Secondary Metabolites from Turkish Astragalus Species

Gülcemal, Derya; Aslanıpour, Behnaz; Bedіr, Erdal

doi:10.1007/978-3-030-03344-6_2

Cited by 7 publications

(4 citation statements)

References 83 publications

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“…In addition, a large number of isoflavone-type compounds have been isolated from Astragalus species. For example, acicerone [ 37 ] from Astragalus cicer , maackiain from Astragalus trojanus [ 38 ], diadzen, genisten, and 7-hydroxy-3′,5′-dimethoxyisoflavone from Astragalus peregrines [ 39 ], 5,5′-dihydroxy-3′-methoxy-isoflavone-7-O-β-d-glucoside, genistin, sissotrin, and 5,4′-dimethoxy-isoflavone-7-O-β-D-glucopyranoside from Astragalus lycius Boiss [ 40 ].…”

Section: Resultsmentioning

confidence: 99%

First determination of anticancer, cytotoxic and in silico ADME evaluation of secondary metabolites of endemic Astragalus leucothrix Freyn & Bornm

2021

Turk J Chem

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Isolation and characterization of anticancer activity guided secondary metabolites of endemic Astragalus leucothrix FREYN& BORNM were aimed. Aerial parts of the plant were extracted by maceration method in the solvent system methanolchloroform (1:1) at room temperature. The obtained crude extract was dissolved in purified water. Then, the extract was partitioned with n-hexane, chloroform, ethyl acetate and n-butanol, respectively. Anticancer activity tests of all the fractions were performed against HeLa and C6 cancer cells. The chloroform fraction that has highest anticancer activity was subjected to chromatographic methods such as column chromatography and thin layer chromatography. Pentyl tetratetracontanoate (1), alfalone (2), 3,6,8-tribromoquinoline (3) and 3,6,8-tribromochromenium (4) molecules were detected from this plant for the first time. The structure determinations of the isolated molecules were elucidated by methods such as 1D and 2D NMR, HPLC-TOF /MS, and GC-MS analysis. Finally, anticancer and cytotoxic activity tests of the 3 compounds were performed. Literature survive showed that 3,6,8-tribromochromenium is a new compound. IC 50 values of compound 1-2 and compound 3-4 mix were determined 4.50±0.10, 2.81±0.00, 4.33±0.00 µM against C6 cell, respectively. The drug likeness properties of 1-4 were obtained by SwissADME. According to Lipinski's rule of five; 2-4 could be a new potential anticancer agent.

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Section: Resultsmentioning

confidence: 99%

First determination of anticancer, cytotoxic and in silico ADME evaluation of secondary metabolites of endemic Astragalus leucothrix Freyn & Bornm

2021

Turk J Chem

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“…The roots of some Astragalus species represent very old and well-known drugs in traditional medicine for the treatment of nephritis, diabetes, and uterine cancer and as antiperspirant, diuretic, and tonic. In Turkish folk medicine, the aqueous extracts of various Astragalus species are used to treat leukemia as well as for wound healing [7].…”

Section: Introductionmentioning

confidence: 99%

Morpho-anatomical and palynological properties of endemic Astragalus tmoleus var. bounacanthus (Fabaceae)

Kaya

2022

Eur J Life Sci

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Astragalus tmoleus Boiss. var. bounacanthus (Boiss.) Chamberlain is a member of the Pterophorus Bunge section of the Fabaceae family and consists of the spiny cushion-forming shrub. In this study, morphological, anatomical and pollen properties of the plant, an endemic species for Turkey, have been investigated in detail. Morphological characters such as the shape of paripinnate leaves, stipules and bracts, the flower number in the inflorescence, the stenonychioid type of standard and the reniform type of seed can be helpful to distinguish A. tmoleus var. bounacanthus. The stem, leaf and rachis characteristics of the plant were examined in anatomical studies. There is a secondary growth in stem anatomy. The number of vascular bundles is 15-18 in a circle. The shape of the transversal section of the rachis is polygonal or almost orbicular. The sclerenchyma tissue is located on the vascular bundles in the rachis. A. tmoleus var. bounacanthus has equifasial leaves. The stomata type is anomocytic and occurs on both leaflet epidermises. The pollen grains of A. tmoleus var. bounacanthus have tricolpate aperture and they are subprolate-shaped. While the pollen exine sculpturing is microreticulate, the seed surface sculpturing is a prominent undulate-ridged pattern formed by irregular cells. Scanning electron microscopy (SEM) is used to determine pollen and seed morphology.

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“…Results from these studies described imidazoline alkaloids, nitro toxins and selenium derivatives as toxic compounds, while polysaccharides, phenols and saponins as biologically active constituents [6]. Astragalus saponins include both oleanane and cycloartane-type glycosides, yet the former occur far less in nature, thus the Astragalus genus was especially employed as an ideal source to find cycloartane saponins [7].…”

Section: Introductionmentioning

confidence: 99%

“…These compounds were the most extensively studied secondary metabolites from Astragalus , as they exhibited a wide range of biological and pharmacological properties. Indeed, these molecules were found to exert immunomodulatory, anti-cancer, anti-fungal, hepato-, kidney-, neuro- and vascular-protective activities [7,8,9,10,11,12]. So far, the most well-characterized biological effects were those related to their immune stimulant properties, which made these compounds ideal vaccine adjuvant candidates [13].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Characterization and Cytotoxicity Assessment towards Human Colon Cancer Cell Lines of Acylated Cycloartane Glycosides from Astragalus boeticus L.

et al. 2019

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In several European countries, especially in Sweden, the seeds of the species Astragalus boeticus L. were widely used as coffee substitutes during the 19th century. Nonetheless, data regarding the phytochemistry and the pharmacological properties of this species are currently extremely limited. Conversely, other species belonging to the Astragalus genus have already been extensively investigated, as they were used for millennia for treating various diseases, including cancer. The current work was addressed to characterize cycloartane glycosides from A. boeticus, and to evaluate their cytotoxicity towards human colorectal cancer (CRC) cell lines. The isolation of the metabolites was performed by using different chromatographic techniques, while their chemical structures were elucidated by nuclear magnetic resonance (NMR) (1D and 2D techniques) and electrospray-ionization quadrupole time-of-flight (ESI-QTOF) mass spectrometry. The cytotoxic assessment was performed in vitro by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays in Caco-2, HT-29 and HCT-116 CRC cells. As a result, the targeted phytochemical study of A. boeticus enabled the isolation of three new cycloartane glycosides, 6-O-acetyl-3-O-(4-O-malonyl)-β-d-xylopyranosylcycloastragenol (1), 3-O-(4-O-malonyl)-β-d-xylopyranosylcycloastragenol (2), 6-O-acetyl-25-O-β-d-glucopyranosyl-3-O-β-d-xylopyranosylcycloastragenol (3) along with two known compounds, 6-O-acetyl-3-O-β-d-xylopyranosylcycloastragenol (4) and 3-O-β-d-xylopyranosylcycloastragenol (5). Importantly, this work demonstrated that the acetylated cycloartane glycosides 1 and 4 might preferentially inhibit cell growth in the CRC cell model resistant to epidermal growth factor receptor (EGFR) inhibitors.

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Secondary Metabolites from Turkish Astragalus Species

Cited by 7 publications

References 83 publications

First determination of anticancer, cytotoxic and in silico ADME evaluation of secondary metabolites of endemic Astragalus leucothrix Freyn & Bornm

First determination of anticancer, cytotoxic and in silico ADME evaluation of secondary metabolites of endemic Astragalus leucothrix Freyn & Bornm

Morpho-anatomical and palynological properties of endemic Astragalus tmoleus var. bounacanthus (Fabaceae)

Spectroscopic Characterization and Cytotoxicity Assessment towards Human Colon Cancer Cell Lines of Acylated Cycloartane Glycosides from Astragalus boeticus L.

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