Triterpeneglycosides of Astragalus and their genins. XXV. Cyclocanthoside D from Astragalus tragacantha

Fadeev, Yu. M.; Исаев, М. И.; Akimov, Yu. A.; Kintya, P. K.; Gorovits, M. B.; Abubakirov, N. K.

doi:10.1007/bf00597576

Cited by 6 publications

(5 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, compound 2 was elucidated as 6-O-β-D-xylopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane. Additionally, cycloastragenol (3) [4], cyclocanthoside E (4) [28], astragaloside IV (5) [29], astragaloside VIII (6) [30], cycloascauloside B (7) [31], cyclocephaloside I (8) [3], astrachrysoside A ( 9) [32] 25-epoxycycloartane ( 12) [9], cyclocephalosoide I (13) [16], 6-O-β-D-glucopyranosyl-3β,6α,16β,24α-tetrahydroxy-20(R),25-epoxycycloartane ( 14) [33] and cyclocanthoside A ( 15) [34] were also isolated from Astragalus karjaginii, and identified based on comparison of their spectroscopic data with literature values.…”

Section: Resultsmentioning

confidence: 99%

Secondary metabolites from Astragalus karjaginii BORISS and the evaluation of their effects on cytokine release and hemolysis

et al. 2017

View full text Add to dashboard Cite

A new cycloartane sapogenol and a new cycloartane xyloside were isolated from Astragalus karjaginii BORISS along with thirteen known compounds. The structures of the new compounds were established as 3-oxo-6α,16β,24(S),25-tetrahydroxycycloartane (1) and 6-O-β-d-xylopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane (2) by 1D- and 2D-NMR experiments as well as ESIMS and HRMS analyses. The presence of the keto function at position 3 was reported for the first time for cyclocanthogenol sapogenin of Astragalus genus. In vitro immunomodulatory effects of the new compounds (1 and 2) along with the n-BuOH and MeOH extracts of A. karjaginii at two different doses (3 and 6μg) were tested on human whole blood for in vitro cytokine release (IL-2, IL-17A and IFN-γ) and hemolytic activities. The results confirmed that compound 2, a monodesmosidic saponin, had the strongest effect on the induction of both IL-2 (6μg, 6345.41±0.12pg/mL (×5), P<0.001) and a slight effect upon IL-17A (3μg, 5217.85±0.72pg/mL, P<0.05) cytokines compared to the other test compounds and positive controls (AST VII: Astragaloside VII; and QS-21: Quillaja saponin 21). All tested extracts and molecules also induced release of IFN-γ remarkably ranging between 5031.95±0.05pg/mL, P<0.001 for MeOH extract (6μg) and 5877.08±0.06pg/mL, P<0.001 for compound 1 (6μg) compared to QS-21 (6μg, 5924.87±0.1pg/mL, P<0.001). Administration of AST VII and other test compounds did not cause any hemolytic activity, whereas QS-21 resulted a noteworthy hemolysis.

show abstract

Section: Resultsmentioning

confidence: 99%

Secondary metabolites from Astragalus karjaginii BORISS and the evaluation of their effects on cytokine release and hemolysis

et al. 2017

View full text Add to dashboard Cite

show abstract

“…It must be mentioned that the chemical shift of C-24 could be deemed to be a typical parameter in the determination of the configuration of C-24 [16]. In the case of the 24(S) configuration, the chemical shift for C-24 gives a resonance at δ C 77.0-78.2 [17][18][19], while for the 24(R) configuration, the chemical shift for C-24 gives a resonance at δ C 79.9-80.6 [20][21][22][23]. Hence, the configuration of C-24 (δ C 80.2) was determined to be R. According to the available data in the literature [24], the 20(S)-configuration was decided by the chemical shift of C-21 (δ C 27.5).…”

Section: Five New Triterpenoid Saponins From the Rhizomes Of Panacis mentioning

confidence: 99%

Five New Triterpenoid Saponins from the Rhizomes of Panacis majoris and Their Antiplatelet Aggregation Activity

Liu

Jin

et al. 2016

Planta Med

View full text Add to dashboard Cite

Five new triterpenoid saponins (-) and four known triterpenoid saponins, ginsenoside Re (), majonoside R (), 24()-majonoside R (), and ginsenoside Rf (), were isolated from the rhizomes of . The structures of new compounds were elucidated as (20,24,25*)-6-O-[-D-glucopyranosyl-(1 → 2)--D-glucopyranosyl]-dammar-20,24-epoxy-3,6,12,25,26-pentaol (), (20,24,25)-6-O-[-D-glucopyranosyl-(1 → 2)--D-glucopyranosyl]-dammar-20,24-epoxy-3,6,12,25,26-pentaol (), (20)-6-O-[-D-glucopyranosyl-(1 → 2)--D-glucopyranosyl]-dammar-20,25-epoxy-3,6,12,24-tetraol (), 6-O-[-D-glucopyranosyl-(1 → 2)--D-glucopyranosyl]-dammar-3,6,12,20,24,25-hexaol (), and 6-O-[-D-glucop-yranosyl-(1 → 2)--D-glucopyranosyl]-dammar-25(26)-ene-3,6,12,20,24-pentaol () on the basis of extensive spectral analysis and chemical methods. Ginsenoside Re was isolated from the plant for the first time. The similarities of the nine compounds lie in the fact that their aglycones are conjoined with the same glucopyranose moieties, the same linkage of the glycosyl chains, and the same glycosylation sites, while they have a varied C-17 side chain. Compounds and exhibited moderate antiplatelet aggregation activities induced by adenosine diphosphate with IC values of 23.24 and 18.43 µM, respectively. Compound displayed moderate inhibition of arachidonic acid-induced platelet aggregation with an IC value of 30.11 µM.

show abstract

“…Besides the two elemanes ( 84) and ( 85) 4 eudesmane derivatives, a-D-arabinopyranosides of a-eudesmol (96) and p-eudesmol (97) and their 3',4'-di-O-acetyl derivatives (98) and ( 99) have been characterized. Also new eudesmanolidetype glucosides have been found in Sonchus oleraceus (see 3.3), such as sonchuside C (100) and D (101).60…”

Section: Eudesmanesmentioning

confidence: 99%

Terpenoid glycosides

Pfander¹,

Stoll²

1991

Nat. Prod. Rep.

View full text Add to dashboard Cite

Triterpeneglycosides of Astragalus and their genins. XXV. Cyclocanthoside D from Astragalus tragacantha

Cited by 6 publications

References 5 publications

Secondary metabolites from Astragalus karjaginii BORISS and the evaluation of their effects on cytokine release and hemolysis

Secondary metabolites from Astragalus karjaginii BORISS and the evaluation of their effects on cytokine release and hemolysis

Five New Triterpenoid Saponins from the Rhizomes of Panacis majoris and Their Antiplatelet Aggregation Activity

Terpenoid glycosides

Contact Info

Product

Resources

About