Nitric Oxide Inhibitory Activity Research Articles

Diterpenoid glycosides from the flower of Trollius chinensis Bunge and their nitric oxide inhibitory activities

Trolliusditerpenosides A-Q (1–17), seventeen new labdane-diterpenoid glycosides, were isolated from the dried flowers of Trollius chinensis Bunge, a plant that has been commonly used as both an anti-inflammatory folk medicine and a healthcare tea for its therapeutic and anti-viral and antibacterial properties. Their structures were corroborated via comprehensive spectroscopic analysis, ECD calculations, and single-crystal X-ray diffraction analysis. Furthermore, the inhibitory activities on lipopolysaccharide (LPS)-induced NO production in RAW 264.7 macrophages of all compounds (1–17) were evaluated in vitro. Compounds 3, 6, 7, and 11 displayed significant inhibitory activities against NO production, with IC50 values ranging from 1.6 ± 0.1 to 14.4 ± 0.2 μM. In addition, compounds 3, 6, 7, and 11 all down-regulated the mRNA expression of iNOS, COX-2, and IL-1β in RAW 264.7 cells mediated by LPS. These findings not only support the chemical context of genus Trollius but also the exploration of new chemical entities with pharmacological significance from this genus.

Rubichaetoglobin A, a new cytochalasan alkaloid isolated from the plant endophytic fungus Chaetomium tectifimeti S104

Rubichaetoglobin A (1), a new cytochalasan alkaloid, together with nine closely related known ones (2-10), were isolated from the ethyl acetate extracts of the endophytic fungus Chaetomium tectifimeti S104 harbored in the root of Rubia podantha Diels. Their structures were elucidated based on comprehensive spectroscopic analysis. All isolated compounds were tested for cytotoxic, antibacterial, and nitric oxide inhibitory activities. The results showed that 2, 4, and 5 possessed moderate cytotoxicity against MDA-MB-231 cells with the IC50 values of 19.14, 11.43, and 10.27 μM, respectively.

Phytochemical profiling of Azima tetracantha Lam. leaf methanol extract and elucidation of its potential as a chain-breaking antioxidant, anti-inflammatory and anti-proliferative agent.

Azima tetracantha, a traditional medicinal plant included in the order Brassicales and family Salvadoraceae, is widely used as a dietary supplement in folklore medicines. The plant is also used for the treatment of rheumatism, diarrhea and other inflammatory disorders. The present investigation focused on the phytochemical composition, radical scavenging, reducing potential and anti-proliferative activities of the A. tetracantha leaves. Quantitative estimation of the polyphenols and flavonoids revealed significantly elevated levels in the methanol extract. Corroborating with this, methanol extract exhibited higher in vitro anti-radical scavenging effect against 2,2-diphenyl-1- picrylhydrazyl (34.14 ± 2.19 μg/mL), and hydrogen peroxide (44.96 ± 1.77 μg/mL), as well as ferric reducing properties (58.24 ± 6.98 μg/mL). The methanolic extract also showed strong lipoxygenase (71.42 ± 6.36 μg/mL) and nitric oxide inhibitory activities (94.23 ± 8.11 μg/mL). Cytotoxic activity against MCF7 cells was found to be higher (IC50= 37.62 ± 2.94 μg/mL), than that of MDAMB231 cells (IC50= 69.11 ± 5.02 μg/mL). The qPCR-based analysis indicated dose-dependent increase in the expression of the pro-apoptotic genes such as executioner caspases and apoptotic protease activating factor-1. Overall, the results indicated the possible use of methanol extract of A. tetracantha leaves as a chain-breaking antioxidant molecule and are capable of inhibiting inflammatory enzymes and the proliferative potential of breast cancer cells.

Chromone glycosides and phenolic glycoside from Scindapsus officinalis (Roxb.) Schott.

• We provided more information about the chemical constituents of Scindapsus officinalis . • We found one anti-inflammatory chromone glycoside reported firstly in literature. • Structures were elucidated by NMR, mass spectrometry and acid hydrolysis methods. Phytochemical and pharmacological investigations of the plants of Scindapsus officinalis (Roxb.) Schott, rendered the isolation of two new chromone glycosides and one phenolic glycoside, named officinalisides F, G (1, 2) and 4- O -[ α - l -rhamnopyranosyl-(1–3)- β - d -glucopyranosyl]-( E )-3-(4-hydroxy-3-methoxyphenyl) acrylic acid (3). Structures of the three undescribed compounds were elucidated by NMR spectroscopic and acid hydrolysis experiments. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production assay in vitro . As indicated in the results, compound 2 exhibited significant NO inhibitory effects with IC 50 value of 8.02 μM, while the other two ones showed weak NO inhibitory activities.

A versatile tailoring tool for pentacyclic triterpenes of Penicillium griseofulvum CICC 40293

In the biosynthetic pathway of pentacyclic triterpenes (PTs), tailoring reactions can produce a wide range of end products from a small number of common scaffolds and the microbial transformation has also been established as an alternative technique for this purpose. In this study, we explored the tailoring reactions involved in the microbial transformation of pentacyclic triterpenes by Penicillium griseofulvum CICC 40293. Preparative biotransformation of eight different PTs from three scaffolds resulted in the isolation of thirteen metabolites. The structures of metabolites were elucidated by HR-ESI-MS, 1D, and 2D NMR spectroscopy. We discovered the highly efficient regio- and stereo-selective hydroxylation of inactivated sp3 CH2 and CH3 on the position of 2α, 7β, 15α, 21β, 23(angular methyl), and 30−COOH glycosylation, this versatile tailoring system for PTs would provide an effective method for expanding their structural diversities. In addition, all compounds were subjected to the bioassay on the model of lipopolysaccharide (LPS)-stimulated RAW 264.7 cells to evaluate their anti-inflammatory activity through nitric oxide (NO) inhibition activity. Compounds 2a and 5a exhibited excellent NO inhibitory activity with IC50 values of 8.35 ± 2.81 μM and 19.60 ± 4.25 μM, respectively.

Lignans with NO inhibitory activity from Tinospora sinensis.

Two new lignan glucosides, tinsinlignans A and B (1 and 2), two new oxyneolignans, tinsinlignans C and D (3 and 4), along with one known analogue (5), were isolated from the stems of Tinospora sinensis. The structures of the new compounds were elucidated based on analysis of spectroscopic data, and the absolute configuration of 1 was determined through electronic circular dichroism (ECD) calculation based on the time-dependent density functional theory (TD-DFT). Compounds 1-4 were evaluated for their inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine RAW264.7 macrophage cells and compounds 1 and 2 exhibited moderate inhibitory activities with IC50 values of 18.5 ± 2.0 and 28.8 ± 1.2 μmol·L-1, respectively.

Panabipinoside A and panabipinoside B, two new oleanane triterpenoid saponins from the roots of Panax bipinnatifidus with nitric oxide inhibitory activity

Panax bipinnatifidus belongs to the ginseng genus and it is used in traditional Vietnamese and Chinese medicine. Phytochemical studies of the roots of this plant led to the isolation of two new oleanane triterpenoid saponins, panabipinoside A and panabipinoside B, and three known compounds, ginsennoside Ro, 3- O- β-D-glucopyranosyl-(1→3)- β-glucuronopyranosyl oleanolic acid, and spinasaponin A 28- O-glucoside. Their structures are established by extensive spectroscopic analysis (IR, high-resolution electrospray ionization mass spectrometry, and nuclear magnetic resonance) and by comparison of the spectral data with those reported in the literature. The anti-inflammatory activity of the isolated compounds is evaluated by their inhibition of nitric oxide production in lipopolysaccharide stimulated RAW 264.7 cells. Compounds 2–5 showed inhibitory effects on nitric oxide production with IC50 values of 0.62 ± 0.09, 0.21 ± 0.04, 0.30 ± 0.03, and 0.45 ± 0.05 µg/mL, respectively, compared to value of 8.08 ± 0.09 µg/mL for the positive control compound, NG-monomethyl-L-arginine.

Diterpenoids from Rosmarinus officinalis L. and their nitric oxide inhibitory activity

AbstractOne icetexane diterpenoid, demethylsalvicanol (1) and four abietane diterpenoids, sageone (2), 20‐deoxocarnosol (3), 11,12,20‐trihydroxy‐abieta‐8,11,13‐triene (4), and 7αα‐ethoxyrosmanol (5) were isolated from the n‐hexane layer of the leaves and twigs of Rosmarinus officinalis L. Chemical structures of compounds were identified by ESI‐MS, 1D‐, 2D‐NMR spectra and by comparison of the spectral data in the literature. Compounds 1‐5 were evaluated anti‐inflammatory activity by inhibitory NO production, LPS stimulated on RAW 264.7 cells. At a concentration of 100 μM, compound 4 exhibited inhibitory percentage of 34.7±1.8 %, meanwhile compounds 1‐3 and 5 showed cytotoxic effect. After dilution to concentration of 20 μM, except compound 1 and 2, compounds 3‐5 did not show cytotoxic effect. Their NO inhibitory productions were ranging from 20.5±2.4 % to 26.7±1.9 %. Compounds 1, 3 and 4 have been reported for the first time from the Rosmarinus genus.

Antibacterial, anti-inflammatory and antioxidant activities of Mahanintangtong and its constituent herbs, a formula used in Thai traditional medicine for treating pharyngitis

BackgroundMahanintangtong is listed in the Thailand’s National List of Essential Medicines (NLEM). It is used to treat non-specific fevers and illnesses such as pharyngitis and chickenpox. In this study, we investigated the biological activities of the different medicinal plants used in the Mahanintangtong formula.MethodsThe plant materials were extracted by maceration and decoction. Antimicrobial activity, assessed by disc diffusion method, the minimum inhibitory concentration (MIC), and minimum bactericidal concentration (MBC) were compared with commercially available standard antibiotics. To elucidate the anti-inflammatory mechanisms, inhibition of nitric oxide (NO), tumor necrosis factor α (TNF-α), and interleukin 6 (IL-6) production was tested by Griess and ELISA techniques. Antioxidant activity was measured by ABTS and DPPH scavenging assays.ResultsThe extracts with the best antimicrobial activities were carbonized Tectona grandis showing against Streptococcus pyogenes, Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa. The ethanol extract of Dracaena loureiroi wood exhibited the highest NO and IL-6 inhibitory activity with IC50 values of 9.42 ± 1.81 and 12.02 ± 0.30 μg/mL, respectively. The ethanol extract of Pogostemon cablin had the highest TNF-α inhibitory with IC50 values of 10.68 ± 0.02 μg/mL. In anti-free radical testing, the ethanol extract of D. loureiroi displayed high antioxidant activity by both ABTS and DPPH assays.ConclusionThe ethanol extracts from carbonized T. grandis and Mahanintangtong showed good antimicrobial activity, especially against S. pyogenes, and good anti-inflammatory activity. These findings are relevant to the pathogenesis of pharyngitis and justify additional studies to see if Mahanintangtong could have clinical utility.

Anti-inflammatory effect of leaves of Vernonia zeylanica in lipopolysaccharide-stimulated RAW 264.7 macrophages and carrageenan-induced rat paw-edema model

Ethnopharmacological relevanceVernonia zeylanica (L.) Less (Family: Compositae) is a medicinal plant used as external applications for boils, bone fractures, eczema and internally for asthma in traditional medicine in Sri Lanka. Anti-nociceptive, anti-bacterial and anti-proliferative activities have been reported previously. Aim of the studyTo investigate the anti-inflammatory activity of methanol/dichloromethane extract (MDE) of leaves of V. zeylanica by assessing in vivo inhibition of rat paw-edema, in vitro inhibition of the production of nitric oxide (NO) and superoxide and inhibitory effect on inducible nitric oxide synthase (iNOS) gene expression. Materials and methodsIn vivo anti-inflammatory activity of MDE was tested at the dose of 1500 mg/kg using rat paw-edema model. Indomethacin and Gum acacia was used as the positive and vehicle control respectively. In vitro NO inhibitory activity of 7.8–250 μg/ml MDE was tested using lipopolysaccharide (LPS)-stimulated (1 μg/ml) mouse macrophages (RAW264.7 cells) and rat peritoneal cells (RPC) obtained following carrageenan-induction (5 mg/Kg). Griess method was used to quantify the nitrite levels in culture supernatants. In vitro inhibition of superoxide production of Phorbal 12-myristate 13-acetate (PMA)-stimulated RAW cells was determined by quantitative Nitroblue Tetrazolium (NBT) assay. N-monomethyl-L-arginine acetate (NMMA) (1 mM) and Diphenyleneiodonium chloride (DPI) (10 μM) were used as the positive controls for inhibitory activity of NO and superoxide production respectively. Reverse transcriptase polymerase chain reaction (RT-PCR) analysis was carried out to test the inhibitory effect on mRNA expression of iNOS gene. ResultsTreatment with MDE of V. zeylanica at 1500 mg/kg showed significant inhibition of paw-edema from 1st-5th hour (P < 0.01) compared with the control. The reference drug, indomethacin showed a biphasic pattern and its highest inhibition was (98.3 ± 7.1%) at 4th h (P < 0.01). MDE of V. zeylanica showed similar inhibition of paw-edema with highest inhibition recorded as 94.5 ± 5.28%, at 5th h (P < 0.01). The inhibitory concentration (IC50) of MDE for in vitro NO inhibitory activity was 105 μg/ml for RAW cells and 80 μg/ml for RPCs. Both NO inhibitory activities showed significant dose-dependency (r = 0.998 and r = 0.915 respectively; p < 0.05). MDE concentration of 250 μg/ml showed 55% inhibition of ROS production in RAW cells. NMMA showed 78% and 70.1% inhibition of NO production with RAW cells and RPCs whereas DPI showed 61% superoxide inhibitory activity with RAW cells. NO inhibitory activity of MDE on RAW cells was confirmed by the significant reduction (99.1%) in iNOS gene expression. ConclusionThese results demonstrated potent anti-inflammatory activity of MDE of V. zeylanica reflected by its significant in vivo inhibition of rat paw-edema, in vitro inhibition of NO and superoxide production, and the reduction of iNOS gene expression. Thus, further purification and isolation of bioactive compounds from V. zeylanica are emphasized.

Phytochemical profile and biological activities of Sudanese baobab (Adansonia digitata L.) fruit pulp extract

The present work aimed to investigate the phytochemical profile and biological activities of Sudanese baobab (Adansonia digitata L.) fruit pulp extract. Baobab fruit pulp serves as food, and has been used in traditional medicine in Africa for the treatment of several diseases, and believed to possess many biological activities. The sample of baobab fruit was collected from Blue Nile State in Sudan. The fruit pulp was obtained from baobab pods, sieved, extracted with methanol (80%), and analysed for its antioxidant activity, and alpha-glucosidase and nitric oxide (NO) inhibitory activities. The phytochemical constituents of the pulp were determined by LC-MS and 1H-NMR techniques. The results for antioxidant activity evaluated by DPPH and FRAP for methanolic extract were 232.70 mg Ascorbic Acid Equivalent Antioxidant Capacity (AEAC)/g and 222.28 mmol/g of Fe2+, respectively. Baobab pulp extract showed greater capability in inhibiting the generation of NO from the stimulated RAW264.7 cells at 98.45% inhibition and IC50 of 36.55 µg/mL; and α-glucosidase enzyme activity at 97.94% inhibition and IC50 of 58.59 µg/mL. The LC-MS/MS analysis of the baobab extract showed that 52 compounds were found in the baobab pulp, including 19 flavonoids, ten phenolic acids, four lipids (glycero-3-phosphocholine derivative, 1,2-didodecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol), 1-pentadecanoyl-2-(13Z,16Z-docosadienoyl)-glycero-3-phosphate, and glycero-3-hosphocholine derivative), sugars, organic acid, iridoids, adenosine, scopoletin, and taraxerone. The NMR detected 21 metabolites from baobab pulp extract including carbohydrates, organic acids, vitamin, amino acids, phenolic compounds, alkaloids, and fatty acids. The present work is the first of its kind in comprehensively analysing the Sudanese baobab fruit pulp, combined with qualitative characterisation of chemical components using NMR, LC-MS, α-glucosidase, and NO inhibitors. Baobab fruit pulp contains several beneficial phytochemicals and biological activities, and it has potential positive effect on general human’s health.

Pentacyclic triterpenes with nitric oxide inhibitory activity from Potentilla chinensis

Three new ursane-type triterpenes (1–3) and twenty-one known triterpenoids (4–24) were isolated from the methanolic extract of the whole plants of Potentilla chinensis. Their structures were elucidated by extensive spectroscopic analysis of 1D and 2D NMR (HSQC, HMBC, COSY and ROESY) and HRESIMS data. The bioassay screening revealed the inhibitory effects on nitric oxide production of compounds 2, 5, 7, 9, 10, and 13–24 in LPS-induced RAW264.7 macrophages.

Structurally diverse steroids with nitric oxide inhibitory activities from Aglaia lawii leaves

Eleven previously uncharacterized steroids, along with three analogs were isolated from Aglaia lawii leaves. Their structures were definitely characterized by the methods of NMR, MS, IR, ECD and X-ray crystallography study. Among these unreported compounds, 3-epi-dyscusin C, 3-epi-lansisterone E and (Z)-2α-hydroxyaglawone were C-21 pregnane steroids incorporating a highly oxygenated ring A, while others were Δ5-3β-hydroxy-7-ketosteroids bearing different ring D and C-17 aliphatic chains. All isolates were evaluated for nitric oxide (NO) inhibitory activities. 3-Epi-dyscusin C, 3-epi-lansisterone E, (Z)-2α-hydroxyaglawone and 17(20)E-dyscusin B showed significant anti-inflammatory activities with IC50 values of NO inhibition less than 10 μM (in the range from 4.47 ± 0.36 to 7.67 ± 0.46 μM).

Polygokingiasides A and B: Two New Spirostane Glycosides From the Roots of Polygonatum kingianum With Nitric Oxide Inhibitory Activity

Two new spirostane glycosides, named polygokingiaside A (1) and polygokingiaside B (2), and 6 known spirostane glycosides, (25 R)-26- O-( β-d-glucopyranosyl)-furost-5-en-3 β,22 α,26-triol 3- O-β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (3), (25 S)-26- O-( β-d-glucopyranosyl)-furost-5-en-3 β,22 α,26-triol 3- O-β-d-glucopyranosyl-(1→2)- β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (4), (25 R)-26- O-( β-d-glucopyranosyl)-furost-5-en-3 β,22 α,26-triol 3- O-β-d-glucopyranosyl-(1→2)- β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (5), (23 S,25 R)-spirostan-5-en-3 β,23-dihydroxy-12-one-3- O-β-d-glucopyranosyl-(1→2)- β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (6), (24 S,25 R)-spirostan-5-en-3 β,24-dihydroxy-12-one-3- O-β-d-glucopyranosyl-(1→2)- β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (7), and (25 R)-spirostan-5-en-3 β-hydroxy-12-one-3- O-β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (8), were isolated from the roots of Polygonatum kingianum Collett &amp; Hemsl. (Asparagaceae). Their structures were determined by extensive analysis of high-resolution electron spray ionization mass spectrometry and nuclear magnetic resonance spectral data, as well as by comparison of the spectral data with those reported in the literature. Anti-inflammatory activity of compounds 1-8 was evaluated by their inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. At a concentration of 20 µM, compounds 1-8 exhibited a modest inhibitory effect on NO production in LPS-stimulated RAW246.7 cells with inhibitory values ranging from 9.5 ± 0.8% to 33.8 ± 2.1%.

Structurally diverse triterpenes obtained from the fruits of Ziziphus jujuba Mill. as inflammation inhibitors by NF-κB signaling pathway.

Twenty-nine triterpenes were obtained from the fruits of Ziziphus jujuba Mill. through various chromatography methods, and their stereo-structures were confirmed by spectroscopic methods. Among them, 2α,3β,20-trihydroxylupane-28-oic acid (1) was identified as a new compound, and the 1H and 13C NMR data of 7, 8 and 23, as well as the 13C NMR data of 17 are reported here for the first time. Meanwhile, the nitric oxide (NO) inhibitory activities of all compounds were examined in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. As results, compounds 2, 7, 10-13, 15, 16, 18-21, 26-29 were found to play important roles in suppressing NO production at 5 μM. The structure-activity relationships (SARs) on NO inhibition indicated that the ursolic and oleanolic acid skeletons, p-coumaroyl group substitution, six-membered A ring, and deoxygenation (loss of C[double bond, length as m-dash]O) in the C ring showed a more positive effect on the NO inhibitory activity of triterpenes, while the reduction of the A ring C[double bond, length as m-dash]O to OH was a negative factor. Moreover, it was found that compounds 15 and 19 could suppress the phosphorylation of IκBα and NF-κB/p65 to prevent it from shifting into the nucleus and downregulate the expression of inflammatory factors, such as iNOS, IL-6 and TNF-α. Our investigations revealed that the NO inhibitory effects of the active triterpenes obtained from Z. jujuba were mediated, at least in part, through the NF-κB signaling pathway.

Effects of drying methods on compositional characterization and functional characteristics of Blighia sapida aril oil

The composition of Blighia sapida fruits is reported to differ based on its origin, variety, and preservation technique. In this study, the effect of drying method on the composition as well as the antioxidant activity of oven-dried and sun-dried B. sapida aril flour and oil were examined using standard procedures. Sun-dried B. sapida aril flour had significantly higher protein and fat content compared to the oven-dried flour. In addition, sun-dried B. sapida aril flour contained a more diverse phytochemical profile compared to the oven-dried flour. However, oven-dried B. sapida aril oil (ODAO) showed a higher percentage of unsaturated fatty acids compared to oil from the sun-dried B. sapida flour (SDAO). On the other hand, SDAO showed significantly higher DPPH scavenging and nitric oxide inhibitory activities compared to ODAO. Based on these findings, sun-drying is recommended for both nutritional purposes and other health-promoting usage such as antioxidant, over oven-drying.

Bioactive sesquiterpene derivatives from mangrove endophytic fungus Phomopsis sp. SYSU-QYP-23: Structures and nitric oxide inhibitory activities

Eight new sesquiterpene derivatives (2, 4–6 and 10–13), along with five known analogues were isolated from the mangrove endophytic fungus Phomopsis sp. SYSU-QYP-23. Their structures of new compounds were established by spectroscopic methods, and the absolute configurations were confirmed by single-crystal X-ray diffraction analysis and comparison of the experimental ECD spectra. The absolute configuration of the side chain in 1 was first defined by modified Mosher’s method. Compounds 1–7 showed potent inhibitory activities against nitric oxide (NO) production in lipopolysaccharides (LPS) induced RAW 264.7 cells with IC50 values ranging from 8.6 to 14.5 μM. The molecular docking results implied that the bioactive sesquiterpenes may directly bind with targeting residues in the active cavity of iNOS protein.

Identification and characterization of the chemical components of Iris tectorum Maxim. and evaluation of their nitric oxide inhibitory activity.

Iris tectorum Maxim. is a traditional medicinal herb that is commonly used to treat inflammatory conditions. The present study investigated the fragmentation patterns of isoflavone glycosides and their qualitative analysis. In addition, lipopolysaccharide (LPS)-induced RAW264.7 macrophages were used to evaluate the anti-inflammatory properties of I. tectorum Maxim. samples collected at different time points during the year. High-performance liquid chromatography/quadrupole time-of-flight tandem mass spectrometry (HPLC/QTOF-MS/MS) and HPLC with diode-array detection were employed for qualitative and quantitative analysis. The fragmentation patterns of the isoflavones were observed in negative electrospray ionization mode with collision-induced dissociation (CID). Their anti-inflammatory activity was assessed via nitric oxide (NO) production in LPS-treated RAW264.7 macrophages. A total of 15 chemical components were observed and tentatively identified using HPLC/QTOF-MS/MS. At low collision energy, the relative abundances of the aglycone radical anions Y0 - , [Y0 - H]-• , [Y0 - CH3 ]-• and [Y0 - H- CH2 ]-• were used for the structural characterization of tectoridin and tectorigenin-4'-O-β-D-glucoside. The radical ions [Y0 - CH3 ]-• and [Y0 - H - 2CH3 ]-• were also employed to differentiate between iristectorin A and iristectorin B based upon their high-energy CID spectra. Levels of 9.02 mg/g of tectoridin and 1.04 mg/g of tectorigenin were found in samples collected in June, which exhibited 69.7% NO inhibitory activity. The characteristic fragmentation patterns enabled us to reliably identify isoflavone glycosides. The results of the quantitative determination and NO inhibitory activity offer insight into the optimal I. tectorum Maxim. harvesting time.

A New Phenylethanoid Glycoside From the Leaves of Rosmarinus officinalis With Nitric Oxide Inhibitory Activity

A new phenylethanoid glycoside, named rosmacinalis (1), and 6x known compounds {2-phenylethyl O-α-L-rhamnopyranosyl-(1‴→6″)- O-β-D-glucopyranoside (2), clinopodiolide C (3), rosmanol (4), 7 α-methoxyrosmanol (5) 7 β-methoxyrosmanol (6) and carnosol (7)} were isolated from the leaves of Rosmarinus officinalis. Their structures were determined by extensive analysis of high-resolution electron spray ionization mass spectrum and nuclear magnetic resonance spectral data, as well as by comparison of the spectral data with those reported in the literature. Anti-inflammatory activity of compounds 1‐7 was evaluated by their inhibition of NO production in lipopolysaccharide-stimulated RAW 264.7 cells. At a concentration of 100 µM, compounds 1 and 2 exhibited inhibitory rates of 47.1% ± 2.2% and 44.5% ± 1.3%, respectively, while compounds 3‐7 showed a cytotoxic effect. After dilution to a concentration of 20 µM, except compound 7, compounds 1‐6 did not show a cytotoxic effect. Their NO inhibitory rates ranged from 14.2% ± 1.3% to 31.1% ± 1.9%.

Anti-Inflammatory ent-Kaurane Diterpenoids from Isodon serra.

Ten new ent-kaurane diterpenoids, including two pairs of epimers 1/2 and 4/5 and a 6,7-seco-ent-kauranoid 10, were obtained from the aerial parts of Isodon serra. The structures of the new compounds were confirmed by extensive spectroscopic methods and electronic circular dichroism (ECD) data analysis. An anti-inflammatory assay was applied to evaluate their nitric oxide (NO) inhibitory activities by using LPS-stimulated BV-2 cells. Compounds 1 and 9 exhibited notable NO production inhibition with IC50 values of 15.6 and 7.3 μM, respectively. Moreover, the interactions of some bioactive diterpenoids with inducible nitric oxide synthase (iNOS) were explored by employing molecular docking studies.