Polyphenols from Sophora yunnanensis, and their inhibitory effects on nitric oxide production

A new flavonoid, (2R,3R)-3,7,4'-trihydroxy-3',5'-dimethoxyflavanone, named sophorayunnanol (1), together with eight known polyphenols (2-9), were isolated from the roots of Sophora yunnanensis C.Y.MA (Leguminosae). The structure including absolute stereochemistry of 1 was determined by spectroscopic (high resolution (HR)-MS, 1D- and 2D-NMR, and circular dichroism (CD)) methods. The inhibitory activity of these compounds was examined against nitric oxide (NO) production by lipopolysaccharide (LPS) and interferon (IFN)-γ activated macrophages, RAW264.7 cells. 3,7,3',5'-Tetrahydroxy-4'-methoxyflavone (6) and piceatannol (9) showed potent inhibitory activity against the production of NO with IC(50) values of 14.4±2.5 and 12.9±1.8 μM, respectively. This article is the first report on phytochemical study of S. yunnanensis.     

New Labdane diterpenes from Hedychium yunnanense with cytotoxicity and inhibitory effects on nitric oxide production

Two new labdane diterpenes, hedychenoids A (1) and B (2), were isolated from the rhizomes of Hedychium yunnanense, together with four known ones hedychenone (3), forrestin A (4), villosin (5) and calcaratarin C (6). Their structures were determined on the basis of NMR (1D and 2D) and mass spectroscopic analysis. Compounds 2, 3 and 5 exhibited cytotoxicity against SGC-7901 with IC₅₀ values of 14.88 ± 0.52, 7.08 ± 0.21 and 7.76 ± 0.21 μg/ml, 3 and 5 against HeLa with IC₅₀ values of 9.76 ± 0.48 and 13.24 ± 0.63 μg/ml, respectively. Compounds 2, 5 showed inhibitory effects against nitric oxide production in LPS and IFN-γ-induced RAW 264.7 murine macrophages with IC₅₀ values of 6.57 ± 0.88 and 5.99 ± 1.20 μg/ml, respectively.     

Chemical constituents from Curcuma longa L. and their inhibitory effects of nitric oxide production

A new bisabolane-type sesquiterpenoid, turmerone Q (1), along with six known compounds (2–7), were isolated from the rhizomes of Curcuma longa L. The structural elucidation of the new compound was conducted using ¹H NMR, ¹³C NMR, HSQC, HMBC and NOESY spectroscopic analyses. The absolute configuration of 1 was elucidated by comparison of the experimental and calculated ECD spectra. The anti-inflammatory effects of 1–7 were evaluated through lipopolysaccharide-induced nitric oxide (NO) production in RAW 264.7 macrophages assays, and compounds 6 and 7 showed potent inhibitory activity against NO production.     

Sesquiterpene coumarins from Ferula fukanensis and nitric oxide production inhibitory effects

Four new sesquiterpene coumarin derivatives, fukanemarin B (1), fukanefuromarin E (2), fukanefuromarin F (3) and fukanefuromarin G (5) were isolated from a 80% aqueous methanol extract of the roots of Ferula fukanensis. The structures were elucidated based on spectral evidence, especially heteronuclear multiple-bond connectivity (HMBC) and high-resolution MS. The 80% aqueous methanol extract of the roots of Ferula fukanensis (FFE) and the sesquiterpene coumarin derivatives inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma).     

A New Triterpene from the Orchid Pholidota yunnanensis

A new triterpene, 25-methylenecyclopholidonyl p-hydroxy-trans-cinnamate, was isolated from a orchid Pholidota yunnanensis. The structure elucidation and ^1H, ^13C-NMR assignments were achieved by spectral and chemical method.     

New lignans from Kadsura coccinea and their nitric oxide inhibitory activities

In vitro anti-allergic screening of medicinal herbal extracts revealed that the chloroform extract of the rhizoma of Kadsura coccinea inhibited nitric oxide (NO) production in a lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma) activated murine macrophage like cell line RAW 264.7. Further fractionation of the chloroform extract led to the isolation of three new lignans, including two dibenzocyclooctadiene lignans and one arylnaphthalene lignan, together with other three known dibenzocyclooctadiene lignans. This is the first report of NO production inhibitory activity of Kadsura coccinea and first report about the isolation of arylnaphthalene lignan from K. coccinea.     

Flavonoids from Daphne aurantiaca and their inhibitory activities against nitric oxide production

Chemical examination of the methanolic extract from the stem bark of Daphne aurantiaca led to the isolation of three new flavonoids (1-3), and 29 known flavonoids. All 32 compounds were isolated for the first time from Daphne aurantiaca. The isolates were tested for inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophages. Compounds 21 and 24 showed potent inhibitory activities against the production of NO with IC?? values of 0.006 and 0.076 μM, respectively.     

Humulene derivatives from Zingiber zerumbet with the inhibitory effects on lipopolysaccharide-induced nitric oxide production

A new humulene sesquiterpene, 5-hydroxyzerumbone (5-hydroxy-2E,6E,9E-humulatrien-8-one) (1) and a known compound, zerumboneoxide (2) were isolated from the rhizomes of Zingiber zerumbet (Zingiberaceae), and found to inhibit lipopolysaccharide-induced nitric oxide production in murine macrophage RAW 264.7 cells with IC50 values of 14.1 and 23.5 microM, respectively, by bioassay-guided fractionation (positive control: N(omega)-monomethyl-L-arginine, IC50=21.3 microM). The structure of 1 was determined by spectroscopic methods including 1D and 2D-NMR.     

Melampolides from the leaves of Smallanthus sonchifolius and their inhibitory activity of lps-induced nitric oxide production

Two new melampolide-type sesquiterpene lactones, 8beta-epoxyangeloyloxy-9alpha-ethoxy-14-oxo-acanthospermolide (1) and 8beta-angeloyloxy-9alpha-ethoxy-14-oxo-acanthospermolide (2), were isolated from the leaves of yacon [Smallanthus sonchifolia (POEPP. et ENDL.) H. Robinson] along with eleven known melampolides, allo-schkuhriolide (3), enhydrin (4), polymatin A (5), fluctuanin (6), 8beta-angeloyloxy-9alpha-acetoxy-14-oxo-acanthospermolide (7), 8beta-angeloyloxy-14-oxo-acanthospermolide (8), 8beta-methacryloyloxymelampolid-14-oic acid methyl ester (9), uvedalin (10), polymatin B (11), 8beta-tigloyloxymelampolid-14-oic acid methyl ester (12), and sonchifolin (13). Their structures were established on the basis of spectroscopic evidence including 1D- and 2D-NMR experiments. All isolates were evaluated for inhibition of LPS-induced nitric oxide production in murine macrophage RAW 264.7 cells.     

New seco-dibenzocyclooctadiene lignans with nitric oxide production inhibitory activity from the roots of Kadsura longipedunculata

Four new seco-dibenzocyclooctadiene lignans,kadlongilignans A-D(1-4),consisting of a rare 6,7-seco-(1),two 15,16-seco-(2 and 3) and a 9,10-seco-dibenzocyclooctadiene(4) lignans,were isolated from the roots of Kadsura longipedunculata.Their structures were elucidated by spectroscopic analysis,including extensive NM R,MS and ECD(electronic circular dichroism) spectra.Compounds 3 and 4 exhibited potent inhibitory activities against NO(nitric oxide) production of LPS(lipopolysaccharide)-induced murine macrophages with the inhibition rates of 36.3% and 26.9%,respectively.     

A new triterpenoid saponin from Gleditisia sinensis and structure-activity relationships of inhibitory effects on lipopolysaccharide-induced nitric oxide production

A phytochemical investigation of the anomalous fruits of Gleditisia sinensis led to one new oleanane-type triterpenoid saponin acylated with one monoterpenic acid, 3-O-beta-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)-[(6S,2E)-6-hydroxy-2,6-dimethyl-2,7-octadienoyl-(1 --> 6)]-beta-D-glucopyranosyl ester, named gleditsioside Z (1), together with nine known ones (2-10). Their structural details were mainly established on the basis of 1D, 2D NMR and HR-MS analysis as well as some chemical methods. Structure-activity relationships of the isolated saponins that affected nitric oxide production from cultured mouse macrophages (RAW 264.7 cell lines) induced by lipopolysaccharide were discussed.     

Neolignans from Piper futokadsura and their inhibition of nitric oxide production

From a MeOH extract of the aerial part of Piper futokadsura, the tetrahydrofuran lignans, futokadsurin A [(7S,8S,7'S,8'R)-3,4,3'-trimethoxy-4'-hydroxy-7,7'-epoxylignan], futokadsurin B [(7R,8R,7'R,8'S)-3,4-dimethoxy-3',4'-methylenedioxy-7,7'-epoxylignan], and futokadsurin C [(7R,8R,7'S,8'S)-3,4-methylenedioxy-3',4'-dimethoxy-7,7'-epoxylignan] were isolated, together with nine known neolignans. In addition, L-tryptophan, pellitorine, phytol, elemicin, and 1,2,4-trimethoxyphenyl-5-aldehyde were isolated. The structures of the new compounds were elucidated using spectroscopic methods. These lignans inhibited nitric oxide production by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide and interferon-gamma.     

Highly-oxygenated isopimarane-type diterpenes from Orthosiphon stamineus of Indonesia and their nitric oxide inhibitory activity

From the methanolic extract of Indonesian Orthosiphon stamineus, nine new highly-oxygenated isopimarane-type diterpenes [7-O-deacetylorthosiphol B (1), 6-hydroxyorthosiphol B (2), 3-O-deacetylorthosiphol I (3), 2-O-deacetylorthosiphol J (4), siphonols A-E (5-9)] have been isolated together with nine known diterpenes [orthosiphols H (10), K (11), M (12) and N (13); staminols A (14) and B (15); neoorthosiphols A (16) and B (17); norstaminol A (18)]. Their structures were determined based on the spectroscopic data. The isolated diterpenes inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophage-like J774.1 cells. Compounds 4-7, 9, 10, 14, and 17 showed inhibitory activities more potent (IC(50), 10.8-25.5 microM) than a positive control N(G)-monomethyl-L-arginine (L-NMMA; IC(50), 26.0 microM).     

Lignans from Arctium lappa and their inhibition of LPS-induced nitric oxide production

A new butyrolactone sesquilignan, isolappaol C (1), together with four known lignans, lappaol C (2), lappaol D (3), lappaol F (4), and diarctigenin (5), were isolated from the methanolic extract of the seeds from the Arctium lappa plant. The structure of isolappaol C (1) was determined by spectral analysis including 1D- and 2D-NMR. All the isolates were evaluated for their inhibitory effects on the LPS-induced nitric oxide production using murine macrophage RAW264.7 cells. Lappaol F (4) and diarctigenin (5) strongly inhibited NO production in the LPS-stimulated RAW264.7 cells with IC(50) values of 9.5 and 9.6 microM, respectively.     

Sesquiterpenes from an Egyptian herbal medicine, Pulicaria undulate, with inhibitory effects on nitric oxide production in RAW264.7 macrophage cells

The methylene chloride-methanol (1?:?1) extract from the air-dried aerial parts of wild Pulicaria undulata collected in North Sinia, Egypt, showed inhibitory effects on lipopolysaccharide (LPS)-induced production of nitric oxide (NO) in RAW264.7 macrophages. From the extract, three new sesquiterpenes named 5α-hydroperoxyivalin, 8-epi-xanthanol, and 8-epi-isoxanthanol were isolated together with four known sesquiterpenes. The structure of each new sesquiterpenes was determined on the basis of physicochemical and chemical evidence. In addition, all the sesquiterpenoids significantly inhibited the production of NO. Ivalin (IC50=2.0?μM) and 2α-hydroxyalantolactone (1.8?μM) showed particularly strong inhibitory effects, but had strong cytotoxic effects as well. Furthermore, ivalin and 2α-hydroxyalantolactone concentration-dependently reduced inducible NO synthase (iNOS) protein levels in RAW264.7 cells.     

New method of detecting nitric oxide production.

Nitric oxide (NO) reacts with H2O2 to produce a rise in potent luminol-dependent chemiluminescence under neutral pH conditions. We applied this reaction to the continuous detection of NO released from the rat isolated perfused kidney with simultaneous pressure changes. Acetylcholine increased NO release dose-dependently with the pressure reduction. An NO synthesis inhibitor, NG-monomethyl-L-arginine, abolished the release. This inhibition was reversed by the addition of L-arginine.     

Lignans from the roots of Wikstroemia indica and their DPPH radical scavenging and nitric oxide inhibitory activities

In our investigation of in vitro anti-allergic screening of medicinal herbal extracts, the ethyl acetate extract of the root of Wikstroemia indica was observed to inhibit nitric oxide (NO) production in a lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma) activated murine macrophage-like cell line, RAW 264.7. Fractionation of the active extract led to the isolation of two new lignan dimer bis-5,5-nortrachelogenin (1) and bis-5,5'-nortrachelogenin (2), and three known lignans. Compound 1 and lirioresinol B (5) inhibited NO production with IC50 values at 48.6 and 53.5 microM, respectively. Compound 5 also showed free radical scavenging effect on 1,1-diphenyl-2-picrylhydrazil (DPPH) at IC50 values at 19.5 microM.     

Antiallergic agents from natural sources. 3. Structures and inhibitory effects on nitric oxide production and histamine release of five novel polyacetylene glucosides from Bidens parviflora WILLD

Five new polyacetylene glucosides, bidensyneosides A1, A2, B, C (1-4), and 3-deoxybidensyneoside B (5), have been isolated from the air-dried whole plant of Bidens parviflora WILLD. The structures were identified based on spectroscopic analysis, physicochemical properties, and application of the modified Mosher method to be 3(R),8(E)-8-decene-4,6-diyne-1,3-diol 1-O-beta-D-glucopyranoside (1), deca-3(R),8(Z) 8-decene-4,6-diyne-1,3-diol 1-O-beta-D-glucopyranoside (2), 3(R)-deca-4,6,8-triyne-1,3-diol 1-O-beta-D-glucopyranoside (3), 3(R),8(E)-8-decene-4,6-diyne-1,3,10-triol 1-O-beta-D-glucopyranoside (4), and 8(E)-8-decene-4,6-diyne-1,10-diol 1-O-beta-D-glucopyranoside (5), respectively. These compounds inhibited nitric oxide (NO) production in lipopolysaccharide and interferon-gamma activated murine macrophages (RAW264.7) and also inhibited histamine release from rat mast cells stimulated by the antigen-antibody reaction.     

Stilbene derivatives from Pholidota chinensis and their anti-inflammatory activity

Ethyl acetate extract of Pholidota chinensis L. showed strong NO production inhibitory activity in murine macrophage-like cell line, RAW 264.7, which was activated by a lipopolysaccharide (LPS) and interferon-gamma (IFN-gamma). Fractionation of the active extract led to the isolation of two new stilbene derivatives, 2,3'-dihydroxy-5-methoxy-3,4-methylenedioxydihydrostilbene (Pholidotol A) and 2-hydroxy-5-methoxy-3,4,3',4'-dimethylenedioxydihydrostilbene (Pholidotol B) together with six known stilbene derivatives. Pholidotols A both B and inhibited Nitric oxide (NO) production with an IC(50) value at 24.3 and 17.1 microM, respectively.