New Nitric Oxide Inhibitory Spirostane Glycosides from Polygonatum kingianum  Collett & Hemsl

Two new spirostane glycosides, (25 R)-12 β-hydroxyspirost-5-en-3 β-yl O- β-D-glucopyranosyl-(1→4)- β-D-galactopyranoside (1) and (25 S)-spirost-5-en-7-one-3 β-yl O- β-D-glucopyranosyl-(1→2)- β-D-glucopyranosyl-(1→4)- β-D-galactopyranoside (2), and a known spirostane glycoside, funkioside C (3), were isolated from the roots of Polygonatum kingianum Collett & Hemsl. (Asparagaceae). Their structures were determined by extensive analysis of mass spectrometry 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. Compound 2 showed inhibitory effects on nitric oxide production in the lipopolysaccharide stimulated RAW 264.7 cells with an IC50 value of 8.78 ± 0.05 µM compared to a value of 7.12 ± 0.08 µM for the positive control compound, NG-monomethyl-L-arginine.

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A New β-Carboline Alkaloid From the Aerial Part of Hedyotis capitellata

Natural Product Communications ◽

10.1177/1934578x211047705 ◽

2021 ◽

Vol 16 (10) ◽

pp. 1934578X2110477

Author(s):

Le Thi Huyen ◽

Nguyen Thi Thu Hau ◽

Hoang Son Vu ◽

Nguyen Thi Lan Huyen ◽

Bui Huu Tai ◽

...

Keyword(s):

Aerial Part ◽

2D Nmr ◽

Positive Control ◽

Raw 264.7 Cells ◽

No Production ◽

Ionization Mass ◽

Inhibitory Effects ◽

One Dimensional ◽

A Value ◽

Control Compound

A new β-carboline alkaloid, 10-hydroxy-capitelline (1) together with three known anthraquinones, hedanthroside B (2), hedanthroside C (3), and rubiadin (4) were isolated from the aerial part methanol extract of Hedyotis capitellata. Their structures were established by spectroscopic data (one-dimensional, two-dimensional nuclear magnetic resonance (1D, 2D-NMR) and high-resolution-electrospray ionization-mass spectrometry, HR-ESI-MS) and comparison with those reported in the literature. The anti-inflammatory activity of the isolated compounds is 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 to 4 showed weak inhibitory effects on NO production with inhibitory values ranging from 1.2% to 23.9% compared to a value of 74.5% for the positive control compound, NG-monomethyl-L-arginine (L-NMMA).

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

Natural Product Communications ◽

10.1177/1934578x20969088 ◽

2020 ◽

Vol 15 (10) ◽

pp. 1934578X2096908

Author(s):

Le Thi Huyen ◽

Le Thi Oanh ◽

Nguyen Thi Son ◽

Nguyen Thi Minh Thu ◽

Nguyen Huy Hoang ◽

...

Keyword(s):

Spectral Data ◽

Cytotoxic Effect ◽

Rosmarinus Officinalis ◽

Raw 264.7 Cells ◽

No Production ◽

Ionization Mass ◽

Phenylethanoid Glycoside ◽

Extensive Analysis ◽

Resolution Electron ◽

Ionization Mass Spectrum

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%.

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

Natural Product Communications ◽

10.1177/1934578x20985634 ◽

2021 ◽

Vol 16 (1) ◽

pp. 1934578X2098563

Author(s):

Tran Thi Thu Ha ◽

Trinh Quang Huy ◽

Pham The Chinh ◽

Phan Van Kiem

Keyword(s):

Nitric Oxide ◽

Mass Spectrometry ◽

Spectral Data ◽

Inhibitory Effect ◽

Raw 264.7 Cells ◽

No Production ◽

Ionization Mass ◽

Raw 264.7 ◽

Extensive Analysis ◽

Resolution Electron

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 & 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%.

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

Journal of Chemical Research ◽

10.1177/17475198211018988 ◽

2021 ◽

pp. 174751982110189

Author(s):

Phan Van Kiem ◽

Vu DinhHoang ◽

Nguyen Thi Hoang Anh ◽

Dinh Thi Phuong Anh ◽

Do Thi Trang ◽

...

Keyword(s):

Nitric Oxide ◽

Positive Control ◽

Raw 264.7 Cells ◽

Ionization Mass ◽

Nitric Oxide Production ◽

Triterpenoid Saponins ◽

Oxide Production ◽

Control Compound ◽

Phytochemical Studies ◽

Oleanane Triterpenoid

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.

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Diarylheptanoids of Curcuma comosa with Inhibitory Effects on Nitric Oxide Production in Macrophage RAW 264.7 Cells

Natural Product Communications ◽

10.1177/1934578x1501000123 ◽

2015 ◽

Vol 10 (1) ◽

pp. 1934578X1501000 ◽

Cited By ~ 1

Author(s):

Nilubon Sornkaew ◽

Yuan Lin ◽

Fei Wang ◽

Guolin Zhang ◽

Ratchanaporn Chokchaisiri ◽

...

Keyword(s):

Nitric Oxide ◽

Inhibitory Activity ◽

Raw 264.7 Cells ◽

Racemic Mixture ◽

Raw 264.7 ◽

Nitric Oxide Production ◽

Inhibitory Effects ◽

Curcuma Comosa ◽

Oxide Production ◽

Potent Inhibitory Activity

Eight new diarylheptanoids, a 1.2:1 mixture of (3S)- and (3 R)-1-(4-hydroxyphenyl)-7-phenyl-(4 E,6 E)-4,6-heptadien-3-ol (1a and 1b), a racemic mixture of (3S)- and (3 R)-1-(4-hydroxyphenyl)-3-methoxy-7-phenyl-(4 E,6 E)-4,6-heptadiene (2a and 2b), a ca. 1:1 mixture of (3S)- and (3 R)-1-(4-hydroxy-3-methoxyphenyl)-3-methoxy-7-phenyl)-(4 E,6 E)-4,6-heptadiene (3a and 3b), 3-acetoxy-1-(3,4-dihydroxyphenyl)-7-phenylheptan-5-ol (4), (3 R)-1-(4,5-dihydroxyphenyl)-7-phenyl-(6 E)-6-hepten-3,2′-epoxide (5), and thirteen known diarylheptanoids, 6-12, a 3:1 mixture of 13a and 13b, and 14-17, were isolated from the rhizomes of Curcuma comosa from Sakon Nakhon, northeastern part of Thailand. The isolated compounds were evaluated for their antiinflammatory activities on the inhibition of lipopolysaccharide-induced nitric oxide production in macrophage RAW 264.7 cells and the diarylheptanoids 1a and 1b mixture and 14 exhibited potent inhibitory activity.

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Urea inhibits inducible nitric oxide synthase in macrophage cell line

AJP Cell Physiology ◽

10.1152/ajpcell.1997.273.6.c1882 ◽

1997 ◽

Vol 273 (6) ◽

pp. C1882-C1888 ◽

Cited By ~ 46

Author(s):

Sharma S. Prabhakar ◽

Guillermo A. Zeballos ◽

Martin Montoya-Zavala ◽

Claire Leonard

Keyword(s):

Nitric Oxide ◽

Raw 264.7 Cells ◽

Contributory Factor ◽

No Production ◽

Uremic Toxin ◽

Inhibitory Effects ◽

Macrophage Dysfunction ◽

Oxide Synthase ◽

Dose Dependent ◽

Inducible Nitric Oxide

Macrophage dysfunction is considered an important contributory factor for increased propensity of infections in uremia. Because nitric oxide (NO) is believed to be an effector molecule of macrophage cytotoxicity, we propose that the dysfunction may be related to impaired NO synthesis. To verify this hypothesis, we evaluated macrophage NO synthesis in the presence of urea, a compound that accumulates in renal failure and is believed by some to be a uremic toxin. Macrophages (RAW 264.7 cells) were incubated with bacterial lipopolysaccharide to induce NO synthesis, whereas the test groups had various concentrations of urea in addition. NO synthesis was measured by assaying the supernatant for nitrites and nitrates by chemiluminescence. We observed that urea consistently produced a dose-dependent reversible inhibition of inducible NO production in macrophages, whereas parathormone, another toxin retained in uremia, had no such inhibitory effects. Further studies revealed that mRNA for inducible NO synthase was not inhibited by urea. We thus conclude that urea inhibits inducible NO synthesis in macrophages by a posttranscriptional mechanism and that this may be important in macrophage dysfunction of uremia.

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ANTI-INFLAMMATORY ACTIVITY OF TINOCRISPOSIDE BY INHIBITING NITRIC OXIDE PRODUCTION IN LIPOPOLYSACCHARIDES-STIMULATED RAW 264.7 CELLS

Asian Journal of Pharmaceutical and Clinical Research ◽

10.22159/ajpcr.2018.v11i4.23739 ◽

2018 ◽

Vol 11 (4) ◽

pp. 149 ◽

Cited By ~ 1

Author(s):

Adek Zamrud Adnan ◽

Muhammad Taher ◽

Tika Afriani ◽

Annisa Fauzana ◽

Dewi Imelda Roesma ◽

...

Keyword(s):

Nitric Oxide ◽

Inflammatory Diseases ◽

Positive Control ◽

Inflammatory Activity ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

Dependent Manner ◽

Anti Inflammatory

Objective: The aim of this study was to investigate in vitro anti-inflammatory activity of tinocrisposide using lipopolysaccharides (LPS)-stimulated RAW 264.7 macrophage cells. Tinocrisposide is a furano diterpene glycoside that was isolated in our previous study from Tinospora crispa.Methods: Anti-inflammatory effect was quantified spectrometrically using Griess method by measuring nitric oxide (NO) production after the addition of Griess reagent.Results: The sample concentrations of 1, 5, 25, 50, and 100 μM and 100 μM of dexamethasone (positive control) have been tested against the LPS-stimulated RAW 264.7 cells, and the results showed NO level production of 39.23, 34.00, 28.9, 20.25, 16.3, and 13.68 μM, respectively, and the inhibition level of 22.67, 33.00, 43.03, 60.10, 68.00, and 73%, respectively.Conclusions: From the study, it could be concluded that tinocrisposide was able to inhibit the formation of NO in the LPS-stimulated RAW 264.7 cells in concentration activity-dependent manner, with half-maximal inhibition concentration 46.92 μM. It can be developed as anti-inflammatory candidate drug because NO is a reactive nitrogen species which is produced by NO synthase. The production of NO has been established as a mediator in inflammatory diseases.

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