Structure of Cyclogaleginoside E from<i>Astragalus galegiformis</i>

Gigoshvili, T. I.; Alaniya, M. D.; Tsitsishvili, Vladimer; Foure, R.; Debrauver, L.; Кемертелидзе, Э. П.

doi:10.1023/b:conc.0000003419.24465.3f

Cited by 8 publications

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“…As the summarized results shown in Table 1, Table 2 and Table 3 and Figure 1, Figure 2, Figure 3 and Figure 4, 46 kinds of Astragalus species have been studied for their chemical constituents in recent years [9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63,64,65,66,67,…”

Section: Phytochemistrymentioning

confidence: 99%

A Review of Recent Research Progress on the Astragalus Genus

Li¹,

Qu²,

Dong³

et al. 2014

Molecules

249

148

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Astragalus L., is one of the largest genuses of flowering plants in the Leguminosae family. Roots of A. membranaceus Bge. var. mongholicus (Bge.) Hsiao, A. membranaceus (Fisch.) Bge. and its processed products are listed in the China Pharmacopeia for "qi deficiency" syndrome treatment. However, more and more researches on other species of Astragalus have been conducted recently. We summarize the recent researches of Astragalus species in phytochemistry and pharmacology. More than 200 constituents, including saponins and flavonoids, obtained from 46 species of Astragalus genus were collected for this article. In pharmacological studies, crude extracts of Astragalus, as well as isolated constituents showed anti-inflammatory, immunostimulant, antioxidative, anti-cancer, antidiabetic, cardioprotective, hepatoprotective, and antiviral activities. The goal of this article is to provide an overview of chemical and pharmacological studies on the Astragalus species over the last 10 years, which could be of value to new drug or food supplement research and development. OPEN ACCESS

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Section: Phytochemistrymentioning

confidence: 99%

A Review of Recent Research Progress on the Astragalus Genus

Li¹,

Qu²,

Dong³

et al. 2014

Molecules

249

148

View full text Add to dashboard Cite

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“…The IR, PMR, and 13 C NMR spectra indicated that the studied glycoside was a cycloartane derivative [3,4]. The PMR spectrum of 1 showed resonances at 0.20 and 0.52 ppm for protons of an isolated cyclopropane methylene.…”

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confidence: 93%

Cycloascauloside b from Astragalus caucasicus

et al. 2008

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“…Alkaline hydrolysis of 1 gave glycoside 2, which was identified as cyclogaleginoside E [3]. Therefore, cyclogaleginoside D is cyclogaleginoside E monoacetate.…”

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confidence: 98%

“…42, No. 3, 2006 We have previously isolated from A. galegiformis L. stems and identified cycloartane glycosides cyclogaleginosides A, B, and E [2,3]. In continuation of chemical research on isoprenoids from plants of the genus Astragalus (Leguminosae) [1], we isolated in addition to the aforementioned glycosides another two polar glycosides C and D. Herein the structure of cyclogaleginoside D (1) is examined.…”

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Cyclogaleginoside D from Astragalus galegiformis stems

2006

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Astragalus galagiformis stems. The structure of the glycoside was established using chemical transformations and IR, PMR, and 13 C NMR spectral data.We have previously isolated from A. galegiformis L. stems and identified cycloartane glycosides cyclogaleginosides A, B, and E [2, 3]. In continuation of chemical research on isoprenoids from plants of the genus Astragalus (Leguminosae) [1], we isolated in addition to the aforementioned glycosides another two polar glycosides C and D. Herein the structure of cyclogaleginoside D (1) is examined.The PMR spectrum of 1 contained a 1H doublet for an AX system at 0.38 and 0.54 ppm with SSCC 2 J = 4.5 Hz in addition to signals for seven methyls in the range 0.91-1.41 ppm. This indicated that the compound was a triterpenoid cycloartane [1]. This was consistent with the isolation of cyclogalegigenin (3) as the genin from the acid-hydrolysis products of cyclogaleginoside D. Paper chromatography detected D-xylose and D-glucose in the carbohydrate part of the acid-hydrolysis products. The PMR and 13 C NMR spectra of 1 (Table 1) contained signals for two carbohydrate units and indicated that the studied glycoside was a bioside.A 3H singlet at 2.10 ppm in the PMR spectrum of 1 was consistent with one acetic acid moiety. As expected, the 13 C NMR spectrum of 1 contained signals for C atoms of one acetyl at 21.1 and 169.5 ppm.Alkaline hydrolysis of 1 gave glycoside 2, which was identified as cyclogaleginoside E [3]. Therefore, cyclogaleginoside D is cyclogaleginoside E monoacetate.The attachment site of the acetyl was found by comparing the 13 C NMR spectra of 1 and 2. Atoms C-6 and C-16 of 1 resonated in the 13 C NMR spectrum of 1 at 69.07 and 74.40 ppm, respectively. These values were practically the same as those in the 13 C NMR spectrum of 2. This means that the acetyl is not located on the genin of 1.

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Structure of Cyclogaleginoside E fromAstragalus galegiformis

Cited by 8 publications

References 0 publications

A Review of Recent Research Progress on the Astragalus Genus

A Review of Recent Research Progress on the Astragalus Genus

Cycloascauloside b from Astragalus caucasicus

Cyclogaleginoside D from Astragalus galegiformis stems

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