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proanthocyanidins prevent tau protein aggregation and disintegrate tau filaments

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Chinese Journal of Chemical Engineering 2023年第5期57卷 63-71页

作者： Huan-Huan Yin Yin-Lei Han Xiao Yan Yi-Xin Guan College of Chemical and Biological Engineering Zhejiang UniversityHangzhou 310027China Max Planck Institute of Molecular Cell Biology and Genetics Dresden 01307Germany

Occurrence of neurofibrillary tangles of the tau protein is a hallmark of tau-related neurodegenerative diseases, i.e. Alzheimer's disease(AD) and frontotemporal dementia. The pathological mechanism underlying AD remains poorly understood, and effective treatments are still unavailable to mitigate the disease.Inhibiting of tau aggregation and disrupting the existing fibrils are key targets in drug discovery towards preventing or curing AD. In this study, grape seed proanthocyanidins(GSPs) was found to effectively inhibit the repeat domain of tau(tau-RD) aggregation and disaggregate tau-RD fibrils in a concentrationdependent manner by inhibiting β-sheet formation of tau-RD. In cells, GSPs relieved cytotoxicity induced by tau-RD aggregates. Molecular dynamics simulations indicated that strong hydrogen bonding,hydrophobic interaction and π-π stacking between GSPs and tau-RD protein were major reasons why GSPs had high inhibitory activity on tau-RD fibrillogenesis. These results provide preliminary data to develop GSPs into medicines, foodstuffs or nutritional supplements for AD patients, suggesting that GSPs could be a candidate molecule in the drug design for AD therapeutics.

关键词： Protein Aggregation Disaggregation Molecular simulation proanthocyanidins Alzheimer’s disease(AD)

Identification of novel bioactive proanthocyanidins with potent antioxidant and anti-proliferative activities from kiwifruit leaves

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Food Bioscience 2022年第2期46卷 539-549页

作者： Ji-Min Lv Mostafa Gouda Alaa El-Din Bekhit Ya-Ke He Xing-Qian Ye Jian-Chu Chen College of Biosystems Engineering and Food Science National-Local Joint Engineering Laboratory of Intelligent Food Technology and EquipmentZhejiang Key Laboratory for Agro-Food ProcessingZhejiang Engineering Laboratory of Food Technology and EquipmentZhejiang UniversityHangzhou310058China Department of Nutrition and Food Science National Research CentreDokki12622GizaEgypt Department of Food Science University of OtagoOtagoNew Zealand

Agro-wastes contribute major social,economic,and environmental challenges for food production and circular economy systems.The current increasing demand for clean label food production and use of natural bioactive compounds could turn these challenges into opportunities providing avenues for proper utilization of agro-wastes to produce valuable products.This study aimed to investigate the potential use of kiwifruit(Actinidia chinensis)leaves as a source of proanthocyanidins(PAs)bioactive phenolic phytochemicals.Kiwifruit leaves PAs were extracted,purified,identified,and evaluated for their antioxidant and anti-proliferative activities.The structural composition of the purified PAs was characterized using HPLC-QTOF-MS/MS and MALDI-TOF-MS.The results showed that purified kiwifruit leaves PAs(PKLPs)comprised mainly procyanidins,propelargonidins,and prodelphindins ranging from dimers to hexamers with(epi)catechin as terminal units and(epi)afzelechin or(epi)gallocatechin as dominant extension units.This study reports the structure of novel PKLPs monomer fractions was unique compared to the PAs that extracted from the other plant sources.The PKLPs exhibited higher phenolic content than the skin and flesh of several kiwifruit cultivars.Moreover,the PKLPs exhibited higher in vitro antioxidant activity in chemical-based(DPPH,ABTS,and FRAP)assays and H2O2-induced injury cell model than ascorbic,Trolox,and catechin(p<0.01).A remarkable dose-dependent anti-proliferation activity(IC_(50)=186.04±2.61μg/mL)against HepG2 cells was observed.In conclusion,this study demonstrated that kiwifruit leaves waste could serve as a sustainable and low-cost source of PAs,a group of multi-functional bioactive compounds that plays a key role in the food and pharmaceutical industries.

关键词： proanthocyanidins Agro-waste valorisation HPLC-QTOF-MS/MS Antioxidant potential Anti-proliferative activity

proanthocyanidins Inhibit Seed Germination by Maintaining a High Level of Abscisic Acid in Arabidopsis thaliana

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Journal of Integrative Plant Biology 2012年第9期54卷 663-673页

作者： Liguo Jia Qiuyu Wu Nenghui Ye Rui Liu Lu Shi Weifeng Xu Hui Zhi A. N. M. Rubaiyath Bin Rahman Yiji Xia Jianhua Zhang Department of Biology Hong Kong Baptist University Hong Kong China School of Life Sciences and State Key Laboratory of Agrobiotechnology The Chinese University of Hong Kong Hong Kong China

proanthocyanidins （PAs） are the main products of the flavonoid biosynthetic pathway in seeds, but their biological function during seed germination is still unclear. We observed that seed germination is delayed with the increase of exogenous PA concentration in Arabidopsis. A similar inhibitory effect occurred in peeled Brassica napus seeds, which was observed by measuring radicle elongation. Using abscisic acid （ABA）, a biosynthetic and metabolic inhibitor, and gene expression analysis by real-time polymerase chain reaction, we found that the inhibitory effect of PAs on seed germination is due to their promotion of ABA via de novo biogenesis, rather than by any inhibition of its degradation. Consistent with the relationship between PA content and ABA accumulation in seeds, PA-deficient mutants maintain a lower level of ABA compared with wild-types during germination. Our data suggest that PA distribution in the seed coat can act as a doorkeeper to seed germination. PA regulation of seed germination is mediated by the ABA signaling pathway.

关键词： Abscisic acid Arabidopsis Brassica napus proanthocyanidins seed germination.

Protective effect of ginkgo proanthocyanidins against cerebral ischemia/reperfusion injury associated with its antioxidant effects

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Neural Regeneration Research 2016年第11期11卷 1779-1783页

作者： Wang-li Cao Hai-bo Huang Ling Fang Jiang-ning Hu Zhu-ming Jin Ru-wei Wang Zhejiang Modern Chinese Medicine and Natural Drug Research Academy Co. Ltd. Hangzhou Zhejiang Province China Zhejiang Conba Pharmaceutical Co. Ltd. Hangzhou Zhejiang Province China Zhejiang Key Laboratory of Traditional Chinese Medicine Pharmaceutical Technology Hangzhou Zhejiang Province China

proanthocyanidins have been shown to effectively protect ischemic neurons, but its mechanism remains poorly understood. Ginkgo proan-thocyanidins （20, 40, 80 mg/kg） were intraperitoneally administered 1, 24, 48 and 72 hours before reperfusion. Results showed that ginkgo proanthocyanidins could effectively mitigate neurological disorders, shorten infarct volume, increase superoxide dismutase activity, and de-crease malondialdehyde and nitric oxide contents. Simultaneously, the study on grape seed proanthocyanidins （40 mg/kg） confirmed that different sources of proanthocyanidins have a similar effect. The neurological outcomes of ginkgo proanthocyanidins were similar to that of nimodipine in the treatmen＇t of cerebral ischemia/reperfusion injury. （Sur results suggestthat-ginkgo proanthocyanidins can effectively lessen cerebral ischemia/reperfusion injury and protect ischemic brain tissue and these effects are associated with antioxidant properties.

关键词： nerve regeneration cerebral ischemia/reperfusion injury proanthocyanidins nimodipine superoxide dismutase malondialdehyde nitric oxide neural regeneration

Modulation of Anti-Oxidation Ability by proanthocyanidins during Germination of Arabidopsis thaliana Seeds

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Molecular Plant 2012年第2期5卷 472-481页

作者： Li-Guo Jia Zi-Wei Sheng Wei-Feng Xu Ying-Xuan Li Ying-Gao Liu Yi-Ji Xia Jian-Hua Zhang Department of Biology Hong Kong Baptist University Hong Kong China State Key Laboratory of Soil and Sustainable Agriculture Institute of Soil Science Chinese Academy of Sciences Nanjing 210008 Jiangsu China State Key Laboratory of Crop Biology College of Life Sciences Shandong Agricultural University Taian Shandong 271018 China

proanthocyanidins （PAs） as the end products of flavonoid biosynthetic pathway mainly accumulate in seed coat but their biological function is largely unknown. We studied the anti-oxidation ability in seed coat and germination changes under externally applied oxidative stresses in PAs-deficient mutants of Arabidopsis. Germination of PAs-deficient mutant seeds was faster than that of wild-type under low or no oxidative stress, suggesting a PAs-induced inhibition of germination. When the applied oxidative stress was high, germination of PAs-deficient mutants was lower than that of wild-type, suggesting a loss of PAs-related anti-oxidation ability in the mutants. Using ABA signaling mutants, our studies demonstrated that both ABA signaling pathway and PAs were important for the response to serve oxidative stress during seed germination. However, the discrepancy of the response between abi mutants and PAs mutants to oxidative stress suggests that ABA signaling pathway may not play a major role in PAs＂ action in alleviating oxidative stress. Under low or no oxidative stress, germination was mainly determined by the ABA content in seed and the PAs-deficient mutant seeds germinated faster due to their lower ABA content than wild-type. However, oxidative injury inhibited germination when PAs-deficient seeds germinated under high oxidative stress, Wild-type exhibited higher germination under the high ox- idative stress due to the PAs＇ anti-oxidation ability. Oxidative stress applied externally led to changes in endogenous PAs contents that coincided with the expression changes of PAs biogenesis genes. PAs modulated the activities of some key enzymes that controlled the levels of reactive oxygen species and the anti-oxidation capacity during the seed germination. This work suggests that PAs contribute to the adaptive mechanism that helps germination under environmental stresses by playing dual roles in both germination control and anti-oxidation reaction.

关键词： abscisic acid anti-oxidation ability oxidative stress proanthocyanidins reactive oxygen species seed germination Arabidopsis.

Protective effects of proanthocyanidins on beta-amyloid peptide (25-35)-induced PC12 cell apoptosis by blocking S-phase and increasing p53 gene expression

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Neural Regeneration Research 2010年第2期5卷 108-112页

作者： Hanfang Mei Zhaoyang Xie Qifeng Zhu Department of Biochemistry and Molecular Biology Guangdong Pharmaceutical University Guangzhou 510006 Guangdong Province China School of Pubfic Health and Tropical Medicine Southem Medical University Guangzhou 510515 Guangdong Province China Institute of Biochemistry and Molecular Biology Guangdong Medical College Zhanjiang 524023 Guangdong Province China

BACKGROUND： Current studies related to the effects of proanthocyanidins on Alzheimer＇s disease have focused primarily on the signal transduction pathway of cellular apoptosis. However, the influence of p53 gene expression on cell cycle regulation, with regard to the protective mechanisms of proanthocyanidins, has not been reported. OBJECTIVE： To observe the effect of proanthocyanidins on cell cycle distribution, cellular apoptosis and p53 gene expression in β-amyloid peptide （25-35）（Aβ25-35）-induced PC12 cells cultured in serum-free media, and to investigate the molecular neuroprotective mechanisms of proanthocyanidins with regard to cell cycle regulation. DESIGN, TIME AND SETTING： A parallel, controlled, at the Institute of Biochemistry and Molecular Biology cellular, and molecular study was performed Guangdong Medical College from July 2006 to July 2008. MATERIALS： proanthocyanidins were provided by Nanjing Xuezi Medical and Chemical Research Center, China; Aβ25-35 was provided by Sigma, USA; PC12 cells were provided by the Institute of Basic Medical Science, Academy of Military Medical Sciences; and rabbit anti-p53 polyclonal antibody was provided by Santa Cruz Biotechnology, USA. METHODS： PC12 cells were cultured in serum-free media for 24 hours. Cells from the model group were treated with 25 μmol/L Aβ25-35 for 24 hours. Cells in the drug protection group were pre-treated with 30 mg/L proanthocyanidins for 1 hour and then treated with 25 μmol/LAβ2^-35 for 24 hours. The control group was not treated. MAIN OUTCOME MEASURES： Flow cytometry was used to detect cell cycle distribution and rate of apoptosis; reverse-transcriptase polymerase chain reaction was used to detect p53 mRNA expression; and Western blot was used to detect p53 protein expression. RESULTS： After treating with 25 μmol/LAβ25-35 for 24 hours, the rate of apoptosis and the percentage of cells in S phase were significantly increased （P 〈 0.01 ）, and p53 mRNA and protein expressions were decreased. Pretreatment with proanthocyanidins for 1 hour bl

关键词： proanthocyanidins β-amyloid peptide （25-35） Alzheimer＇s disease PC12 cells p53 gene neural regeneration

BnbHLH92a negatively regulates anthocyanin and proanthocyanidin biosynthesis in Brassica napus

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The Crop Journal 2023年第2期11卷 374-385页

作者： Ran Hu Meichen Zhu Si Chen Chengxiang Li Qianwei Zhang Lei Gao Xueqin Liu Shulin Shen Fuyou Fu Xinfu Xu Ying Liang Liezhao Liu Kun Lu Hao Yu Jiana Li Cunmin Qu Chongqing Rapeseed Engineering Research Center College of Agronomy and BiotechnologySouthwest UniversityChongqing 400715China Academy of Agricultural Sciences Southwest UniversityChongqing 400715China Engineering Research Center of South Upland Agriculture Ministry of EducationChongqing 400715China Department of Biological Sciences Faculty of ScienceNational University of SingaporeSingapore 117558Singapore Agriculture and Agri-Food Canada Saskatoon Research Centre107 Science PlaceSaskatoonSaskatchewan S7N 02XCanada Temasek Life Sciences Laboratory National University of SingaporeSingapore 117604Singapore

Yellow seed trait is a desirable characteristic with potential for increasing seed quality and commercial value in rapeseed,and anthocyanin and proanthocyanidins(PAs)are major seed-coat pigments.Few transcription factors involved in the regulation of anthocyanin and PAs biosynthesis have been characterized in rapeseed.In this study,we identified a transcription factor gene BnbHLH92a(BnaA06T0441000ZS)in rapeseed.Overexpressing BnbHLH92a both in Arabidopsis and in rapeseed reduced levels of anthocyanin and PAs.Correspondingly,the expression profiles of anthocyanin and PA biosynthesis genes(TT3,BAN,TT8,TT18,and TTG1)were shown by quantitative real-time PCR to be inhibited in BnbHLH92a-overexpressing Arabidopsis seeds,indicating that BnbHLH92a represses the anthocyanin and PA biosynthesis pathway in Arabidopsis.BnbHLH92a physically interacts with the BnTTG1 protein and represses the biosynthesis of anthocyanins and PAs in rapeseed.BnbHLH92a also binds directly to the BnTT18 promoter and represses its expression.These results suggest that BnbHLH92a is a novel upstream regulator of flavonoid biosynthesis in B.napus.

关键词： Brassica napus L BnbHLH92a Anthocyanin proanthocyanidins Flavonoid pathway

The contribution of different polyphenol compositions from chokeberry produced in China to cellular antioxidant and antiproliferative activities

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Food Science and Human Wellness 2023年第5期12卷 1590-1600页

作者： Ningxuan Gao Xu Si Wenzhong Han Ersheng Gong Chi Shu Jinlong Tian Yuehua Wang Jiyue Zhang Binxu Li Bin Li Department of Food Science College of FoodShenyang Agricultural UniversityShenyang 110161China National R&D Professional Center For Berry Processing Shenyang 110161China Agriculture and Forest Institute in Arid of Liaoning Chaoyang 122000China

Abundant polyphenols make chokeberry have beneficial antioxidant and antiproliferative activity. In order to explore the contribution of different polyphenols in chokeberry to these activities, this study was conducted to determine polyphenol composition from 7 chokeberry varieties produced in China. Totally, 11 kinds of main polyphenol monomers were identified and quantified by UPLC-Q-TOF-MS and UPLC-PDA. HepG2 cells were used to evaluate their cellular antioxidant and antiproliferative activities. Partial least squares method was utilized to analyze multivariate correlations between proportion of different composition and monomers in total polyphenols with these activities. The results showed that the highest proportion in chokeberry polyphenols was proanthocyanidins. In comparing the bioactivities of 7 varieties of chokeberry, ‘Viking' and purple chokeberry had the strongest antioxidant activity, while 'Fukangyuan 1#' had the strongest antiproliferative activity. In terms of the contribution sources of these bioactivities, the total antioxidant activity of chokeberry mainly depended on the contribution of free polyphenols. As the main source of cellular antioxidant activity, anthocyanins and neochlorogenic acid can provide more contribution. The antiproliferative activity mainly depended on the proportion of free polyphenols and proanthocyanidins in total polyphenols. The results may provide some new possibilities for the comprehensive utilization of polyphenols from chokeberry.

关键词： Chokeberry Anthocyanins proanthocyanidins Antioxidant Antiproliferation

New N-acetyl-L-cysteine derivatives synthesized by the degradation of proanthocyanidins as high biological activity antioxidants

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Journal of Polyphenols 2021年第1期3卷 14-31页

作者： Yuxuan Wang Ruifang Bai Siqi Luo Meng Huang Yan Cui School of Pharmacy Shenyang Pharmaceutical UniversityShenyang 110016China Faculty of Functional Food and Wine Shenyang Pharmaceutical UniversityShenyang 110016China

A novel degradation method was investigated to synthesize highly biologically active flavan-3-ol derivatives in the presence of N-acetyl-L-cysteine(NAC)as a nucleophile under acidic conditions for polymerized proanthocyanidins degradation.The reaction conditions were optimized by the combination of single-factor test and central composite experimental design(CCD).Grape seed proanthocyanidins were reacted with NAC at a ratio of 1:3 with 0.3 M methanolic HC1,a temperature of 55°C,and a reaction time of 50 mins.Most of the degradation products were separated and prepared by one-step high-speed countercurrent chromatography(HSCCC)and preparative high-performance liquid chromatography(prep-HPLC).Three monomeric pro anthocyanidins and four new N-acetyl-L-cysteine derivatives were isolated from degradation products with total degradation yield of 55.44%and high purity over 95%.Furthermore,the neuroprotective abilities of these compounds to H2O2-treated PC-12 neuroblastoma cells were evaluated.NAC derivatives showed better antioxidant activity than their corresponding underivatized monomers and NAC,indicating that they had a better performance in protecting PC-12 cells from oxidative stress damage.

关键词： N-acetyl-L-cysteine proanthocyanidins HSCCC antioxidant activity