Sesquiterpene lactones and flavonoids from Centaurea aspera

Cardona, Luz; Fernández, Isabel; Pedro, José R.; Perez, Beatriz

doi:10.1016/0031-9422(91)83643-y

Cited by 22 publications

(4 citation statements)

References 14 publications

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“…Previous studies have confirmed that this genus is a source of novel bioactive compounds. Phytochemical investigations on this genus generally revealed the isolation of sesquiterpene lactones, flavonoids, phenyl propanoids, lignans and phenolic compounds (Astari et al, 2013;Baykan-Erel et al, 2010;Bruno et al, 2013;Cardona et al, 1997Cardona et al, , 1991Erel et al, 2011;Gulcemal et al, 2010;Karamenderes et al, 2007aKaramenderes et al, , 2007bSkaltsa et al, 1999). Composition of the essential oil of Centaurea polyclada was previously reported (Erel et al, 2013).…”

Section: Introductionmentioning

confidence: 90%

Specialized metabolites from the aerial parts of Centaurea polyclada DC.

2017

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The genus Centaurea L. (Asteraceae) is represented by 200 taxa in the flora of Turkey and several Centaurea species are used as herbal remedies against different conditions. Previous phytochemical investigations on this genus generally revealed the isolation of sesquiterpene lactones and flavonoid derivatives. In our continuous search on Centaurea genus, a phytochemical study was performed on Centaurea polyclada DC., an endemic of West Anatolia. Previously undescribed two sesquiterpene-amino acid conjugates, an elemane and an eudesmane derivative were isolated from the aerial parts of Centaurea polyclada, together with eight known compounds; two elemane derivatives, three flavonoids, a lignan, a phenolic glucoside and a phenylpropanoid glucoside. Structural elucidation of the compounds was based on spectroscopic evidence, including 1D and 2D NMR and high-resolution mass spectrometry, chemical degradation results and reference data comparison. Sesquiterpene-amino acid conjugates are representatives of an unusual group of sesquiterpenes, and elemane-amino acid conjugates are herein reported for the first time in nature.

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Section: Introductionmentioning

confidence: 90%

Specialized metabolites from the aerial parts of Centaurea polyclada DC.

2017

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“…Cytotoxic properties of the Centaurea plant extracts are usually related to their chemical composition. The majorities of compounds in aqueous extracts (AE) belong, but are not limited to the groups of sesquiterpene lactones (SQLs), acetylenes, phenolics, flavonoids, glycosides, lignans, coumarines, and others . Sesquiterpene lactones, phenols, flavonoids, and lignans are usually regarded as a group of compounds responsible for diverse biological activity of Centaurea plant extracts.…”

Section: Introductionmentioning

confidence: 99%

Qualitative HPLC‐DAD/ESI‐TOF‐MS Analysis, Cytotoxic, and Apoptotic Effects of Croatian Endemic Centaurea ragusina L. Aqueous Extracts

Radan

Carev

Tešević

et al. 2017

Chemistry & Biodiversity

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Centaurea ragusina L., an endemic Croatian plant species, revealed a good cytotoxic activity of aqueous extracts (AE) on human bladder (T24) and human glioblastoma (A1235) cancer cell lines. The chemical constituents were tentatively identified using high performance liquid chromatography HPLC-DAD/ESI-TOF-MS in negative ionization mode. The main compounds of herba extract were sesquiterpene lactones: solstitialin A 3,13-diacetate and epoxyrepdiolide; organic acid: quinic acid. The main compounds of flower extract were organic acids: quinic acid, citric acid, and malic acid; sesquiterpene lactone: cynaropicrin; phenolic compounds: chlorogenic acid and phenylpropanoid: syringin. The AE of C. ragusina were investigated for correlation of their effects on human bladder (T24) and human glioblastoma (A1235) cancer cell lines using the MTT assay. Although both extracts showed significant dose- and time-dependent cytotoxic activity against both cancer cell lines, the flower extract exhibited slightly higher activity. In order to determine type of cell death induced by treatment, cell lines were exposed subsequently to a treatment with both flower and herba AE. The majority of the cells died by induced apoptosis treatment. Flower AE (26.25%), compared to a leaf AE (22.15%) showed slightly higher percentage of an apoptosis in T24 cells, when compared to a non-treated cells (0.04%).

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“…Concerning the secondary metabolites of Centaurea sp., sesquiterpene lactones are predominant and are of taxonomic significance [7][8][9][10][11][12]. In addition, flavonoids, lignans, steroids, hydrocarbons, polyacetylenes and alkaloids have also been isolated from this genus [13][14][15][16][17]. Previous phytochemical investigations on the volatile compounds have focused on the relationship between chemical composition and taxonomy [18][19][20][21].…”

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confidence: 99%

Chemical Composition and Antimicrobial Activity of Essential Oils from Centaurea Pannonica and C. Jacea

Milosevic

Argyropoulou

Solujić

et al. 2010

Natural Product Communications

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The chemical composition and antimicrobial activity of the essential oils obtained by hydrodistillation from Centaurea pannonica (Heufel) Simonkai and C. jacea L. (Asteraceae), were investigated. The essential oils were analyzed by GC and GC-MS. Forty five and twenty nine compounds were identified in the two oils, respectively. C. pannonica oil was rich in fatty acids (43.7%), with 9-octadecanoic acid (34.0%) and (Z,Z)-9,12-octadecadienoic acid (8.6%) as the major compounds. In contrast, the essential oil of C. jacea was dominated by oxygenated sesquiterpenes (43.2%), among which caryophyllene oxide (23.5%) and spathulenol (8.9%) were the major constituents. However, the oil was also characterized by an important fatty acid fraction (15.5%), with 9-octadecanoic acid (8.9%) and hexadecanoic acid (6.6%) being the main components. The antimicrobial activities of the essential oils were evaluated by the microdilution method against three Gram-positive and three Gram-negative bacteria, and one yeast. Both oils exhibited significant antimicrobial activity, especially against Gram-positive bacteria.

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Sesquiterpene lactones and flavonoids from Centaurea aspera

Cited by 22 publications

References 14 publications

Specialized metabolites from the aerial parts of Centaurea polyclada DC.

Specialized metabolites from the aerial parts of Centaurea polyclada DC.

Qualitative HPLC‐DAD/ESI‐TOF‐MS Analysis, Cytotoxic, and Apoptotic Effects of Croatian Endemic Centaurea ragusina L. Aqueous Extracts

Chemical Composition and Antimicrobial Activity of Essential Oils from Centaurea Pannonica and C. Jacea

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