Secondary Metabolites from Astragalus lycius and Their Cytotoxic Activities (original) (raw)
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TURKISH JOURNAL OF CHEMISTRY, 2021
Introduction Cancer is a major global public health problem. In addition, the incidence and mortality rates of cancer continue to increase. There will be an estimated 18.1 million new cancer cases and 9.6 million cancer deaths in 2018 [1]. Various systemic treatments such as surgery, chemotherapy, radiotherapy, and hormone therapy are used in cancer treatment [2,3]. Despite these treatment methods, neither a decrease in the number of patients with this disease nor a decrease in the mortality rate is observed [3]. In addition, cancer drugs cause toxicity in normal cells and tissues, causing serious side effects such as vomiting, nausea, hair loss, and resistance development [3-6]. Potential anticancer activities of many medicinal drugs and plant extracts have been investigated in order to avoid these undesirable side effects [3, 7-12]. Therefore, it is extremely important to develop more effective treatments by plants. Astragalus L. (Fabaceae) taxon is one of the largest genera in the world with 2500-3000 taxa [13-16]. In the studies conducted on Astragalus taxa in Turkey, it has been reported that there are 425-450 taxa, 201-224 of which are endemic and the rate of endemism varies between 47% and 50% [16,17]. Astragalus ssp. includes saponins, flavonoids, and polysaccharides as main classes of compounds [18]. Also, the species contents anthraquinones, alkaloids, amino acids, β-sitosterol, and metallic elements [19]. Astragalus species are used as hepatoprotective, antioxidative, immunostimulant, antiviral [20], antidiabetic, cardioprotective, antiinflammatory [19], for the treatment of wounds and leukemia [21, 22], and anticancer [23] at folk medicine. Also, immunomodulatory and anticancer activity of Astragalus genus were reported in some studies [24-26]. This pharmacological activity has been determined to be caused by three groups of chemical substances: polyholosites, saponins, and phenolics [20]. To our knowledge, there is no study about the anticancer activity and isolation of endemic A. leucothrix Freyn & Bornm. Thus, the main purpose of the research was to investigate the isolation, structural elucidation, biological activities, and in silico ADME evaluation.
Current Issues in Molecular Biology
Some of the most effective anticancer compounds are still derived from plants since the chemical synthesis of chiral molecules is not economically efficient. Rapid discovery of lead compounds with pronounced biological activity is essential for the successful development of novel drug candidates. This work aims to present the chemical diversity of antitumor bioactive compounds and biotechnological approaches as alternative production and sustainable plant biodiversity conservation. Astragalus spp., (Fabaceae) and Gloriosa spp. (Liliaceae) are selected as research objects within this review because they are known for their anticancer activity, because they represent two of the largest families respectively in dicots and monocots, and also because many of the medicinally important plants are rare and endangered. We summarized the ethnobotanical data concerning their anticancer application, highlighted the diversity of their secondary metabolites possessing anticancer properties such a...
Secondary Metabolites of Astragalus cruciatus Link. and Their Chemotaxonomic Significance
Records of Natural Products
In continuation of our chemical studies on the secondary metabolites of Algerian saharan species, we report on the isolation, from the methanol extract of the whole plant Astragalus cruciatus Link., of seven known compounds including two saponins named azukisaponin V (1) and astragaloside VIII (2), four flavonoids called narcissin (3), nicotiflorin (4), kaempferol 3-O-α-L-rhamnopyranosyl-(1→ 4)-α-L-rhamnopyranosyl-(1→ 6)-β-Dglucopyranoside (5) and 5,7,2'-trihydroxyflavone (6) and one phytosterol glycoside, daucosterol (7). All the isolated compounds were characterized by using spectroscopic methods especially 1D and 2D NMR and ESI mass spectrometry and comparison with literature data. The chemotaxonomic and systematic characters of the genus Astragalus are summarized in this study to show its interesting chemodiversity throughout the world, as well as to establish the chemotaxonomical classification of this genus.
Secondary metabolites of genus Astragalus: Structure and biological activity
Studies in Natural Products Chemistry, 2002
Astragalus L. is the largest genus in the family Leguminosae (subfamily Papilionideae, tribe Galegeae). Widely distributed throughout the temperate region of the world, is principally located in Europe, Asia and North America, but also on mountains in Africa and South America. They are annual and perennial herbs or small shrubs. Astragalus species are divided in two main groups: the medicinal plants and the poisonous species. "Astragali radix" (dried roots of ^4. membranaceous Bunge and other Astragalus spp.) represents a very old and well known drug in traditional Chinese medicine. They are officially listed in the Chinese Pharmacopoeia and prescribed mainly as an antiperspirant, a diuretic and a tonic, but also for their hepatoprotective, antioxidative, immunostimulant and antiviral properties. The other most common use of Astragalus is as forage for liverstock and wild animals; however a number of species are toxic for cattle and in many cases this toxicity could be transferred to humans through meat and milk. From a chemical point of view the biologically active principles of Astragalus species consist of saponins, polysaccharides and phenolics, while the toxic compounds include imidazoline alkaloids, nitro toxins and selenium derivatives. This review deals with the chemistry, purification procedures, structure elucidation methods and biological activity of triterpenoidic sapogenins and saponins, the most widely studied secondary metabolites from Astragalus. However the other important metabolites, such as phenolics, polysaccharides, alkaloids, nitro compounds and seleniferous derivatives, have been considered and a brief summary of their important biological properties has also been included. BNTRODUCnON Astragalus L. is the largest genxis in the Leguminosae (Fabaceae) family and one of the largest genera of vascular plants on Earth, comprising ca. 2500 species of herbs or shrubs, mostly perennial, grouped into more than 100 subdivisions [51]. Astragalus is cosmopolitan, distributed in cool, temperate, arid and semiarid continental region of SouthWestern Asia (the largest centre of distribution with 1000-1500 spp.), Sino-03 !2 *o c a u H CD 60 c c lit s so
Secondary Metabolites from the Roots of Astragalus zahlbruckneri
Journal of Natural Products, 2001
Four new phenolic glycosides, -apiofuranosyl-(1f2)--glucopyranosides (1-4), along with the cycloartane triterpenes 20(R),25-epoxy-3 ,6R,16 ,24R-tetrahydroxycycloartane (5) and 20(R),24(S)-epoxy-3 ,6R,25trihydroxycycloartan-16-one (6) were isolated from roots of Astragalus zahlbruckneri. The structure elucidation of all compounds was based on their 1 H and 13 C NMR spectral data including 1D-TOCSY, DQF-COSY, HSQC, and HMBC experiments.
New Flavonol Tetraglycosides from Astragalus caprinus
Chemical and Pharmaceutical Bulletin, 2002
Astragalus caprinus MAIRE (Fabaceae) is an endemic of North Africa, the leaves of which are used as an antihaemorrhoidal in Tunisian folk medicine. Our previous paper describing the structure of a new 3-O-tetraglycoside of kaempferol from this plant was the first phytochemical report on this species. 1) Here we report the isolation and structural elucidation of five new flavonol glycosides. Results and Discussion The methanolic extract of dried leaves from A. caprinus, once prepurified, was fractionated by repeated column and preparative thin-layer chromatography to give 1-5. Analysis of the 1 Hand 13 C-NMR spectra of compound 1 (Table 1; all assignments based on heteronuclear single quantum coherence-total correlation spectroscopy (HSQC-TOCSY) and heteronuclear multiple bond correlation (HMBC) experiments) showed the presence of one aromatic system and four sugar moieties. The 1 H-NMR resonances of two metacoupled doublets at d 6.19 and 6.38 ppm (1H, Jϭ1.9 Hz), correlated with the carbons at 99.8 and 94.7 ppm, respectively, in the HSQC spectrum, characterized the 6-and 8-protons of a flavonoid 5,7 dihydroxy A-ring. 2) Ring B was assigned as a 1,4-substituted benzene ring (d H 8.07, d, 2H, Jϭ8.8 Hz; 6.89, d, 2H, Jϭ8.8 Hz) from a HMBC experiment. Thus, the aglycone of 1 was identified as 3,5,7,4Ј-tetrahydroxyflavone (kaempferol), as suggested by its UV spectral properties. A HSQC-TOCSY experiment was performed to identify the spin systems of sugar units, starting from anomeric protons at d 5.57 (d, Jϭ7.8 Hz), 5.22 (s), 4.52 (s) and 4.32 (d, Jϭ7.4 Hz); on the basis of the chemical shifts, multiplicity of the signals and values of the coupling constants, the sugars were identified as b-galactopyranosyl (Gal), a-rhamnopyranosyls (Rha a and Rha b) and b-xylopyranosyl (Xyl). 3) The common D-configuration for Gal and Xyl, and the L-configuration for Rha were assumed according to those most often encountered among the plant glycosides. HMBC experiments showed long-range correlations between Gal H-1 (d 5.57) and Kaempferol C-3 (d 134.5), Rha a H-1/C-1 (d 5.22/102.6) and Gal C-2/H-2 (d 77.5/3.93), Rha b H-1/C-1 (d 4.52/101.8) and Gal C-6/H-6 (d 67.5/3.68), Xyl H-1/C-1 (d 4.32/106.4) and Rha b C-3/H-3 (d 82.3/3.55). Thus, compound 1 was identified as kaempferol-3-O-{[b-Dxylopyranosyl(1→3)-a-L-rhamnopyranosyl(1→6)][a-Lrhamnopyranosyl(1→2)]}-b-D-galactopyranoside. This identification was corroborated by electrospray ionization mass July 2002 Notes Chem. Pharm. Bull. 50(7) 981-984 (2002) 981
Cytotoxicity of Astragalus hamosus Phenolic Compounds on Cancer Cell Lines AMJ13 and SK-GT-4
Astragalus hamosus L. is a globally used herb for treating various diseases. This work was conducted to find out the cytotoxicity effects of phenolic compounds isolated from Astragalus hamosus root (PAR) to introduce a substitute approach in treating breast cancer and oesophageal cancer. Herein, the determination of the antioxidant activity the PAR extract was performed using the method of 1,1-diphenyl-2-picryl-hydrazyl (DPPH) employing ascorbic acid as positive antioxidant control. Moreover, its toxicity on liver and kidneys of albino mice was assessed. The acute cytotoxicity of PAR extract was studied in mice model in addition to two cell lines AMJ13 and SK-GT-4 representing breast and oesophageal cancers, respectively using an MTT assay. The finding of this study indicated that the PAR extract demonstrated improved antioxidant activity. Furthermore, the results revealed no death or behavioral changes among the treated animals. Interestingly, the liver and kidney tissues of treated animals displayed normal features. Markedly, the PAR extract exerted a noteworthy cytotoxic activity against both studied cell lines with IC50 of 1.807 and 6.581 μg /ml, respectively. The constituents of the PAR extract provide significant protection against the presence of anticancer activity. In conclusion, PAR extract may replace the traditional treatment policy of cancer once it fully studied in terms of other pharmacological investigations.
Secondary metabolites from the roots of Astragalus maximus
2017
Background and objectives: Astragalus is one of the most abundant genera of flowering plants in Iran. There are a few reports on phytochemical investigation of this valuable genus. Saponins, flavonoids and polysaccharides have been reported as the most important metabolites in Astragalus species. In the present research, we aimed to identify the foremost constituents of Astragalus maximus. Method: Phytochemical analysis of the ethyl acetate (EtOAc) fraction of Astragalus maximus roots was performed using different methods of chromatography such as HPLC, SPE and preparative TLC. The structures of the isolated compounds were elucidated on the basis of extensive spectral evidence from 1D and 2D NMR including DQF-COSY, HSQC, HMBC, and DEPT, in comparison with reported values in the literature. Results: Analysis of the extract yielded three flavonoids namely liquiritigenin, formononetin, isoquercitrin and one acylated cycloartane-type saponin, astragaloside I. Conclusion: According to th...
Triterpene glycosides from Astragalus icmadophilus
Phytochemistry, 2010
Six cycloartane-type triterpene glycosides were isolated from Astragalus icmadophilus along with two known cycloartane-type glycosides, five known oleanane-type triterpene glycosides and one known flavonol glycoside. The structures of the six compounds were established as 3-O-[a-L-arabinopyranosyl-
Secondary Metabolites from the Roots of Astragalus trojanus
Journal of Natural Products, 1999
Six novel cycloartane-type glycosides were isolated from the roots of Astragalus trojanus. Two of these, compounds 1 and 2, have (20R, 24S)-epoxy-3beta,6alpha,16beta,25-tetrahydroxycycloartane as the aglycon, while compounds 3-6 possess 3beta,6alpha,16beta,(24S), 25-pentahydroxycycloartane as the aglycon. The saccharide moieties linked to the C-3, C-6, and C-24 or C-25 positions of the aglycons in 1-6 contained either xylopyranose, glucopyranose, rhamnopyranose, or arabinopyranose units. Structure elucidation of compounds 1-6 was accomplished through the extensive use of 1D and 2D NMR techniques. In addition, a new oleanene glycoside (7) and a new tryptophan derivative (8) were also isolated and characterized.