Two cycloartane-type glycosides from the roots of Astragalus glycyphyllos

Linnek, Jens; Mitaine-Offer, Anne Claire; Miyamoto, Tomofumi; Lacaille-Dubois, M. A.

doi:10.1055/s-0028-1084486

Cited by 7 publications

(5 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Phytochemical investigation of A. glycyphyllos led to the isolation of six saponins, and their structures are partially elucidated [ 66 , 67 ]. After acid hydrolysis of a saponin mixture obtained from the aerial parts of the plant, soyasapogenol B and 3β,22β,24-trihidroxyolean-12-en-19-one are identified [ 68 ]. Cycloartane saponins askenoside C and F [ 68 ] and 17 (R) , 20 (R) -3 β ,6 α ,16 β -trihydroxycycloartanyl-23-carboxylic acid 16-lactone 3- O - β -D-glucopyranoside are later isolated from the species [ 69 ].…”

Section: Resultsmentioning

confidence: 99%

“…After acid hydrolysis of a saponin mixture obtained from the aerial parts of the plant, soyasapogenol B and 3β,22β,24-trihidroxyolean-12-en-19-one are identified [ 68 ]. Cycloartane saponins askenoside C and F [ 68 ] and 17 (R) , 20 (R) -3 β ,6 α ,16 β -trihydroxycycloartanyl-23-carboxylic acid 16-lactone 3- O - β -D-glucopyranoside are later isolated from the species [ 69 ]. Several known flavonoids, including the rare camelliaside A, are also identified [ 53 , 69 ].…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Anticancer Secondary Metabolites: From Ethnopharmacology and Identification in Native Complexes to Biotechnological Studies in Species of Genus Astragalus L. and Gloriosa L.

Йонкова

Shkondrov

Zarev

et al. 2022

CIMB

View full text Add to dashboard Cite

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 as saponins, flavonoids, and alkaloids, and revealed the potential of the in vitro cultures as an alternative way of their production. Since the natural supply is limited, it is important to explore the possibility of employing plant cell or organ in vitro cultures for the biotechnological production of these compounds as an alternative.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Anticancer Secondary Metabolites: From Ethnopharmacology and Identification in Native Complexes to Biotechnological Studies in Species of Genus Astragalus L. and Gloriosa L.

Йонкова

Shkondrov

Zarev

et al. 2022

CIMB

View full text Add to dashboard Cite

show abstract

“…In addition, the available –OH group at C-24 is glycosylated (L-Ara) in compound S1 . The saponin S1 has a structural similarity with the triperpenoids previously isolated from the roots of the species, i.e., askendosides C and F—the aglycone is the same and, like askendoside F, is a bisdesmoside [ 7 ]. The differences are the type of sugars and the attachment position.…”

Section: Discussionmentioning

confidence: 99%

“…A phytochemical investigation of the overground parts of the species was initiated in Bulgaria 35 years ago and led to the isolation of some sapogenins (soyasapogenol B and 3 β ,22 β ,24-trihydroxyolean-12-en-19-one) after acid hydrolysis [ 5 , 6 ]. In later research, the saponins askendoside C and F were isolated from the roots of the plant [ 7 ]. Recently, from its aerial parts, an epoxycycloartane saponin 17( R ),20( R )-3 β ,6 α ,16 β -trihydroxycycloartanyl-23-carboxilic acid 16-lactone 3- O - β -D-glucopyranoside [ 8 ] was isolated.…”

Section: Introductionmentioning

confidence: 99%

Cycloartane Saponins from Astragalus glycyphyllos and Their In Vitro Neuroprotective, Antioxidant, and hMAO-B-Inhibiting Effects

et al. 2023

View full text Add to dashboard Cite

Astragalus glycyphyllos (Fabaceae) is used in the traditional medicine of many countries against hepatic and cardiac disorders. The plant contains mainly flavonoids and saponins. From a defatted methanol extract from its overground parts, a new triterpenoid saponin, 3-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-xylopyranosyl]-24-O-α-L-arabinopyranosyl-3β,6α,16β,24(R),25-pentahydroxy-20R-cycloartane, together with the rare saponin astrachrysoside A, were isolated using various chromatography methods. The compounds were identified via extensive high resolution electrospray ionisation mass spectrometry (HRESIMS) and NMR analyses. Both saponins were examined for their possible antioxidant and neuroprotective activity in three different in vitro models. Rat brain synaptosomes, mitochondria, and microsomes were isolated via centrifugation using Percoll gradient. They were treated with the compounds in three different concentrations alone, and in combination with 6-hydroxydopamine or tert-butyl hydroperoxide as toxic agents. It was found that the compounds had statistically significant dose-dependent in vitro protective activity on the sub-cellular fractions. The compounds exhibited a weak inhibitory effect on the enzyme activity of human recombinant monoamine oxidase type B (hMAO-B), compared to selegiline.

show abstract

“…There are two main groups of secondary metabolites in A. glycyphyllos: flavonoids [3] and triterpenoid saponins [4]. The latter group include both cycloartane-type saponins: askendoside C and F [5] and 17(R),20(R)-3b,6a,16b-trihydroxycycloartanyl-23-carboxylic acid 16lactone 3-O-b-D-glucopyranoside [6]; and oleanane-type saponins: soyasapogenol B and 3b,22b,24-trihydroxyolean-12-ene-19-one [7,8]. Cycloartane saponins possess numerous pharmacological activities [4], incl.…”

Section: Introductionmentioning

confidence: 99%

Production of saponins from in vitro cultures of Astragalus glycyphyllos and their antineoplastic activity

Shkondrov

Krasteva

Йонкова

et al. 2019

Biotechnology & Biotechnological Equipment

View full text Add to dashboard Cite

In the last decade the need of plant-derived cytotoxic compounds exceeds the possibilities for obtaining them from naturally grown sources. In vitro plant biotechnology offers a unique and often invaluable alternative for production of complex biologically active substances without harming the flora. Astragalus glycyphyllos L. (Fabaceae) is a plant native to Bulgaria that has been reported to contain triterpenoid saponins and flavonoids. It is used in folk medicine as an antihypertensive, diuretic, anti-inflammatory, anti-tumour, laxative, expectorant agent, etc. The aim was to study the saponin content of A. glycyphyllos cultures grown in vitro and their antiproliferative activity. Three types of cultures were developed: callus, shoot and suspension cultures. Murashige and Skoog's, as well as other media, supplemented with various concentrations and combinations of plant growth regulators and different photoperiods were used. In all cultures the saponin content was determined by a novel liquid chromatography-mass spectrometry (LC-MS) method. Compared to the wild grown species, in vitro shoot cultures accumulated double the amount of the main saponin (225.00 ng/mg dw) found in the plant. Saponin-rich fractions obtained from shoot cultures were tested for cytotoxicity in a panel of various malignant human cells and half-maximal inhibitory concentration (IC 50) values were determined. Interestingly, the saponin-rich fractions showed higher efficacy against urinary bladder cancer cells with constitutive high expression level of the xenobiotic pump gp170 (MDR1). In vitro cultures of A. glycyphyllos could serve as an alternative way for production of saponins, with promising antineoplastic activity, which deserves further detailed characterization.

show abstract

Two cycloartane-type glycosides from the roots of Astragalus glycyphyllos

Cited by 7 publications

References 0 publications

Anticancer Secondary Metabolites: From Ethnopharmacology and Identification in Native Complexes to Biotechnological Studies in Species of Genus Astragalus L. and Gloriosa L.

Anticancer Secondary Metabolites: From Ethnopharmacology and Identification in Native Complexes to Biotechnological Studies in Species of Genus Astragalus L. and Gloriosa L.

Cycloartane Saponins from Astragalus glycyphyllos and Their In Vitro Neuroprotective, Antioxidant, and hMAO-B-Inhibiting Effects

Production of saponins from in vitro cultures of Astragalus glycyphyllos and their antineoplastic activity

Contact Info

Product

Resources

About