Syringin in some species of the subtribe Centaureinae of the Asteraceae

Cis, Joanna; Nowak, Gerard; Horoszkiewicz-Hassan, Małgorzata; Kisiel, Wanda

doi:10.5586/asbp.2003.013

Cited by 7 publications

(3 citation statements)

References 4 publications

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“…The genus Psephellus was previously reported to be a rich source of sesquiterpenes and lignans [17,18]; moreover P. pyrrhoblepharus was published to accumulate essential oil, containing monoterpene and sesquiterpene hydrocarbons, and carbonylic compounds in substantial quantities [19].…”

Section: Introductionmentioning

confidence: 99%

Sesquiterpene Lactones and Flavonoids from Psephellus pyrrhoblepharus with Antiproliferative Activity on Human Gynecological Cancer Cell Lines

et al. 2019

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Multistep chromatographic separations of the chloroform extract of the Turkish endemic plant Psephellus pyrrhoblepharus (Boiss.) Wagenitz (syn. Centaurea pyrrhoblephara Boiss.) resulted in the isolation of six guaianolid-type sesquiterpenes, chlorojanerin (1), 19-deoxychlorojanerin (2), 15-hydroxyjanerin (3), aguerin B (4), cynaropicrin (5), eleganin (6); three flavonoids, apigenin, 6-methoxyluteolin and jaceosidine; two glycosides, benzyl-1-O-β-d-glucoside and 3(Z)-hexenyl-1-O-β-d-glucoside; and the coumarin scopoletin. The structures were established by the interpretation of their ESI-MS and 1D and 2D NMR data including 1H-NMR, JMOD, 1H,1H-COSY, HSQC, HMBC, and NOESY experiments. All compounds were isolated for the first time from P. pyrrhoblepharus. Compounds 1–6, the isolated flavonoids and scopoletin were evaluated for their antiproliferative activities on human gynecological cancer cell lines (SiHa, HeLa, and MDA-MB-231 cells) using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Chlorojanerin (1), 19-deoxychlorojanerin (2), aguerin B (4), cynaropicrin (5), eleganin (6) were shown to have noteworthy effects on all of the tested cell lines, while apigenin, jaceosidine, and 6-methoxyluteolin were moderately active on HeLa cells. The highest activities were demonstrated by the chlorine-containing derivatives chlorojanerin (1) and 19-deoxychlorojanerin (2) with IC50 values of 2.21 and 2.88 µM, respectively, against the triple negative breast cancer model MDA-MB-231 cells.

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Section: Introductionmentioning

confidence: 99%

Sesquiterpene Lactones and Flavonoids from Psephellus pyrrhoblepharus with Antiproliferative Activity on Human Gynecological Cancer Cell Lines

et al. 2019

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“…Up to now, more than 80 secondary metabolites belonging to diverse structural types of lignans, favonoids, coumarins, alkaloids, sterols, triterpenes, volatile oils, and polyphenols have been identifed [33][34][35][36][37][38]. Syringin has also been detected in other plants, including Fraxinus rhynchophylla [21], Musa paradisiaca [39], Centaurea bella Trautv, and many other species [40]. Syringin isolated from Stevia rebaudiana (Bert.)…”

Section: Antibacterial Activity Of the Extractmentioning

confidence: 99%

Antibacterial Activity of a Phenylpropanoid from the Root Extract of Carduus leptacanthus Fresen

Dagne,

Degu,

Abebe

et al. 2023

Journal of Tropical Medicine

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Background. The emergence and rapid spread of antimicrobial drug-resistance microorganisms exacerbate the treatment of infectious diseases, underscoring the importance of finding new, safe, and effective drugs. In Ethiopia, the roots of Carduus leptacanthus have traditionally been employed to treat microbial infectious diseases The aim of this study was to evaluate the antibacterial activity of the root extract and its primary components against six bacterial strains (Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus agalactiae, Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumonia). Methods. The extraction involved maceration of air-dried and powdered roots of C. leptacanthus with 80% methanol. The compound was isolated from the root extract using silica gel column chromatography and recrystallization in CHCl3/MeOH (9 : 1) and was characterized using ESI-MS and 1D-NMR spectroscopy. Antibacterial activity of the extract was assessed using agar well diffusion and broth microdilution methods. Results. Syringin, a phenylpropanoid, was isolated and characterized from the extract of C. leptacanthus. The extract showed the most substantial efficacy against S. epidermidis (MIC = 5.33 mg/ml and inhibition zone diameter of 24 mm at 200 mg/m). Syringin also elicited antibacterial activity against S. aureus (MIC = 13.33 mg/ml), S. epidermidis (MIC = 16 mg/ml), and S. agalactiae (MIC = 16 mg/ml). Despite being tested up to a maximum concentration of 16 mg/ml, syringin did not exhibit antibacterial activity against the Gram-negative bacteria (P. aeruginosa, E. coli, and K. pneumonia). Conclusions. In conclusion, the findings suggest that syringin exhibits partial involvement in the root extract’s antibacterial activity, thereby potentially supporting the traditional medicinal use of the plant.

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“…This phenolic glycosides (syn. eleutheroside B) were found to possess an immunomodulatory, anti-allergic and inhibitory on bone resorption effects [10]. In Klasea Cass.…”

Section: Introductionmentioning

confidence: 99%

Detection of Pharmacological Active Compounds of the Asteraceae Family and their Chemotaxonomical Implications

Urbańska¹,

Nawrot²,

Dawid-Pać³

et al. 2014

JPS

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It can be assumed that sesquiterpene lactones and natural phytosteroids (ecdysones) are the characteristic compounds of the plants from the Asteraceae family. They display certain pharmacological properties and thus are helpful in chemical descriptions of the Asteraceae tribes, subtribes and species. Also some phenolic glycosides found in genus Klasea Cass, and in genus Centaurea L. may be of medical and chemotaxonomical significance. Our studies on the species of the aforementioned taxons and the isolation of several compounds allowed for interesting conclusions of phytochemical and taxonomical nature.

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Syringin in some species of the subtribe Centaureinae of the Asteraceae

Cited by 7 publications

References 4 publications

Sesquiterpene Lactones and Flavonoids from Psephellus pyrrhoblepharus with Antiproliferative Activity on Human Gynecological Cancer Cell Lines

Sesquiterpene Lactones and Flavonoids from Psephellus pyrrhoblepharus with Antiproliferative Activity on Human Gynecological Cancer Cell Lines

Antibacterial Activity of a Phenylpropanoid from the Root Extract of Carduus leptacanthus Fresen

Detection of Pharmacological Active Compounds of the Asteraceae Family and their Chemotaxonomical Implications

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