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1.
J Breath Res ; 4(2): 026005, 2010 Jun.
Article in English | MEDLINE | ID: mdl-21383473

ABSTRACT

Recently, we reported that myrsinoic acid B purified from Myrsine seguinii inhibited methyl mercaptan (CH(3)SH) production by Fusobacterium nucleatum JCM8532. Since hydrogen sulfide (H(2)S) is the main component of physiological halitosis, while CH(3)SH is involved in pathological oral halitosis, the objective of this study is to determine whether myrsinoic acid B inhibits H(2)S production by oral microorganisms. F. nucleatum, Porphyromonas gingivalis and Treponema denticola were incubated with myrsinoic acid B and a substrate such as l-cysteine or l-methionine. H(2)S or CH(3)SH concentration in the headspace air, was determined using a gas chromatograph. The concentration of myrsinoic acid B inhibiting 50% (IC(50)) of H(2)S production by F. nucleatum was 0.142 µg ml(-1), and the IC(50) of P. gingivalis and T. denticola were 2.71 µg ml(-1) and 28.9 µg ml(-1), respectively. The presence of pyruvate, a by-product of H(2)S production, was determined. The IC(50) values of myrsinoic acid B for pyruvate production were 22.9 µg ml(-1) for F. nucleatum, 87.7 µg ml(-1) for P. gingivalis and 165 µg ml(-1) for T. denticola. We concluded that myrsinoic acid B inhibited the production of both H(2)S and pyruvate by periodontal pathogens.


Subject(s)
Alkenes/pharmacology , Benzofurans/pharmacology , Enzyme Inhibitors/pharmacology , Fusobacterium nucleatum/metabolism , Hydrogen Sulfide/metabolism , Porphyromonas gingivalis/metabolism , Sulfhydryl Compounds/metabolism , Chlorides/pharmacology , Humans , Treponema denticola/metabolism , Zinc Compounds/pharmacology
2.
Chem Pharm Bull (Tokyo) ; 56(12): 1691-7, 2008 Dec.
Article in English | MEDLINE | ID: mdl-19043241

ABSTRACT

Two new sempervirol type diterpenes, inumakiols A, B, and six new totarol type diterpenes, inumakiols C-H, were isolated from a methanolic extract of bark of Podocarpus macrophyllus (Podocarpaceae), along with one known abietane, two known totarol type diterpenes, and one known totarol type diterpene dimer. The structures of the new compounds were elucidated by the spectroscopic methods. Some of them possessed antibacterial activity against oral pathogenic microorganisms with minimum inhibitory concentration (MIC) values ranging from 3.1 to 25 ppm.


Subject(s)
Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Diterpenes/isolation & purification , Diterpenes/pharmacology , Plants/chemistry , Bacteria/drug effects , Chromatography, High Pressure Liquid , Crystallography, X-Ray , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Models, Molecular , Mouth/microbiology , Plant Bark/chemistry , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet
3.
Biosci Biotechnol Biochem ; 72(9): 2411-4, 2008 Sep.
Article in English | MEDLINE | ID: mdl-18776663

ABSTRACT

A methioninase inhibitor from Myrsine seguinii was purified and identified as myrsinoic acid B. Its inhibitory activities as to crude methioninase from periodontal bacteria such as Fusobacterium nucleatum, Porphyromonas gingivalis, and Treponema denticola were determined. The IC50 values were 10.5, 82.4, and 30.3 microM respectively.


Subject(s)
Alkenes/chemistry , Alkenes/pharmacology , Benzofurans/chemistry , Benzofurans/pharmacology , Carbon-Sulfur Lyases/antagonists & inhibitors , Primulaceae/chemistry , Alkenes/isolation & purification , Benzofurans/isolation & purification , Butyrates/antagonists & inhibitors , Fusobacterium nucleatum/metabolism , Inhibitory Concentration 50 , Methylmercury Compounds/antagonists & inhibitors , Molecular Structure , Periodontitis/microbiology , Porphyromonas gingivalis/metabolism , Species Specificity , Treponema denticola/metabolism
4.
Mol Pharmacol ; 66(3): 667-74, 2004 Sep.
Article in English | MEDLINE | ID: mdl-15322259

ABSTRACT

We investigated the effect of gamma-mangostin purified from the fruit hull of the medicinal plant Garcinia mangostana on spontaneous prostaglandin E(2) (PGE(2)) genase release and inducible cyclooxy-2 (COX-2) gene expression in C6 rat glioma cells. An 18-h treatment with gamma-mangostin potently inhibited spontaneous PGE(2) release in a concentration-dependent manner with the IC(50) value of approximately 2 microM, without affecting the cell viability even at 30 microM. By immunoblotting and reverse-transcription polymerase chain reaction, we showed that gamma-mangostin concentration-dependently inhibited lipopolysaccharide (LPS)-induced expression of COX-2 protein and its mRNA, but not those of constitutive COX-1 cyclooxygenase. Because LPS is known to stimulate inhibitor kappaB (IkappaB) kinase (IKK)-mediated phosphorylation of IkappaB followed by its degradation, which in turn induces nuclear factor (NF)-kappaB nuclear translocation leading to transcriptional activation of COX-2 gene, the effect of gamma-mangostin on the IKK/IkappaB cascade controlling the NF-kappaB activation was examined. An in vitro IKK assay using IKK protein immunoprecipitated from C6 cell extract showed that this compound inhibited IKK activity in a concentration-dependent manner, with the IC(50) value of approximately 10 microM. Consistently gamma-mangostin was also observed to decrease the LPS-induced IkappaB degradation and phosphorylation in a concentration-dependent manner, as assayed by immunoblotting. Furthermore, luciferase reporter assays showed that gamma-mangostin reduced the LPS-inducible activation of NF-kappaB-and human COX-2 gene promoter region-dependent transcription. gamma-Mangostin also inhibited rat carrageenan-induced paw edema. These results suggest that gamma-mangostin directly inhibits IKK activity and thereby prevents COX-2 gene transcription, an NF-kappaB target gene, probably to decrease the inflammatory agent-stimulated PGE(2) production in vivo, and is a new useful lead compound for anti-inflammatory drug development.


Subject(s)
Gene Expression/drug effects , I-kappa B Proteins/antagonists & inhibitors , Isoenzymes/biosynthesis , Lipopolysaccharides/pharmacology , Prostaglandin-Endoperoxide Synthases/biosynthesis , Xanthones/pharmacology , Animals , Brain Neoplasms , Cyclooxygenase 1 , Cyclooxygenase 2 , Dinoprostone/metabolism , Drug Interactions , Glioma , I-kappa B Kinase , Isoenzymes/genetics , Isoenzymes/metabolism , Male , Membrane Proteins , NF-kappa B/antagonists & inhibitors , Pain/chemically induced , Pain/drug therapy , Prostaglandin-Endoperoxide Synthases/genetics , Prostaglandin-Endoperoxide Synthases/metabolism , Protein Serine-Threonine Kinases/physiology , RNA, Messenger/drug effects , RNA, Messenger/metabolism , Rats , Rats, Wistar , Transcriptional Activation/drug effects , Tumor Cells, Cultured , Xanthones/therapeutic use
5.
Eur J Oral Sci ; 112(3): 249-52, 2004 Jun.
Article in English | MEDLINE | ID: mdl-15154923

ABSTRACT

Cacao bean husk extract (CBH) has been shown to possess antibacterial and antiglucosyltransferase activities through its unsaturated fatty acids and epicatechin polymers, respectively. In the present study, the antiplaque activities of CBH were examined in vitro and in vivo. The extract inhibited the adherence of Streptococcus mutans MT8148 to saliva-coated hydroxyapatite and reduced the accumulation of artificial dental plaque by S. mutans MT8148 on orthodontic wire. The number of mutans streptococci in dental plaque was also significantly reduced when human dental plaque was exposed to CBH from 21 children at 37 degrees C for 1 h. For the in vivo study, 28 volunteers aged 19-29 yr old rinsed their mouth with CBH, before and after each intake of food and before sleeping at night for 4 d without using other oral hygiene procedures. Plaque depositions and the numbers of mutans streptococci were reduced in the subjects, compared with rinsing with 1% ethanol alone. These results indicate that CBH possesses significant antiplaque activity in vitro and in vivo.


Subject(s)
Bacterial Adhesion/drug effects , Cacao , Dental Plaque/drug therapy , Mouthwashes/pharmacology , Phytotherapy , Plant Extracts/pharmacology , Streptococcus mutans/drug effects , Adult , Analysis of Variance , Dental Plaque/microbiology , Durapatite , Female , Humans , Male , Mouthwashes/therapeutic use , Orthodontic Wires , Plant Extracts/therapeutic use , Saliva/microbiology , Seeds
6.
J Biosci Bioeng ; 96(2): 199-202, 2003.
Article in English | MEDLINE | ID: mdl-16233510

ABSTRACT

For one-step enzymatic synthesis of eugenyl alpha-glucoside as a promising pro-drug for a hair restorer and a derivative of spices, selective alpha-glucosylation of eugenol was carried out using the alpha-glucosyl transfer enzyme of Xanthomonas campestris WU-9701. When 130 micromol eugenol and crude enzyme showing 1.0 unit of alpha-glucosyl transfer activity were shaken in 2 ml of 10 mM H3BO3-NaOH-KCl buffer (pH 8.0) containing 1.2 M maltose as a glucosyl donor at 40 degrees C, only one form of eugenyl glucoside was selectively obtained as a product and identified as eugenyl alpha-D-glucopyranoside (alpha-EG) by 13C-NMR, 1H-NMR, and two-dimensional heteronuclear multiple-bond coherence analyses. In the reaction, no other glucosylated products such as maltotriose or eugenyl maltoside were detected in the reaction mixture. The reaction at 40 degrees C for 48 h under the above conditions yielded 68 mumol alpha-EG in 2 ml suspension, and the maximum molar conversion yield based on the amount of eugenol supplied reached 52%.

7.
Biol Pharm Bull ; 25(9): 1137-41, 2002 Sep.
Article in English | MEDLINE | ID: mdl-12230104

ABSTRACT

The fruit hull of mangosteen, Garcinia mangostana L. has been used as a Thai indigenous medicine for many years. However, its mechanism of action as a medicine has not been elucidated. The present study was undertaken to examine the effects of mangosteen extracts (100% ethanol, 70% ethanol, 40% ethanol and water) on histamine release and prostaglandin E2 synthesis. We found that the 40% ethanol extract of mangosteen inhibited IgE-mediated histamine release from RBL-2H3 cells with greater potency than the water extract of Rubus suavissimus that has been used as an anti-allergy crude drug in Japan. All extracts of mangosteen potently inhibited A23187-induced prostaglandin E2 synthesis in C6 rat glioma cells, while the water extract of Rubus suavissimus had no effect. The 40% ethanol extract of mangosteen inhibited the prostaglandin E2 synthesis in a concentration-dependent manner with relatively lower concentrations than the histamine release. In addition, passive cutaneous anaphylaxis (PCA) reactions in rats were significantly inhibited by this ethanol extract as well as by the water extract of Rubus suavissimus. These results suggest that the 40% ethanol extract of mangosteen has potent inhibitory activities of both histamine release and prostaglandin E2 synthesis.


Subject(s)
Dinoprostone/antagonists & inhibitors , Dinoprostone/biosynthesis , Garcinia mangostana , Histamine Release/drug effects , Animals , Dose-Response Relationship, Drug , Fruit , Histamine Release/physiology , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Leaves , Plants, Medicinal , Rats , Thailand , Tumor Cells, Cultured
8.
Chem Pharm Bull (Tokyo) ; 50(9): 1163-8, 2002 Sep.
Article in English | MEDLINE | ID: mdl-12237530

ABSTRACT

To reverse the adverse reactions of alkylxanthines and to develop novel inhibitors of cyclic AMP phosphodiesterase 4 (PDE4), a series of heterocycle [a]-, [b]-, [c,d]-, and [i]-condensed purines were designed and synthesized. Although all compounds did not display PDE1 and PDE3 inhibitory activities, several heterocycle [i]-condensed purines strongly inhibited PDE4. Especially, dl-3,4-dipropyl-8-methyl-4,5,7,8-tetrahydro-1H-imidazo[2,1-i]purin-5-one (dl-7c) exhibited comparable PDE4 inhibitory activity (IC(50)=1.9 microM) to rolipram and denbufylline (DBF).


Subject(s)
3',5'-Cyclic-AMP Phosphodiesterases/antagonists & inhibitors , Heterocyclic Compounds/chemical synthesis , Heterocyclic Compounds/pharmacology , Phosphodiesterase Inhibitors/chemical synthesis , Phosphodiesterase Inhibitors/pharmacology , Purines/chemical synthesis , Purines/pharmacology , Chemical Phenomena , Chemistry, Physical , Cyclic Nucleotide Phosphodiesterases, Type 1 , Cyclic Nucleotide Phosphodiesterases, Type 4 , Indicators and Reagents , Isoenzymes/antagonists & inhibitors , Magnetic Resonance Spectroscopy , Phosphodiesterase I , Phosphoric Diester Hydrolases/metabolism
9.
J Agric Food Chem ; 50(8): 2400-3, 2002 Apr 10.
Article in English | MEDLINE | ID: mdl-11929303

ABSTRACT

In a search for possible antitumor agents from natural sources, megastigmane glycosides and polyphenolic constituents isolated from the leaves of Eriobotrya japonica (Rosaceae) were found to inhibit the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced activation of Epstein-Barr virus early antigen in Raji cells. Roseoside and procyanidin B-2 were among the active compounds found in an in vitro assay; these compounds were further assessed for antitumor activity in vivo in a two-stage carcinogenesis assay on mouse skin. Roseoside significantly delayed carcinogenesis induced by peroxynitrite (initiator) and TPA (promoter), and its potency was comparable to that of a green tea polyphenol, (-)-epigallocatechin 3-O-gallate, in the same assay.


Subject(s)
Antineoplastic Agents/isolation & purification , Antineoplastic Agents/therapeutic use , Biflavonoids , Norisoprenoids , Plant Leaves/chemistry , Proanthocyanidins , Rosaceae/chemistry , 9,10-Dimethyl-1,2-benzanthracene , Animals , Antigens, Viral/analysis , Carcinogens , Catechin/analogs & derivatives , Catechin/isolation & purification , Catechin/therapeutic use , Female , Glucosides/isolation & purification , Glucosides/therapeutic use , Herpesvirus 4, Human/genetics , Herpesvirus 4, Human/growth & development , Herpesvirus 4, Human/immunology , Humans , Mice , Mice, Inbred ICR , Nasopharyngeal Neoplasms/virology , Peroxynitrous Acid , Skin Neoplasms/chemically induced , Skin Neoplasms/drug therapy , Tea/chemistry , Tetradecanoylphorbol Acetate/pharmacology , Virus Activation/drug effects
10.
Phytochemistry ; 59(3): 315-23, 2002 Feb.
Article in English | MEDLINE | ID: mdl-11830140

ABSTRACT

Callus tissue cultures induced from an axenic leaf of Eriobotrya japonica (Rosaceae) produced triterpenes in large amounts (ca. 50 mg/g dry wt). Nine triterpenes were characterized as ursolic acid, oleanolic acid, 2alpha-hydoxyursolic acid, maslinic acid, tormentic acid, 2alpha, 19alpha-dihydroxy-3-oxo-urs-12-en-28-oic acid, hyptadienic acid and a mixture of 3-O-cis-p-coumaroyltormentic acid and 3-O-trans-p-coumaroyltormentic acid. The triterpene composition in the callus tissues was noticeably different from that in intact leaves. The contents of tormentic acid with antidiabetic action, and 2alpha, 19alpha-dihydroxy-3-oxo-urs-12-en-28-oic acid with anti-HIV activity, were much larger than those in the intact leaves. All of the triterpenes isolated from the callus tissues showed an inhibitory effect comparable to (-)-epigallocatechin gallate (EGCG) of green tea on the activation of Epstein-Barr virus early antigen (EBV-EA) induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). 2alpha, 19alpha-Dihydroxy-3-oxo-urs-12-en-28-oic acid was the most potent inhibitor among them and caused a significant delay of two-stage carcinogenesis on mouse skin.


Subject(s)
Rosaceae/metabolism , Triterpenes/metabolism , Animals , Antigens, Viral/drug effects , Antineoplastic Agents/pharmacology , Carcinoma, Squamous Cell/pathology , Cell Division/drug effects , Cell Transformation, Neoplastic , Chromatography, High Pressure Liquid , Culture Techniques , Humans , Magnetic Resonance Spectroscopy , Mice , Mouth Neoplasms/pathology , Salivary Gland Neoplasms/pathology , Skin Neoplasms/pathology , Spectrometry, Mass, Electrospray Ionization , Triterpenes/pharmacology , Tumor Cells, Cultured
11.
J Biosci Bioeng ; 93(3): 328-30, 2002.
Article in English | MEDLINE | ID: mdl-16233209

ABSTRACT

Alpha-arbutin, a useful cosmetic ingredient, was selectively synthesized by alpha-anomer-selective glucosylation of hydroquinone with maltose as a glucosyl donor using lyophilized cells of Xanthomonas campestris WU-9701 as a biocatalyst. When 45 mM hydroquinone and 120 mg of lyophilized cells showing 11 nkat of alpha-glucosyl transfer activity were shaken in 2 ml of 10 mM H3BO3NaOHKCl buffer (pH 7.5) containing 1.2 M maltose at 40 degrees C, only one form of hydroquinone glucoside was selectively obtained as a product and identified as hydroquinone 1-O-alpha-D-glucopyranoside (alpha-arbutin) by 13C-NMR, 1H-NMR and two-dimensional HMBC analysis. Although hydroquinone has two phenolic -OH groups at the para position in its structure, only one -OH group, but not both -OHs, was glucosylated and no other glucosylated products such as maltotriose were detected in the reaction mixture. The reaction at 40 degrees C for 36 h under optimum conditions yielded 42 mM alpha-arbutin, and the maximum molar conversion yield based on the amount of hydroquinone supplied reached 93%.

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