cinidon-ethyl and procyanidin

Lotus seedpod oligomeric procyanidins (LSOPC) are potent inhibitors of advanced glycation end products (AGEs), whose gastrointestinal susceptibility to degradation limits their use in vivo. In this study, carboxymethyl chitosan-lotus seedpod oligomeric procyanidin nanoparticles (CMC-LSOPC NPs) were constructed with a binding ratio of 1:6.51. CMC-LSOPC NPs significantly inhibited the release of AGEs from glycated casein (G-CS) during digestion, increasing the inhibition rate by 25.76% in the gastric phase and by 14.33% in the intestinal phase compared with LSOPC alone. To further investigate the inhibition mechanism, fluorescence microscopy, scanning electron microscopy and FTIR were used to find that CMC-LSOPC NPs could form cohesions to encapsulate G-CS in the gastric phase and hinder G-CS hydrolysis. In the intestinal phase, LSOPC was targeted for release and bound to trypsin through hydrophobic interactions and hydrogen bonding, resulting in protein peptide chain rearrangement, changes in secondary structure and significant reduction in trypsin activity. In addition, CMC-LSOPC NPs increased the antioxidant capacity of digestive fluid and could reduce the oxidative stress in the gastrointestinal tract caused by the release of AGEs. It's the first time that CMC-LSOPC NPs were constructed to enhance the stability of LSOPC during digestion and explain the mechanism by which CMC-LSOPC NPs inhibit the release of AGEs from G-CS in both stomach and intestine. This finding will present a novel approach for reducing AGEs during gastrointestinal digestion.

Topics: Caseins; Chitosan; Dietary Advanced Glycation End Products; Digestion; Lotus; Nanoparticles; Proanthocyanidins; Seeds; Trypsin

Glycation of protein results in the formation of advanced glycation end-products (AGEs), which are further absorbed by the body through digestion in the gastrointestinal tract. The inhibitory properties of procyanidin for the release of AGEs from glycated proteins are of great significance in promoting, accelerating or stabilizing gastrointestinal folding intermediates, although the mechanism of action remains unclear. With the background of dairy processing, the study investigated the inhibitory effect of lotus seedpod oligomeric procyanidins (LSOPC) and its three monomers on AGE release from glycated casein (G-CS) during gastrointestinal digestion. In gastrointestinal microenvironments, multispectral and microscopy analysis were used to investigate interaction mechanisms. Results showed that the binding force of the protein-procyanidin complexes were hydrogen bonding and hydrophobic interaction and LSOPC leaded the G-CS secondary structure transformations furtherly. In the gastric environment, all monomers displayed stronger binding to pepsin but in the intestinal environment, results were opposite. Molecular docking showed that procyanidins were bound in the internal cavity of G-CS, pepsin and pancreatin, thereby forming a relatively stable binding conformation. Moreover, procyanidins enhanced the antioxidant capacity of G-CS, which could attenuate postprandial oxidative stress in the gastrointestinal tract caused by the release of AGEs. Together, this study improves our understanding of dietary AGEs during gastrointestinal digestion.

Topics: Biflavonoids; Caseins; Catechin; Digestion; Lotus; Molecular Docking Simulation; Proanthocyanidins; Seeds

To solve the potential problem of hindered β-galactosidase activity by procyanidins, carboxymethylated Pachyman (CMP), a negatively-charged carboxymethylated (1 → 3)-β-d-glucan, was applied to mitigate inhibition by procyanidins. The mechanisms underlying this effect were explored through enzyme kinetic analysis, fluorescence quenching assays, circular dichroism, and molecular docking studies. The results indicated that the introduction of CMP could decrease the inhibition rate of high-concentration lotus seedpod oligomeric procyanidins (LSOPC) from 98.7 to 46.5%, and enabled low-concentration LSOPC to activate β-galactosidase in vitro and in vivo. The competitive/noncompetitive inhibition constants, fluorescence quenching constants, and molecular docking results indicated that the mechanism of this effect might be CMP competing with β-galactosidase to bind procyanidins, resulting in restoration of the catalytic centre and key active site of procyanidin-bound lactase. Additionally, it was affected by procyanidin-CMP noncovalent interactions. This study illustrates a promising strategy for mitigating the anti-nutritional properties of procyanidins and activating β-galactosidase to promote intestinal health.

Topics: beta-Galactosidase; beta-Glucans; Biflavonoids; Catechin; Kinetics; Lotus; Methylation; Proanthocyanidins; Protein Binding

This study investigated the modulatory effects of lotus seedpod oligomeric procyanidins (LSOPC) on the advanced glycation endproducts (AGEs)-induced liver injury via advanced glycation end-product receptors (RAGE)-mitogen-activated protein kinases (MAPK)-nuclear factor-kappa B (NF-κB) signaling pathways in a mice model. To examine the antioxidation properties of LSOPC, a model of high-AGEs-diet were established using Sprague Dawley (SD) male mice fed with a normal AIN-93G diet, a high AGEs diet (H), or H plus 0.5 or 0.2% (w/w) LSOPC for 12 weeks. Our results showed that LSOPC inhibited the AGEs formation and alleviated AGEs-induced liver injury by suppressing the nuclear translocation of NF-κB and activation of the MAPK signaling pathway. Additionally, LSOPC inhibited the genes expression of tumor necrosis factor-α (TNF-α) and interleukin 6 (IL-6). Taken together, LSOPC treatment potentially inhibited the AGEs formation and modulated liver injury with long-term dietary AGEs by suppressing RAGE-MAPK-NF-κB pathways.

Topics: Animals; Biflavonoids; Catechin; Diet; Glycation End Products, Advanced; Lotus; Mice; NF-kappa B; Proanthocyanidins; Receptor for Advanced Glycation End Products; Seeds; Signal Transduction

The potential protective effect of nanoliposomes loaded with lotus seedpod oligomeric procyanidin (LSOPC) against melanogenesis and skin damaging was investigated. Fluorescence spectroscopy showed that, after encapsulation, the LSOPC-nanoliposomes still possessed strong inhibitory effects against melanogenesis, reducing the activity of both monophenolase and diphenolase. Molecular docking indicated that LSOPC could generate intense interactive configuration with tyrosinase through arene-H, arene-arene, and hydrophobic interaction. An ultraviolet radiated cell-culture model (human foreskin fibroblast cell (HFF-1)) was used to determine the protective effects of the LSOPC-nanoliposomes against skin aging and damage. Results showed that LSOPC-nanoliposomes exerted the highest protective effects against both ultraviolet B (UVB) and ultraviolet A (UVA) irradiation groups compared with non-encapsulated LSOPC and a control (vitamin C). Superoxide dismutase (SOD) and malonaldehyde (MDA) assays demonstrated the protection mechanism may be related to the anti-photooxidation activity of the procyanidin. Furthermore, a hydroxyproline assay suggested that the LSOPC-nanoliposomes had a strong protective effect against collagen degradation and/or synthesis after UVA irradiation.

Topics: Ascorbic Acid; Biflavonoids; Catechin; Cell Line; Humans; Liposomes; Lotus; Malondialdehyde; Proanthocyanidins; Skin; Superoxide Dismutase; Ultraviolet Rays

Lotus seed epicarp, the main by-product of lotus seed processing, is abundant in polyphenols. In this study, polyphenols in lotus seed epicarp were separated by Sephadex LH-20 gel filtration chromatography to yield Fraction-I (F-I), Fraction-II (F-II), and Fraction-III (F-III). The polyphenol compounds in the three fractions were identified by UPLC-MI-TOF-MS. Six kinds of polyphenol compounds including cyanidin-3-

Topics: Anthocyanins; Antioxidants; Biflavonoids; Catechin; Chromatography, High Pressure Liquid; Glucosides; Lotus; Plant Extracts; Polyphenols; Proanthocyanidins; Seeds

Dietary polyphenols have shown hypolipidemic effects by reducing triglyceride absorption. The mechanisms may involve modifying fat emulsion during digestion in the gastrointestinal tract and suppressing lipase during hydrolysis in the small intestine. In an in vivo study, lotus seedpod oligomeric procyanidin (LSOPC) decreased total serum triglyceride and total cholesterol and elevated the high-density lipoprotein level in the hyperlipidemic rat model. In addition, LSOPC suppressed de novo lipogenesis-related gene expressions. In an in vitro study, the LSOPC-enriched emulsion decreased the mean droplet size from 0.36 to 0.33 μm and increased the viscosity of the emulsion. Moreover, the LSOPC-enriched emulsion improved the antioxidant properties. A digestion model was developed and showed that the particle size of the LSOPC-enriched emulsion increased in the oral cavity. However, an increase and then a significant drop of the particle size was measured in the stomach and small intestine. The free fatty acid release rate was decreased in the LSOPC-enriched emulsion partly ascribed to the inhibition of lipase by LSOPC.

Topics: Animals; Biflavonoids; Catechin; Digestion; Emulsions; Fats; Gastric Mucosa; Homeostasis; Humans; Hyperlipidemias; Intestinal Mucosa; Intestines; Lipid Metabolism; Lotus; Male; Mice; Mice, Inbred ICR; Particle Size; Plant Extracts; Proanthocyanidins; Rats; Rats, Sprague-Dawley; Seeds

This study investigated the protective properties of lotus seedpod oligomeric procyanidins (LSOPC) against nonalcoholic fatty liver disease (NAFLD) and its underlying mechanism. Sprague-Dawley (SD) male rats were fed a basic diet, a high-fat diet (HFD), or HFD plus 0.2 or 0.5% (w/w) LSOPC for 12 weeks. Administration of LSOPC markedly reduced serum and hepatic biochemical parameters and protein expression of advanced glycation endproducts (AGEs). Additionally, 0.5% (w/w) LSOPC treatment remarkably reversed the increasing tendency of receptor of advanced glycation endproduct (RAGE) to normal level. Furthermore, dietary LSOPC significantly decreased the protein levels of mitogen-activated protein kinases (MAPK) and nuclear factor-kappa B (NF-κB) and down-regulated genes involved in pro-inflammatory cytokines and adhesion molecules. Taken together, these findings demonstrate that LSOPC may protect obese rats with long-term HFD-induced NAFLD against RAGE-MAPK-NF-κB signaling suppression.

Topics: Animals; Biflavonoids; Catechin; Diet, High-Fat; Glycation End Products, Advanced; Humans; Lotus; Male; Mitogen-Activated Protein Kinases; NF-kappa B; Non-alcoholic Fatty Liver Disease; Plant Extracts; Proanthocyanidins; Rats; Rats, Sprague-Dawley; Receptor for Advanced Glycation End Products; Seeds; Signal Transduction

Lotus seedpod procyanidins (LSPCs) could effectively prevent learning and memory damage and oxidative damage caused by extremely low frequency electromagnetic field (ELF-EMF) exposure. However, LSPCs protect neurons from ELF-EMF-induced damage by mechanisms currently not clear. An excessive release of glutamate is considered to be one of the molecular mechanisms of neuronal damage in several neurological diseases. In this study we determined whether the ELF-EMF (50 Hz, 8 mT, 28 days) exposure induced alterations of glutamate release in mice hippocampus and explored the possible mechanism, and if LSPC treatment normalized its alterations. The results showed that ELF-EMF exposure induced the increased contents of glutamate, GABA, excessively activated NMDA receptors, increasing the number of NMDA receptor 2B (NR2B) and intracellular Ca(2+) concentration [Ca(2+)]i in hippocampus. In addition, ELF-EMF exposure decreased the ERK1/2 and CREB phosphorylation, which suggested that the Ca(2+) influx induced by the ELF-EMF exposure stimulated activity of the ERK, in turn, influences the expression of downstream proteins in this signaling pathway. Besides, ELF-EMF exposure also increased JNK1/2 phosphorylation through the activated ASK1, which plays a pivotal role in hippocampal neuronal cell death. However, oral administration of LSPCs (especially 60 and 90 mg kg(-1)) markedly improved expressions of p-CREB, p-ERK1/2 and p-JNK1/2, accompanied by decreased levels of glutamate, GABA, [Ca(2+)]i and NR2B. Thus, the results from the present study suggest that p-ERK1/2, p-JNK1/2, [Ca(2+)]i and p-CREB expression normalized, possibly via a NMDA receptor-channel through the changes of GABA, glutamate and NR2B, which might be responsible for the neuroprotective or memory enhancing effects of LSPCs.

Topics: Animals; Biflavonoids; Catechin; Cognition Disorders; CREB-Binding Protein; Glutamic Acid; Hippocampus; Humans; Lotus; Male; MAP Kinase Signaling System; Mice; Mice, Inbred ICR; Phosphorylation; Plant Extracts; Proanthocyanidins

Several lines of evidence suggested that B-type procyanidin oligomers from lotus seedpod (LSOPC) may effectively modulate the formation of advanced glycation end products (AGEs). In vivo, LSOPC is metabolized by intestinal flora to become various kinds of phenolic compounds that possess potent antioxidant activities. However, few reports of the absorption and metabolism of LSOPC have been revealed. In the present study, rats were orally administered with LSOPC at a dose of 300 mg/kg body weight. The metabolites of LSOPC in urine were elucidated by HPLC-MS/MS analysis 24 h post-administration. Eight major metabolites were significantly increased by the administration of 300 mg/kg of LSOPC (p < 0.01). The anti-glycative activity of LSOPC and its metabolites were investigated. The results showed that LSOPC and catechin had greater anti-glycative activities than other metabolites, which were positively correlated to their carbonyl scavenging activities and antioxidant capacities.

Topics: Animals; Antioxidants; Biflavonoids; Catechin; Chromatography, High Pressure Liquid; Glycation End Products, Advanced; Inhibitory Concentration 50; Lotus; Male; Phenols; Plant Extracts; Proanthocyanidins; Rats; Rats, Sprague-Dawley; Seeds; Tandem Mass Spectrometry

The butanol-HCl spectrophotometric assay is widely used for quantifying extractable and insoluble condensed tannins (CT, syn. proanthocyanidins) in foods, feeds, and foliage of herbaceous and woody plants, but the method underestimates total CT content when applied directly to plant material. To improve CT quantitation, we tested various cosolvents with butanol-HCl and found that acetone increased anthocyanidin yields from two forage Lotus species having contrasting procyanidin and prodelphinidin compositions. A butanol-HCl-iron assay run with 50% (v/v) acetone gave linear responses with Lotus CT standards and increased estimates of total CT in Lotus herbage and leaves by up to 3.2-fold over the conventional method run without acetone. The use of thiolysis to determine the purity of CT standards further improved quantitation. Gel-state (13)C and (1)H-(13)C HSQC NMR spectra of insoluble residues collected after butanol-HCl assays revealed that acetone increased anthocyanidin yields by facilitating complete solubilization of CT from tissue.

Topics: Anthocyanins; Biflavonoids; Catechin; Chemical Fractionation; Chemistry Techniques, Analytical; Lotus; Plant Extracts; Proanthocyanidins

To study the protective effect of procyanidins from the seedpod of the lotus (LSPC) on myocardial ischemia and reperfusion in rats.. Myocardial injury model was made by ligating the coronary artery for 30 min followed by reperfusion for 45 min in anesthetized rat and 30 min of ischemia followed by 30 min of reperfusion in the isolated rat heart. All animals were given the medicine or normal saline before the experiment. ET, Ang I, Ang II in the serum, the MDA content, SOD activity, NO level, the recovery rate of coronary flow (CF) and heart rate (HR) after reperfusion and CK, XO from the myocardial cells were observed.. LSPC was shown to inhibit the release of ET, Ang II (P < 0.05) , and the increase of MDA content (P < 0.05). It was also found to increase the SOD activity (P < 0.05) and NO level (P < 0.01). LSPC was found to increase the recovery rate of the coronary flow (CF) and heart rate (HR) after reperfusion (P < 0.05 or P < 0.01), decrease the release of CK from the myocardial cells (P < 0.01), depress the XO activity of myocardial tissue (P < 0.05), as well as improve the myocyte ultrastructural pathological injury.. The anti-ischemia effect of LSPC was related to the mechanism of scavenging the oxygen free radicals directly, cutting off the source of free radicals, reducing tissue peroxidation, stabilizing the cells membrane, depressing the production of EDCF and increasing the NO level as well.

Topics: Animals; Biflavonoids; Cardiotonic Agents; Catechin; Coronary Circulation; Lotus; Male; Myocardial Ischemia; Myocardial Reperfusion Injury; Myocardium; Proanthocyanidins; Rats; Rats, Wistar