Triterpenoids from Astragalus Plants

Mamedova, R. P.; Исаев, М. И.

doi:10.1023/b:conc.0000048246.16075.62

Cited by 48 publications

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“…Genus Astragalus is the richest source of cycloartane compounds. About 400 cycloartane-type saponins were isolated and 160 of them were isolated from genus Astragalus (Mamedova and Isaev, 2004). present study.…”

Section: Introductionmentioning

confidence: 72%

Isolation of Astragaloside-IV and Cyclocephaloside-I from Astragalus gummifera and Evaluation of Astragaloside-IV on CCl4 Induced Liver Damage in Rats

Ranganath

Balakrishna

Pramila

et al. 2014

Asian J. of Biological Sciences

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Two Cycloartane saponins, astragaloside-IV and cyclocephaloside-I, were isolated from the roots of Astragalus gummifera. Their structures were determined by utilizing 1D and 2D NMR experiments. Hepatoprotective effects of astragaloside-IV against carbon tetrachloride (CCl 4 ) induced nephrotoxicity and hepatotoxicity in rats was studied. The rats (200-230 g) of either sex were divided into 6 groups (6 rats each). Injection of a single dose of CCl 4 increases the level of serum AST, ALT, GGT, ALP and total bilirubin activities, decreases non-protein sulfhydryls (NP-SH) and total proteins (TPs), increases malondialdehyde (MDA) and produces changes in hepatic and nephritic tissue structure. Administration of doses of 25, 50 and 75 mg kgG 1 of astragaloside-IV reversed significantly (p<0.001) the liver diagnostic blood markers as well as stricture of nephrotoxicity and hepatotoxicity of the treated groups when compared to the control group. The present finding indicated that astragaloside-IV is an active hepatoprotective agent that restores the affected biochemical markers and nephritic and hepatic tissues.

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Section: Introductionmentioning

confidence: 72%

Isolation of Astragaloside-IV and Cyclocephaloside-I from Astragalus gummifera and Evaluation of Astragaloside-IV on CCl4 Induced Liver Damage in Rats

Ranganath

Balakrishna

Pramila

et al. 2014

Asian J. of Biological Sciences

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“…The PMR and 13 C NMR spectra indicated that the cyclopropane ring was missing and that seven methyls were present. Therefore, 1 was not a lanostane or cucurbitane triterpenoid, which are biologically related to cycloartanes [2]. In other words, 1 retained the 9,19-and 10,19-bonds.…”

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confidence: 98%

Triterpene glycosides and their genins from Astragalus. LXXXIV. Secomacrogenin B, a new 9,10-seco-cycloartane

2010

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The structure of a new triterpenoid, secomacrogenin B, which was isolated from Astragalus macropus Bunge (Leguminosae) roots and is 24R-9,10-seco-cycloartan-1(10),9(11)-dien-3E,7E,24,25-tetraol, was elucidated. In continuation of structural investigations of triterpenoids from Astragalus macropus Bunge (Leguminosae), we showed that the chromatographically homogeneous compound C [1] was not a pure compound. Rechromatography of this mixture over a column produced two fractions. The first contained a mixture of compounds. The second was a pure compound. Herein we present data on the structure elucidation of the latter, which we called secomacrogenin B (1).The molecular formula of the new compound 1, C 30 H 50 O 4 , which was derived from NMR spectral data [1] and confirmed by quasi-molecular ions in positive-and negative-ion electrospray mass spectra (ESI-MS and ESI-MS), indicated that it was triterpenoid in nature. An examination of PMR and 13 C NMR spectra confirmed this conclusion ( Table 1) and indicated that all O atoms were hydroxyls, three of which were secondary and one of which was tertiary. Therefore, 1 had six degrees of unsaturation. Because 1 contained two double bonds, it should have consisted of four rings, which is one ring less than for cycloartane triterpenoids. The PMR and 13 C NMR spectra indicated that the cyclopropane ring was missing and that seven methyls were present. Therefore, 1 was not a lanostane or cucurbitane triterpenoid, which are biologically related to cycloartanes [2]. In other words, 1 retained the 9,19-and 10,19-bonds. That meant that the 9,10-bond had been lost and, therefore, the new triterpenoid 1 was a 9,10-seco-cycloartane triterpenoid.The PMR spectrum of 1 showed 1H doublets for an AX system of an isolated methylene at G 2.77 and 3.03. The doublet at G 2.77 in the HMBC spectrum had cross-peaks with four olefinic C atoms (G 139.49, 135.82, 126.23, 117.17) and two methine C atoms that resonated at G 44.99 and 55.74.Because the last resonances belonged to C-5 and C-8, respectively, the isolated methylene was CH 2 -19. Therefore, the double bonds were located on C-1-C-10 and C-9-C-11 and 1 had a 9,10-seco-cycloart-1(10),9(11)-diene C skeleton.The same PMR spectrum showed only one methyl group as a doublet. This defined the location of the tertiary hydroxyl as C-25.

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“…To the best of our knowledge, there are no phytochemical studies on this species to date. In this article, we describe the isolation and structural elucidation of two new acylated tridesmosides of a 20,24-epoxycycloartane-type aglycone from the roots of A. armatus, named armatosides I (1) and II (2), together with two known cycloartane-type glycosides, trigonoside II (3) [6] and trojanoside H (4) [7]. The new compounds showed unique chemical substitutions which are not frequently found in the genus Astragalus.…”

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confidence: 99%

“…Saponins with aglycones of the cycloartane-, lanostane-and oleanane-type were isolated from many Astragalus species, but the cycloartane glycosides dominate the triterpenoids of this genus [2] [3] (cycloartane ¼ 9,19-cyclolanostane). Among the cycloartane-type skeletons, cycloastragenol (also known as cyclosiversigenin and astramembrangenin) is the most widely distributed genin of the glycosides in Astragalus genus [2]. The identified saponins were found to be diversified by their glycosylation types, degrees, and attachment points at the genin; moreover, several of them were acetylated.…”

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confidence: 99%

“…-Astragalus is a great legume genus including more than 2200 species growing worldwide [1]. Saponins with aglycones of the cycloartane-, lanostane-and oleanane-type were isolated from many Astragalus species, but the cycloartane glycosides dominate the triterpenoids of this genus [2] [3] (cycloartane ¼ 9,19-cyclolanostane). Among the cycloartane-type skeletons, cycloastragenol (also known as cyclosiversigenin and astramembrangenin) is the most widely distributed genin of the glycosides in Astragalus genus [2].…”

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confidence: 99%

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Two New Acylated Tridesmosidic Saponins from Astragalus armatus

Semmar

Miyamoto

Mrabet

et al. 2010

Helvetica Chimica Acta

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Two new tridesmosidic glycosides of (3b,6a,16b,20R,24S)-20,24-epoxycycloartane-3,6,16,25-tetrol (¼ cycloastragenol), armatosides I and II (1 and 2, resp.), were isolated from the roots of Astragalus armatus (Fabaceae) as well as the known bidesmosidic glycosides of cycloastragenol, trigonoside II (3) and trojanoside H (4). Their structures were elucidated as (3b,6a,16b,20R,24S) -3,6,16,25-tetrol (1), and (3b,6a,16b,20R,24S) 6,16,25-tetrol (2). These structures were established by extensive NMR and MS analyses and by comparison with literature data.Introduction. -Astragalus is a great legume genus including more than 2200 species growing worldwide [1]. Saponins with aglycones of the cycloartane-, lanostane-and oleanane-type were isolated from many Astragalus species, but the cycloartane glycosides dominate the triterpenoids of this genus [2] [3] (cycloartane ¼ 9,19-cyclolanostane). Among the cycloartane-type skeletons, cycloastragenol (also known as cyclosiversigenin and astramembrangenin) is the most widely distributed genin of the glycosides in Astragalus genus [2]. The identified saponins were found to be diversified by their glycosylation types, degrees, and attachment points at the genin; moreover, several of them were acetylated. These different structural characteristics lead to specific chemical traits which could be used as fingerprints to distinguish different Astragalus species from each other. Astragalus armatus Willd. (Fabaceae) is an endemic shrub species in the region of Maghreb. It mainly grows in arid regions where pastoral activity is important because of its low palatability [4] [5]. To the best of our knowledge, there are no phytochemical studies on this species to date. In this article, we describe the isolation and structural elucidation of two new acylated tridesmosides of a 20,24-epoxycycloartane-type aglycone from the roots of A. armatus, named armatosides I (1) and II (2), together with two known cycloartane-type glycosides, trigonoside II (3) [6] and trojanoside H (4) [7]. The new compounds showed unique chemical substitutions which are not frequently found in the genus Astragalus.

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Triterpenoids from Astragalus Plants

Cited by 48 publications

References 33 publications

Isolation of Astragaloside-IV and Cyclocephaloside-I from Astragalus gummifera and Evaluation of Astragaloside-IV on CCl4 Induced Liver Damage in Rats

Isolation of Astragaloside-IV and Cyclocephaloside-I from Astragalus gummifera and Evaluation of Astragaloside-IV on CCl4 Induced Liver Damage in Rats

Triterpene glycosides and their genins from Astragalus. LXXXIV. Secomacrogenin B, a new 9,10-seco-cycloartane

Two New Acylated Tridesmosidic Saponins from Astragalus armatus

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