α-Glucosidase inhibitory and anti-inflammatory activities of dammarane triterpenoids from the leaves of Cyclocarya paliurus

Li, Chenguo; Deng, Shengping; Liu, Wei; Zhou, Dexiong; Huang, Yan; Liang, Cheng-Qin; Hao, Lili; Zhang, Gaorong; Su, Shanshan; Xu, Xia; Yang, Ronghua; Li, Jun; Huang, Xishan

doi:10.1016/j.bioorg.2021.104847

Cited by 26 publications

(11 citation statements)

References 30 publications

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“…The Cui group reported that cyclocarioside K isolated from the ethanol leaf extracts of C. paliurus has potential for the treatment of diabetes by the network pharmacological approach (Lin et al, 2020). In related literature (Li et al, 2021), cyclocarioside J was found to display moderate inhibitory activity against α ‐glucosidase, with IC 50 values ranging from 451.22 to 478.15 μ M .…”

Section: Resultsmentioning

confidence: 80%

“…The dry extractum was dissolved and diluted to 50 mg mL −1 with 5% ethanol solution. The resulting sample solution was subjected to column chromatography (25 × 3 cm) on D101 macroporous resin, and then eluted successively using water and 30, 50, 70 and 95% ethanol solutions at a flow rate of 2.0 mL min −1 (Feng et al, 2021; Li et al, 2021). The eluates were collected separately and evaporated to dryness under reduced pressure, yielding the five eluate fractions.…”

Section: Methodsmentioning

confidence: 99%

Section: Gray Relational Analysismentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 80%

Section: Methodsmentioning

confidence: 99%

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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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“…Compound 1 was treated with anhydrides or carboxylic acids in the presence of N , N’ -dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) to yield compounds 2 – 8 with acyl groups at C-3, compounds 9 – 15 with acyl groups at C-12 and di-esterified products 16 – 21 . Oxidation of compound 1 using pyridinium chlorochromate (PCC) afforded ketones 22 – 24 with different oxidation location at C-3 and C-12, while compound 22 could be selectively obtained in 70% yield via Oppenauer oxidation [ 24 ]. When compound 22 and hydroxylamine hydrochloride were heated in the presence of sodium acetate trihydrate, the oxime derivative 25 was afforded in 93% yield [ 25 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of (20S,24R)-epoxy-dammarane-3β,12β,25-triol derivatives as α-glucosidase and PTP1B inhibitors

Yang

Geng

et al. 2022

Med Chem Res

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The dammarane triterpenoid (20 S ,24 R )-epoxy-dammarane-3 β ,12 β ,25-triol obtained from Cyclocarya paliurus in our previous study showed inhibitory activity on α -glucosidase in vitro with an inhibitory ratio of 32.2% at the concentration of 200 μM. In order to reveal the structure-activity relationships (SARs) and get more active compounds, 42 derivatives of (20 S ,24 R )-epoxy-dammarane-3 β ,12 β ,25-triol were synthesized by chemical modification on the hydroxyls (C-3 and C-12), rings A and E, and assayed for their α -glucosidase and PTP1B inhibitory activities. Two compounds ( 8 , 26 ) increased activity against α -glucosidase, and four compounds ( 8 , 15 , 26 , 42 ) significantly inhibited PTP1B. It was noted that compounds 8 and 26 could inhibit both α -glucosidase and PTP1B as dual-target inhibitors with IC 50 values of 489.8, 467.7 μM ( α -glucosidase) and 319.7, 269.1 μM (PTP1B). Compound 26 was revealed to be a mix-type inhibitor on α -glucosidase and a noncompetitive-type inhibitor on PTP1B based on enzyme kinetic study. Furthermore, compound 42 could selectively inhibited PTP1B as a mix-type inhibitor with IC 50 value of 134.9 μM, which was 2.5-fold higher than the positive control, suramin sodium (IC 50 339.0 μM), but not inhibit α -glucosidase.

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“…The total triterpenoid content of C. paliurus has also been shown to ameliorate glucose and lipid metabolism disorders [ 20 ]. A total of 137 triterpenoids are found in C. paliurus leaves [ 10 ], as described in Table 2 , many of which promote glucose uptake [ 21 , 44 , 45 ] and improve lipid metabolism [ 46 , 47 ].…”

Section: Active Components Of C Paliurusmentioning

confidence: 99%

Progress in Research on the Alleviation of Glucose Metabolism Disorders in Type 2 Diabetes Using Cyclocarya paliurus

et al. 2022

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Globally, the incidence of diabetes is increasing annually, and China has the largest number of patients with diabetes. Patients with type 2 diabetes need lifelong medication, with severe cases requiring surgery. Diabetes treatment may cause complications, side-effects, and postoperative sequelae that could lead to adverse health problems and significant social and economic burdens; thus, more efficient hypoglycemic drugs have become a research hotspot. Glucose metabolism disorders can promote diabetes, a systemic metabolic disease that impairs the function of other organs, including the heart, liver, and kidneys. Cyclocarya paliurus leaves have gathered increasing interest among researchers because of their effectiveness in ameliorating glucose metabolism disorders. At present, various compounds have been isolated from C. paliurus, and the main active components include polysaccharides, triterpenes, flavonoids, and phenolic acids. C. paliurus mainly ameliorates glucose metabolism disorders by reducing glucose uptake, regulating blood lipid levels, regulating the insulin signaling pathway, reducing β-cell apoptosis, increasing insulin synthesis and secretion, regulating abundances of intestinal microorganisms, and exhibiting α-glucosidase inhibitor activity. In this paper, the mechanism of glucose metabolism regulation by C. paliurus was reviewed to provide a reference to prevent and treat diabetes, hyperlipidaemia, obesity, and other metabolic diseases.

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α-Glucosidase inhibitory and anti-inflammatory activities of dammarane triterpenoids from the leaves of Cyclocarya paliurus

Cited by 26 publications

References 30 publications

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

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

Synthesis and biological evaluation of (20S,24R)-epoxy-dammarane-3β,12β,25-triol derivatives as α-glucosidase and PTP1B inhibitors

Progress in Research on the Alleviation of Glucose Metabolism Disorders in Type 2 Diabetes Using Cyclocarya paliurus

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