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procyanidins
FOOD RESEARCH INTERNATIONAL · 2024 · IF 7

Identification of procyanidins as α-glucosidase inhibitors, pancreatic lipase inhibitors, and antioxidants from the bark of Cinnamomum cassia by multi-bioactivity-labeled molecular networking

Jun Dai,Zihan Liu,Lei Ma,Chunliu Yang,Ligai Bai,Dandan Han,Qi Song,Hongyuan Yan,Zhiqiang Wang

This study examined the suppressive effects of 16 selected plant-based foods on α-glucosidase and pancreatic lipase and their antioxidant properties. Among these, the bark of Cinnamomum cassia (Cinnamon, WLN-FM 15) showed the highest inhibitory activity against α-glucosidase and the highest antioxidant activity. Additionally, WLN-FM 15 showed promising results in the other tests. To further identify the bioactive constituents of WLN-FM 15, a multi-bioactivity-labeled molecular networking approach was used through a combination of GNPS-based molecular networking, DPPH-HPLC, and affinity-based ultrafiltration-HPLC. A total of nine procyanidins were identified as antioxidants and inhibitors of α-glucosidase and pancreatic lipase in WLN-FM 15. Subsequently, procyanidins A1, A2, B1, and C1 were isolated, and their efficacy was confirmed through functional assays. In summary, WLN-FM 15 has the potential to serve as a functional food ingredient with the procyanidins as its bioactive constituents. These results also suggest that the multi-bioactivity-labeled molecular networking approach is reliable for identifying bioactive constituents in plant-based foods.

研究领域: 植物化学 · 食品科学 · 药理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Journal of Food Measurement and Characterization · 2022 ·Vol. 16 ·期 5 ·3618-3629 · IF 3.006

An alkaline-trigged and procyanidins-stabilized microparticle prepared by extruding the mixture of corn starch, zein and procyanidins

Song Jialin,Jiang Lijun,Qi Mingming,Li Xiaoyu,Li Ruihong,Ma Chengye,Chen Shanfeng,Li Hongjun,Zhang Dongliang

An alkaline-trigged release of microparticle was prepared. The microparticle was prepared by extruding the mixture of corn starch, zein and procyanidins, and the characteristics of microparticle were detected. The 90% of procyanidins was released at the beginning in pH9 buffer solution and decreased following the chasing time. Even under the extreme alkaline condition (pH 11), approximately 50% of procyanidins was detected after 2 days chasing. The microparticle prepared by extruding the mixture of corn starch and procyanidins (SP) and microparticle prepared by extruding the mixture of corn starch, zein and procyanidins (SZP) showed high antioxidant ability, and the SP displayed five times more ABTS·+ scavenging ratio than SZP. Both of them maintained the constant procyanidins release ratio of 60% and 15% in digestive juice, respectively. The change of morphology, disintegration of crystal and breakage of chemical bonds specified the relationship between procyanidins release and damage of microparticle structure. Graphical abstract

研究领域: 食品科学 · 生物化学
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FOOD CHEMISTRY · 2018 · IF 4.946

A semisynthetic approach for the simultaneous reaction of grape seed polymeric procyanidins with catechin and epicatechin to obtain oligomeric procyanidins in large scale

Ruifang Bai,Yan Cui,Lanxin Luo,Danbing Yuan,Zongmin Wei,Weichao Yu,Baoshan Sun

Polymeric procyanidins (PPCs) were the major constituents of procyanidins, while they have poor bioactivity. To better utilize PPCs, a semisynthetic approach for converting PPCs to oligomeric procyanidins (OPCs) was proposed. Grape seed PPCs were simultaneously reacted with catechin (C) and epicatechin (EC) under acid condition. Combining response surface methodology (RSM) and single-factor experiments, an optimized semisynthetic condition was confirmed with the ratio of PPCs with C and EC of 1:1:1, temperature of 40 °C, reaction time of 20 min and 0.1 M methanolic HCl. High-speed counter-current chromatography (HSCCC) was adopted to obtain three fractions from semisynthetic products and preparative-HPLC was used to isolate individual procyanidins. Thirteen B-type procyanidins including monomers, dimers and trimers were got with high yield of 0.8–17.8 mg from 200 mg semisynthetic products and high purity over 91%. The developed semisynthesis combined with separation method was efficient to obtain individual OPCs in preparative scale.

CAS / MDL: 108-73-6
研究领域: 植物化学 · 天然产物化学 · 药物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2017 · IF 2.329

Adsorption of procyanidins onto chitosan-modified porous rice starch

Suwei Jiang,Zhenyu Yu,Hailiang Hu,Jian Lv,Hualin Wang,Shaotong Jiang

Polyphenolic bioflavonoids are easily oxidized when exposed to oxygen during the processing or storage. This research developed a porous chitosan-modified starch for the adsorption of procyanidins . The modified starch was fabricated by a facile surface modification of chitosan on porous rice starch. Besides the investigation of the morphologies and structures of starches, the adsorption kinetics of procyanidins onto starches was evaluated. The modified starch was mesoporous with a relative moderate specific surface area at 1.13 ± 0.05 m 2 /g, and the interactions between starch and chitosan were intermolecular hydrogen bonds. The modification of chitosan resulted in the positive zeta potential of starch at pH 2-10. The enzymolysis reduced starch size slightly and induced a decrease in the apparent viscosity of starch suspension, while the modification of chitosan increased starch size and induced an increase in the apparent viscosity of the suspension. The adsorption capacity of the modified starch towards procyanidins was significantly improved and reached 96 ± 3% of the total amount of procyanidins, and the adsorption was chemisorption or strong surface complexation rather than mass transport. The results suggested that the porous chitosan-modified starch might be used as an efficient adsorbent for polyphenols.

研究领域: 食品科学 · 生物化学
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ADVANCED FUNCTIONAL MATERIALS · 2023 · IF 19

Procyanidins Boost the Neuroprotective Effect of Minocycline for Intracerebral Haemorrhage

Taoyang Yuan,Tianyou Wang,Jianhua Zhang,Shun Shi,Zhipeng Gu,Yiwen Li,Jianguo Xu

Poor prognosis is often expected after the treatment of intracerebral haemorrhage (ICH) when the approach lacks effective neuroprotective interventions. Minocycline (Mino) is a promising clinical neuroprotective candidate for acute ICH therapy that mainly inhibits activation of microglia/macrophages. However, to address iron neurotoxicity, ferroptosis, and oxidative stress-induced multiple neuroinjury mechanisms, the neuroprotective effect of minocycline still urgently needs to be enhanced. To address this issue, procyanidins (PACs), typical natural polyphenols, is used to improve the neuroprotective effect of Mino by constructing PACs-Mino nanoparticles (NPs) using 3-aminophenylboronic acid as the crosslinker. The yielding NPs possessed improved antioxidant and iron-removing capacities in vitro. More importantly, PACs-Mino NPs exerted excellent therapeutic effects on ICH, showing improved neuroprotective activity and resulting in neurobehavioral recovery, in an in vitro cellular model and an in vivo ICH rat model. This study can provide a general strategy that uses natural polyphenols to boost the performance of drugs for ICH treatment, and the results may be further extended to other injuries of the central nervous system, such as brain injury and spinal cord injury.

研究领域: 神经科学 · 药理学 · 纳米技术 · 神经病学
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BIO-MEDICAL MATERIALS AND ENGINEERING · 2015 · IF 1.091

Preparation of decellularized vascular matrix by co-crosslinking of procyanidins and glutaraldehyde

Wang Xiaotong,Ma Bing,Chang Jiang

BACKGROUND: Vascular extracellular matrices (vECMs) have shown potential for small-diameter blood vessel tissue engineering applications. However, problems such as chemical instability and easy calcification are still remained. Chemical crosslinking using crosslinkers such as glutaraldehyde (GA) can improve mechanical properties and proteolysis resistance of vECMs, but leads to calcification and cytotoxicity. Procyanidins (PC) can crosslink ECMs with anti-calcification property and cytocompatibility, but the mechanical properties and chemical stability are unsatisfactory. OBJECTIVE: A novel co-crosslinking technique using PC and GA was developed, which combines the advantages of both PC and GA for enhancing mechanical properties and stability of vECMs with reduced calcification and cytotoxicity. METHODS: Fresh carotid were decellularized and then crosslinked by PC and subsequent GA for 6 h respectively. The mechanical properties, dynamic release of PC, enzymatic degradation, calcification and cytotoxicity of crosslinked samples were evaluated. RESULTS: The co-crosslinked vECMs showed enhanced tensile strength, chemical and biological stability, comparable anti-calcification property as compared to pure PC-crosslinked samples. Cytotoxicity assay showed that the co-crosslinked vECMs were cytocompatible for supporting the adhesion and proliferation of HUVECs. CONCLUSIONS: Co-crosslinking with PC and GA might be a useful method for preparation of vECM scaffolds with potential applications in small-diameter blood vessel tissue engineering.

研究领域: 组织工程 · 生物材料科学 · 生物医学工程
✓ 已验证 DOI PubMed 高影响因子
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Acta Biomaterialia · 2015 · IF 6.025

Procyanidins-crosslinked aortic elastin scaffolds with distinctive anti-calcification and biological properties

Xiaoya Wang,Wanyin Zhai,Chengtie Wu,Bing Ma,Jiamin Zhang,Hongfeng Zhang,Ziyan Zhu,Jiang Chang

Elastin , a main component of decellularized extracellular matrices and elastin-containing materials, has been used for tissue engineering applications due to their excellent biocompatibility. However, elastin is easily calcified, leading to the decrease of life span for elastin-based substitutes. How to inhibit the calcification of elastin-based scaffolds, but maintain their good biocompatibility, still remains significantly challenging. Procyanidins (PC) are a type of natural polyphenols with crosslinking ability. To investigate whether pure elastin could be crosslinked by PC with anti-calcification effect, PC was first used to crosslink aortic elastin. Results show that PC can crosslink elastin and effectively inhibit elastin-initiated calcification. Further experiments reveal the possible mechanisms for the anti-calcification of PC crosslinking including (1) inhibiting inflammation cell attachment , and secretion of inflammatory factors such as MMPs and TNF-α, (2) preventing elastin degradation by elastase , and (3) direct inhibition of mineral nucleation in elastin. Moreover, the PC-crosslinked aortic elastin maintains natural structure with high pore volume (1111   μL/g), large pore size (10–300   μm) and high porosity (75.1%) which facilitates recellularization of scaffolds in vivo , and displays excellent hemocompatibility, anti-thrombus and anti-inflammatory potential. The advantages of PC-crosslinked porous aortic elastin suggested that it can serve as a promising scaffold for tissue engineering .

研究领域: 生物材料 · 组织工程 · 生物医学工程
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES · 2016 · IF 2.687

Preparative separation of cacao bean procyanidins by high-speed counter-current chromatography

Lingxi Li,Shuting Zhang,Yan Cui,Yuanyuan Li,Lanxin Luo,Peiyu Zhou,Baoshan Sun

In this work, an efficient method for preparative separation of procyanidins from raw cacao bean extract by high-speed counter-current chromatography (HSCCC) was developed. Under the optimized solvent system of n -hexane-ethyl acetate-water (1:50:50, v/v/v) with a combination of head–tail and tail–head elution modes, various procyanidins fractions with different polymerization degrees were successfully separated. UPLC, QTOF-MS and 1 H NMR analysis verified that these fractions contained monomer up to pentamer respectively. Dimeric procyanidin B2 (purity   >   86%) could be isolated by HSCCC in a single run. Other individual procyanidins in these fractions could be further isolated and purified by preparative HPLC. The developed HSCCC together with preparative HPLC techniques appeared to be a useful tool for large preparation of different procyanidins from cacao beans. Furthermore, by antioxidant activity assays, it was proved that both fractions and individual procyanidins possessed greater antioxidant activities compared to standard trolox. The antioxidant activities of procyanidins increase as the increase of their polymerization degree.

CAS / MDL: 108-73-6
研究领域: 食品科学 · 分析化学 · 植物化学
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2019 · IF 3.714

Preparation and characterization of oxidized starch-chitosan complexes for adsorption of procyanidins

Ying Ji,Xun Lin,Jicheng Yu

This study developed oxidized starch-chitosan complexes for the adsorption of procyanidins . Oxidized starch-chitosan complexes were prepared in two steps. Native cornstarch was first oxidized with a 2,2,6,6-tetramethyl piperidinyloxy (TEMPO) mediated reaction and then surface coated with chitosan to adsorb procyanidins. This study evaluated the morphologies and structures of starches in addition to the adsorption properties of procyanidins onto oxidized starch-chitosan complexes. The zeta potential revealed that the optimal weight ratio of oxidized starch and chitosan in the complexes was 1:0.4. The UV–visible spectrum of the complexes showed absorption spectra at about 255 nm, which has never been observed for oxidized starch. X-ray analysis and SEM indicated that the complexes changed the crystallinity and morphology of native starch. The ATR-FTIR spectra suggested that electrostatic interactions may be present between the -COO - of oxidized starch and –NH 3 + of chitosan. The adsorb experiments suggested that the oxidized starch-chitosan complexes could potentially be applied as carriers of bioactive compounds . This paper provides a good reference for an efficient adsorbent of polyphenols by oxidized starch-chitosan complexes.

研究领域: 材料科学 · 食品科学 · 化学工程 · 分析化学
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Antioxidants · 2022 ·Vol. 11 ·期 11 ·2098 · IF 7.675

The Peanut Skin Procyanidins Attenuate DSS-Induced Ulcerative Colitis in C57BL/6 Mice

Na Wang,Weixuan Chen,Chenxu Cui,Yuru Zheng,Qiuying Yu,Hongtao Ren,Zhigang Liu,Chao Xu,Gaiping Zhang

Polyphenols from peanut skin have been reported to possess many beneficial functions for human health, including anti-oxidative, antibacterial, anticancer, and other activities. To date, however, its anti-inflammatory effect and the underlying mechanism remain unclear. In this study, the anti-inflammatory effect of peanut skin procyanidins extract (PSPE) and peanut skin procyanidins (PSPc) were investigated by a dextran sodium sulfate (DSS)-induced colitis mouse model. The results showed that both PSPE and PSPc supplementation reversed the DSS-induced body weight loss and reduced disease activity index (DAI) values, accompanied by enhanced goblet cell numbers and tight junction protein claudin-1 expression in the colon. PSPE and PSPc treatment also suppressed the inflammatory responses and oxidative stress in the colon by down-regulating IL-1β, TNF-α, and MDA expressions. Meanwhile, PSPE and PSPc significantly altered the gut microbiota composition by increasing the relative abundance ofClostridium XlVbandAnaerotruncus, and inhibiting the relative abundance ofAlistipesat the genus level. PSPE and PSPc also significantly elevated the production of short-chain fatty acids (SCFAs) in mice with colitis. The correlation analysis suggested that the protective effects of PSPE and PSPc on colitis might be related to the alteration of gut microbiota composition and the formation of SCFAs. In conclusion, the current research indicates that supplementation of PSPE and PSPc could be a promising nutritional strategy for colitis prevention and treatment.Keywords:peanut skin;procyanidins;DSS-induced;ulcerative colitis

研究领域: 营养学 · 免疫学 · 胃肠病学 · 药理学
✓ 已验证 DOI PubMed 高影响因子
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Journal of Functional Foods · 2014 · IF 4.48

Chemical characterization of procyanidins from Spatholobus suberectus and their antioxidative and anticancer activities

Wenting Li,Jing Liu,Ronggui Guan,Jianping Chen,Depo Yang,Zhimin Zhao,Dongmei Wang

Spatholobus suberectus (SS) is an excellent functional and medicinal food source of dietary procyanidins, which have numerous health benefits. Ten procyanidin fractions with different polymerization degrees were prepared from SS. For the first time, trimers to 11-mers were detected in SS extracts, and their compositions were elucidated through thiolysis, ESI-MS and MALDI-TOF-MS analyses. The results determined that the mean polymerization degree (mDP) of the crude SS procyanidins was 5.2 and that the mass distribution of the monomer and the oligomers (mDP of 1.0–5.7) was 70.4%, whereas that of the polymers (mDP of 6.2–11.8) was 25.6%. Catechin and epicatechin were the main monomeric units with minor quantities of epigallocatechin and gallocatechin. The observed interflavan linkages were both A-type (minor type) and B-type (major type). The fractions enriched in the monomer and oligomers showed the highest activities, including antioxidant activity and inhibitory activities on both the proliferation of MCF-7 breast cancer cells and lactate dehydrogenase A (LDH-A). These results suggested that the monomer- and oligomer-enriched procyanidin fractions from SS could undergo further development to become a beneficial source of antioxidants, LDH-A inhibitors, and potential inhibitors of breast cancer.

研究领域: 食品科学 · 植物化学 · 癌症研究 · 天然产物化学 · 抗氧化研究
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COLLOIDS AND SURFACES B-BIOINTERFACES · 2025 · IF 5.6

Preparation and characterization of hyaluronic acid nanoparticles for procyanidins hepatocellular and mitochondrial targeting delivery

Mengmeng Xue,Yanyan Li,Shanshan Tie,Yunling Zhang,Xue Zhang,Shichang Li,Jianrui Sun,Dongyang Zhu,Yuwan Li,Shaobin Gu

The purpose of this study was to design and fabricate hepatocyte and mitochondria dual-targeted nanoparticles for improving the stability and utilization of procyanidins (PC). PC nanoparticles were prepared by emulsion solvent evaporation method using (5-carboxypentyl) (triphenyl) phosphonium bromide modified PC as core materials, lactobionic acid and 3-amino phenylboronic acid modified hyaluronic acid as wall materials. The obtained nanoparticles were spherical, with small size, high encapsulation efficiency (> 80 %) and strong antioxidant capacity. Compared with free PC, the stability of loaded PC was improved under high temperature, UV radiation, long-term storage, freeze-thaw cycles, simulated digestion and other conditions. In vitro studies proved that nanoparticles had reactive oxygen species-responsive, hepatocyte and mitochondria dual targeting functional properties. In addition, dual-targeted PC nanoparticles could also inhibit the elevation of intracellular reactive oxygen species level and the decrease of mitochondrial membrane potential caused by high-fat. This work proposes a new strategy to deliver active compounds to hepatocytes and even mitochondria, which can provide new ideas for nutritional interventions in liver-related chronic diseases induced by high-fat diets.

CAS / MDL: 603-35-0 96-82-2
研究领域: 纳米医学 · 药物递送 · 制药技术 · 营养生物化学 · 线粒体生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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