Anti-inflammatory properties from isolated compounds of<i>Cyclolepis genistoides</i>

Sosa, Ángela; Fusco, María del Rosario; Rossomando, Pedro C.; Juárez, Américo; Robles, Sebastián; Petenatti, Elisa M.; Pelzer, Lilian Eugenia

doi:10.3109/13880200903431467

Cited by 12 publications

(10 citation statements)

References 10 publications

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“…Compound 4 has already been reported as a constituent of C. ragusina L. ( Mahmoud et al, 1986 ) and other Centaurea species with anti-inflammatory and cytotoxic activity ( González et al, 1977 ; Sosa et al, 2011 ).…”

Section: Resultsmentioning

confidence: 93%

Biological Activity of Flavonoids and Rare Sesquiterpene Lactones Isolated From Centaurea ragusina L.

et al. 2018

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The endemic Croatian species Centaurea ragusina L., like other species from the genus Centaurea, has been traditionally used in Croatia as an antibacterial agent and for the treatment of gastrointestinal and urogenital disorders. In several chromatographic steps, three flavonoids and three sesquiterpene lactones (STLs) were isolated and identified from the most active fractions of the ethanol extract. Two STLs, one for which we created the trivial name ragusinin, and hemistepsin A are here reported for the first time as constituents of the genus Centaurea. All six compounds were screened for their effect on several tumor and one normal cell lines. Among them, ragusinin showed the best bioactivity and high specificity to affect tumor murine SCCVII, human HeLa and Caco-2 cell lines, but not the viability of normal V79 fibroblasts. Due to these characteristics the action of ragusinin was investigated in more detail. Since DNA is the primary target for many drugs with antibacterial and anticancer activity, we studied its interaction with ragusinin. Rather moderate binding affinity to DNA excluded it as the primary target of ragusinin. Due to the possibility of STL interaction with glutathione (GSH), the ubiquitous peptide that traps reactive compounds and other xenobiotics to prevent damage to vital proteins and nucleic acids, its role in deactivation of ragusinin was evaluated. Addition of the GSH precursor N-acetyl-cysteine potentiated the viability of HeLa cells, while the addition of GSH inhibitor L-buthionine sulfoximine decreased it. Moreover, pre-treatment of HeLa cells with the inhibitor of glutathione-S-transferase decreased their viability indicating the detoxifying role of GSH in ragusinin treated cells. Cell death, derived by an accumulation of cells in a G2 phase of the cell cylce, was shown to be independent of poly (ADP-ribose) polymerase and caspase-3 cleavage pointing toward an alternative cell death pathway.

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Section: Resultsmentioning

confidence: 93%

Biological Activity of Flavonoids and Rare Sesquiterpene Lactones Isolated From Centaurea ragusina L.

et al. 2018

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“…The mixture of elemanolides 72 and 73 from C. chilensis showed anti-inflammatory activity when tested against carrageenan-induced edema in the guinea pig hindpaw (Negrete et al, 1993) and desacylcynaropicrin (149) isolated from the aerial parts of Cyclolepis genistoides produced a significant inhibition of carrageenan-induced inflammation at doses of 75 and 100 mg/kg, respectively (Sosa et al, 2011). Cnicin (19) showed an anti-inflammatory activity in the rat paw edema screen which was nearly equivalent to that of indomethacin (Schneider and Lachner, 1987).…”

Section: Anti-inflammatorymentioning

confidence: 99%

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties

et al. 2013

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“…A previous study reported that DAC manifests an anti-inflammatory effect (Sosa et al, 2011). Therefore, the secretions of LPS-induced inflammatory cytokines including TNF-α, IL-1β, and IL-6 from BMMs were detected by ELISA in vitro .…”

Section: Resultsmentioning

confidence: 96%

“…Importantly, in this study, we found that DAC, as a monomer component of C. genistoides or the flowers of H. lyrata Bunge with natural biological activity, may prevent and treat Ti particle-induced osteolysis and aseptic loosening of artificial joints. Previous studies have reported that DAC has been used to treat inflammation (Sosa et al, 2011). However, the application of DAC for the prevention and treatment of RANKL-induced osteoclastogenesis and LPS-induced inflammatory osteolysis has not been reported.…”

Section: Discussionmentioning

confidence: 99%

“…Researchers are increasingly interested in alternative materials that can be used for prevention and therapy of osteoporosis. Deacylcynaropicrin (DAC), isolated from the aerial parts of Cyclolepis genistoides or the flowers of Hemisteptia lyrata Bunge, has been demonstrated to inhibit carrageenan-induced inflammation (Ha et al, 2003; Sosa et al, 2011). Other research revealed that DAC presents moderate antibacterial activity against Staphylococcus aureus and its cytotoxic activities against cancer cells (Ha et al, 2003; Shakeri et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

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Deacylcynaropicrin Inhibits RANKL-Induced Osteoclastogenesis by Inhibiting NF-κB and MAPK and Promoting M2 Polarization of Macrophages

Zhu

et al. 2019

Front. Pharmacol.

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Inflammation can promote the maturity of osteoclasts and bone resorption in many bone disease such as osteoporosis and arthritis. Here, we aimed to investigate the inhibitory effects of deacylcynaropicrin (DAC) on osteoclastogenesis and bone resorption induced by RANKL. Bone-marrow-derived macrophages were used for assessing the influence of DAC on polarization of macrophages and osteoclastogenesis in vitro . Inducible nitric oxide synthase (iNOS) and CD206, as well as osteoclastogenesis markers, nuclear factor of activated T-cells 1 (NFATc1), and c-Fos, were qualitatively analyzed by immunofluorescence, flow cytometry, reverse transcription polymerase chain reaction, and Western blotting. The results showed that DAC significantly inhibited osteoclastogenesis by suppressing the expression levels of c-Fos and NFATc1 through nuclear factor-κB, c-Jun N-terminal kinase (JNK), and Akt pathway. Moreover, immunohistochemistry and enzyme-linked immunosorbent assays showed that DAC reduced the release of tumor necrosis factor-α, interleukin (IL)-1β, and IL-6 in vivo . Finally, DAC also promoted macrophage polarization from M1 to M2 types. In conclusion, these results demonstrated that DAC suppressed RANKL-induced inflammation and osteoclastogenesis and therefore it can be used as a potential treatment for osteoporosis, arthritis, osteolysis, and aseptic loosening of artificial prostheses.

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Anti-inflammatory properties from isolated compounds ofCyclolepis genistoides

Cited by 12 publications

References 10 publications

Biological Activity of Flavonoids and Rare Sesquiterpene Lactones Isolated From Centaurea ragusina L.

Biological Activity of Flavonoids and Rare Sesquiterpene Lactones Isolated From Centaurea ragusina L.

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties

Deacylcynaropicrin Inhibits RANKL-Induced Osteoclastogenesis by Inhibiting NF-κB and MAPK and Promoting M2 Polarization of Macrophages

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