NO Production Inhibitory Activity Research Articles

Search for New Liverwort and Fern Constituents of Biological Interest

Over several hundred new compounds have been isolated from the liverworts and more than 40 new carbon skeletal terpenoids (1,2) and aromatic compounds (3) have been found in this class. The biological activity ascribed to liverworts is due mainly to lipophilic sesqui- and diterpenoids, phenolic compounds and acetogenins which are constituents of oil bodies. Most of liverworts elaborate characteristic odiferous, hot tasting and bitter compounds many of which show allergenic contact dermatitis, cytotoxicity, insecticide, anti-HIV, antimicrobial, antifungal and antiinfluenza, superoxide anion radical release, plant growth regulatory, neurotrophic, NO production inhibitory, muscle relaxing and antiobesity activity.[1 – 3] Several ferns produce pungent, bitter or sweet substances. Thelypteris hispidula and Blechnum fluviatile produce a large amount of polygodial, responsible for their pungency and its related drimanes. Elaphoglossum and Hymenophyllum species elaborate bitter styrene glucosides, and hemiterpene glucosides (4) with phenylacetic acid, respectively. [4 – 6]

A Comparison between Water and Ethanol Extracts of Rumex acetosa for Protective Effects on Gastric Ulcers in Mice

Rumex acetosa is a perennial herb that is widely distributed across eastern Asia. Although the hot water extract of R. acetosa has been used to treat gastritis or gastric ulcers as a folk medicine, no scientific report exists for the use of this plant to treat gastric ulcers. Hence, the present study was undertaken to assess the anti-ulcer activity of water and 70% ethanol extracts obtained from R. acetosa, using an HCl/ethanol-induced gastric ulcer model in mice. Anti-inflammatory and free radical-scavenging activities of these two extracts were also evaluated and compared. As a result, the administration of R. acetosa extracts significantly reduced the occurrence of gastric ulcers. However, significant differences in protective activity against gastric ulcers were observed between the two samples. In the case of the group pretreated with an ethanol extract dosage of 100 mg/kg, the protective effect (90.9%) was higher than that of water extract (41.2%). Under histological evaluation, pretreatment with R. acetosa extracts reversed negative effects, such as inflammation, edema, moderate hemorrhaging and loss of epithelial cells, presented by HCl/ ethanol-treated stomachs. Meanwhile, R. acetosa extracts showed potent DPPH radical-scavenging activity and decreased NO production in a murine macrophage cell line, RAW 264.7, in a dose-dependent manner without affecting cellular viability. The greater anti-ulcer and NO production inhibitory activities exhibited by ethanol extracts compared to water extracts could be ascribed to the higher emodin levels, a major anthraquinone component of this plant.

Phytochemical and biological studies of bryophytes

The bryophytes contain the Marchantiophyta (liverworts), Bryophyta (mosses) and Anthocerotophyta (hornworts). Of these, the Marchantiophyta have a cellular oil body which produce a number of mono-, sesqui- and di-terpenoids, aromatic compounds like bibenzyl, bis-bibenzyls and acetogenins. Most sesqui- and di-terpenoids obtained from liverworts are enantiomers of those found in higher plants. Many of these compounds display a characteristic odor, and can have interesting biological activities. These include: allergenic contact dermatitis, antimicrobial, antifungal and antiviral, cytotoxic, insecticidal, insect antifeedant, superoxide anion radical release, 5-lipoxygenase, calmodulin, hyaluronidase, cyclooxygenase, DNA polymerase β, and α-glucosidase and NO production inhibitory, antioxidant, piscicidal, neurotrophic and muscle relaxing activities among others. Each liverwort biosynthesizes unique components, which are valuable for their chemotaxonomic classification. Typical chemical structures and biological activity of the selected liverwort constituents as well as the hemi- and total synthesis of some biologically active compounds are summarized.

Design and synthesis of carbamate and thiocarbamate derivatives and their inhibitory activities of NO production in LPS activated macrophages

Series of carbamate and thiocarbamate derivatives were designed and synthesized and their inhibitory activities of NO production in lipopolysaccharide-activated macrophages were evaluated. Several thoicarbamate derivatives revealed promising inhibitory activity. The structure–activity relationship study of these compounds is also reported. Among these compounds, compound 12b was the most potent with 6.5μM of IC50. They inhibited NO production through the suppression of iNOS protein and mRNA expression and nuclear translocation of p65.

Liverworts-Potential Source of Medicinal Compounds

The bryophytes contain the Marchantiophyta (liverworts), Bryophyta (mosses) and Anthocerotophyta (hornworts) among which the Marchantiophyta contain cellular oil body and they produce a number of terpenoids, aromatic compounds and acetogenins, several of which show interesting biological activity such as allergenic contact dermatitis, insecticide, insect antifeedant, cytotoxic, piscicidal, muscle relaxing, plant growth regulatory, anti-HIV, DNA polymerase beta inhibitory, anti-obesity, neurotrophic, NO production inhibitory, antimicrobial and antifungal activities. The isolation and chemical structures of biologically active compounds and their total synthesis are reviewed.

Phenolic Compounds of Abies nephrolepis and Their NO Production Inhibitory Activities

Two new, i.e., 1 and 2, and 69 known phenolics were isolated from the aerial parts of Abies nephrolepis. These chemical constituents included 22 lignans, 30 flavonoids, and 19 other phenols. Their structures were determined mainly by analysis of the 1D- and 2D-NMR spectroscopic data. All the 71 isolates were evaluated for their inhibitory activities against lipopolysaccharide (LPS)-induced NO production in RAW 264.7 macrophages. Compound 1 exhibited a potent effect with an IC(50) value of 13.7 μg/ml.

Clerodane Diterpenoids fromTinospora sagittata(Oliv.) Gagnep

Three new clerodane diterpene glycosides, tinospinosides A (1), B (2), and C (3) were isolated from the roots of Tinospora sagittata (Oliv.) Gagnep. Their structures were determined to be (2 S,4a R,6a R,9 R,10a S,10b S)-2-(3-furanyl)-9-( β-D-glucopyranosyloxy)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-6a,10b-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester (1), (2 S,4a S,6a R,9 R,10a R,10b S)-2-(3-furanyl)-9-( β-D-glucopyranosyloxy)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-4a-hydroxyl-6a,10b-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester (2) and (2 S,4a R,6a R,9 R,10a R,10b S)-2-(3-furanyl)-9-( β-D-glucopyranosyloxy)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-4a-hydroxyl-6a,10b-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester (3), by various spectroscopic analyses, chemical reactions, and computer-assisted calculations. The inhibitory activities of NO production by these compounds and their chemical derivatives in lipopolysaccharide and TNF γ-activated macrophage-like cell line J774.1 were tested. Tinospin A, 12- EPI-tinospin A, tinospinoside B, and tinospinoside C showed inhibitory activities of NO production with the IC(50) values of 162, 182, 290, and 218 µM, respectively.

A new iridoid glycoside and NO production inhibitory activity of compounds isolated from Russelia equisetiformis

From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Russelia equisetiformis, one new iridoid glucoside was isolated along with 24 known compounds, comprising iridoids and iridoid glucosides, phenyl propane glucosides, phenyl ethanoids, lignan glucosides, and flavonoid glucosides. The structure of the new compound was elucidated to be 10-O-cinnamoyl sinuatol. Of the 25 compounds isolated, rehmaglutin B exhibited moderate inhibitory activity toward NO production, which was not associated with cytotoxicity.

Chisomicines A−C, Limonoids from Chisocheton ceramicus

Three new limonoids, chisomicines A-C (1-3), have been isolated from the bark of Chisocheton ceramicus. Their structures were determined by 2D NMR, CD spectroscopic methods, and X-ray analysis. Chisomicine A (1) exhibited NO production inhibitory activity in J774.1 cells stimulated by LPS dose-dependently at high cell viability.

Kojyl thioether derivatives having both tyrosinase inhibitory and anti-inflammatory properties

This study was conducted to examine the tyrosinase inhibitory and anti-inflammatory activities of kojic acid derivatives. A series of kojic acid derivatives containing thioether, sulfoxide, and sulfone linkages were synthesized. In the tyrosinase assay, kojyl thioether derivatives containing appropriate lipophilic alkyl chains (pentane, hexane, and cyclohexane) showed potent inhibitory activity. However, sulfoxides and sulfones exhibited decreased activity. Similar experimental results were obtained with inhibitory activities of NO production being induced by LPS. The presence of thioether linkage and appropriated lipophilic acid moiety was critical for the tyrosinase inhibitory and anti-inflammatory activities.

ChemInform Abstract: Synthesis of Heterocycle‐Linked Thiourea and Their Inhibitory Activities of NO Production in LPS Activated Macrophages.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis of Heterocycle-linked Thioureas and Their Inhibitory Activities of NO Production in LPS Activated Macrophages

A series of thioureas were synthesized as inhibitors of NO production in lipopolysaccharide-activated macrophages. We investigated the effect of lipophilic moiety and N-substituents of the thioureas on the activity. Phenoxazine and carbazole-containing derivatives revealed higher activity than indole-containing thioureas. The appropriate spacer between lipophilic tail and thiourea head and methyl substituent at N3 position of thiourea brought beneficial effect on the inhibition of NO production. Among prepared compounds, phenoxazine-containing derivative 2a was the most potent with 2.32 μM of IC 50 value. RT-PCR analysis suggested that the prepared thioureas inhibited NO production through the suppression of iNOS mRNA expression.

제주 재래식된장의 생리적 특성

제주재래식된장의 생리적 특성을 측정하기 위하여 제주도내 전통된장업체로부터 된장제품 4종(JTD1-4)을 수거하여, 유기용매로 추출, 분획하여 총 페놀 함량, 항산화활성(DPPH 유리기 소거능, superoxide 유리기 소거능), ACE 및 α-glucosidase 저해능, 항염 및 항암효과를 측정하였다. 에틸아세테이트 분획물에서 총 페놀 함량(201.8～305.4 ㎍/ g)과 DPPH 유리기 소거활성(37.5～59.9%)이 가장 높았다. Superoxide anion radical 소거활성은 부탄올 분획물에서 56.3～85.1%로 가장 높았는데, JTD1(81.7%)과 JTD4(85.1%)의 소거활성은 양성대조구로 사용한 ascorbic acid의 소거활성(82.2%)과 유사하였다. ACE 저해활성은 메탄올 추출물에서 23.6～74.5%로 가장 높았다. α-Glucosidase 저해활성은 디클로로메탄 분획물에서 72.0～80.2%로 양성대조구인 acarbos의 57.4%보다 높았다. RAW 264.7 세포를 대상으로한 NO 생성 저해활성(IC<SUB>50</SUB>: 17.3～29.0 ㎍/mL)은 에틸아세테이트 분획물이 가장 높았지만, 세포독성은 모든 분획물에서 관찰되지 않았다. 에틸아세테이트 분획물의 세포증식 저해활성은 정상세포주인 피부섬유아세포(HS-68)에서 JTD1-3은 100 ㎍/mL 이하의 농도에서 나타내지 않았으나, JTD4는 21%의 세포독성을 나타내었다. 대장암 세포주(HT-29)에 대해서는 JTD1과 JTD2는 세포증식이 저해되지 않았으나, JTD3과 JTD4는 50 ㎍/mL 이상에서 증식저해 효과를 나타내었다. 유방암 세포주(MCF-7)는 100 ㎍/mL에서 JTD3은 30.9%, JTD4는 34.7%의 세포증식 저해효과를 보였다.

Tannins with LPS-induced NO production inhibitory activity from Juglans sigillata bark

Juglans sigillata Dode (Juglandaceae), a deciduous tree indigenous to China, has been extensively used in folk medicines to cure esophageal, gastric, cardiac and lung cancer [1–3], though its chemical constituents have never been reported. The Inhibitory effect of J. sigillata bark constituents against LPS-induced NO production in murine microglial BV2 cells was investigated. Bioactivity-guided fractionation and purification of a 70% acetone extract of the bark led to the isolation of 9 tannins and their structures were elucidated as gallic acid (1), ellagic acid (2), 1,2,6-tri-O-galloyl-β-D-glucose (3), 1,3,6-tri-O-galloyl-β-D-glucose (4), 1,2,3,6-tetra-O-galloyl-β-D-glucose (5), 1,2,3,4,6-penta-O-galloyl-β-D-glucose (6), 2,3-O-4,4′,5,5′,6,6′-HHDP-(α/β)-D-glucose (7), 4,6-O-4,4′,5,5′,6,6′-HHDP-(α/β)-D-glucose (8), and pedunculagin (9) on the basis of spectral and chemical evidence. All the nine tannins exhibited significant inhibition of LPS-induced NO production compared with NAME (positive control). A structure-activity relationship analysis revealed that the introduction of galloyl and HHDP groups increased the inflammation inhibitory effect. Total tannin content of J. sigillata bark was 178mg/100g which was measured indirectly using Folin-Ciocalteu after being removed with PVPP.

ChemInform Abstract: Synthesis and NO Production Inhibitory Activities of Ursolic Acid and Oleanolic Acid Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Chemical analysis, antioxidant, antiinflammatory and anticholinesterase activities of Origanum ehrenbergii Boiss and Origanum syriacum L. essential oils

Abstract The essential oils of Origanum ehrenbergii and O. syriacum collected in Lebanon were analysed by GC and GC–MS and evaluated for their anticholinesterase, NO production inhibitory activities, and antioxidant properties. O. ehrenbergi essential oil was characterised by the presence of 37 components, representing 94.9% of the total oil of which thymol (19%) and p -cymene (16.1%) were the main abundant compounds. Thirty-six compounds characterised the O. syriacum essential oil, representing 90.6% of the total oil. The most abundant components were thymol (24.7%) and carvacrol (17.6%). O. ehrenbergii demonstrated interesting scavenging effects on DPPH with an IC 50 value of 0.99 μg/ml. In addition, both O. ehrenbergii and O. syriacum oils inhibited oxidation of linoleic acid after 30 min of incubation, as well as after 60 min of incubation with IC 50 values of 42.1 and 33.6 μg/ml, and 46.9 and 58.9 μg/ml, respectively. Interestingly, O. ehrenbergii oil inhibited NO production in the murine monocytic macrophage cell line RAW 264.7 with an IC 50 value of 66.4 μg/ml. Acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition was assessed by modifications of the Ellman’s method. O. ehrenbergii exhibited a strong activity against both cholinesterases with IC 50 values of 0.3 μg/ml. The data suggest that O. ehrenbergii and O. syriacum oils could be used as a valuable new flavour with functional properties for food or nutriceutical products with particular relevance to supplements for the elderly.

Synthesis and NO Production Inhibitory Activities of Ursolic Acid and Oleanolic Acid Derivatives

Ursolic acid and oleanolic acid are pentacyclic triterpenoid compounds with 30 carbon atoms, biosynthetically derived from the cyclization of squalene. Since these triterpenes are widely distributed in food, medicinal herbs and other plants, these compounds can be integral part of the human diet.

Bryophytes: Bio- and Chemical Diversity, Bioactivity and Chemosystematics

The bryophytes contain the Marchantiophyta (liverwort), Bryophyta (moss) and Anthocerotophyta (hornwort) among which the Marchantiophyta contain cellular oil body and they produce a number of mono-, sesqui- and diterpenoids, aromatic compounds like bibenzyl, bis(bibenzyls) and acetogenins. Several of these compounds show interesting biological activity such as insecticide, insect antifeedant, cytotoxic, piscicidal, muscle relaxing, allergenic contact dermatitis, anti-HIV, DNA polymerase p, 5-lipoxygenase, calmodium inhibitory, anti-obesity, neurotrophic, cyclooxygenase, hyaluronidase and NO production inhibitory, antimicrobial and antifungal activities. Each liverwort biosynthesizes peculiar components, which are valuable for classification of liverworts. The typical chemical structures and bioactivity of the selected liverwort constituents as well as chemosystematics of several species of the Marchantiophyta are surveyed.

Liverworts-Potential Source of Medicinal Compounds

The bryophytes contain the Marchantiophyta (liverworts), Bryophyta (mosses) and Anthocerotophyta (hornworts) among which the Marchantiophyta contain cellular oil body and they produce a number of terpenoids, aromatic compounds and acetogenins, several of which show interesting biological activity such as allergenic contact dermatitis, insecticide, insect antifeedant, cytotoxic, piscicidal, muscle relaxing, plant growth regulatory, anti-HIV, DNA polymerase beta inhibitory, anti-obesity, neurotrophic, NO production inhibitory, antimicrobial and antifungal activities. The isolation and chemical structures of biologically active compounds and their total synthesis are reviewed.

Marchantiophyta and inedible mushrooms: marvelous sources of bioactive molecules

The biological activity ascribed to the Marchantiophyta is due mainly to sesqui- and diterpenoids and phenolic compounds. Novel terpenoids, phenolics and acetogenins showing characteristic scent, hot-taste, allergenic contact dermatitis, cytotoxicity, insect antifeedant, anti-HIV, superoxide radical release inhibitory, antimicrobial, antifungal, muscle relaxing, apoptosis inducing activity against HL-60, NO production inhibitory activity, liver X receptors agonist/antagonist activity have been isolated from the Marchantiophyta (Blasiaceae, Frullaniaceae, Jungermanniaceae, Lejeuneaceae, Marchantiaceae, Pelliaceae, Plagiochialceae, Porellaceae and Aytoniaceae) species. The chemical constituents of 24 inedible mushroom species belonging to five families, Scutigeraceae, Polypolaceae, Xylariaceae, Thelephoraceae and Paxillaceae were studied. Various type of chemical substances including p-terphenyls, cytochalacines, pregnanes, azaphilones, binaphthyls, lanostanes, 3(R)-hydroxybutyric acid, its dimmer and trimer which showed a broad activity of in many biological systems, such as antimicrobial, antinematicidal, NO production and TNF-α release inhibitory activity, anti-HIV, anti-HSV and antioxidant activities were isolated and their structures characterized.