Flavonoids in Subtribe Centaureinae (<scp>Cass.</scp>)<scp>Dumort.</scp>(Tribe Cardueae, Asteraceae): Distribution and<sup>13</sup>C‐NMR Spectral Data

Formisano, Carmen; Rigano, Daniela; Senatore, Felice; Bancheva, Svetlana; Maggio, Antonella; Rosselli, Sergio; Bruno, Maurizio

doi:10.1002/cbdv.201100208

Cited by 51 publications

(26 citation statements)

References 209 publications

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“…Centaurea species have been the object of various phytochemical studies, with a diversity of bioactive phytochemicals and prevalence of flavonoids 2 , flavonoid aglycones 3 , lignans 4 , sesquiterpene lactones 5 , essential oils 6 , alkaloids 7 and other biologically active constituents. Some species of the genus Centaurea have been used as medicinal plants in folk medicine for their uses in gastrointestinal 8 and inflammatory disorders 9 , cytotoxic activity 4,10 , in addition to the anti-microbial 11,12 and antioxidant activities 13 .…”

Section: Genusmentioning

confidence: 99%

Phenolic Compounds and Hepatoprotective Activity of Centaurea aegyptiaca L. on Carbon Tetrachloride-induced Hepatotoxicity in Rats

Senosy

Kamal

El‐Toumy

et al. 2018

Journal of Advanced Pharmacy Research

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Objectives: This study aimed to isolate phenolic compounds from the 70% aqueous methanol extract of the aerial parts (leaves, flowers and stems) of Centaurea aegyptiaca , evaluate in-vivo hepatoprotective activity and determine total phenolic and total flavonoid contents. Methods: 70% aqueous methanol extract of the aerial parts subjected to different chromatographic separation techniques. The identities of the isolated compounds were established on the basis of their spectral data and comparing with previously reported data. The crude extract was evaluated for invivo hepatoprotective activity on CCl4-induced hepatotoxicity in rats. Total phenolic and total flavonoid contents of the aqueous methanol extract were determined using Folin-Ciocalteu and aluminum chloride colorimetric methods, respectively. Results: The aqueous methanol extract of the aerial parts of Centaurea aegyptiaca afforded seven compounds. A phenolic acid ester; protochatechuic acid methyl ester (1) along with six known flavonoids; apigenin-6-C-β-D-glucopyranoside (isovitexin) (2), apigenin-8-C-β-D-glucopyranoside (vitexin) (3), quercetin-3-O--Dglucopyranoside (isoquercetin) (4), apigenin (5), 3-O-methylquercetin (6) and quercetin (7). Administration of the extract at doses of 100 and 200 mg/kg b.wt showed a hepatoprotective activity similar to that of the standard drug; silymarin at a dose of 25 mg/kg b.wt. Comparative histopathological study of liver exhibited moderate changes in liver histoarchitecture when compared to the CCl4 group. The methanolic extract showed high concentration of phenolic and flavonoid contents. Conclusion: The aqueous methanol extract of the aerial parts of C. aegyptiaca afforded seven phenolic compounds for the first time from this species, with promising in-vivo hepatoprotective activity.

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Section: Genusmentioning

confidence: 99%

Phenolic Compounds and Hepatoprotective Activity of Centaurea aegyptiaca L. on Carbon Tetrachloride-induced Hepatotoxicity in Rats

Senosy

Kamal

El‐Toumy

et al. 2018

Journal of Advanced Pharmacy Research

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“…C. calcitrapa is used in traditional medicine as antidiabetic and diuretic [3,4]. Several previous chemical studies have been reported on the genus [5][6][7][8][9].…”

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“…C. calcitrapa is used in traditional medicine as antidiabetic and diuretic [3,4]. Several previous chemical studies have been reported on the genus [5][6][7][8][9].Continuing our research on the chemical constituents of Algerian Centaurea species [10-16], we report here the isolation of six flavonoids and a sesquiterpene lactone, cnicin, from the chloroform exudate of the aerial parts of Centaurea calcitrapa L.Fresh aerial parts (1.8 kg) were extracted with a mixture of toluene-ethyl acetate (6:4) twice during 15 min. The obtained solutions were combined and concentrated.…”

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confidence: 99%

Flavonoids of the Exudate of Centaurea calcitrapa

Kitouni

Benayache

2015

Chem Nat Compd

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The large genus Centaurea (Asteraceae) comprises about 500 species mostly distributed around the Mediterranean area and in Western Asia [1]. About 50 species grow in Algeria, among which Centaurea calcitrapa, known as Bou Neggar, is largely distributed [2]. C. calcitrapa is used in traditional medicine as antidiabetic and diuretic [3,4]. Several previous chemical studies have been reported on the genus [5][6][7][8][9].Continuing our research on the chemical constituents of Algerian Centaurea species [10-16], we report here the isolation of six flavonoids and a sesquiterpene lactone, cnicin, from the chloroform exudate of the aerial parts of Centaurea calcitrapa L.Fresh aerial parts (1.8 kg) were extracted with a mixture of toluene-ethyl acetate (6:4) twice during 15 min. The obtained solutions were combined and concentrated. During the concentration, a precipitate was formed. This precipitate was filtered and washed with petroleum ether to give a pure white compound 1 (2.65 g) as a major component, identified as cnicin [12]. The residual solution was concentrated to give 11.52 g of extract, which was chromatographed on a silicagel column eluted with a gradient of chloroform-acetone to yield eight fractions, which were purified on preparative TLC Silica gel 60 GF plates eluted with a mixture of CHCl 3 -MeOH-H 2 O (80:9:1) to give compounds 2-7. Purification of each compound for spectral analysis was carried out using MeOH over a Sephadex LH-20 column.The structures of these compounds were established using UV spectroscopy, 1 H and 13 C NMR, and MS analyses. All the data were in good agreement with the respective literature data.Compound 1. C 20 H 26 O 7 , mp 143qC. IR spectrum (KBr, Q, cm -1 ): 1756 (J-lactone), 1707 (C=O conjugated ester), 3385 (OH). Mass spectrum (FAB + , 70 eV), m/z: 379 [M + H] + , 247 [(1c,2c-OH -Et) acrylic acid], 229 [247 -H 2 O]. 1 H NMR (250 MHz, CDCl 3 + 2 drops CD 3 OD, G, ppm, J/Hz): 6.3 (1H, s, H-18c), 6.25 (1H, d, J 13c, 7 = 3.3, H-13c), 6.1 (1H, s, H-18), 5.75 (1H, d, J 13, 7 = 2.7, H-13), 5.2 (1H, t, J 6,5 = J 6,7 = 8.2, H-6), 5.15 (1H, m, H-8), 5.05 (1H, m, H-1), 4.

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“…Many members of this genus are used in traditional folk medicine, such as Centaurea pulchella used to treat skin problems such as to resolve the abscess [4a]. Although biological activity of many Centaurea species have been investigated in different countries and Turkey [3][4][5][6][7][8], cytotoxic effect of C. patula, C. pulchella and C. tchihatcheffii has not been studied yet.…”

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Effect of Three Centaurea Species Collected from Central Anatolia Region of Turkey on Human Melanoma Cells

Russo

Cardile

Graziano

et al. 2016

Natural Product Communications

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Centaurea is the largest genus within the Asteraceae family. Many members of this genus are used in traditional folk medicine, such as Centaurea pulchella used to treat skin problems such as to resolve the abscess. Although biological activities of many Centaurea species have been investigated in different countries and Turkey, cytotoxic effect of C. patula, C. pulchella and C. tchihatcheffii has not been studied yet. Melanoma is one of the most invasive and deadly forms of skin cancer. Therefore, in an ongoing effort to identify new natural anticancer products for the treatment and/or prevention of melanoma cancer, the present study was undertaken to investigate the effect of these Centaurea species, collected from Central Anatolia region of Turkey on cell growth and death in human melanoma cell line, A375.The results revealed that all extracts were able to inhibit, after 48 h of treatment, the growth of cancer cells, that could be related to an overall action of the phenolic compounds present. In fact, C. pulchella, with the highest level of phenolics, showed a major activity followed by C. patula and C. tchihatcheffii. Our data also demonstrate that these natural products induce apoptotic cell death. In conclusion, the study of plant extracts for their cytotoxic and apoptotic properties has shown that medicinal herbs from Centaurea species might have also importance in the prevention and treatment of melanoma.

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Flavonoids in Subtribe Centaureinae (Cass.)Dumort.(Tribe Cardueae, Asteraceae): Distribution and¹³C‐NMR Spectral Data

Abstract: This review reports the occurrence of flavonoids in subtribe Centaureinae of Asteraceae family. It extensively covers the literature up to 2010 and collects all available (13)C-NMR data.

Cited by 51 publications

References 209 publications

Phenolic Compounds and Hepatoprotective Activity of Centaurea aegyptiaca L. on Carbon Tetrachloride-induced Hepatotoxicity in Rats

Phenolic Compounds and Hepatoprotective Activity of Centaurea aegyptiaca L. on Carbon Tetrachloride-induced Hepatotoxicity in Rats

Flavonoids of the Exudate of Centaurea calcitrapa

Effect of Three Centaurea Species Collected from Central Anatolia Region of Turkey on Human Melanoma Cells

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Flavonoids in Subtribe Centaureinae (Cass.)Dumort.(Tribe Cardueae, Asteraceae): Distribution and13C‐NMR Spectral Data

Abstract: This review reports the occurrence of flavonoids in subtribe Centaureinae of Asteraceae family. It extensively covers the literature up to 2010 and collects all available (13)C-NMR data.

Cited by 51 publications

References 209 publications

Phenolic Compounds and Hepatoprotective Activity of Centaurea aegyptiaca L. on Carbon Tetrachloride-induced Hepatotoxicity in Rats

Phenolic Compounds and Hepatoprotective Activity of Centaurea aegyptiaca L. on Carbon Tetrachloride-induced Hepatotoxicity in Rats

Flavonoids of the Exudate of Centaurea calcitrapa

Effect of Three Centaurea Species Collected from Central Anatolia Region of Turkey on Human Melanoma Cells

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Flavonoids in Subtribe Centaureinae (Cass.)Dumort.(Tribe Cardueae, Asteraceae): Distribution and¹³C‐NMR Spectral Data