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Protein tyrosine phosphatase 1B inhibitory activity of lavandulyl flavonoids from roots of Sophora flavescens.
Planta Med.
PUBLISHED: 04-29-2014
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Protein tyrosine phosphatase 1B is a non-transmembrane protein tyrosine phosphatase and major negative regulator in insulin signaling cascades, and much attention has been paid to protein tyrosine phosphatase 1B inhibitors as potential therapies for diabetes. The screening of a natural compound library led to the discovery of five lavandulyl flavonoids, which were isolated from the roots of Sophora flavescens, as novel PTP1B inhibitors: kuraridin (1), norkurarinone (2), kurarinone (3), 2'-methoxykurarinone (4), and kushenol T (5). The three most potent compounds, 1, 2, and 4 (IC50
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Anti-influenza sesquiterpene from the roots of Reynoutria japonica.
Nat Prod Commun
PUBLISHED: 04-03-2014
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One new flavonol glycoside, 4'-O-methylmyricitrin 3'-O-beta-D-glucopyranoside (1), one new sesquiterpene, reynoudiol (11), as well as the 12 known compounds (2-10, 12-14) quercetin 3-O-methyl ether (2), quercitrin (3), isorhamnetin 3-alpha-L-rhamnopyranoside (4), tamarixetin 3-alpha-L-rhamnopyranoside (5), myricitrin (6), 4'-O-methylmyricitrin (7), isorhamnetin 3-O-beta-D-xylopyranosyl (1-2)-O-beta- D-glucopyranoside (8), isorhamnetin 3-O-beta- D-apiofuranosyl(1-2)-O-beta- D-glucopyranoside (9), (+)-catechin (10), 7-drimene-3,11,12-triol (12), clovane-2 beta,9 alpha-diol (13), and a-cadinol (14), were isolated from the methanol extract of Reynoutria japonica roots. Based on in vitro screening of the anti-influenza activity of the isolated compounds, reynoudiol showed significantly higher activity than that of oseltamivir phosphate at the same concentration, and did not induce any detectable cytopathic effect in MDCK cells. The CC50 of reynoudiol was above 50 micro M and could inhibit influenza virus infection with an IC50 of 0.29 +/- 0.01 microM. The therapeutic index (TI) of reynoudiol against influenza infection was 172.4, and thus, this compound can be potentially used to treat oseltamivir-resistant influenza virus infection.
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Penicillinolide A: a new anti-inflammatory metabolite from the marine fungus Penicillium sp. SF-5292.
Mar Drugs
PUBLISHED: 10-09-2013
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In the course of studies on bioactive metabolites from marine fungi, a new 10-membered lactone, named penicillinolide A (1) was isolated from the organic extract of Penicillium sp. SF-5292 as a potential anti-inflammatory compound. The structure of penicillinolide A (1) was mainly determined by analysis of NMR and MS data and Moshers method. Penicillinolide A (1) inhibited the production of NO and PGE2 due to inhibition of the expression of iNOS and COX-2. Penicillinolide A (1) also reduced TNF-?, IL-1? and IL-6 production, and these anti-inflammatory effects were shown to be correlated with the suppression of the phosphorylation and degradation of I?B-?, NF-?B nuclear translocation, and NF-?B DNA binding activity. In addition, using inhibitor tin protoporphyrin (SnPP), a competitive inhibitor of HO activity, it was verified that the inhibitory effects of compound 1 on the production of pro-inflammatory mediators and NF-?B DNA binding activity were partially associated with HO-1 expression through Nrf2 nuclear translocation.
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Anti-inflammatory components of the starfish Astropecten polyacanthus.
Mar Drugs
PUBLISHED: 06-20-2013
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Inflammation is important in biomedical research, because it plays a key role in inflammatory diseases including rheumatoid arthritis and other forms of arthritis, diabetes, heart disease, irritable bowel syndrome, Alzheimers disease, Parkinsons disease, allergies, asthma, and even cancer. In the present study, we describe the inhibitory effect of crude extracts and steroids isolated from the starfish Astropecten polyacanthus on pro-inflammatory cytokine (Interleukin-12 (IL-12) p40, interleukin-6 (IL-6), and tumor necrosis factor ? (TNF-?)) production in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells (BMDCs). Among those tested, compounds 5 and 7 showed potent inhibitory effects on the production of all three pro-inflammatory cytokines with IC50 values ranging from 1.82 ± 0.11 to 7.00 ± 0.16 ?M. Potent inhibitory activities were also observed for compound 1 on the production of IL-12 p40 and IL-6 with values of 3.96 ± 0.12 and 4.07 ± 0.13 ?M, respectively, and for compounds 3 and 4 on the production of IL-12 p40 with values of 6.55 ± 0.18 and 5.06 ± 0.16 ?M, respectively. Moreover, compounds 2 (IC50 = 34.86 ± 0.31 ?M) and 6 (IC50 = 79.05 ± 2.05 ?M) exhibited moderate inhibitory effects on the production of IL-12 p40, whereas compounds 3 (IC50 = 22.80 ± 0.21 ?M) and 4 (IC50 = 16.73 ± 0.25 ?M) moderately inhibited the production of TNF-? and IL-6, respectively.
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Inhibitory effects of oleanane-type triterpenes and saponins from the stem bark of Kalopanax pictus on LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells.
Arch. Pharm. Res.
PUBLISHED: 02-27-2013
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Kalopanax pictus (Araliaceae) is a deciduous tree distributed in Korea, Japan, and China. The stem bark of K. pictus has been functionally used as a traditional crude drug for the treatment of various inflammatory diseases. In the present study, we describe the inhibitory effects of oleanane-type triterpenes and saponins isolated from the stem bark of K. pictus on production of pro-inflammatory cytokines in LPS-stimulated bone marrow-derived dendritic cells. Of the compounds tested, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3?,6?,23-trihydroxyolean-12-en-28-oic acid 28-O-?-D-glucopyranoside (3), nipponogenin E (6), 3?,6?,23-trihydroxyolean-12-en-28-oic acid (7), and caulophyllogenin (19) significantly inhibited the production of IL-12 p40 and IL-6 with IC50 values ranging from 3.3 to 9.1 ?M. Compounds 2, 3, 7, and 19 significantly suppressed the secretion of TNF-? with IC50 ranging from 8.8 to 20.0 ?M. These data provide scientific support for the use of K. pictus stem bark and its triterpene and saponin components in the inhibition of pro-inflammatory cytokine secretion, including IL-12 p40, IL-6, and TNF-?, and for prevention and treatment of inflammatory diseases.
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Outcomes of antiretroviral therapy in Vietnam: results from a national evaluation.
PLoS ONE
PUBLISHED: 02-15-2013
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Vietnam has significantly scaled up its national antiretroviral therapy (ART) program since 2005. With the aim of improving Vietnams national ART program, we conducted an outcome evaluation of the first five years of the program in this concentrated HIV epidemic where the majority of persons enrolled in HIV care and treatment services are people who inject drugs (PWID). The results of this evaluation may have relevance for other national ART programs with significant PWID populations.
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Oleanolic triterpene saponins from the roots of Panax bipinnatifidus.
Chem. Pharm. Bull.
PUBLISHED: 11-02-2011
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Ten oleanane-type saponins (1-10), including three new compounds, namely bifinosides A-C (1-3), were isolated from the roots of Panax bipinnatifidus SEEM. Their structures were elucidated on the basis of chemical and spectroscopic methods.
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Oleanane-type triterpene saponins from the bark of Aralia elata and their NF-?B inhibition and PPAR activation signal pathway.
Bioorg. Med. Chem. Lett.
PUBLISHED: 06-22-2011
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Two new oleanane-type triterpene saponins, tarasaponin IV (1) and elatoside L (2), and four known; stipuleanoside R(2) (3), kalopanax-saponin F (4), kalopanax-saponin F methylester (5), and elatoside D (6) were isolated from the bark of Aralia elata. Kalopanax-saponin F methyl ester was isolated from nature for the first time. Their chemical structures were elucidated using the chemical and physical methods as well as good agreement with those of reported in the literature. Oleanane-type triterpene saponins are the main component of A. elata. All compounds were investigated the anti-inflammatory activity. We measured their inhibition of NF-?B and activation of PPARs activities in HepG2 cells using luciferase reporter system. As results, compounds 2 and 4 were found to inhibit NF-?B activation stimulated by TNF? in a dose-dependent manner with IC(50) values of 4.1 and 9.5 ?M, respectively, when compared with that of positive control, sulfasalazine (0.9 ?M). Compounds 2 and 4 also inhibited TNF?-induced expression of iNOS and COX-2 mRNA. Furthermore, compounds 1-6 were evaluated PPAR activity using PPAR subtype transactivation assays. Among of them, compounds 4-6 significantly increased PPAR? transactivation. However, compounds 4-6 did not activate in any other PPAR subtypes.
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Effect of triterpenes and triterpene saponins from the stem bark of Kalopanax pictus on the transactivational activities of three PPAR subtypes.
Carbohydr. Res.
PUBLISHED: 06-16-2011
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Kalopanax pictus (Araliaceae) is a deciduous tree that grows in East Asian countries. Its stem bark and leaves have been used in traditional medicine to treat rheumatic arthritis, neurotic pain, and diabetes mellitus. A phytochemical study on a methanol extract of the stem bark of K. pictus resulted in the isolation of three new compounds, 6?,16?-dihydroxy-hederagenin 3-O-?-D-glucuronopyranoside (1), 3-O-?-D-glucuronopyranosyl-28-O-?-D-glucopyranosyl-6?,16?-dihydroxy-oleanolic acid (2), and 3-O-?-D-galactopyranosyl(1?3)-?-L-arabinopyranosyl hederagenin 28-O-?-D-glucopyranosyl-(1?6)-?-D-glucopyranosyl ester (3), along with eight known compounds (4-11). Their structures were established on the basis of chemical and spectroscopic methods (IR, 1D and 2D NMR, and HRESITOFMS). Compounds 1-6 and 8-10 upregulated PPARs transcriptional activity in a dose-dependent manner in HepG2 cells, with EC(50) values in the range 0.20-15.5 ?M. Moreover, the specific PPAR transactivational effects of compounds 1-6 and 8-10 on separate PPAR subtypes, PPAR?, -?, and -?(?) were further investigated. Compounds 4, 5, 8, and 10 showed significant PPAR? transactivational activity, with EC(50) values of 7.8, 8.0, 10.3, and 17.3 ?M, respectively. Compounds 2, 4, 6, and 8-10 exhibited PPAR? dose-dependent transactivational activity, with EC(50) values of 14.7, 15.5, 14.8, 10.9, 17.1, and 16.3 ?M, whereas compounds 8 and 10 significantly upregulated PPAR?(?) transcriptional activity, with EC(50) values of 15.7 and 17.7 ?M, respectively.
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An evaluation of the RNase H inhibitory effects of Vietnamese medicinal plant extracts and natural compounds.
Pharm Biol
PUBLISHED: 05-20-2011
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Acquired immune deficiency syndrome (AIDS) is a severe pandemic disease especially prevalent in poor and developing countries. Thus, developing specific, potent antiviral drugs that restrain infection by human immunodeficiency virus type 1 (HIV-1), a major cause of AIDS, remains an urgent priority.
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Multiple component quantitative analysis for the pattern recognition and quality evaluation of Kalopanacis Cortex using HPLC.
Arch. Pharm. Res.
PUBLISHED: 05-11-2011
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A quantitative and pattern recognition analyses were conducted for quality evaluation of Kalopanacis Cortex (KC) using HPLC. For quantitative analysis, four bioactive compounds, liriodendrin, pinoresinol O-?-D-glucopyranoside, acanthoside B and kalopanaxin B, were determined. The analysis method was optimized and validated using ODS column with mobile phase of methanol and aqueous phosphoric acid. The validation gave acceptable linearities (r > 0.9995), recoveries (98.4% to 101.9%) and precisions (RSD < 2.20). The limit of detection of compounds ranged from 0.4 to 0.9 ?g/mL. Among the four compounds, liriodendrin was recommended as a marker compound for the quality control of KC. The pattern analysis was successfully carried out by analyzing thirty two samples from four species, and the authentic KC samples were completely discriminated from other inauthentic species by linear discriminant analysis. The results indicated that the method was suitable for the quantitative analysis of liriodendrin and the quality evaluation of KC.
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Anti-inflammatory activity on LPS-stimulated dendritic cells of lupanetype triterpenoids from the leaves of Acanthopanax koreanum.
Arch. Pharm. Res.
PUBLISHED: 03-27-2011
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Acanthopanax koreanum is well known herb in traditional Korean, Chinese, and Japanese anti-inflammatory action without any adverse effects. In the current study, we investigated the inhibitory effects of isolated compounds 1-13 from the leaves of A. koreanum on the lipopolysaccharide-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. Of these lupane-type triterpenoids, 1 exhibited particularly high inhibitory effect on lipopolysaccharide-stimulated TNF-?, IL-6, and IL-12 production with the values ranging from 45.0 to 84.5% at a concentration of 50 ?M. These results warrant further studies concerning the potential anti-inflammatory benefits of medicinal foods containing the leaves of A. koreanum.
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A new iridoid and effect on the rat aortic vascular smooth muscle cell proliferation of isolated compounds from Buddleja officinalis.
Bioorg. Med. Chem. Lett.
PUBLISHED: 03-04-2011
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A new iridoid, named methylscutelloside (1) together with 19 known compounds belonging to the iridoids (2-4), monoterpenoids (5), flavonoids (6-8), triterpenoids (9-14), and phenylethanoids (15-20) were isolated from the flowers of Buddleja officinalis. Their chemical structures were elucidated on the basis of physicochemical properties, and by spectroscopic methods including 1D, 2D NMR, and MS. All isolated compounds were tested in vitro for their effects on the proliferation of rat aortic vascular smooth muscle cells (VSMCs). Among them, iridoids were the main active components and showed significant inhibitory effects on PDGF-BB-induced proliferation in rat aortic VSMCs.
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Inhibitory effect of ginsenosides from steamed ginseng-leaves and flowers on the LPS-stimulated IL-12 production in bone marrow-derived dendritic cells.
Arch. Pharm. Res.
PUBLISHED: 02-10-2011
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Interleukin-12, a heterodimeric cytokine comprising p40 and p35 subunits, plays an essential role in the regulating the differentiation of Th cells, which establish and maximize the capabilities of the immune system. The aim of present study is to screen the effect of 21 ginsenosides from steamed ginseng-leaves and flowers on IL-12 production in bone marrow-derived dendritic cells induced by lipopolysaccharide. Noticeably, ginsenoside Rg(6) (12) and ginsenoside F(4) (13) exhibited particularly inhibitory effect on LPS-induced IL-12 production with the inhibition values of 80 and 82%; and ginsenoside ST(1) (4), ginsenoside SL(2) (8), ginsenoside SL(3) (9), ginsenoside Rh(3) (14), ginsenoside Rk(2) (15), and ginsenoside Rs(4) (18) showed moderate effects with inhibition rates of 63, 65, 67, 68, 71, 73, and 67%, respectively. These results warrant further studies concerning potential of saponin extracts of steamed ginseng-leaves and flowers for medicinal uses.
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Cytotoxic and PPARs transcriptional activities of sterols from the Vietnamese soft coral Lobophytum laevigatum.
Bioorg. Med. Chem. Lett.
PUBLISHED: 01-26-2011
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A new unusual sterol, named lobophytosterol (1), and five known metabolites (2-6) were isolated from the methanol extract of the soft coral Lobophytum laevigatum. Their chemical structures were elucidated by extensive spectroscopic analysis and comparison with those reported in the literature. The absolute stereochemistry of 1 was determined using a modified Moshers method. Compounds 1-3 showed cytotoxic activity against HCT-116 cells with IC(50) values of 3.2, 6.9 and 18.1 ?M, respectively. Compound 1 additionally displayed cytotoxic effects on A549 and HL-60 cells with IC(50) values of 4.5 and 5.6 ?M, respectively. Treatment of these cells with compound 1 resulted in an induction of apoptosis evident by chromatin condensation in treated cells. Besides, compounds 2, 4, and 6 significantly upregulated PPARs transcriptional activity dose-dependently in Hep-G2 cells. Taken together, these data suggest that compound 1 might inhibit the growth of the cancer cells by the induction of apoptosis, and compounds 2, 4, and 6 might act as specific agonists for PPAR?, PPAR?, and PPAR? and may therefore regulate cellular glucose, lipid, and cholesterol metabolism.
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A new ursane-type triterpenoid glycoside from Centella asiatica leaves modulates the production of nitric oxide and secretion of TNF-? in activated RAW 264.7 cells.
Bioorg. Med. Chem. Lett.
PUBLISHED: 01-18-2011
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One new ursane-type triterpenoid glycoside, asiaticoside G (1), five triterpenoids, asiaticoside (2), asiaticoside F (3), asiatic acid (4), quadranoside IV (5), and 2?,3?,6?-trihydroxyolean-12-en-28-oic acid 28-O-[?-L-rhamnopyranosyl-(1?4)-?-D-glucopyranosyl-(1?6)-?-D-glucopyranosyl] ester (6), and four flavonoids, kaempferol (7), quercetin (8), astragalin (9), and isoquercetin (10) were isolated from the leaves of Centella asiatica. Their chemical structures were elucidated by mass, 1D- and 2D-nuclear magnetic resonance (NMR) spectroscopy. The structure of new compound 1 was determined to be 2?,3?,23,30-tetrahydroxyurs-12-en-28-oic acid 28-O-[?-L-rhamnopyranosyl-(1?4)-?-D-glucopyranosyl-(1?6)-?-D-glucopyranosyl] ester. The anti-inflammatory activities of the isolated compounds were investigated on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Asiaticoside G (1) potently inhibited the production of nitric oxide and tumor necrosis factor-? with inhibition rates of 77.3% and 69.0%, respectively, at the concentration of 100 ?M.
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Cytotoxic and anti-inflammatory cembranoids from the Vietnamese soft coral Lobophytum laevigatum.
Bioorg. Med. Chem.
PUBLISHED: 01-14-2011
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Four new cembranoids, namely laevigatol A-D (1-4), and six known metabolites (5-10), were isolated from the Vietnamese soft coral Lobophytum laevigatum. The structures of these compounds were elucidated by extensive spectroscopic analyses, and the absolute stereochemistry of 1 was determined using the modified Moshers method. Compounds 5, and 7-10 exhibited cytotoxic activity against selected human cancer cell lines. Compounds 1, 2, 8, and 9 showed dose-dependent inhibitory effects on the TNF?-induced NF-?B transcriptional activity in Hep-G2 cells. Moreover, compounds 1, 2, 8, and 9 significantly inhibited the induction of COX-2 and iNOS mRNA dose-dependently, indicating that these compounds attenuated the synthesis of these transcripts at the transcriptional level.
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alpha-Glucosidase inhibition properties of cucurbitane-type triterpene glycosides from the fruits of Momordica charantia.
Chem. Pharm. Bull.
PUBLISHED: 05-13-2010
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Fourteen cucurbitane-type triterpene glycosides (1-14) were isolated from a methanol extract of Momordica charantia fruits, including three new compounds, charantosides A-C (1, 5, 6). Their structures were elucidated by chemical and spectroscopic methods. All isolated compounds were evaluated for alpha-glucosidase inhibitory effect. Of which, 12 and 13 showed moderate inhibitory activity against alpha-glucosidase. Whereas, 2, 3, 6-11, and 14 showed weak inhibitory activity, and 1, 4, and 5 were inactive.
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Cucurbitane-type triterpene glycosides from the fruits of Momordica charantia.
Magn Reson Chem
PUBLISHED: 03-13-2010
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The chemical study of Momordica charantia fruits led to the isolation of three new cucurbitane triterpene glycosides, momordicosides U, V, and W (1-3). The structures of these compounds were determined to be (19R, 23R)-5beta, 19-epoxy-19-methoxycucurbita-6,24-diene-3beta, 23-diol 3-O-beta-D-allopyranoside (1), (23R)-5beta, 19-epoxycucurbita-6,24-diene-3beta, 23-diol 3-O-beta-D-allopyranoside (2), and (19R)-5beta, 19-epoxy-19,25-dihydroxycucurbita-6,23(E)-diene-3beta-ol 3-O-beta-D-glucopyranoside (3), by chemical and spectroscopic methods.
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Chemical components from the Vietnamese soft coral Lobophytum sp.
Arch. Pharm. Res.
PUBLISHED: 01-21-2010
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Chromatographic separation resulted in the identification of one new squalene derivative, named lobophytene (1), three cembranoid diterpenes (2-4), and two sterols (5 and 6) from the Vietnamese marine soft coral Lobophytum sp. Their structures were identified on the basis of extensive spectroscopic data and comparison of those with reported data. Compounds 1 and 2 showed significant cytotoxic activities against lung (A549) and colon (HT-29) cell lines with IC(50) values of 8.2 and 5.6 microM for 1; 5.1 and 1.8 microM for 2, respectively.
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Two new megastigmane sulphonoglucosides from Mallotus anisopodus.
Nat Prod Commun
PUBLISHED: 09-08-2009
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Phytochemical study of the methanol extract of Mallotus anisopodus led to the isolation of two new megastigmane sulphonoglucosides, namely anisoposides A (1) and B (2), along with junipetrioloside A (3), bergenin (4), os-tocopherol, and N1-methyl-2-pyridone-5-carboxamide. Their structures were deduced by spectroscopic and spectrometric methods including 1D-, 2D-NMR, ESI-MS, and HRESI-MS.
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Chemical constituents of the fruits of Gleditschia australis Hemsl.
Nat Prod Commun
PUBLISHED: 04-18-2009
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From the methanolic extract of the fruits of Gleditschia australis Hemsl., a new flavonoid derivative 3"-O-menthiafoloylisovitexin (1) and a new carbohydrate ester of cinnamic acid 1-O-E-cinnamoyl-[2-O-E-cinnamoyl-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside] (2) have been isolated along with four known compounds, 1-O-E-cinnamoyl-[3-O-E-cinnamoyl-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside], isovitexin, luteolin, and quercetin. Their structures were elucidated on the basis of physical and spectroscopic evidence.
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Inhibition of TNF-?-mediated NF-?B Transcriptional Activity in HepG2 Cells by Dammarane-type Saponins from Panax ginseng Leaves.
J Ginseng Res
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Panax ginseng (PG) is a globally utilized medicinal herb. The medicinal effects of PG are primarily attributable to ginsenosides located in the root and leaf. The leaves of PG are known to be rich in various bioactive ginsenosides, and the therapeutic effects of ginseng extract and ginsenosides have been associated with immunomodulatory and anti-inflammatory activities. We examined the effect of PG leaf extract and the isolated ginsenosides, on nuclear factor (NF)-?B transcriptional activity and target gene expression by applying a luciferase assay and reverse transcription polymerase chain reaction in tumor necrosis factor (TNF)-?-treated hepatocarcinoma HepG2 cells. Air-dried PG leaf extract inhibited TNF-?-induced NF-?B transcription activity and NF-?B-dependent cyclooxygenase (COX)-2 and inducible nitric oxide synthase (iNOS) gene expression more efficiently than the steamed extract. Of the 10 ginsenosides isolated from PG leaves, Rd and Km most significantly inhibited activity in a dose-dependent manner, with IC50 values of 12.05±0.82 and 8.84±0.99 ?M, respectively. Furthermore, the ginsenosides Rd and Km inhibited the TNF-?-induced expression levels of the COX-2 and iNOS gene in HepG2 cells. Air-dried leaf extracts and their chemical components, ginsenoside Rd and Km, are involved in the suppression of TNF-?-induced NF-?B activation and NF-?B-dependent iNOS and COX-2 gene expression. Consequently, air-dried leaf extract from PG, and the purified ginsenosides, have therapeutic potential as anti-inflammatory.
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Inhibitory effect on TNF-?-induced IL-8 secretion in HT-29 cell line by glyceroglycolipids from the leaves of Ficus microcarpa.
Arch. Pharm. Res.
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Bioassay-guided fractionation based on the anti-inflammatory activity of a methanol extract of Ficus microcarpa leaves led to the isolation of seven galactolipids: 2(S)-3-O-octadeca-9Z,12Z,15Z-trienoylglyceryl-O-?-D-galactopyranoside (1), (2S)-2,3-O-dioctadeca-9Z,12Z,15Z-trienoylglyceryl-O-?-D-galactopyranoside (2), (2S)-2,3-O-dioctadeca-9Z,12Z-dienoylglyceryl-O-?-D-galactopyranoside (3), (2S)-3-O-octadeca-9Z,12Z,15Z-trienoylglyceryl-6-O-(?-D-galactopyranosyl)-?-D-galactopyranoside (4), (2S)-2,3-O-dioctadeca-9Z,12Z,15Z-trienoylglyceryl-6-O-(?-D-galactopyranosyl)-?-D-galactopyranoside (5), gingerglycolipid B (6), and (2S)-2,3-O-dioctadeca-9Z,12Z-dienoylglyceryl-6-O-(?-D-galactopyranosyl)-?-D-galactopyranoside (7). Their chemical structures were elucidated by mass, 1D-, and 2D-NMR spectroscopic methods as well as chemical methods. The antiinflammatory effect of these compounds on TNF-? induced IL-8 secretion in the HT-29 cell line was evaluated. All above galactolipids showed significant inhibition ranging 40% at a concentration of 50 ?M. The results suggest that galactolipids from the leaves of F. microcarpa may be used as potent anti-inflammatory agents.
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Diterpenoids from the soft coral Sinularia maxima and their inhibitory effects on lipopolysaccharide-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells.
Chem. Pharm. Bull.
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Nine new diterpenoids, termed sinumaximols A-I (1-3, 5-9, 12), together with three known compounds (4, 10, 11), were isolated from the methanol extract of the soft coral Sinularia maxima. Their structures were elucidated on the basis of extensive spectroscopic methods, including one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS). The isolated compounds were evaluated for their inhibitory effects on the lipopolysaccharide (LPS)-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells (BMDCs). Among them, compounds 2, 3, and 11 were potent inhibitors of LPS-stimulated interleukin-12 (IL-12) p40 with half-maximal inhibitory concentration (IC(50)) values ranging from 4.35±0.12 to 18.04±0.21?µM. Compounds 2, 3, and 11 showed moderate inhibitory activity on IL-6 production with IC(50) values ranging from 17.72±0.31 to 59.77±2.34?µM.
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Plantagiolides I and J, two new withanolide glucosides from Tacca plantaginea with nuclear factor-kappaB inhibitory and peroxisome proliferator-activated receptor transactivational activities.
Chem. Pharm. Bull.
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A novel withanolide glucoside, plantagiolide I (1), a new withanolide glucoside, plantagiolide J (2), and six known compounds (3-8) were isolated from the whole plant of Tacca plantaginea. Their structures were determined by spectroscopic and chemical methods. Compound 3 significantly inhibited tumor necrosis factor alpha (TNF?)-induced nuclear factor-kappaB (NF-?B) transcriptional activity in HepG2 cells in a dose-dependent manner, with IC(50) values of 9.0?µM. Compounds 1-8 enhanced the transcriptional activity of peroxisome proliferator-activated receptors (PPARs) in a dose-dependent manner, with EC(50) values ranging from 1.6 to 49.7?µM. In addition, the transactivational effects of compounds 1-8 on three individual PPAR subtypes, including PPAR?, ?(?), and ? were evaluated. Compounds 1-8 significantly activated the transcriptional activity of PPAR?(?), with EC(50) values in a ranging from 4.1 to 29.6?µM. These results provide scientific support for the use of T. plantaginea and its components for the prevention and treatment of inflammatory and metabolic diseases.
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Anti-inflammatory norditerpenoids from the soft coral Sinularia maxima.
Bioorg. Med. Chem. Lett.
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Chemical investigation of the soft coral Sinularia maxima resulted in the isolation of seven norditerpenoids, including two new compounds, 12-hydroxy-scabrolide A (2) and 13-epi-scabrolide C (6). The structures of the isolated compounds were elucidated based on extensive spectroscopic evidence including Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS) and both one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR, respectively), in comparison with reported data. Compound 6 potently inhibited IL-12 and IL-6 production in LPS-stimulated bone marrow derived dendritic (BMDCs) with IC(50) values of 5.30 ± 0.21 and 13.12 ± 0.64 ?M, respectively. Compound 1 exhibited moderate inhibitory activity against IL-12 and IL-6 production with IC(50) values of 23.52 ± 1.37 and 69.85 ± 4.11 ?M, respectively.
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Anti-Inflammatory and PPAR transactivational properties of flavonoids from the roots of Sophora flavescens.
Phytother Res
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Anti-inflammatory and peroxisome proliferator-activated receptors (PPARs) transactivational effects of nine compounds (1?-?9) from the roots of Sophora flavescens were evaluated using NF-?B-luciferase, reverse transcriptase polymerase chain reaction, peroxisome proliferator response element (PPRE)-luciferase, and GAL-4-PPAR chimera assays. Compounds 4 and 8 significantly inhibited TNF?-induced NF-?B transcriptional activity in HepG2 cells in a dose-dependent manner, with IC?? values of 4.0 and 4.4??M, respectively. Furthermore, the transcriptional inhibitory function of these compounds was confirmed by a decrease in cyclooxgenase 2 and inducible nitric oxide synthase gene expression levels in HepG2 cells. Compounds 1, 3, 5, 6, 8, and 9 significantly activated the transcription of PPARs in a dose-dependent manner, with EC?? values ranging from 1.1 to 13.0??M. Compounds 1, 3, 5, 6, 8, and 9 exhibited dose-dependent PPAR? transactivational activity, with EC?? values in a range of 0.9?-?16.0??M. Compounds 1, 3, 8, and 9 also significantly upregulated PPAR? activity in a dose-dependent manner, with EC?? values of 10.5, 6.6, 15.7, and 1.6??M, whereas compounds 1, 8, and 9 demonstrated transactivational PPAR?(?) effects with EC?? values of 11.4, 10.3, and 1.5??M, respectively. These results provide a scientific rationale for the use of the roots of S. flavescens and warrant further studies to develop new agents for the prevention and treatment of inflammatory and metabolic diseases.
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Diarylheptanoid glycosides from Tacca plantaginea and their effects on NF-?B activation and PPAR transcriptional activity.
Bioorg. Med. Chem. Lett.
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In the screening search for NF-?B inhibitory and PPAR transactivational agents from medicinal plants, a methanol extract of the whole plant of Tacca plantaginea and its aqueous fraction showed the significant activities. Bioassay-guided fractionation combined with repeated chromatographic separation of the aqueous fraction of the methanol extract of T. plantaginea resulted in the isolation of two new diarylheptanoid glycosides, plantagineosides A (1) and B (2), an unusual new cyclic diarylheptanoid glycoside, plantagineoside C (3), and three known compounds (4-6). Their structures were determined by extensive spectroscopic and chemical methods. Compounds 3-6 significantly inhibited TNF?-induced NF-?B transcriptional activity in HepG2 cells in a dose-dependent manner, with IC(50) values ranging from 0.9 to 9.4 ?M. Compounds 1-6 significantly activated the transcriptional activity of PPARs in a dose-dependent manner, with EC(50) values ranging from 0.30 to 10.4 ?M. In addition, the transactivational effects of compounds 1-6 were evaluated on three individual PPAR subtypes, including PPAR?, ?, and ?(?). Compounds 1-6 significantly enhanced the transcriptional activity of PPAR?(?), with EC(50) values in a range of 11.0-30.1 ?M. These data provide the rationale for using T. plantaginea and its components for the prevention and treatment of inflammatory and metabolic diseases.
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Anti-inflammatory and PPAR transactivational effects of secondary metabolites from the roots of Asarum sieboldii.
Bioorg. Med. Chem. Lett.
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Phytochemical study on the roots of Asarum sieboldii resulted in the isolation of one new compound, (1R,2S,5R,6R)-5-O-methylpluviatilol (1) and 12 known compounds (2-13). Their structures were determined by extensive spectroscopic methods, including 1D and 2D NMR, and MS spectra. The absolute configuration of compound 1 was established using CD spectrum. Compounds 4, 5, and 12/13 significantly inhibited TNF?-induced NF-?B transcriptional activity in HepG2 cells in a dose-dependent manner, with IC(50) values ranging from 6.4 to 9.4 ?M. Furthermore, the transcriptional inhibitory function of these compounds was confirmed based on decreases in COX-2 and iNOS gene expression in HepG2 cells. Compounds 1-3, 6,7, 10, and 11 significantly activated the transcriptional activity of PPARs in a dose-dependent manner, with EC(50) values ranging from 1.7 to 20.9 ?M. Compounds 7, 10, and 11 exhibited significant dose-dependent PPAR? transactivational activity, with EC(50) values of 19.5, 15.7, and 4.0 ?M, respectively. Compounds 1, 6, 7, 10, and 11 activated PPAR? transcriptional activity, with EC(50) values ranging from 3.6 to 22.6 ?M, whereas compounds 10 and 11 significantly increased PPAR?(?) transactivational activity, with EC(50) values of 22.6 and 4.9 ?M, respectively. These results provide a scientific support for the use of the roots of A. sieboldii and warrant further studies to develop new agents for the prevention and treatment of the inflammatory and metabolic diseases.
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Anti-inflammatory and PPAR transactivational effects of components from the stem bark of Ginkgo biloba.
J. Agric. Food Chem.
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Ginkgo biloba, which is considered a "living fossil", has been used for medicinal purposes for thousands of years. Currently, extracts of G. biloba are some of the most widely used herbal products and/or dietary supplements in the world. In this study, three new compounds, (2E,4E,1R,3S,5R,8S)-dihydrophaseic acid 3-O-?-D-glucopyranoside (1), 7,8-dihydro-(R)-7-methoxyconiferyl alcohol (2), and (8S)-3-methoxy-8,4-oxyneolignan-4,9,9-triol 3-O-?-D-glucopyranoside (3), and 13 known compounds (4-16) were isolated from the stem bark of G. biloba. Their structures were determined by extensive spectroscopic methods, including 1D and 2D NMR, MS, and circular dichroism spectra. Four of the compounds (1, 2, 7, and 10) inhibited TNF?-induced NF-?B transcriptional activity significantly in HepG2 cells in a dose-dependent manner, with IC?? values ranging from 6.9 to 9.1 ?M. Furthermore, the transcriptional inhibitory function of these compounds was confirmed based on decreases in COX-2 and iNOS gene expression in HepG2 cells. Compounds 1-5, 7, 9, 10, and 12-14 significantly activated the transcriptional activity of PPARs in a dose-dependent manner, with EC?? values ranging from 0.7 to 12.8 ?M. Compounds 2, 3, and 12 exhibited dose-dependent PPAR? transactivational activity, with EC?? values of 7.0, 3.3, and 10.1 ?M, respectively. Compounds 1-3 activated PPAR? transcriptional activity, with EC?? values of 11.9, 11.0, and 15.3 ?M, whereas compounds 1 and 3 promoted the transactivational activity of PPAR?(?) with EC?? values of 10.7 and 11.2 ?M, respectively. These results provide a scientific support for the use of G. biloba stem bark for the prevention and treatment of inflammatory and metabolic diseases. Moreover, these data provide the rationale for further studies of the potential of G. biloba stem bark in functional foods.
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Cytotoxic oleane-type triterpene saponins from Glochidion eriocarpum.
Arch. Pharm. Res.
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The anticancer activity of ten compounds from the aerial parts of Glochidion eriocarpum were evaluated on two human cancer cell lines, HL-60 and HCT-116. Compounds 1-4 displayed highly potent cytotoxic activity on the HCT-116 cancer cell line with IC(50) values ranging of 0.41?1.16 ?M. Compounds 1-4 significantly inhibited the HL-60 cell line with IC(50) values ranging of 4.51?6.33 ?M. These results suggested that the benzoyl group at the C-22 position in oleane-type triterpene saponins was essential for cytotoxicity towards tumor cells. Moreover, compounds 2 and 3 showed more potent cytotoxicity than compounds 1 and 4 against HL-60 and HCT-116 cells. With respect to the mechanism underlying cytotoxicity, compounds 1-4 increased chromatin condensation, a typical apoptotic characteristic in HL-60 and HCT-116 cells. In the mechanism of apoptosis induction, compounds 1-4 reduced Bcl-2 expression, whereas the expression of Bax was increased compared to controls in HCT-116 cells. In addition, compounds 1-4 decreased the level of procaspase-3. The cleavage of poly (ADP-ribose) polymerase (PARP), a vital substrate of effector caspase, was observed in HCT-116 cells. Furthermore, the induction of apoptosis was also accompanied by an activation of extracellular signal-regulated kinase (ERK) and p38 kinase in HCT-116 cells. These findings provide evidence demonstrating that the pro-apoptotic effects of compounds 1-4 are mediated through the activation of ERK and p38 in HCT-116 cells.
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Inhibition of nuclear transcription factor-?B and activation of peroxisome proliferator-activated receptors in HepG2 cells by cucurbitane-type triterpene glycosides from Momordica charantia.
J Med Food
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Momordica charantia is used to treat various diseases, including inflammatory conditions. Previous reports indicated that the extract of this plant inhibits activation of nuclear transcription factor-?B (NF-?B) but activates peroxisome proliferator-activated receptor (PPAR). Additionally, cucurbitane-type triterpene glycosides are the main bioactive components of the fruit of M. charantia. Therefore, we investigated the anti-inflammatory activity of 17 cucurbitane-type triterpene glycosides (1-17) isolated from this plant. Their inhibition of NF-?B and activation of PPAR activities in HepG2 cells were measured using luciferase reporter and PPAR subtype transactivation assays. Compounds 6 and 8 were found to inhibit NF-?B activation stimulated by tumor necrosis factor-? (TNF?) in a dose-dependent manner. With 50% inhibition concentration (IC(50)) values of 0.4??M, compounds 6 and 8 were more potent inhibitors than the positive control, sulfasalazine (IC(50)=0.9??M). Compounds 4, 6, and 8 also inhibited TNF?-induced expressions of inducible nitric oxide synthase and cyclooxygenase-2 mRNA. However, only compound 13 significantly increased PPAR? transactivation.
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