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1.
Biosci Biotechnol Biochem ; 83(3): 551-560, 2019 Mar.
Article in English | MEDLINE | ID: mdl-30526376

ABSTRACT

This study was undertaken to determine the effects of enzyme-treated Zizania latifolia (ETZL) and of its major compound tricin on skin photo-aging and to investigate the mechanisms involved. It was found ETZL and tricin suppressed matrix metalloproteinase (MMP) production and increased type I-procollagen production in UVB-irradiated human dermal fibroblasts (HDFs). Furthermore, ETZL and tricin significantly up-regulated the expressions of the antioxidant enzymes HO-1 and SOD1, reduced UVB-induced reactive oxygen species (ROS) generation and mitogen-activated protein kinase (MAPK) induction by ROS and thereby attenuated activator protein-1 (AP-1) expression. In addition, ETZL and tricin both reduced the phosphorylations of IκBα and IKKα/ß and κB blocked the nuclear translocation of nuclear factor-κB (NF-κB) p65. These results show that ETZL have skin protective effects against UVB and suggest tricin as major efficacious material in ETZL protecting skin photoaging.


Subject(s)
Enzymes/metabolism , Fibroblasts/drug effects , Flavonoids/pharmacology , Poaceae/chemistry , Radiation-Protective Agents/pharmacology , Skin/cytology , Ultraviolet Rays/adverse effects , Fibroblasts/cytology , Fibroblasts/metabolism , Fibroblasts/radiation effects , Flavonoids/isolation & purification , Flavonoids/metabolism , Humans , Mitogen-Activated Protein Kinases/metabolism , NF-kappa B/metabolism , Radiation-Protective Agents/isolation & purification , Radiation-Protective Agents/metabolism , Reactive Oxygen Species/metabolism , Signal Transduction/drug effects , Signal Transduction/radiation effects , Skin Aging/drug effects , Skin Aging/radiation effects , Transcription Factor AP-1/metabolism
2.
Food Sci Biotechnol ; 27(6): 1833-1842, 2018 Dec.
Article in English | MEDLINE | ID: mdl-30483448

ABSTRACT

The aim of this study was to identify sleep-promoting substance from Polygonatum sibiricum rhizome extract (PSE) with the regulation of sleep architecture. PSE showed a decrease in sleep latency time and an increase in the sleeping time. In the electroencephalography analysis of rats, PSE (150 mg/kg) showed an increase of non-rapid eye movement by 38% and a decrease of rapid eye movement by 31% compared to the control. This sleep-promoting activity was found to be involved in the GABAA-BDZ receptor. The chemical structure of the pure compound was determined by the 1H and 13C nuclear magnetic resonance spectroscopy and gas chromatography mass spectrometry analysis; active compound was glyceryl-1-monolinoleate. The commercial standard glyceryl-1-monolinoleate showed a similar inhibitory concentration on [3H]-flumazenil binding to GABAA-BDZ receptors with final active fraction of PSE. The results indicate that glyceryl-1-monolinoleate is a major active compound responsible for the PSE-derived sleep promotion.

3.
J Microbiol ; 56(12): 910-916, 2018 Dec.
Article in English | MEDLINE | ID: mdl-30484159

ABSTRACT

Zizania latifolia is a perennial herb belonging to the family Gramineae that has been used as a health food in Asian countries. In this study, we investigated the antimicrobial effect of Z. latifolia, which increased human beta-defensin 2 (hBD2) expression in HaCaT cells. hBD2 expression was further increased in cells treated with Z. latifolia extracts and subsequently infected with Staphylococcus aureus. Inversely, S. aureus infection decreased after treatment. The induction of hBD2 in HaCaT cells was mediated by the Toll-like receptor 2 (TLR2) signaling pathway, including the activation of extracellular signal-regulated kinase (ERK) and activator protein 1 (AP-1). Further study using siRNA revealed that hBD2 played an important role in the inhibition of S. aureus infection in HaCaT cells. Our data suggest that Z. latifolia extracts can be used as an antimicrobial ingredient for skin treatment formulas.


Subject(s)
Anti-Bacterial Agents/pharmacology , Plant Extracts/pharmacology , Poaceae/chemistry , Staphylococcal Skin Infections/therapy , Staphylococcus aureus/drug effects , beta-Defensins/metabolism , Cell Line/drug effects , Extracellular Signal-Regulated MAP Kinases/metabolism , Gene Expression Regulation/drug effects , Humans , Immunity, Innate/drug effects , RNA, Small Interfering , Signal Transduction , Toll-Like Receptor 2/metabolism , Transcription Factor AP-1/metabolism , Water , beta-Defensins/drug effects
4.
Molecules ; 20(11): 20823-31, 2015 Nov 23.
Article in English | MEDLINE | ID: mdl-26610451

ABSTRACT

A phytochemical investigation of the whole plants of Adonis multiflora Nishikawa & Koki Ito. resulted in the isolation and identification of two new cardenolides--adonioside A (1) and adonioside B (6)--as well as four known cardenolides: tupichinolide (2) oleandrine (3), cryptostigmin II (4), and cymarin (5). Their structures were elucidated on the basis of NMR, MS, and IR spectroscopic analyses. Compounds 1, 2, 5, and 6 showed significant cytotoxicity against six human cancer cell lines (HCT-116, HepG2, HeLa, SK-OV-3, and SK-MEL-5, and SK-BR-3).


Subject(s)
Adonis/chemistry , Cardenolides/chemistry , Cardenolides/pharmacology , Plant Extracts/chemistry , Plant Extracts/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Cardenolides/isolation & purification , Cell Line, Tumor , Cell Survival/drug effects , Hep G2 Cells , Humans , Inhibitory Concentration 50 , Nuclear Magnetic Resonance, Biomolecular , Plant Extracts/isolation & purification
5.
Molecules ; 20(4): 5616-24, 2015 Mar 30.
Article in English | MEDLINE | ID: mdl-25830790

ABSTRACT

Two new flavonolignan glycosides, tricin-4'-O-(threo-ß-guaiacylglyceryl) ether 7''-O-ß-D-glucopyranose (4) and tricin-4'-O-(erythro-ß-guaiacylglyceryl) ether 7''-O-ß-D-glucopyranose (5) were isolated from the roots of Zizania latifolia, together with tricin-7-O-ß-D-glucopyranose (1), tricin-4'-O-(threo-ß-guaiacylglyceryl) ether 7-O-ß-D-glucopyranose (2), and tricin-4'-O-(erythro-ß-guaiacylglyceryl) ether 7-O-ß-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.


Subject(s)
Flavonolignans/isolation & purification , Glycosides/isolation & purification , Plant Extracts/chemistry , Poaceae/chemistry , Flavonolignans/chemistry , Glycosides/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Components, Aerial/chemistry , Plant Roots/chemistry
6.
Biosci Biotechnol Biochem ; 79(5): 700-6, 2015.
Article in English | MEDLINE | ID: mdl-25559019

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-ß-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 ß-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.


Subject(s)
Anti-Allergic Agents/pharmacology , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Flavonoids/chemistry , Poaceae/chemistry , Animals , Anti-Allergic Agents/chemistry , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Cell Line/drug effects , Drug Evaluation, Preclinical/methods , Flavones/chemistry , Flavones/pharmacology , Flavonoids/pharmacology , Flavonolignans/chemistry , Flavonolignans/isolation & purification , Flavonolignans/pharmacology , Immunoglobulin E/pharmacology , Lignans/chemistry , Lignans/pharmacology , Lipopolysaccharides/pharmacology , Mice , Molecular Structure , Nitric Oxide/metabolism , Plant Components, Aerial/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Rats , beta-N-Acetylhexosaminidases/antagonists & inhibitors , beta-N-Acetylhexosaminidases/metabolism
7.
Exp Biol Med (Maywood) ; 239(10): 1325-34, 2014 Oct.
Article in English | MEDLINE | ID: mdl-24939823

ABSTRACT

Angiogenesis, the growth of new blood vessels from pre-existing vasculature, plays an important role in physiological and pathological processes such as embryonic development wound healing and revascularization of tissues after exposure to ischemia. We investigated the effects of jaceosidin, a main constituent of medicinal herbs of the genus Artemisia, on angiogenesis and signaling pathways in endothelial cells. Jaceosidin stimulated proliferation, migration and tubulogenesis of ECs as well as ex vivo sprouting from aorta rings, which are phenomena typical of angiogenesis. Jaceosidin activated vascular endothelial growth factor receptor 2 (VEGFR2, FLk-1/KDR) and angiogenic signaling molecules such as focal adhesion kinase, phosphatidylinositol 3-kinase, and its downstream target, the serine-threonine kinase AKTWe also demonstrated that jaceosidin activated the NF-κB-driven expression of a luciferase reporter gene and NF-κB binding to DNA. Jaceosidin-induced proliferation and migration of human umbilical vascular endothelial cells were strongly inhibited by the phosphatidylinositol 3-kinase inhibitor LY294002 and NF-κB inhibitor BAY11-7082, indicating that the PI3K/AKT/NF-κB signaling pathway is involved in jaceosidin-induced angiogenesis. Our results suggest that jaceosidin stimulates angiogenesis by activating the VEGFR2/FAK/PI3K/AKT/NF-κB signaling pathway and that it may be useful in developing angiogenic agents to promote the growth of collateral blood vessels in ischemic tissues.


Subject(s)
Angiogenesis Inducing Agents/metabolism , Endothelial Cells/drug effects , Flavonoids/metabolism , Neovascularization, Physiologic/drug effects , Signal Transduction/drug effects , Animals , Artemisia/chemistry , Cell Movement/drug effects , Cell Proliferation/drug effects , Cells, Cultured , Flavonoids/isolation & purification , Focal Adhesion Kinase 1/metabolism , Gene Expression Regulation/drug effects , Humans , Male , NF-kappa B/metabolism , Phosphatidylinositol 3-Kinase/metabolism , Proto-Oncogene Proteins c-akt/metabolism , Rats, Sprague-Dawley , Vascular Endothelial Growth Factor Receptor-2/metabolism
8.
Int J Mol Med ; 34(1): 145-52, 2014 Jul.
Article in English | MEDLINE | ID: mdl-24789471

ABSTRACT

Stewartia koreana (S. koreana) has been used in the treatment of inflammatory diseases, such as acute gastroenteritis and aches, in Korean folk medicine and has been reported to have a number of biological activities, such as anti-inflammatory activity and the promotion of angiogenesis. In this study, we aimed to determine the effects of S. koreana extract (SKE) and its components on dermal fibroblast growth and migration, and to investigate the wound healing activity of the extract in mice. In vitro experiments revealed that the numbers of SKE-treated cells increased by approximately 2.5-­ and 3.7-fold with 50 and 100 µg/ml of SKE, respectively. 5-bromo-2'-deoxy-uridine (BrdU) incorporation was also increased in the SKE-treated cells by 2.3-fold. SKE promoted the migration of human skin fibroblasts and, among the isolated compounds, hyperin increased the proliferation and migration of the fibroblasts to almost the same degree as SKE. Western blot analysis demonstrated that SKE stimulated the MEK/ERK1/2 and PI3K/Akt signaling pathways. In in vivo experiments, the SKE-treated wound lesions of mice decreased by approximately 7% in diameter after 2 days of treatment with SKE compared with the wound lesions on the 1st day of the experiment. On the 9th day of treatment, the diameter of the lesions was further reduced by approximately 83% in the SKE-treated wound areas compared with the wound areas on the 1st day of treatment. Our results demonstrate that methanol extracts of S. koreana leaves promote the proliferation and migration of skin fibroblasts and possess effective wound healing activity through the activation of the MEK/ERK1/2 and PI3K/Akt signaling pathways. Hyperin was identified as an active compound responsible for the stimulation of fibroblast growth and migration.


Subject(s)
Fibroblasts/drug effects , Flavonoids/pharmacology , Plant Extracts/pharmacology , Theaceae/chemistry , Wound Healing/drug effects , Animals , Cell Movement/drug effects , Cell Proliferation/drug effects , Cell Survival , Cells, Cultured , Fibroblasts/cytology , Fibroblasts/metabolism , Flavonoids/isolation & purification , Gene Expression Regulation , Humans , MAP Kinase Signaling System , Methanol , Mice , Mice, Inbred BALB C , Mitogen-Activated Protein Kinase 1/genetics , Mitogen-Activated Protein Kinase 1/metabolism , Mitogen-Activated Protein Kinase 3/genetics , Mitogen-Activated Protein Kinase 3/metabolism , Phosphatidylinositol 3-Kinases/genetics , Phosphatidylinositol 3-Kinases/metabolism , Plant Extracts/chemistry , Proto-Oncogene Proteins c-akt/genetics , Proto-Oncogene Proteins c-akt/metabolism , Solvents
9.
Food Chem Toxicol ; 66: 96-106, 2014 Apr.
Article in English | MEDLINE | ID: mdl-24468670

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 phosphorylation mediated 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.


Subject(s)
Acetates/chemistry , Arthritis, Experimental/prevention & control , Brassica rapa/chemistry , Inflammation/prevention & control , NF-kappa B/antagonists & inhibitors , Plant Extracts/pharmacology , Animals , Arthritis, Experimental/metabolism , Base Sequence , Cell Line , Chromatography, High Pressure Liquid , DNA Primers , Inflammation/genetics , Inflammation/metabolism , Macrophages/drug effects , Macrophages/metabolism , Male , Mice , NF-kappa B/metabolism , Plant Roots/chemistry , Rats , Rats, Sprague-Dawley , Real-Time Polymerase Chain Reaction , Reverse Transcriptase Polymerase Chain Reaction
10.
Nat Prod Res ; 27(23): 2244-7, 2013.
Article in English | MEDLINE | ID: mdl-23822726

ABSTRACT

Nine phenolic compounds, phloracetophenone-4-O-ß-D-glucopyranoside (1), p-hydroxybenzoic acid-4-O-ß-D-glucopyranoside (2), leonuriside A (3), 3-methoxy-4-hydroxyphenol-1-O-ß-D-glucopyranoside (4), cis-p-coumaric acid-4-O-ß-D-glucopyranoside (5), trans-p-coumaric acid-4-O-ß-D-glucopyranoside (6), trans-p-coumaric acid-9-O-ß-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.


Subject(s)
Lipopolysaccharides/pharmacology , Macrophages/drug effects , Nitric Oxide/antagonists & inhibitors , Plant Extracts/pharmacology , Rhus/chemistry , Animals , Cell Line , Macrophages/metabolism , Magnetic Resonance Spectroscopy , Mass Spectrometry , Mice , Nitric Oxide/biosynthesis
11.
Arch Pharm Res ; 36(4): 423-9, 2013 Apr.
Article in English | MEDLINE | ID: mdl-23435947

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 (SiO2), 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 IC50 values ranging from 15.0 to 35.0 µM and against LDL-oxidation with IC50 values ranging from 2.9 to 7.1 µM.


Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Antioxidants/pharmacology , Brassica rapa , Cell Proliferation/drug effects , Diarylheptanoids/pharmacology , Lipoproteins, LDL/metabolism , Neoplasms/pathology , Phenanthrenes/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antioxidants/chemistry , Antioxidants/isolation & purification , Brassica rapa/chemistry , Diarylheptanoids/chemistry , Diarylheptanoids/isolation & purification , Dose-Response Relationship, Drug , HCT116 Cells , HeLa Cells , Humans , Inhibitory Concentration 50 , MCF-7 Cells , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Phenanthrenes/chemistry , Phenanthrenes/isolation & purification , Phytotherapy , Plant Roots , Plants, Medicinal , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet
12.
Biochem Biophys Res Commun ; 427(2): 236-41, 2012 Oct 19.
Article in English | MEDLINE | ID: mdl-22943853

ABSTRACT

A phytosterol derivative, 3-O-ß-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/ß 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.


Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Chemokine CCL17/antagonists & inhibitors , Dermatologic Agents/pharmacology , Keratinocytes/drug effects , NF-kappa B/antagonists & inhibitors , STAT1 Transcription Factor/antagonists & inhibitors , Stigmasterol/analogs & derivatives , Cell Line , Chemokine CCL17/biosynthesis , Dermatitis, Atopic/drug therapy , Dermatitis, Atopic/metabolism , Humans , Interferon-gamma/pharmacology , Janus Kinase 2/metabolism , Keratinocytes/metabolism , Phosphorylation/drug effects , Proto-Oncogene Proteins c-raf/metabolism , Signal Transduction/drug effects , Stigmasterol/pharmacology , Tumor Necrosis Factor-alpha/pharmacology , p38 Mitogen-Activated Protein Kinases/metabolism
13.
Food Chem ; 135(3): 967-75, 2012 Dec 01.
Article in English | MEDLINE | ID: mdl-22953812

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.


Subject(s)
Cytokines/immunology , Inflammation Mediators/immunology , Macrophages/immunology , NF-kappa B/genetics , Nitric Oxide/immunology , Stigmasterol/analogs & derivatives , Undaria/chemistry , p38 Mitogen-Activated Protein Kinases/genetics , Animals , Cell Line , Cytokines/genetics , Down-Regulation/drug effects , Gene Expression Regulation/drug effects , Lipopolysaccharides/immunology , Macrophages/drug effects , Mice , NF-kappa B/immunology , Stigmasterol/isolation & purification , Stigmasterol/pharmacology , p38 Mitogen-Activated Protein Kinases/immunology
14.
Int Immunopharmacol ; 13(3): 264-70, 2012 Jul.
Article in English | MEDLINE | ID: mdl-22595195

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-ß-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-1ß 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/ß 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-1ß 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.


Subject(s)
Macrophage Activation/drug effects , Stigmasterol/analogs & derivatives , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Base Sequence , Cell Line , Cytokines/biosynthesis , Cytokines/genetics , Down-Regulation/drug effects , Glycosides/chemistry , Glycosides/pharmacology , I-kappa B Kinase/metabolism , I-kappa B Proteins/metabolism , Inflammation Mediators/metabolism , Lipopolysaccharides/pharmacology , MAP Kinase Signaling System/drug effects , Macrophage Activation/immunology , Macrophage Activation/physiology , Male , Medicine, Korean Traditional , Mice , Mice, Inbred C57BL , NF-KappaB Inhibitor alpha , NF-kappa B/metabolism , Nitric Oxide/biosynthesis , Nitric Oxide Synthase Type II/genetics , RNA, Messenger/genetics , RNA, Messenger/metabolism , Stigmasterol/chemistry , Stigmasterol/pharmacology , Theaceae/chemistry
15.
Biosci Biotechnol Biochem ; 76(2): 289-93, 2012.
Article in English | MEDLINE | ID: mdl-22313761

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 ß-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.


Subject(s)
Actinidia/chemistry , Anti-Allergic Agents/isolation & purification , Anti-Inflammatory Agents/isolation & purification , Ceramides/isolation & purification , Animals , Ceramides/pharmacology , Chemical Fractionation , Hypersensitivity/drug therapy , Inflammation/drug therapy , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Macrophages/metabolism , Mice , Nitric Oxide/antagonists & inhibitors , Plant Extracts/chemistry , beta-N-Acetylhexosaminidases/metabolism
16.
Arch Pharm Res ; 34(4): 533-42, 2011 Apr.
Article in English | MEDLINE | ID: mdl-21544718

ABSTRACT

The silkworm (Bombyx mori L.) droppings were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned in succession with EtOAc, n-BuOH, and H(2)O. From the EtOAc fraction, five megastigmane sesquiterpenes were isolated through repeated silica gel and ODS column chromatography. According to the results of spectroscopic data, such as NMR, MS, and IR, the chemical structures of the isolated compounds were determined as (3S,5R,8R)-3,5-dihydroxymegastigma-6,7-dien-9-one (1), (S)-dehydrovomifoliol (2), (6R,7E,9R) -9-hydroxy-4,7-megastigmadien-3-one (3), (3S,5R,6S,7E)-3,5,6-trihydroxy-7-megastigmen-9-one (4), (6R,9R)-9-hydroxy-4-megastigmen-3-one (5). Compounds 2 through 5 were isolated for the first time from silkworm droppings. GC/MS analysis indicated silkworm powder contained compound 3, and mulberry leaves contained compound 4. Compounds 1 and 5 increased the expression of heme oxygenase-1 and SIRT1 in HepG2 and HEK239 cells, respectively. Heme oxygenase-1 is considered to be an antioxidant enzyme that catabolizes heme to carbon monoxide, free iron and biliverdin, while SIRT1 is the mammalian homologue of the yeast silent information regulator (Sir)-2, which are involved in the suppression of inflammatory mediators or factors that may be used to improve atopy-related symptoms.


Subject(s)
Bombyx , Heme Oxygenase-1/metabolism , Norisoprenoids/isolation & purification , Sesquiterpenes/isolation & purification , Sirtuin 1/metabolism , Animals , Cell Line , Electrophoresis, Polyacrylamide Gel , Feces/chemistry , Gas Chromatography-Mass Spectrometry , Heme Oxygenase-1/biosynthesis , Humans , Molecular Structure , Norisoprenoids/chemistry , Norisoprenoids/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Sirtuin 1/biosynthesis
17.
Arch Pharm Res ; 34(12): 2029-35, 2011 Dec.
Article in English | MEDLINE | ID: mdl-22210027

ABSTRACT

A new lignan, (7R,7'R,8R,8'R)-8-hydroxypinoresinol 8-O-ß-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-ß-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.


Subject(s)
Flowers/chemistry , Glucosides/pharmacology , Lignans/pharmacology , Nitric Oxide/antagonists & inhibitors , Oleaceae/chemistry , Plant Extracts/pharmacology , Animals , Cell Line , Cell Survival/drug effects , Dose-Response Relationship, Drug , Glucosides/isolation & purification , Lignans/isolation & purification , Mice , Nitric Oxide/metabolism
18.
Phytother Res ; 24(1): 20-5, 2010 Jan.
Article in English | MEDLINE | ID: mdl-19548289

ABSTRACT

Angiogenesis, the growth of new blood vessels from preexisting vasculature, plays an important role in physiological and pathological processes such as embryonic development and wound healing. This study investigated the effects of methanol extracts of Stewartia koreana leaves (SKE) on angiogenesis. Stewartia koreana significantly promoted the proliferation and migration of human umbilical vein endothelial cells in a dose-dependent manner. The SKE induced endothelial cell proliferation in the range of 50 microg/mL without cytotoxicity. Treatment of HUVECs resulted in the activation of the mitogen-activated protein kinases that was correlated with endothelial cell proliferation and migration. SKE also stimulated angiogenesis in a chick chorioallantoic membrane assay, demonstrating promotion of new blood vessel formation in vivo. Local administration of SKE onto skin punched wounds resulted in increased von Willebrand Factor antigen, indicating that it stimulated neovasculization in the wound region. The results suggest that Stewartia koreana extracts may potentially be useful for the development of agents to accelerate vascular wound healing or to promote the growth of collateral blood vessels in ischemic tissues.


Subject(s)
Cell Movement/drug effects , Cell Proliferation/drug effects , Endothelial Cells/drug effects , Plant Extracts/pharmacology , Theaceae/chemistry , Animals , Cells, Cultured , Chick Embryo , Endothelial Cells/metabolism , Humans , Mice , Neovascularization, Physiologic/drug effects , Umbilical Veins/cytology
19.
Arch Pharm Res ; 32(10): 1345-9, 2009 Oct.
Article in English | MEDLINE | ID: mdl-19898795

ABSTRACT

The fruits of Capsicum annuum were extracted using 80% aqueous MeOH, and fractionated using EtOAc and water. Repeated column chromatography using silica gel, octadecyl silica gel, and Sephadex LH-20 for the EtOAc fraction led to the isolation of a new lignan glycoside and a known one, icariside E(5). From the results of spectroscopic data, including EIMS, FABMS, UV, IR, (1)H and (13)C-NMR, DEPT, and 2D-NMR (COSY, HSQC, HMBC), the chemical structure of the new lignan glycoside was determined as (8R)-isodehydrodiconiferyl alcohol-4'-O-(6''-vanilloyl)-beta-D-glucopyranoside named vanilloylicariside E(5). All isolated compounds were tested for antioxidant activities using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Icariside E(5) (2) and (8R)-Isodehydrodiconiferyl alcohol (3) exhibited a strong scavenging effect on DPPH (2: IC(50)=42.1 microM, 3: IC(50)=4.5 microM).


Subject(s)
Antioxidants/pharmacology , Capsicum/chemistry , Lignans/pharmacology , Antioxidants/isolation & purification , Biphenyl Compounds/chemistry , Free Radicals/chemistry , Fruit/chemistry , Lignans/isolation & purification , Molecular Structure , Picrates/chemistry
20.
Chem Pharm Bull (Tokyo) ; 56(8): 1168-72, 2008 Aug.
Article in English | MEDLINE | ID: mdl-18670120

ABSTRACT

Repeated silica gel and octadecyl silica gel (ODS) column chromatography of the aerial parts of Artemisia princeps PAMPANINI (Sajabalssuk) led to the isolation of a new sesquiterpenoid, 3-((S)-2-methylbutyryloxy)-costu-1(10),4(5)-dien-12,6 alpha-olide (2), along with two previously reported sesquiterpenoids: 8 alpha-angeloyloxy-3beta,4 beta-epoxy-6 beta H,7 alpha H,8 beta H-guaia-1(10),11(13)-dien-12,6 alpha-olide (1, carlaolide B) and 3beta,4 beta-epoxy-8 alpha-isobutyryloxy-6 beta H,7 alpha H,8 beta H-guaia-1(10),11(13)-dien-12,6 alpha-olide (3, carlaolide A). The structure of compound 2 was elucidated by spectroscopic data analysis, including one dimensional (1D) and two dimensional (2D) nuclear magnetic resonance (NMR) experiments. Of the isolates, compound 2 exhibited potent cytotoxicity against human cervix adenocarcinoma cells and induced apoptosis.


Subject(s)
Adenocarcinoma/pathology , Apoptosis/genetics , Artemisia/chemistry , Cervix Uteri/pathology , Sesquiterpenes, Guaiane/isolation & purification , Adenocarcinoma/drug therapy , Female , Humans , Molecular Structure , Sesquiterpenes, Guaiane/toxicity , Tumor Cells, Cultured
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