New triterpenoid saponins from the leaves of Cyclocarya paliurus

Cui, Bao‐Song; Li, Shuai

doi:10.1016/j.cclet.2014.11.033

Cited by 29 publications

(17 citation statements)

References 19 publications

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“…Triterpenoids are another major group of bioactive components from C. paliurus . In the present study, six triterpenoids (peaks 12 , 13 , 14 , 15 , 16 and 20 ) were unambiguously identified by comparison with their reference standards’ retention time and MS 2 data, while another three compounds (peaks 17 , 18 and 19 ) were tentatively deduced based on their fragmentation pathways and previous reports of C. paliurus [ 14 , 15 , 37 , 38 ]. Unfortunately, we were unable to identify peak 21.…”

Section: Resultssupporting

confidence: 62%

Chemical Fingerprint and Multicomponent Quantitative Analysis for the Quality Evaluation of Cyclocarya paliurus Leaves by HPLC–Q–TOF–MS

et al. 2017

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Cyclocarya paliurus is an edible and medicinal plant containing various bioactive components with significant health benefits. A combinative method using high-performance liquid chromatography (HPLC) fingerprint and quantitative analysis was developed and successfully applied for characterization and quality evaluation of C. paliurus leaves collected from 18 geographical locations of China. For the fingerprint analysis, 21 common peaks were observed among the 18 samples, and these peaks were identified by high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (HPLC–Q–TOF–MS), while a simultaneous quantification of 16 markers was conducted to interpret the variations of contents of these bioactive compounds among the C. paliurus leaves from different geographical locations. Quantification results showed that the contents of these sixteen investigated compounds varied greatly among the leaves from different locations. The developed new method would be a valuable reference for further study and development of this bioactive plant.

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Section: Resultssupporting

confidence: 62%

Chemical Fingerprint and Multicomponent Quantitative Analysis for the Quality Evaluation of Cyclocarya paliurus Leaves by HPLC–Q–TOF–MS

et al. 2017

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“…The sugar linkage at C-12 was deduced by the HMBC correlation between H-1′ (δ H 4.36) and C-12 (δ C 76.5). The closely comparable NMR spectra for the sugar moiety of 3 to those of co-isolated known compounds 12 , 13 , 14 , and 15 , and the previously reported dammarane derivativesfrom this plant [14,20,21], together with an acid hydrolysis experiment and co-TLC with an authentic d -quinovose sample [22], suggested that the same β- d -quinovopyranosyl unit in 3 . The configuration of 3 was also confirmed by NOESY experiment.…”

Section: Resultssupporting

confidence: 76%

“…Furthermore, a significant HMBC correlation between the anomeric hydrogen H-1′ and C-12 placed the glycoside moiety properly. Moreover, the pentose moiety was assigned as α- l -arabinopyranosyl based on the NMR data and comparison with those dammarane derivatives from this plant [14,20,21], as well as further acid hydrolysis and co-TLC with an authentic l -arabinose sample [22]. The relative configuration of 1 was determined by NOESY experiments (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

“…The β-orientation of H-13, H 3 -18, and H 3 -19 were then verified by NOESY correlations of H-13/H 3 -18 and H 3 -18/H 3 -19. Because free rotation of the C-17–C-20 single bond was restricted to some extent in these triterpenoids with a 20,24-epoxyside chain [14,20], the configurations at C-20 and C-24 were then determined to be 20 S and 24 R based on key NOESY correlations of H-17/H 3 -21 and H 3 -21/H-24, respectively. As the absolute configuration on the main skeleton of these seco -dammarane triterpenoids have already been clarified by techniques such as single-crystal X-ray diffraction analysis with Cu K α irradiation [23], compound 1 was identified as (20 S ,24 R )-20,24-epoxy-25-hydroxy-12β-(α- l -arabinopyranosyloxy)-3,4- seco -dammara-4(28)-en-3-oic acid.…”

Section: Resultsmentioning

confidence: 99%

“…By comparing their NMR data with those reported in the literatures, the eleven known compounds (Table S1) were identified asarjunolic acid ( 5 ) [25], cyclocaric acid B ( 6 ) [26], 1α, 3β-dihydroxy-olean-12-en-28-oic acid ( 7 ) [27], punicaone ( 8 ) [28], olean-12-en-1β,3β,28-triol ( 9 ) [29], ursolic acid ( 10 ) [30], asiatic acid ( 11 ) [31], cyclocarioside K ( 12 ) [20], cyclocarioside H ( 13 ) [14], cyclocariosideI ( 14 ) [32], and cyclocarioside B ( 15 ) [33], respectively.…”

Section: Resultsmentioning

confidence: 99%

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Triterpenoids from Cyclocarya paliurus that Enhance Glucose Uptake in 3T3-L1 Adipocytes

et al. 2019

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Four previously undescribed compounds, including three rarely occurring seco-dammarane triterpenoid glycosides and a pentacyclic triterpenic acid, were isolated from a 70% ethanol extract of the leaves of Cyclocarya paliurus (Juglandaceae), along with eleven known triterpenoids. Their structures were determined by spectroscopic techniques, including 2D NMR and HRESIMS, as well as chemical methods. Among them, several triterpenoids enhanced insulin stimulated glucose uptake in both 3T3-L1 adipocytes and C2C12 myotubes. Furthermore, compound 1 dose-dependently increased glucose uptake through activating AMP-activated protein kinase (AMPK)-p38 pathway. Collectively, triterpenoids from C. paliurus could be developed as insulin sensitizers, which might have therapeutic potential for insulin resistance and hyperglycemia.

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α‐Glucosidase inhibitors screening from Cyclocarya paliurus based on spectrum–effect relationship and UPLC–MS/MS

Yan-jun

Guo

et al. 2022

Biomedical Chromatography

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Cyclocarya paliurus is an edible and medicinal plant exhibiting significant hypoglycemic effect. However, its active components are still unclear and need further elucidation. In this research, the active components of the leaves of C. paliurus responsible for the α-glucosidase inhibitory activity were screened and identified based on a spectrum-effect relationship study in combination with ultra-performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) analysis. The 70% ethanol eluate fraction of the leaves of C. paliurus with the strongest α-glucosidase inhibitory activity was obtained after extraction and purification with macroporous resin.Their chromatographic fingerprints (15 batches) were established by UPLC analysis and 32 common peaks were specified by similarity analysis. Their IC 50 values for α-glucosidase inhibition were measured by an enzymatic reaction. Several multivariate statistical analysis methods including hierarchical cluster analysis, principal component analysis, partial least square analysis and gray relational analysis were applied to explore the spectrum-effect relationship between common peaks and IC 50 values, and the chromatographic peaks making a large contribution to efficacy were screened out. To further elucidate the active components of leaves of C. paliurus, the 70% ethanol eluate fraction was characterized by UPLC-MS/MS analysis, and 10 compounds were identified. This study provides a valuable reference for further research and development of hypoglycemic active components of C. paliurus.

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New triterpenoid saponins from the leaves of Cyclocarya paliurus

Cited by 29 publications

References 19 publications

Chemical Fingerprint and Multicomponent Quantitative Analysis for the Quality Evaluation of Cyclocarya paliurus Leaves by HPLC–Q–TOF–MS

Chemical Fingerprint and Multicomponent Quantitative Analysis for the Quality Evaluation of Cyclocarya paliurus Leaves by HPLC–Q–TOF–MS

Triterpenoids from Cyclocarya paliurus that Enhance Glucose Uptake in 3T3-L1 Adipocytes

α‐Glucosidase inhibitors screening from Cyclocarya paliurus based on spectrum–effect relationship and UPLC–MS/MS

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