpha phosphorylation and nuclear translocation of p65. Potent inhibition of LPS-inducible NO production in macrophages may constitute anti-inflammatory effects of the dibenzylbutyrolactone lignans.