Guaianolides from Ormenis mixta: Structural Insights and Evaluation of Their Anti-inflammatory Profile

AbstractIn this paper, the isolation of five new guaianolides (1 – 5) and four (6 – 9) known sesquiterpenes from Ormenis mixta aerial parts is reported. The structural determination of the guaianolides was obtained by NMR spectroscopic data, as well as MS experiments. Their relative configurations were assigned by a combined quantum mechanical/NMR approach, comparing the experimental 13C/1H NMR chemical shift data and 1 J H-H homonuclear coupling constants with the related predicted values. The isolates were assayed for their anti-inflammatory potential evaluating nitric oxide release and cyclooxygenase-2 expression in J774A.1 macrophages treated with lipopolysaccharide from Escherichia coli. Our results indicated that, among the tested compounds, 1 – 3, and 7 were able to inhibit nitric oxide release, while all were able to inhibit cyclooxygenase-2 expression with different potencies.

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Aspirin Analogues as Dual Cyclooxygenase-2/5-Lipoxygenase Inhibitors: Synthesis, Nitric Oxide Release, Molecular Modeling, and Biological Evaluation as Anti-Inflammatory Agents

ChemMedChem ◽

10.1002/cmdc.201100460 ◽

2011 ◽

Vol 7 (1) ◽

pp. 144-150 ◽

Cited By ~ 13

Author(s):

Jatinder Kaur ◽

Atul Bhardwaj ◽

Zhangjian Huang ◽

Edward E. Knaus

Keyword(s):

Nitric Oxide ◽

Molecular Modeling ◽

Biological Evaluation ◽

Cyclooxygenase 2 ◽

Lipoxygenase Inhibitors ◽

Nitric Oxide Release ◽

Anti Inflammatory

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Controlled Nitric Oxide Release Using Poly(lactic-co-glycolic acid) Nanoparticles for Anti-Inflammatory Effects

Biomacromolecules ◽

10.1021/acs.biomac.0c01176 ◽

2020 ◽

Vol 21 (12) ◽

pp. 4972-4979

Author(s):

Yoogyeong Oh ◽

Hyejoong Jeong ◽

Sungmin Lim ◽

Jinkee Hong

Keyword(s):

Nitric Oxide ◽

Glycolic Acid ◽

Nitric Oxide Release ◽

Anti Inflammatory

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In Vitro Anti-Inflammatory and Immunomodulatory Activities of an Extract from the Roots of Bupleurum rotundifolium

Medicines ◽

10.3390/medicines6040101 ◽

2019 ◽

Vol 6 (4) ◽

pp. 101 ◽

Cited By ~ 2

Author(s):

Cholet ◽

Decombat ◽

Vareille-Delarbre ◽

Gainche ◽

Berry ◽

...

Keyword(s):

Mononuclear Cells ◽

Polymorphonuclear Neutrophils ◽

Ros Production ◽

Peripheral Blood Mononuclear ◽

Aerial Parts ◽

Bupleurum Scorzonerifolium Willd ◽

Anti Inflammatory ◽

Inflammatory Profile ◽

Bupleurum Scorzonerifolium

Background: Some Bupleurum species, such as the Bupleurum chinense DC. or the Bupleurum scorzonerifolium Willd have been extensively studied (especially their roots) for the treatment of inflammation. In contrast, only compounds extracted from the aerial parts of Bupleurum rotundifolium have been studied and showed anti-inflammatory or antiproliferative activities. This study was conducted to investigate the antioxidant, anti-inflammatory, and immunomodulatory effects of Bupleurum rotundifolium roots. Methods: To tackle the various aspects of inflammation, we studied in vitro a methanolic extract from the roots of Bupleurum rotundifolium on peripheral blood mononuclear cells (PBMCs), polymorphonuclear neutrophils (PMNs), and the monocytic cells THP-1. Its antioxidant capacities and iron-chelating activity were assessed. The extract was tested on THP-1 differentiation, reactive oxygen species (ROS) production by leukocytes, neutrophils chemotaxis, cytokines, PGE2 production, and NF-κB activation in PBMCs. Results: The extract showed a decreased ROS production in stimulated cells. It increased PBMC chemokine secretion and up-regulated the differentiation of THP-1 monocytes into macrophage-like cells, indicating a potential interest of the extract in the resolution of acute inflammation. In addition, the analysis of cytokine production suggests that Bupleurum rotundifolium has immunomodulatory properties. Conclusions: Cytokines secretion, especially IL-1β and IL-12p70, provided us with a set of indicators suggesting that the extract might be able to drive the polarization of macrophages and lymphocytes toward a Th2 anti-inflammatory profile in excessive inflammation.

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Differential anti-inflammatory effects of immunosuppressive drugs: Cyclosporin, rapamycin and FK-506 on inducible nitric oxide synthase, nitric oxide, cyclooxygenase-2 and PGE2 production

Inflammation Research ◽

10.1007/pl00000199 ◽

2000 ◽

Vol 49 (1) ◽

pp. 20-26 ◽

Cited By ~ 89

Author(s):

M. G. Attur ◽

R. Patel ◽

G. Thakker ◽

P. Vyas ◽

D. Levartovsky ◽

...

Keyword(s):

Nitric Oxide ◽

Nitric Oxide Synthase ◽

Inducible Nitric Oxide Synthase ◽

Immunosuppressive Drugs ◽

Cyclooxygenase 2 ◽

Pge2 Production ◽

Fk 506 ◽

Anti Inflammatory ◽

Oxide Synthase ◽

Inducible Nitric Oxide

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Phytochemical Analysis of Podospermum and Scorzonera n-Hexane Extracts and the HPLC Quantitation of Triterpenes

Molecules ◽

10.3390/molecules23071813 ◽

2018 ◽

Vol 23 (7) ◽

pp. 1813 ◽

Cited By ~ 4

Author(s):

Özlem Bahadır-Acıkara ◽

Serkan Özbilgin ◽

Gülcin Saltan-İşcan ◽

Stefano Dall’Acqua ◽

Veronika Rjašková ◽

...

Keyword(s):

Hplc Method ◽

Phytochemical Analysis ◽

Qualitative And Quantitative Analysis ◽

Qualitative And Quantitative ◽

Aerial Parts ◽

Hexane Extracts ◽

Lupeol Acetate ◽

Anti Inflammatory

Previously tested n-hexane extracts of the Scorzonera latifolia showed promising bioactivity in vivo. Because triterpenes could account for this activity, n-hexane extracts were analyzed by HPLC to identify and quantify the triterpenes as the most abundant constituents. Other Scorzonera and Podospermum species, potentially containing triterpenic aglycones, were included in the study. An HPLC method for simultaneous determination of triterpene aglycones was therefore developed for analysis of Podospermum and Scorzonera species. n-Hexane extracts of root and aerial parts of S. latifolia, ten other Scorzonera species and two Podospermum species were studied to compare the content of triterpenes. HPLC was used for the qualitative and quantitative analysis of α-amyrin, lupeol, lupeol acetate, taraxasteryl acetate, 3-β-hydroxy-fern-7-en-6-one acetate, urs-12-en-11-one-3-acetyl, 3-β-hydroxy-fern-8-en-7-one acetate, and olean-12-en-11-one-3-acetyl. Limits of detection and quantification were determined for each compound. HPLC fingerprinting of n-hexane extracts of Podospermum and Scorzonera species revealed relatively large amounts of triterpenes in a majority of investigated taxa. Lupeol, lupeol acetate, and taraxasteryl acetate were found in a majority of the species, except S. acuminata. The presence of α-amyrin, 3β-hydroxy-fern-7-en-6-one-acetate, urs-12-en-11-one-3-acetyl, 3β-hydroxy-fern-8-en-7-one-acetate, and olean-12-en-11-one-3-acetyl was detected in varying amounts. The triterpene content could correlate with the analgesic and anti-inflammatory activity of Scorzonera, which was previously observed and Scorzonera species that have been determined to contain triterpenes in large amounts and have not yet been tested for their analgesic activity should be tested for their potential analgesic and anti-inflammatory potential. The presented HPLC method can be used for analysis of triterpene aglycones, for example dedicated to chemosystematic studies of the Scorzonerinae.

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