Inhibition of NF-κB activation and expression of inflammatory mediators by polyacetylene spiroketals from Plagius flosculosus

Calzado, Marco A.; Lüdi, Katharina Schmid; Fiebich, Bernd L.; Ben‐Neriah, Yinon; Bacher, Susanne; Muñóz, Eduardo; Ballero, Mauro; Prosperini, Simona; Appendino, Giovanni; Schmitz, M. Lienhard

doi:10.1016/j.bbaexp.2005.04.007

Cited by 15 publications

(15 citation statements)

References 24 publications

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“…For example, polyacetylenes of Daucus carota L . have been shown to inhibit LPS induced nitric oxide production in the RAW264.7 macrophage cell line (22) and polyacetylene spiroketals from Plagius flosculosus have been identified to inhibit LPS induced IL-1, IL-6, TNF-α, and PGE 2 production, as well as inhibit the degradation of IkB and further DNA binding of NF-kB (23). …”

Section: Discussionmentioning

confidence: 99%

Endogenous Levels ofEchinaceaAlkylamides and Ketones Are Important Contributors to the Inhibition of Prostaglandin E2 and Nitric Oxide Production in Cultured Macrophages

LaLone¹,

Rizshsky²,

Hammer³

et al. 2009

J. Agric. Food Chem.

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Due to the popularity of Echinacea as a dietary supplement, researchers have been actively investigating which Echinacea constituent or groups of constituents are necessary for immune modulating bioactivities. Our prior studies indicate that alkylamides may play an important role in the inhibition of prostaglandin E2 (PGE2) production. HPLC fractionation, employed to elucidate interacting anti-inflammatory constituents from ethanol extracts of E. purpurea, E. angustifolia, E. pallida, and E. tennesseensis identified fractions containing alkylamides and ketones as key anti-inflammatory contributors using lipopolysaccharide induced PGE2 production in RAW264.7 mouse macrophage cells. Nitric oxide (NO) production and parallel cytotoxicity screens were also employed to substantiate an anti-inflammatory response. Echinacea pallida showed significant inhibition of PGE2 with a first round fraction, containing GC-MS peaks for Bauer Ketones 20, 21, 22, 23, and 24, with 23 and 24 identified as significant contributors to this PGE2 inhibition. Chemically synthesized Bauer Ketones 21 and 23 at 1 μM each significantly inhibited both PGE2 and NO production. Three rounds of fractionation were produced from an E. angustifolia extract. GC-MS analysis identified the presence of Bauer Ketone 23 in third round Fraction 3D32 and Bauer Alkylamide 11 making up 96% of third round Fraction 3E40. Synthetic Bauer Ketone 23 inhibited PGE2 production to 83 % of control and synthetic Bauer Alkylamide 11 significantly inhibited PGE2 and NO production at the endogenous concentrations determined to be present in their respective fraction, thus each constituent partially explained the in vitro anti-inflammatory activity of their respective fraction. From this study two key contributors to the anti-inflammatory properties of E. angustifolia were identified as Bauer Alkylamide 11 and Bauer Ketone 23.

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Section: Discussionmentioning

confidence: 99%

Endogenous Levels ofEchinaceaAlkylamides and Ketones Are Important Contributors to the Inhibition of Prostaglandin E2 and Nitric Oxide Production in Cultured Macrophages

LaLone¹,

Rizshsky²,

Hammer³

et al. 2009

J. Agric. Food Chem.

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“…Plagius flosculosus has been investigated, by Calzado et al (2005) and Casu et al (2006), to isolate spiroketal compound with anti-inflammatory effect, but no data on essential oil are reported. In this work, we isolated the essential oils and recorded the following composition: (Z)--farnesene (37.3% in SFE vs. 4.4 in HD), -phellandrene (12.0% vs. 31.3 in HD), myrcene (3.1% vs. 12.0 in Table 2.…”

Section: Volatile Fractionsmentioning

confidence: 99%

Chemical and biological comparisons on supercritical extracts of Tanacetum cinerariifolium (Trevir) Sch. Bip. with three related species of chrysanthemums of Sardinia (Italy)

Marongiu

Piras

Porcedda

et al. 2009

Natural Product Research

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In this manuscript, the authors compare the chemical composition and the biological effects of extracts of some Sardinian plant species: Glebionis coronaria (L.) Spach [=Chrysanthemum coronarium L.], locally known as 'caragantzu', Glebionis segetum (L.) Fourr. [=Chrysanthemum segetum L.], known as 'caragantzu masedu', and Sardinian endemic species Plagius flosculosus (L.) Alavi and Heywood [=Chrysanthemum flosculosus L.], known as 'caragantzu burdu'. In addition, the authors compare the pyrethrins contained in these species with an extract of Tanacetum cinerariifolium (Trevir.) Sch. Bip. [=Chrysanthemum cinerariifolium (Trevir.) Vis.], a commercial species rich in pyrethrins. The volatile fractions from chrysanthemum flowers were obtained by supercritical fluid extraction (SFE) with CO(2) at 90 bar and 50 degrees C and by hydrodistillation. Pyrethrins were extracted, together with other high molecular mass compounds, by SFE at high pressure, 300 bar and 40 degrees C. The composition of the volatile oils is determined by GC-MS analysis and the amount of pyrethrins by HPLC analysis. Moreover, the antibacterial and antimycotic activities of volatile fractions were investigated in order to compare to their traditional uses.

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“…Endemic taxa are very interesting because the geographic isolation has been caused a genetic and metabolic differentiation in these species, as shown by the high number of scientific researches that have been published until now (Fattorusso et al, 2004;Petitto et al, 2009;Ramunno et al, 2005;Serrilli et al, 2005Serrilli et al, , 2010. Some of Sardinian endemism have also shown very interesting biological and pharmacological activities Calzado et al, 2005;Poli et al, 2005).…”

Section: Introductionmentioning

confidence: 98%

Chemical composition and biological activity of Tanacetum audibertii (Req.) DC. (Asteraceae), an endemic species of Sardinia Island, Italy

Maxia

Sanna

Piras

et al. 2015

Industrial Crops and Products

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Inhibition of NF-κB activation and expression of inflammatory mediators by polyacetylene spiroketals from Plagius flosculosus

Cited by 15 publications

References 24 publications

Endogenous Levels ofEchinaceaAlkylamides and Ketones Are Important Contributors to the Inhibition of Prostaglandin E2 and Nitric Oxide Production in Cultured Macrophages

Endogenous Levels ofEchinaceaAlkylamides and Ketones Are Important Contributors to the Inhibition of Prostaglandin E2 and Nitric Oxide Production in Cultured Macrophages

Chemical and biological comparisons on supercritical extracts of Tanacetum cinerariifolium (Trevir) Sch. Bip. with three related species of chrysanthemums of Sardinia (Italy)

Chemical composition and biological activity of Tanacetum audibertii (Req.) DC. (Asteraceae), an endemic species of Sardinia Island, Italy

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