[Show abstract][Hide abstract] ABSTRACT: Two new flavonolignan glycosides, tricin-4'-O-(threo-β-guaiacylglyceryl) ether
7''-O-β-D-glucopyranose (4) and tricin-4'-O-(erythro-β-guaiacylglyceryl) ether
7''-O-β-D-glucopyranose (5) were isolated from the roots of Zizania latifolia, together with
tricin-7-O-β-D-glucopyranose (1), tricin-4'-O-(threo-β-guaiacylglyceryl) ether
7-O-β-D-glucopyranose (2), and tricin-4'-O-(erythro-β-guaiacylglyceryl) ether
7-O-β-D-glucopyranose (3). Their structures were identified on the basis of spectroscopic
techniques, including HR-ESI/MS, 1D-NMR (1H, 13C, DEPT), 2D-NMR (gCOSY,
gHSQC, gHMBC), and IR spectroscopy.
[Show abstract][Hide abstract] ABSTRACT: Methanol extract of Zizania latifolia was partitioned with EtOAc, n-BuOH, and H2O. From the EtOAc layers, a new flavonolignan along with a known flavone and three known flavonolignans, tricin (1), salcolin A (2), salcolin B (3), and salcolin C (4), were isolated through repeated silica gel and ODS column chromatography. The chemical structure of the new flavonolignan was determined to be tricin-4'-O-[erythro-β-guaiacyl-(7″-O-methyl)-glyceryl] ether and was named salcolin D (5) based on physicochemical and spectroscopic data, including FT-NMR and ESI-MS. All compounds were isolated for the first time from this plant. Compounds 2-5, tricin derivatives, all exhibited higher anti-inflammatory and anti-allergy activities than tricin. In particular, salcolin D (5) was shown to have the strongest inhibitory activity against LPS-induced NO production in RAW 264.7 cells as well as β-hexosaminidase release in IgE-sensitized RBL-2H3 cells. These results suggest that the presence of tricin derivatives conveys allergy and inflammation treatment ability to Z. latifolia.
[Show abstract][Hide abstract] ABSTRACT: The roots of Pueraria mirifica were extracted with 70% aqueous ethyl alcohol and partitioned into ethyl acetate (EtOAc), n-butyl alcohol (BuOH), and H2O fractions, successively. From the EtOAc fraction, four norsesquiterpenes were isolated through the repeated silica gel, octadecyl silica gel and Sephadex LH-20 column chromatographies. On the basis of physicochemical and spectroscopic data including nuclear magnetic resonance (NMR), mass spectrometry, and infrared spectroscopy, the chemical structures were identified as megastigm-5-en-3,9-diol (1), linarionoside B (2), 3,5,6,9-tetrahydroxymegastigm-7-ene (3) and 3,4,9-trihydroxymegastigma-5,7-diene (4). Especially, the configuration of the anomer hydroxyl group was determined as â from the coupling constants of the anomer proton (J =8.0 Hz) in the 1H-NMR spectrum. These compounds were isolated for the first time from the roots of P. mirifica in this study.
Journal of Applied Biological Chemistry 12/2014; 57(4):347-352. DOI:10.3839/jabc.2014.055
[Show abstract][Hide abstract] ABSTRACT: The antibacterial activity of chitosan against Escherichia coli and Staphylococcus aureus was investigated in the presence of NaCI, acetic acid, lactic acid, and citric acid to assess its potential use as a food preservative. The inhibitory activity of chitosan decreased slightly upon adding NaCI to culture broth containing 100 ppm of chitosan (MW 3,000), while adding acetic acid, lactic acid, or citric acid enhanced the inhibitory activity of chitosan on growing cells. Our results indicate that food components, such as NaCI, acetic acid, lactic acid, and citric acid, can significantly affect the bactericidal activity of chitosan.
Korean Journal of Microbiology and Biotechnology 12/2014; 42(4):413-416. DOI:10.4014/kjmb.1408.08001
[Show abstract][Hide abstract] ABSTRACT: The flavonoids, wighteone (1), naringenin (2), genistein (3), isoliquiritigenin (4), daidzein (5), daidzin (6), genistein-8-C-β-d-apiofuranosyl-(1→6)-O-β-d-glucopyranoside (7), ambocin (8), and genistin (9) were isolated from roots of Pueraria mirifica. Chemical structures of the compounds were determined based on spectroscopic data analysis. Flavonoids 1, 2, 4, 7, and 8 were isolated for the first time. The contents of 6 flavonoids in P. mirifica roots was determined to be 2.5±0.01 (1), 14.8±0.09 (3), 18.6±0.18 (5), 17.3±0.11 (6), 10.4±0.05 (7), and 6.0±0.02 (9) mg/kg, respectively, using HPLC.
[Show abstract][Hide abstract] ABSTRACT: This study was initiated to search for the most effective method for extraction of anthocyanins from Morus alba Fruits using organic acids and to evaluate the stability of the pigments at various storage environments. The anthocyanins were effectively extracted by addition of organic acids such as citric acid, malic acid and fumaric acid. The anthocyanins were not degraded at and under a fluorescent light with 183 lux, but sharply degraded at .
Journal of Applied Biological Chemistry 03/2014; 57(1). DOI:10.3839/jabc.2014.005
[Show abstract][Hide abstract] ABSTRACT: This study was undertaken to investigate the anti-arthritic potential of a standardized ethyl acetate fraction from the roots of Brassica rapa (EABR) and to explore the molecular mechanisms in adjuvant-induced arthritic rats and macrophages. In AIA-induced arthritic rats, EABR significantly reduced paw swelling, an arthritic index, serum rheumatoid factor, and tissue expression ratio of RANKL/OPG versus vehicle-administered group. This was found to be well correlated with significant suppressions in productions of PGE2, NO, and pro-inflammatory cytokines and in activations of NF-κB in AIA-induced paw tissues and LPS-induced macrophages. EABR attenuated NF-κB activation by reducing the nuclear translocation and phosphorylation of the p65 NF-κB, which were accompanied by parallel reductions in the degradation and phosphorylation of IκBα after blocking the phosphorylationmediated IKK activation. The findings suggest EABR exerts its anti-arthritic and anti-inflammatory properties via NF-κB inactivation in vitro and in vivo, and that EABR is a potential therapeutic for the treatment of arthritis and inflammation-associated disorders.
Food and chemical toxicology: an international journal published for the British Industrial Biological Research Association 01/2014; 66. DOI:10.1016/j.fct.2014.01.025 · 2.90 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: A new benzyl α-D-fructofuranoside (3), along with six known phenol compounds, benzyl-β-D-glucopyranoside (1), dihydrosyringin (2), syringin (4), triandrin (5), phillyrin (6), and neoolivil-4-O-β-D-glucopyranoside (7), was isolated from the roots of Brassica rapa ssp. campestris L. for the first time. The structures of the compounds were established on the basis of NMR, MS, and IR spectroscopic data.
[Show abstract][Hide abstract] ABSTRACT: Nine phenolic compounds, phloracetophenone-4-O-β-d-glucopyranoside (1), p-hydroxybenzoic acid-4-O-β-d-glucopyranoside (2), leonuriside A (3), 3-methoxy-4-hydroxyphenol-1-O-β-d-glucopyranoside (4), cis-p-coumaric acid-4-O-β-d-glucopyranoside (5), trans-p-coumaric acid-4-O-β-d-glucopyranoside (6), trans-p-coumaric acid-9-O-β-d-glucopyranoside (7), (-)-shikimic acid (8) and (-)-methyl shikimate (9), were isolated for the first time from the fruits of Rhus parviflora. Compounds 1, 3-6 and 8 inhibited lipopolysaccharide-stimulated nitric oxide (NO) production and inducible NO synthase expression in RAW 264.7 macrophages with IC50 values of 9.24 ± 1.20, 21.37 ± 2.02, 23.07 ± 1.58, 9.86 ± 0.98, 19.05 ± 1.66 and 11.3 ± 1.54 μM, respectively. The results indicated possible use of compounds for the treatment of inflammatory diseases.
Natural product research 07/2013; 27(23). DOI:10.1080/14786419.2013.814050 · 0.92 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: A new compound, miroestrol-3-O-β-D-glucopyranoside, was isolated from the roots of Pueraria mirifica (white kwao krua). The structure of the compound was established on the basis of NMR, ESI-MS, and IR spectroscopic data.
[Show abstract][Hide abstract] ABSTRACT: The quality of fermented dropwort extract (FDE) and fermented dropwort vinegar (FDV) was assessed for free sugar, organic acid and free and total amino acid content. Major organic acids were lactic acid in FDE and acetic acid in FDV. Free sugars in FDE were fructose and glucose, and those in FDV were fructose, sucrose, and maltose. Aspartic acid was the major free amino acid in both FDE and FDV. Additionally, the main free amino acids in FDE were alanine and -amino-n-butyric acid (GABA), while those in FDV were arginine and valine. Moreover, to investigate the protective effects of FDE and FDV against oxidative stress induced by t-BHP and , C6 cells were treated with FDE or FDV prior to inducing the oxidative damage. FDE and FDV inhibited cell death significantly in a dose-dependent manner. These data imply that FDE and FDV may be effective in neuronal cell protection against oxidative damage.
Korean Journal of Food Science and Technology 06/2013; 45(3). DOI:10.9721/KJFST.2013.45.3.350
[Show abstract][Hide abstract] ABSTRACT: Alcohol extracts from the seeds of Macleaya cordata have shown a significant insecticidal effect against the growth of the cotton aphid, Aphis gossypii Glover. In this study, we aimed to isolate the principal component of M. cordata to manifest its insecticidal effect on A. gossypii. The dried seeds of M. cordata were extracted with 80% aqueous methanol (MeOH), and the concentrated extracts were partitioned successively with ethyl acetate (EtOAc), n-butyl alcohol (n-BuOH), and H2O. During the search for an insecticidal compound against the aphids, activityguided fractionation led to the isolation of two alkaloids from an n-BuOH fraction through repeated silica gel column chromatographic separations. Based on NMR, MS, and IR spectroscopic data, the chemical structures of the compounds were determined to be 8-hydroxydihydrochelerythrine (1) and 8-methoxydihydrosanguinarine (2) This is the first study in which 8-methoxydihydrosanguinarine was isolated from M. cordata. 8-Hydroxydihydrochelerythrine (1) and 8-methoxydihydrosanguinarine (2) decreased the survival of the cotton aphid by 76.1±7.9 and 73.6±14.6% at 100 ppm, respectively.
Journal of the Korean Society for Applied Biological Chemistry 04/2013; 56(2). DOI:10.1007/s13765-013-3013-0 · 0.69 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: Brassica rapa ssp. campestris (Brassicaceae) is a conical, deep purple, edible root vegetable commonly known as a turnip. We initiated phytochemical and pharmacological studies to search for biological active compounds from the roots of B. rapa ssp. campestris. We isolated a novel phenanthrene derivative, 6-methoxy-1-[10-methoxy-7-(3-methylbut-2-enyl)phenanthren-3-yl]undecane-2,4-dione, named brassicaphenanthrene A (3) along with two known diarylheptanoid compounds, 6-paradol (1) and trans-6-shogaol (2), through the repeated silica gel (SiO(2)), octadecyl silica gel, and Sephadex LH-20 column chromatography. The chemical structures of the compounds were determined by spectroscopic data analyses including nuclear magnetic resonance, mass spectrometry, ultraviolet spectroscopy, and infra-red spectroscopy. All compounds exhibited high inhibitory activity against the growth of human cancer lines, HCT-116, MCF-7, and HeLa, with IC(50) values ranging from 15.0 to 35.0 μM and against LDL-oxidation with IC(50) values ranging from 2.9 to 7.1 μM.
Archives of Pharmacal Research 02/2013; 36(4). DOI:10.1007/s12272-013-0068-8 · 2.05 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: It has been reported that fucosterol has anti-diabetic, anti-oxidant, and anti-osteoporotic effects. We investigated the anti-inflammatory effects and the underlying molecular mechanism of fucosterol in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages. Fucosterol suppressed the expressions of inducible nitric oxide synthase (iNOS), tumour necrosis factor-α (TNF-α), and interleukin-6 (IL-6) by downregulating their transcriptions, and subsequently inhibited the productions of nitric oxide, TNF-α, and IL-6. In addition, fucosterol attenuated LPS-induced DNA binding and the transcriptional activity of nuclear factor-κB (NF-κB). These reductions were accompanied by parallel reductions in the phosphorylation and nuclear translocation of NF-κB. Furthermore, fucosterol attenuated the phosphorylations of mitogen-activated protein kinase kinases 3/6 (MKK3/6) and mitogen-activated protein kinase-activated protein kinase 2 (MK2), which are both involved in the p38 MAPK pathway. These results suggest that the anti-inflammatory effects of fucosterol are associated with the suppression of the NF-κB and p38 MAPK pathways.
[Show abstract][Hide abstract] ABSTRACT: Chrysoeriol-7-O-β-d-glucopyranoside (1), luteolin-7-O-β-d-glucopyranoside (2), quercetin-3-O-β-d-glucopyranoside (3), quercetin-3-O-β-d-galactopyranoside (4), and quercetin-3-O-α-l-rhamnopyranoside (5) were isolated for the first time from the fruits of Rhus parviflora. The chemical structures of the compounds were determined using nuclear magnetic resonance, fast atom bombardment mass spectrometry, and infrared spectroscopy. Compound 4 (hyperin) inhibited cyclin dependent kinases (CDK2 and CDK5) in vitro with IC50 values of 21.02 and 10.28 μM, respectively.
Journal of the Korean Society for Applied Biological Chemistry 10/2012; 55(5):689-693. DOI:10.1007/s13765-012-2133-2 · 0.69 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: A phytosterol derivative, 3-O-β-d-glucopyanosylspinasterol (spinasterol-Glc) isolated from leaves of Stewartia koreana was reported to inhibit LPS-induced cytokine production in macrophage cells. Thymus and activation regulated chemokine (TARC/CCL17) is produced in response to pro-inflammatory cytokines in keratinocytes, which is implicated in the development of inflammatory skin diseases. In present study, we investigated the effect of spinasterol-Glc on production of TARC/CCL17 induced by TNF-α and IFN-γ in human HaCaT keratinocytes. Spinasterol-Glc inhibited the mRNA and protein expression of TARC/CCL17 induced by TNF-α/IFN-γ in a dose-dependent manner. Inhibitors of c-Raf-1, p38 MAPK, and JAK2, suppressed the TNF-α/IFN-γ-induced production of TARC/CCL17, and phosphorylation of these signaling molecules were attenuated by spinasterol-Glc. The compound also inhibited phosphorylation of IKKα/β and IκB-α, and reduced translocation of NF-κB to the nucleus. We demonstrated that spinasterol-Glc suppressed the NF-κB-driven and the GAS-driven expression of luciferase reporter gene induced by TNF-α and IFN-γ. In addition, spinasterol-Glc inhibited the DNA binding of NF-κB and STAT1 to its cognate binding site. These results suggest that spinasterol-Glc has effective inhibitory effects on production of TARC/CCL17 in keratinocytes via inhibition of NF-κB as well as STAT activation, and could be utilized for development of a potential therapeutic agent against skin inflammatory diseases.
Biochemical and Biophysical Research Communications 08/2012; 427(2):236-41. DOI:10.1016/j.bbrc.2012.08.087 · 2.30 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: Extracts from the leaves of Stewartia koreana are known to exhibit strong anti-inflammatory activity. Investigation of bioactive compounds from S. koreana has led to the isolation of 3-O-β-d-glucopyanosylspinasterol (spinasterol-Glc), a spinasterol glycoside. In the present study, we examined the effects of spinasterol-Glc on production of nitric oxide (NO) and proinflammatory cytokines in LPS-treated RAW264.7 macrophage cells and in mouse models. Our results showed that spinasterol-Glc inhibited the production of NO and proinflammatory cytokines such as TNF-α, IL-6 and IL-1β in dose-dependent manners in LPS-treated RAW264.7 cells. Spinasterol-Glc inhibited the expression of iNOS and the proinflammatory cytokine genes. Spinasterol-Glc also inhibited phosphorylation of IκB-α and IKKα/β as well as translocation of NF-κB to the nucleus. We demonstrated that spinasterol-Glc reduced transcription of the NF-κB minimal promoter and NF-κB DNA binding activity. Administration of the spinasterol-Glc significantly decreased the plasma levels of these inflammatory mediators including TNF-α, IL-6 and IL-1β in LPS-injected mice and improved survival of septic mice with lethal endotoxemia. These results suggest that spinasterol-Glc has effective inhibitory effects on production of inflammatory mediators via inhibition of MAP kinases/NF-κB activities, and can be used as a potential anti-inflammatory agent for the prevention and treatment of inflammatory diseases.
International immunopharmacology 05/2012; 13(3):264-70. DOI:10.1016/j.intimp.2012.05.005 · 2.47 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: Two new indoles, 2-C-β-D-glucopyranosyl-1-methoxyindole-3-acetonitrile (1) and 6-hydroxy-1-methylindole3-acetonitrile (2), along with two known indoles [caulilexin C (3) and arvelexin (4)], were isolated from turnip roots (Brassica rapa ssp. campestris L.). The structures of the compounds were established on the basis of NMR, FAB-MS, and IR spectroscopic data.
[Show abstract][Hide abstract] ABSTRACT: Actinidia polygama Max. was subjected to supercritical fluid extraction (SFE), and the resulting ethanol extract of marc (SFEM) was subjected to sequential fractionation with various solvents. Each extract and fraction was assayed for anti-inflammatory effect. The ethyl acetate fraction (EtOAc) contained the highest level (70.8% inhibition) of anti-inflammatory activity. In order to identify the active constituents, the EtOAc fraction was further fractionated by silica gel and ODS column chromatography. By activity-guided fractionation, an active ceramide was identified as the anti-inflammatory component, and its structure was determined by NMR and MS analysis. The novel ceramide was named actinidiamide, and was found significantly to inhibit nitric oxide (NO) production (30.6% inhibition at 1 µg/mL) in lipopolysaccaride (LPS)-stimulated RAW 264.7 cells and β-hexosaminidase release (91.8% inhibition at 1 µg/mL) in IgE-sensitized RBL-2H3 cells. Thus the presence of actinidiamide conveys allergy and inflammation treatment ability to A. polygama.
[Show abstract][Hide abstract] ABSTRACT: A new lignan, (7R,7'R,8R,8'R)-8-hydroxypinoresinol 8-O-β-D-glucopyranoside 4'-methyl ether (7), was isolated from the flowers of Osmanthus fragrans var. aurantiacus along with six known lignans: (+)-phillygenin (1), phillyrin (2), (-)-phillygenin (3), (-)-epipinoresinol-β-D-glucoside (4), taxiresinol (5), and (-)-olivil (6). The structure of the new compound was elucidated on the basis of 1D- and 2D-NMR spectroscopic analysis and specific rotation data. The compounds isolated from the flowers of O. fragrans var. aurantiacus were evaluated for inhibitory activities on nitric oxide production in lipopolysaccharide-stimulated macrophage RAW 264.7 cells. (+)-Phillygenin (1), phillyrin (2), and (-)-phillygenin (3) exerted the strongest inhibitory activities on NO production with IC(50) values of 25.5, 18.9, and 25.5 μM, respectively. These compounds may prove beneficial in the development of natural agents for prevention and treatment of inflammatory diseases.
Archives of Pharmacal Research 12/2011; 34(12):2029-35. DOI:10.1007/s12272-011-1204-y · 2.05 Impact Factor