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.     

Abiesanol A, a novel biflavanol with unique six connective hexacyclic rings isolated from Abies georgei

A novel biflavanol with unique six connective hexacyclic rings, abiesanol A (1), was isolated from the aerial parts of Abies georgei together with four known flavanols. The structure of new compound was elucidated mainly by the analysis of 1D and 2D NMR spectroscopic data. In addition, single-crystal X-ray diffraction analysis was adopted to confirm the structure of abiesanol A (1). In biological assay for inhibitory activities against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages, abiesanol A (1) showed potent effects at 50 μg/mL with the inhibition rate of 43.0%. Under the same concentration, abiesanol A (1) did not show any cytotoxicity against RAW264.7 macrophages.     

Acylated flavonoid glycosides from Barringtonia racemosa

Abstract

Using various chromatographic separations, three new acylated flavonoid glycosides, namely barringosides G–I (1–3), were isolated from the water-soluble extract of Barringtonia racemosa branches and leaves. The structure elucidation was performed by extensive analysis of the 1D and 2D NMR and HR-QTOF-MS data. Of the isolated compounds, barringoside I (3) showed moderate inhibitory effects on LPS-induced NO production in RAW264.7 cells with an IC₅₀ of 52.48?±?1.04?µM.     

Three new labdane-type diterpenoids from Callicarpa macrophylla Vahl.

Three new labdane-type diterpenoids, callicapene M3-M5 (1–3) were isolated from the Callicarpa macrophylla Vahl. Their structures were identified by spectroscopic method. The isolated compounds were evaluated for inhibitory activity on NO production in LPS-activated RAW 264.7 macrophage cells by using MTT assays. Compounds 1–3 showed potent inhibitory activity, with IC₅₀ value of 48.15, 46.31 and 38.72?μM respectively.     

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.     

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.     

New nor-oleanane triterpenoids from the fruits of Stauntonia brachyanthera with potential anti-inflammation activity

Abstract

The continuing studies on the fruits of Stauntonia brachyanthera led to the isolations of 6 normal and nor-oleanane triterpenoids, including two new compounds, brachyantheoraside B10 (1) and brachyantheraside C1 (2). Compounds 1–3 showed inhibitory activity on lipopolysaccharide (LPS)-induced nitric oxide production in RAW 264.7 macrophages with the IC₅₀ values of 27.04, 26.22, and 21.41?μM, respectively, which were all stronger than that of indomethacin. The study not only revealed a new type of nor-oleanane triterpenoids, but also confirmed the anti-inflammation abilities of three type nor-oleanane triterpenoids as the inhibitors of NO production.     

Triterpenoids from Hippophae rhamnoides L. and their nitric oxide production-inhibitory and DPPH radical-scavenging activities

In our investigation on the chemical constituents of Hippophae rhamnoides L., the chloroform-soluble fraction of the 80% acetone extract of branch bark was observed to inhibit nitric oxide (NO) production in a lipopolysaccharide and recombinant mouse interferon-gamma-activated murine macrophage-like cell line, RAW 264.7 cells. Two new triterpenoids, 2-O-trans-p-coumaroyl maslinic acid (1) and 2-O-caffeoyl maslinic acid (2), and three known triterpenoids, oleanolic acid (3), 3-O-trans-p-coumaroyl oleanolic acid (4), and 3-O-caffeoyl oleanolic acid (5), and 6-methoxy-2H-1-benzopyran (6) and beta-sitosterol (7) were isolated from the branch bark extract. Their inhibitory activities on the production of NO in RAW 264.7 cells and radical-scavenging activities were examined.     

Two New Sesquiterpenes from Inula salsoloides and Their Inhibitory Activities against NO Production

Two new sesquiterpenes, inulasalene ( 1 ) and inulasalsolide B ( 2 ), as well as 22 known compounds were isolated from the aerial parts of Inula salsoloides. The structures of the new sesquiterpenes were determined on the basis of their spectroscopic data and chemical properties. Compounds 1 – 4 exhibited potent inhibitory activities against NO production with IC₅₀ values range of 0.010–1.290 μg/ml in lipopolysaccharide (LPS)‐stimulated RAW264.7 cells.     

Abiesanordines A-N: fourteen new norditerpenes from Abies georgei

Fourteen new norditerpenoids (abiesanordines A-N, 1-14), including a novel podocarpene bearing a rare enolic structure (abiesanordine A, 1), were isolated from Abies georgei together with eight known ones. Their structures were determined mainly by detailed analysis of 1D and 2D NMR spectroscopic data including HSQC, DQF COSY, HMBC, and NOESY. All the isolates were tested for inhibitory activities against LPS-induced NO production in RAW264.7 macrophages, abiesanordine I (9) showed the strongest activity with the IC₅₀ value of 17.0 μg/mL. Furthermore, it exhibited no cytotoxicity against RAW264.7 macrophages under the concentration of 50 μg/mL.     

New sesquiterpenes from Inula japonica Thunb. with their inhibitory activities against LPS-induced NO production in RAW264.7 macrophages

Twenty-two new sesquiterpenes were isolated from the aerial parts of Inula japonica Thunb., together with fifteen known ones. Their structures were determined by detailed spectroscopic analysis, X-ray diffraction studies, and modified Mosher method. All 37 compounds were evaluated for the inhibition of LPS-induced nitric oxide (NO) production in RAW264.7 macrophages, and most of isolates significantly inhibited the NO production with IC₅₀ values in the range of 3.5-20 μM. Besides, results obtained in our studies provided a structure-activity relationship that would be used to design anti-inflammatory agents in the future.     

New bioactive labdane diterpenoids from Marrubium aschersonii

A phytochemical investigation of the ethanol extract of Marrubium aschersonii Magnus (Lamiaceae) collected from Tunisia led to the isolation and identification of two new labdane diterpenoids, marrubaschs A (1) and B (2), along with two known compounds (3 and 4). Their structures were elucidated by spectroscopic methods including HRESIMS and NMR techniques. All compounds were evaluated for their inhibitory effects on the nitric oxide (NO) production induced by lipopolysaccharide in RAW 264.7 macrophage cells. Compound 2 exhibited weak inhibition of NO production with an IC₅₀ value of 35 ± 1.0 μM.     

New Guaiane Sesquiterpenes from the Fruits of Torilis japonica

Three new guaiane type sesquiterpenes were isolated from the methanolic extract of the fruits of Torilis japonica together with a known compound, torilin (1). Their structures were established as 11-acetoxy-8-isobutyryl-4-guaien-3-one (2), 11-acetoxy-8-methacrylyl-4-guaien-3-one (3), and 11-acetoxy-8-propionyl-4-guaien-3-one (4) by spectroscopic methods. These compounds inhibited lipopolysaccharide (LPS)-induced nitric oxide production in murine macrophages RAW 264.7 cells.     

Six new metabolites produced by Colletotrichum aotearoa 09F0161, an endophytic fungus isolated from Bredia oldhamii

Six new compounds, colletobredins A–D (1–4) and colletomelleins A and B (5 and 6), along with 12 previously identified compounds, were isolated from the culture broth of Colletotrichum aotearoa BCRC 09F0161, a fungal endophyte residing in the leaves of an endemic Formosan plant Bredia oldhamii Hook. f. (Melastomataceae). The structures of the new compounds were established by spectroscopic methods, including UV, IR, HR-ESIMS and extensive 1D and 2D NMR techniques. The effects of some isolates on the inhibition of nitric oxide (NO) production in lipopolysaccharide-activated murine macrophage RAW264.7 cells were evaluated. All these compounds inhibited NO production in activated macrophages without any cytotoxicity at a concentration of 100 μM. Of these isolates, 1 showed weak NO inhibitory activity with IC₅₀ value of 182.2 μM. To the best of our knowledge, this is the first report on isochroman glycoside metabolites (1–4) from the genus Colletotrichum.     

A new β-tetralonyl glucoside from the Santalum album derived endophytic fungus Colletotrichum sp. GDMU-1

A new β-tetralonyl glucoside, methylberchemiaside (1), along with five known compounds (2–6) were isolated from a fungus Colletotrichum sp. GDMU-1 derived from the leaves of Santalum album. Their structures were determined by detailed analysis of spectroscopic data. All compounds were tested for the inhibitory effects on the nitric oxide (NO) production in lipopolysaccharide (LPS)-treated RAW264.7 cells. Among them, compounds 4 and 5 showed moderate anti-inflammatory activity with IC₅₀ value of 30.4 and 8.9 μM, respectively.     

Bioactive triterpenoids from Sambucus javanica Blume

Abstract

A new triterpene, javablumine A (1) along with six known ones were isolated from the aerial parts of Sambucus javanica Blume. They were identified as 3β,23-dihydroxy-11α,12α-epoxy-urs-20(30)-en-28,13β-olide (1), ursolic acid (2), pomolic acid (3), oleanic acid (4), 2α-hydroxy-oleanolic acid (5), α-amyrin (6), and lupeol palmitate (7), respectively. Compounds 1 and 3 exhibited inhibitory effect against nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW264.7 macrophage cell lines with IC₅₀ values of 17.4 and 26.2?μM, respectively.     

Monoterpene glucosides from Ziziphora clinopodioides (Labiatae)

Three new monoterpene glucosides, ziziphoroside A (1), B (2), and C (3), together with fifteen known compounds were isolated from the whole herb of Z. clinopodioides. The structures of new compounds were determined primarily from 1D-, 2D-NMR and circular dichroism (CD) spectroscopic analyses. The isolated compounds were evaluated for their inhibitory activity against nitric oxide (NO) production by lipopolysaccharide (LPS) and interferon (IFN)-γ activated macrophages, RAW 264.7. Shizonepetoside A (8) and flavones (11, 12, 13) showed potent inhibitory activity against NO production.     

Betulinic acid derivatives: a new class of α-glucosidase inhibitors and LPS-stimulated nitric oxide production inhibition on mouse macrophage RAW 264.7 cells

Chemical manipulation studies were conducted on betulinic acid (1), twenty-one new rationally designed analogues of 1 with modifications at C-28 were synthesized for their evaluation of inhibitory effects on α-glucosidase and LPS-stimulated nitric oxide production in mouse macrophage RAW 264.7 cells. Compound 2 (IC₅₀ = 5.4 μM) exhibited an almost 1.4-fold increase in α-glucosidase inhibitory activity on yeast α-glucosidase while analogues 5 (IC₅₀ 16.4 μM) and 11 (IC₅₀ 16.6 μM) exhibited a 2-fold enhanced inhibitory activity on NO-production than betulinic acid.     

Anti-Inflammatory Effects of Mitrephora sirikitiae Leaf Extract and Isolated Lignans in RAW 264.7 Cells

Mitrephora sirikitiae Weeras., Chalermglin & R.M.K. Saunders has been reported as a rich source of lignans that contribute to biological activities and health benefits. However, cellular anti-inflammatory effects of M. sirikitiae leaves and their lignan compounds have not been fully elucidated. Therefore, this study aimed to investigate the anti-inflammatory activities of methanol extract of M. sirikitiae leaves and their lignan constituents on lipopolysaccharide (LPS)-induced inflammation in RAW 264.7 mouse macrophage cells. Treatment of RAW 264.7 cells with the methanol extract of M. sirikitiae leaves and its isolated lignans, including (−)-phylligenin (2) and 3′,4-O-dimethylcedrusin (6) significantly decreased LPS-induced prostaglandin E₂ (PGE₂) and nitric oxide (NO) productions. These inhibitory effects of the extract and isolated lignans on LPS-induced upregulation of PGE₂ and NO productions were derived from the suppression of cyclooxygenase 2 (COX-2) and inducible nitric oxide synthase (iNOS) production, respectively. In addition, treatment with 2-(3,4-dimethoxyphenyl)-6-(3,5-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (3) and mitrephoran (5) was able to suppress LPS-induced tumor necrosis factor alpha (TNF-α) secretion and synthesis in RAW 264.7 cells. These results demonstrated that M. sirikitiae leaves and some isolated lignans exhibited potent anti-inflammatory activity through the inhibition of secretion and synthesis of PGE₂, NO, and TNF-α.     

Sesquiterpenes and other constituents from Dendranthema zawadskii var. latilobum

Six new germacranolides, zawadskinolides A-F (1-6), and a new eudesmane glucoside, chrysantiloboside (7) were isolated from the aerial parts of Dendranthema zawadskii var. latilobum, along with thirteen known constituents. Their structures were elucidated by means of spectroscopic evidence. Bioassay showed that flavonoids such as apigenin (9), (-)-eriodictyol (10) and nepetin (12), as well as the sesquiterpene lactone, zawadskinolide F (6), inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells with IC50 values of 66.15, 132.55, 35.44, and 91.32?μM, respectively.