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Animal studies and clinical trials have shown that dietary polyphenols and polyphenol-rich foods can reduce the risk of type 2 diabetes (T2D) and its complications, but how diabetes regulates the metabolism of polyphenol has not been fully elucidated. This study investigated the effects of diabetes on litchi pericarp oligomeric procyanidin (LPOPC) dynamic metabolism and its major static metabolites in urine. First, a high-fat and streptozotocin (STZ)-induced diabetic Sprague Dawley (SD) rat model was established. In the diabetic rat model, elevated fasting blood glucose, severely impaired glucose tolerance test, and increased reactive oxygen species (ROS) levels in serum and the liver were observed. Subsequently, 200 mg per kg body weight of LPOPC was administrated to control and diabetic SD rats, and the gastrointestinal tract was collected at 0.5 h, 1 h, 3 h, and 6 h. The results showed that the retention time of LPOPC was not changed in our diabetic rat model. However, the gut microbiota were significantly altered, with elevated Proteobacteria and Verrucomicrobia abundance in diabetic rats and decreased short chain fatty acid (SCFA)-producing bacteria. Interestingly, after one dose of 300 mg per kg body weight LPOPC, the total antioxidant capacity of urine in diabetic rats significantly decreased. We then tested the static metabolites of LPOPC, demonstrating that epicatechin had not changed in urine in diabetic rats, but that shikimic acid was significantly reduced in urine in diabetic rats. The changes in shikimic acid may be due to the alteration of gut microbiota and elevated ROS levels in serum.

It has been proven that A-type procyanidins, containing an additional ether bond, compared to B-type procyanidins are also bioavailable in vitro and in vivo. However, their bioavailability and absorption in the gastrointestinal tract remain uncertain. In this study, a model of the human adenocarcinoma stomach cell line (MKN-28) was established to explore the cellular transport of flavanolic monomers and procyanidin dimer A2, which were isolated from the litchi pericarp extract. After the integrity and permeability of the cell monolayer were ensured by measurement of the transepithelial electrical resistance and the apparent permeability coefficient for Lucifer yellow, the transportation of procyanidins A2 and B2, (-)-epicatechin (EC), and (+)-catechin (CC) was studied at pH 3.0, 5.0, or 7.0 in the apical side, with compound concentrations of 0.05 and 0.1 mg/mL based on the cytotoxicity test. High-performance liquid chromatography and liquid chromatography-mass spectrometry analyses indicated that EC, CC, and A2 were transported in the MKN-28 cell line from 30 to 180 min, while B2 showed no transport. The maximal transport efficiencies of EC, CC, and A2 were 23 ± 0.81, 13.16 ± 1.53, and 16.41 ± 1.36%, respectively, existing at 120, 180, and 120 min of transportation. Laser scanning confocal microscopy analysis presented the dynamic transmission of EC, in accordance with the result of concentration determination, suggesting that the A-type procyanidins are possibly absorbed through the stomach barrier, which is pH- and time-dependent.

Extraction with organic solvents is a traditional method to isolate bioactive compounds, which is energy-wasting and time-consuming. Therefore, enzyme and ultrasound treatments were combined to assist the extraction of oligomeric procyanidins from litchi pericarp (LPOPC), as an innovative approach to replace conventional extraction methods. Under optimum conditions (enzyme concentration 0.12 mg/mL, ultrasonic power 300 W, ultrasonic time 80 min, and liquid/solid ratio 10 mL/g), the yield of LPOPC could be improved up to 13.5%. HPLC analysis indicated that the oligomeric procyanidins (OPC) content of LPOPC from proposed extraction was up to 89.6%, mainly including (-)-epicatechin, procyanidin A1, A2, and A-type procyanidin trimer. Moreover, LPOPC powder was added in baked food to inhibit the lipid peroxidation. It was found that 0.2% ( w/w ) of LPOPC could maintain the quality of cookies in the first 7 days, by decreasing the peroxide values. The procyanidin dimers and trimers in LPOPC played more important roles as antioxidants compared to monomers during storage. The results also showed that the combined extraction process can be considered as a useful and efficient method for the extraction of functional components from other plant sources.

Litchi pericarp procyanidins (LPP) are dietary supplements with high antioxidant activity, but poor oral bioavailability and efficacy. Lactobacillus casei (L. casei-01) can transform flavan-3-ols from litchi pericarp and increase their antioxidant ability; thus, L. casei-01 with LPP was administered to rats for four and eight weeks to study the effect of such a combination on metabolic parameters and on phase II metabolism and detoxification pathways in the liver as an indirect measure for phenolic bioavailability. Our data indicated that the T-AOC of the plasma, the liver GSH-Px and GSH-ST activity, and the expression of UGT and SULT isoforms in the liver of the rats were all enhanced after the eight-week administration compared with those of the control. However, at 1 h after administration the concentration of (-)-epicatechin in the combined system was lower than that obtained after the ingestion of LPP alone, suggesting that L. casei-01 enhances the bioavailability of phenolics from LPP by modulating the transformation to other compounds but not by increasing its absorption in the native form.

The bioavailability of A-type procyanidins in vivo has been rarely investigated; as such, this study discusses the effect of A-type linkage and degree of polymerization on the metabolism of procyanidins extracted from litchi pericarp (LPOPC). Sprague-Dawley rats were gavaged with (-)-epicatechin (EC) and LPOPC and sacrificed at different time points after ingestion. A-type linkage procyanidin oligomers inhibited the absorption of EC. Analysis of urinary contents from rats administered with EC, A-type procyanidin dimer (A-2), and A-type procyanidin trimer (A-3) showed distinct native and metabolite profiles for each rat. Rats fed with A-2 and A-3 presented significantly higher levels of shikimic acid and less amount of m(p)-coumaric acid metabolites in vivo and provide insight into the quantitative structure-activity relationship of procyanidin oligomers during metabolism, indicating that procyanidins with A-type linkage could induce an altered metabolic pathway of oligomers in the gastrointestinal system.

The main purpose of this study is to characterize and prepare A-type oligomeric procyanidins from litchi pericarp (Litchi chinensis Baila). The variety of oligomeric procyanidins was characterized by LC-ESI-MS analysis. There were (+)-catechin, (-)-epicatechin, twelve dimers and six trimers of procyanidins were found in litchi pericarp extracts, and A-type procyanidins were much more abundant than B-type procyanidins. The main flavan-3-ol monomer and oligomeric procyanidins in litchi pericarp were (-)-epicatechin, A-type dimers (A1 and A2) and trimer (epicatechin-(4β-8, 2β-O-7)-epicatechin- (4β-8)-epicatechin). Procyanidin A1 (epicatechin-(4β-8, 2β-O-7)-catechin) was identified by NMR in litchi pericarp for the first time. (-)-Epicatechin and oligomeric procyanidins were prepared by the combination of AB-8 column chromatography and Toyopearl HW-40S column chromatography. The results showed that each fraction predominantly owned a single compound and gave a high yield with (-)-epicatechin, A-type dimers (A1 and A2) and trimer, suggesting a useful method to obtain pure (-)-epicatechin and A-type oligomeric procyanidins., (Copyright © 2016. Published by Elsevier B.V.)

Intervention studies with A-type oligomeric procyanidins from litchi (Litchi chinensis) pericarp (LPOPC) suggested its protective effect against cardiovascular diseases. However, there is no consensus on the absorption and metabolism of LPOPC. It was demonstrated that the main components in LPOPC were (-)-epicatechin, A-type procyanidin dimers, trimers and tetramers. Rats were orally administered different levels of LPOPC (150 and 300 mg/kgbw), the procyanidins and their microbial metabolites in urine were identified by HPLC-MS/MS analysis 18 h post-administration. Data indicated that seven aromatic acid metabolites excreted were significantly increased by 300 mg/kgbw of LPOPC (P<0.01). However, only (-)-epicatechin and its methylated derivatives were detected in rat plasma 1h after 300 mg/kgbw of LPOPC administration. The total EC content absorbed in plasma was only 2.54 ± 0.53 μmol/L, indicating that the biological properties of LPOPC should be probably explained by its microbial degraded phenolic acids., (Copyright © 2012 Elsevier Ltd. All rights reserved.)

Litchi chinensis pericarp from litchi processing waste is an important plant source of A-type procyanidins, which were considered a natural dietary supplement because of their high biological activity in vivo. Litchi pericarp oligomeric procyanidins (LPOPCs) did not selectively modify the growth of Streptococcus thermophilus and Lactobacillus casei -01 at concentrations of 0.25 and 0.5 mg/mL, and it was demonstrated that the two strains could transform procyanidins during their log period of growth by two different pathways. S. thermophilus was able to metabolize procyanidin A2 to its isomer, and L. casei could decompose flavan-3-ols into 3,4-hydroxyphenylacetic acid, 4-hydroxyphenylpropionic acid, m-coumaric acid, and p-coumaric acid. The total antioxidant capability (T-AOC) of LPOPCs before and after microbial incubation was estimated, and the results suggested that probiotic bacteria bioconversion is a feasible and efficient method to convert litchi pericarp procyanidins to a more effective antioxidant agent.

Theoretically, lactic acid bacteria (LABs) could degrade polyphenols into small molecular compounds. In this study, the biotransformation of lotus seedpod and litchi pericarp procyanidins by Lactobacillus plantarum 90 (Lp90), Streptococcus thermophilus 81 (ST81), Lactobacillus rhamnosus HN001 (HN001), and Pediococcus pentosus 06 (PP06) were analysed. The growth curve results indicated that procyanidins did not significantly inhibit the proliferation of LABs. Ultra-high-performance liquid chromatography high-resolution mass spectrometry (UPLC–HRMS) revealed that procyanidin B2 and procyanidin B3 in lotus seedpod decreased by 62.85% and 25.45%, respectively, with ST81 metabolised, while kaempferol and syringetin 3-O-glucoside content increased. Although bioconversion did not increase the inhibitory function of procyanidins against glycosylation end-products in vitro, the 2,2′-Azinobis-(3-ethylbenzthiazoline-6-sulphonate) free radical scavenging capacity and ferric reducing antioxidant power of litchi pericarp procyanidins increased by 157.34% and 6.8%, respectively, after ST81 biotransformation. These findings may inspire further studies of biological metabolism of other polyphenols and their effects on biological activity. [ABSTRACT FROM AUTHOR]

The low stability of anthocyanins limits their use in industry, which can be surpassed by gliadins linkage. This work was aimed to study the anthocyanins-gliadins bonding properties. HPLC-DAD-ESI-MS2 analysis indicated that the main litchi pericarp anthocyanin (LPA) was cyanidin-3-glucoside-5-rhamnoside (C3G5R). Ultraviolet and fluorescence data revealed the presence of anthocyanin-protein complexes, with strong binding affinity by a combination of hydrogen bonds and van der Waals forces. The combination of C3G5R and gliadins changed its secondary structure. The scavenging effect of the anthocyanin-protein complex over 2,2-diphenyl-1-picrylhydrazyl was comparable to LPA alone. These results may broaden gluten usage to stabilize anthocyanins and so their use in the food, pharmaceutic, and cosmetic industries due to their potential use as colorants and antioxidants. [ABSTRACT FROM AUTHOR]

Litchi pericarp procyanidins (LPP), which were mainly A-types, inhibit cardiovascular disease in vivo significantly. In order to know the pharmacokinetics of LPP, procyanidin (PC) metabolites were examined in various organs of rats at different time points after LPP ingestion. Plasma, liver, kidneys, spleen, brain, together with gastrointestinal (GI) tract of rats were collected over a 24-h period. The PC metabolic product residuals were extracted and identified by HPLC-Trap-MS-MS and LC/Q-trap-MS analyses. According to the data, there were eight PC metabolites with glucuronide, sulfate, and methyl ethers detected, in which brain was the first target of (−)-epicatechin, A-type dimers, and trimer, reaching their maximum values at 0.5 h post-administration. Liver was the major organ for glucuronidated, sulfated, and methylated transform during PC metabolism. GI tract was the primary system to recover PCs. Furthermore, all the litchi pericarp flavan-3-ols and PCs were eliminated from the stomach and GI tract 24 h after administration. (−)-Epicatechin conjugates, which were detected in plasma and brain as the major PC metabolites, demonstrating that flavan-3-ols and their metabolic products can cross the blood-brain barrier. And the results were also considerably helpful for us to know that A-type PCs are bioavailable in body. [ABSTRACT FROM AUTHOR]