The Gastrointestinal Tract Metabolism and Pharmacological Activities of Grosvenorine, a Major and Characteristic Flavonoid in the Fruits of <i>Siraitia grosvenorii</i>

Wang, Mengyue; Xing, Shihua; Luu, Thithanhthuy; Fan, Min; Li, Xiaobo

doi:10.1002/cbdv.201400397

Cited by 18 publications

(8 citation statements)

References 19 publications

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“…[ 44 ] and others. The kaempferol diglycoside is often accompanied by α-rhamnoisorobin (aRh), afzelin and kaempferol that may be the degradation products, resultant of hydrolysis of the Krg molecule [ 47 , 50 ]. The most known pharmacological activity of Krg is its hypoglycemic effect [ 48 , 51 , 52 ].…”

Section: Discussionmentioning

confidence: 99%

Neuroprotective Properties of Kempferol Derivatives from Maesa membranacea against Oxidative Stress-Induced Cell Damage: An Association with Cathepsin D Inhibition and PI3K/Akt Activation

Jantas

Malarz

et al. 2021

IJMS

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As components of the human diet with potential health benefits, flavonols are the subject of numerous studies, confirming their antioxidant, free radical scavenging and anti-inflammatory activity. Taking into consideration the postulated pathogenesis of certain CNS dysfunctions characterized by neuronal degradation, flavonols may prevent the decay of neurons in multiple pathways. Leaves of Maesa membranacea yielded several flavonol glycosides including α-rhamnoisorobin (kaempferol 7-O-α-rhamnoside) and kaempferitrin (kaempferol 3,7-di-O-α-rhamnoside). The latter compound was a major constituent of the investigated plant material. Neuroprotective effects of kaempferitrin and α-rhamnoisorobin were tested in vitro using H2O2-, 6-OHDA- and doxorubicin-induced models of SH-SY5Y cell damage. Both undifferentiated and differentiated neuroblastoma cells were used in the experiments. α-Rhamnoisorobin at a concentration range of 1–10 µM demonstrated cytoprotective effects against H2O2-induced cell damage. The compound (at 1–10 µM) was also effective in attenuating 6-OHDA-induced neurotoxicity. In both H2O2- and 6-OHDA-induced cell damage, kaempferitrin, similar to isoquercitrin, demonstrated neuroprotective activity at the highest of the tested concentrations (50 µM). The tested flavonols were not effective in counteracting doxorubicin-induced cytotoxicity. Their caspase-3- and cathepsin D-inhibitory activities appeared to be structure dependent. Inhibition of the PI3-K/Akt pathway abolished the neuroprotective effect of the investigated flavonols.

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Section: Discussionmentioning

confidence: 99%

Neuroprotective Properties of Kempferol Derivatives from Maesa membranacea against Oxidative Stress-Induced Cell Damage: An Association with Cathepsin D Inhibition and PI3K/Akt Activation

Jantas

Malarz

et al. 2021

IJMS

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“…Compound 1 : yellowish powder; UV at 264 nm and 342 nm; its molecular formula C 33 H 40 O 19 was determined according to the high resolution ESI–MS molecular ion at m/z 741.2246 [M+H] + ; 1 H NMR (DMSO‐ d , 500 Mz) δ: 12.61 (1H, s, OH‐5), 10.91 (1H, s, OH‐4′), 7.81 (2H, d, J = 8.5 Hz, H‐2′, 6′), 6.93 (2H, d, J = 8.5 Hz, H‐3′, 5′), 6.82 (1H, s, H‐8), 6.49 (1H, s, H‐6); 3‐Rha: 5.31 (1H, s, H‐1′′), 4.00 (1H, s, H‐2′′), 3.48∼3.49 (1H, m, H‐3′′), 3.15∼3.16 (2H, m, H‐4′′, 5′′), 0.81 (3H, s, H‐6′′); 7‐Rha: 5.91 (1H, s, H‐1′′′), 3.95 (1H, s, H‐2′′′), 3.68 (1H, m, H‐3′′′), 3.29∼3.31 (1H, m, H‐4′′′), 3.38∼3.39 (1H, m, H‐5′′′), 1.15 (3H, d, J = 6.0 Hz H‐6′′′); 7‐Glu: 4.39 (1H, d, J = 7.0 Hz, H‐1′′′′), 3.07∼3.09 (2H, m, Ha‐2′′′′, H‐4′′′′), 3.16∼3.18 (2H, m, H‐3′′′′, 5′′′′), 3.48∼3.51 (1H, m, Ha‐6′′′′), 3.67 (1H, m, Hb‐6′′′′). Compound 1 was identified as grosvenorine (kaempferol 3‐ O ‐rhamno‐7 ‐O ‐rhamno‐glucoside) .…”

Section: Resultsmentioning

confidence: 99%

Systematic characterization of flavonoids from Siraitia grosvenorii leaf extract using an integrated strategy of high‐speed counter‐current chromatography combined with ultra high performance liquid chromatography and electrospray ionization quadrupole time‐of‐flight mass spectrometry

Lü

Zhu

et al. 2020

J of Separation Science

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The chemical constituents of the Siraitia grosvenorii leaf extract were studied. Firstly, high‐speed counter‐current chromatography was applied to the one‐step separation of four compounds from S. grosvenorii leaf extract with the solvent system composed of 0.01% acetic acid water/n‐butanol/n‐hexane/methanol (5:3:1:1, v/v/v/v). In this work, 270 mg of crude sample yielded four compounds, a new kaempferol O‐glycoside derivative, kaempferol 3‐O‐α‐L‐[4‐O‐(4‐carboxy‐3‐hydroxy‐3‐methylbutanoyl)]‐rhamnopyranoside‐7‐O‐α‐L‐rhamnopyranoside, named kaempferitrin A (2.1 mg, 90%), and three known compounds, grosvenorine (3.4 mg, 93%), kaempferitrin (14.4 mg, 99%) and afzelin (4 mg, 98%), and the structures of these compounds were identified by NMR spectroscopy and mass spectrometry. Then, ultra high performance liquid chromatography with electrospray ionization quadrupole time‐of‐flight mass spectrometry was used to illustrate the dominant flavonoids in S. grosvenorii leaf extract. 34 flavonoids including 19 kaempferol O‐glycosides, 4 quercetin O‐glycosides, 6 flavanone derivatives, and 5 polymethoxyflavones, were accurately or tentatively identified by carefully comparing their retention times, UV data, precise masses, the typical fragments of the standards and literature data. Most of these compounds were reported for the first time. This study establishes a foundation for the further development and utilization of S. grosvenorii leaves in future.

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“…The mixture of mogrosides is 300 times sweeter than sucrose ( 14 ), but only mogrosides with mogrol aglycone and with more than three sugar moieties possess the sweet taste ( 15 , 16 ). Flavonoids are also important compounds in monk fruit and exert antibacterial and antioxidant effects ( 17 ). In addition, there are various sugars found in monk fruit.…”

Section: Introductionmentioning

confidence: 99%

Chemical Comparison of Monk Fruit Products Processed by Different Drying Methods Using High-Performance Thin-Layer Chromatography Combined With Chemometric Analysis

Hong

Yang

et al. 2022

Front. Nutr.

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Monk fruit, also named Luo Han Guo, is the fruit of Siraitia grosvenorii (Swingle) C. Jeffrey ex A. M. Lu et Z. Y. Zhang and has been used as both food and traditional Chinese medicine. Due to preservation concerns, monk fruit is usually processed by hot-air drying or using low-temperature techniques after harvest. In this study, high-performance thin-layer chromatography (HPTLC) method was developed for the analysis of 13 mogrosides, 1 flavonoid, and 3 sugars in monk fruit products. Then chemometric analysis was applied to investigate the chemical characteristics in the samples dried by different methods. The results showed that the contents of mogroside V, 11-oxo-mogroside V, isomogroside V, and sucrose in monk fruits dried at low temperature were much higher than those in traditional hot-air drying samples, which was also confirmed by HPTLC-scanning. These findings indicate that HPTLC combined with chemometric analysis provides a reliable tool to understand the chemical differences between the monk fruit products processed by different drying methods, which will be helpful for their quality evaluation.

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The Gastrointestinal Tract Metabolism and Pharmacological Activities of Grosvenorine, a Major and Characteristic Flavonoid in the Fruits of Siraitia grosvenorii

Cited by 18 publications

References 19 publications

Neuroprotective Properties of Kempferol Derivatives from Maesa membranacea against Oxidative Stress-Induced Cell Damage: An Association with Cathepsin D Inhibition and PI3K/Akt Activation

Neuroprotective Properties of Kempferol Derivatives from Maesa membranacea against Oxidative Stress-Induced Cell Damage: An Association with Cathepsin D Inhibition and PI3K/Akt Activation

Systematic characterization of flavonoids from Siraitia grosvenorii leaf extract using an integrated strategy of high‐speed counter‐current chromatography combined with ultra high performance liquid chromatography and electrospray ionization quadrupole time‐of‐flight mass spectrometry

Chemical Comparison of Monk Fruit Products Processed by Different Drying Methods Using High-Performance Thin-Layer Chromatography Combined With Chemometric Analysis

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