New cascarosides from <i>Rhamnus purshiana</i> and fragmentation studies of the class by ion trap mass spectrometry

Demarque, Daniel P.; Pinho, Danielle R.; Callejon, Daniel R.; Oliveira, Gibson Gomes de; Silva, Denise B.; Carollo, Carlos Alexandre; Lopes, Norberto P.

doi:10.1002/rcm.7883

Cited by 9 publications

(10 citation statements)

References 14 publications

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“…11 Based on a thorough conformational analysis including molecular dynamic simulations, we briefly confirm the validity of the NMR-and ECD-spectroscopic approaches for the determination of the AC at C 10 . 11 Based on a thorough conformational analysis including molecular dynamic simulations, we briefly confirm the validity of the NMR-and ECD-spectroscopic approaches for the determination of the AC at C 10 .…”

Section: Introductionmentioning

confidence: 53%

“…In this contribution, we revisit the important stereochemistry at C 10 of the cascarosides A, B, and C (1-3), as well as of the only very recently isolated and characterized 10-hydroxy-cascarosides A and B (4 and 5). 11 Based on a thorough conformational analysis including molecular dynamic simulations, we briefly confirm the validity of the NMR-and ECD-spectroscopic approaches for the determination of the AC at C 10 . Furthermore, we discuss the results of a VCD spectroscopic characterization of these five compounds, which allow us to establish another set of empirical spectra-structure correlations for the class of (ox-)anthrones.…”

Section: Introductionmentioning

confidence: 53%

“…11 The chemical structures of the isolated compounds were confirmed by NMR and mass spectrometry. 11 The chemical structures of the isolated compounds were confirmed by NMR and mass spectrometry.…”

Section: Isolation and Characterization Of The Cascarosidesmentioning

confidence: 97%

“…The five cascarosides were extracted from the bark of R. purshiana by percolation with ethanol followed by several chromatographic steps as reported previously. 11 The chemical structures of the isolated compounds were confirmed by NMR and mass spectrometry. The stereochemistry of the glucopyranosyl moieties was determined by 1 H-coupling constants and comparison with the literature data.…”

Section: Isolation and Characterization Of The Cascarosidesmentioning

confidence: 97%

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Revisiting empirical rules for the determination of the absolute configuration of cascarosides and other (ox‐)anthrones

et al. 2018

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The introduction of the C -stereocenter of (ox-)anthrones by plant organisms is not stereospecific. Consequently, often, both (10S)- and (10R)-diastereomers can be found in the same plant. Motivated by the importance of a correct assignment of the configuration at C , this study revisits the nuclear magnetic resonance and electronic circular dichroism-based empirical rules for the determination of the absolute configuration by molecular dynamic simulations and electronic circular dichroism spectrum calculations. Furthermore, a vibrational circular dichroism spectroscopic characterization of these large and conformationally very flexible molecules reveals spectral signatures, which can be used to specifically distinguish the C stereochemistry. A detailed analysis of the underlying vibrational modes suggests that the observed spectral pattern of the investigated cascarosides may be generally characteristic for the C -stereocenter of (ox-)anthrones and that they can be used for empirical spectra-structure correlations.

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Section: Introductionmentioning

confidence: 53%

Section: Introductionmentioning

confidence: 53%

Section: Isolation and Characterization Of The Cascarosidesmentioning

confidence: 97%

Section: Isolation and Characterization Of The Cascarosidesmentioning

confidence: 97%

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Revisiting empirical rules for the determination of the absolute configuration of cascarosides and other (ox‐)anthrones

et al. 2018

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“…Phytochemical studies have demonstrated that anthraquinone diglucosides, namely, cascarosides A–F, are the characteristic constituents of cascara sagrada and that cascarosides A and B, especially, are the main anthraquinone glycosides while cacarosides C–F are the relatively minor ones [8–11]. Concerning the chemical structures of the cascarosides, the aglycones of cascarosides A–F were classified into three groups: the aloe‐emodin (cascarosides A and B), chrysophanol (cascarosides C and D), and emodin (cascarosides E and F) types, and two glucosyl moieties, 8‐ C‐ glucose and 10‐ O‐ glucose (Figure 1), were linked to each aglycone.…”

Section: Introductionmentioning

confidence: 99%

Isolation of six anthraquinone diglucosides from cascara sagrada bark by high‐performance countercurrent chromatography

Rho

Kil

Seo

et al. 2020

J of Separation Science

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In this study, high‐performance countercurrent chromatography was employed to isolate six anthraquinone diglucosides, namely, cascarosides A–F, from cascara sagrada (Rhamnus purshiana DC [Rhamnaceae]) bark. The n‐butanol–soluble extract of cascara sagrada was separated by off‐line two‐dimensional high‐performance countercurrent chromatography. The first‐dimensional high‐performance countercurrent chromatography resolved the n‐butanol‐soluble extract (510 mg) of cascara sagrada using the flow‐rate gradient method with a chloroform–methanol–isopropanol–water (6:6:1:4, v/v/v/v, normal‐phase mode) system to afford four anthraquinone diglucoside fractions (groups I [cascarosides C–D, 71 mg], II [cascarosides E–F, 56 mg], III [cascaroside A, 53 mg], and IV [cascaroside B, 31 mg]). Groups I and II were separated by the second‐dimensional high‐performance countercurrent chromatography using an ethyl acetate–n‐butanol–water (7:3:10, v/v/v, normal‐phase mode) system to yield cascarosides C (34 mg), D (26 mg), E (19 mg), and F (15 mg). Additionally, one‐step preparative‐scale high‐performance countercurrent chromatography method was developed to isolate large amounts of cascarosides A (389 mg) and B (187 mg) from the water‐soluble extract (2.1 g) of cascara sagrada using an ethyl acetate–n‐butanol–water (2:8:10, v/v/v, normal‐phase mode) system. The current study demonstrated that high‐performance countercurrent chromatography is a powerful technique for the isolation of marker compounds from herbal materials.

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Antitussive, Expectorant and Antipyretic Effect of the Ethanolic Extract of the Leaves of Momordica charantia L.

Feitosa Ribeiro,

Carvalho de Souza,

Cícero de Lima Araújo

et al. 2024

Chemistry & Biodiversity

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The traditional use of the M. charantia L. plant to treat coughs, fever and expectoration is widely practiced in different cultures, but its effectiveness and safety still require scientific investigation. This study sought to perform a chemical analysis and evaluate the antitussive, expectorant and antipyretic effects of the ethanolic extract of M. charantia leaves (EEMc) in rats and mice. The EEMc was subjected to chemical analysis by HPLC‐DAD, revealing the presence of the flavonoids astragalin and isoquercetin. Acute oral toxicity in mice did not result in deaths, although changes in liver weight and stool consistency were observed. EEMc demonstrated an antitussive effect at doses of 100 and 300 mg/kg in mice subjected to cough induction by citric acid nebulization. Furthermore, it showed expectorant activity at a dose of 300 mg/kg, assessed based on the elimination of the phenol red marker in bronchoalveolar lavage. In the evaluation of antipyretic activity in rats, fever induced by Saccharomyces cerevisiae was reduced at all doses tested during the first hour after treatment. This innovative study identified the presence of astragalin and isoquercetin in EEMc and indicated that the extract has antitussive, expectorant and antipyretic properties.

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New cascarosides from Rhamnus purshiana and fragmentation studies of the class by ion trap mass spectrometry

Cited by 9 publications

References 14 publications

Revisiting empirical rules for the determination of the absolute configuration of cascarosides and other (ox‐)anthrones

Revisiting empirical rules for the determination of the absolute configuration of cascarosides and other (ox‐)anthrones

Isolation of six anthraquinone diglucosides from cascara sagrada bark by high‐performance countercurrent chromatography

Antitussive, Expectorant and Antipyretic Effect of the Ethanolic Extract of the Leaves of Momordica charantia L.

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