Proanthocyanidin metabolites associated with dietary fibre from in vitro colonic fermentation and proanthocyanidin metabolites in human plasma

Proanthocyanidins (PAs) or condensed tannins, a major group of dietary polyphenols, are oligomers and polymers of flavan‐3‐ol and flavan‐3, 4‐diols widely distributed in plant foods. Most literature data on PAs' metabolic fate deal with PAs that can be extracted from the food matrix by aqueous‐organic solvents ( extractable proanthocyanidins). However, there are no data on colonic fermentation of non‐extractable proanthocyanidins (NEPAs), which arrive almost intact to the colon, mostly associated to dietary fibre (DF). The aim of the present work was to examine colonic fermentation of NEPAs associated with DF, using a model of in vitro small intestine digestion and colonic fermentation. Two NEPA‐rich materials obtained from carob pod (Ceratonia siliqua L. proanthocyanidin) and red grapes (grape antioxidant dietary fibre) were used as test samples. The colonic fermentation of these two products released hydroxyphenylacetic acid, hydroxyphenylvaleric acid and two isomers of hydroxyphenylpropionic acid, detected by HPLC‐ESI‐MS/MS. Differences between the two products indicate that DF may enhance the yield of metabolites. In addition, the main NEPA metabolite in human plasma was 3,4‐dihydroxyphenyl acetic acid. The presence in human plasma of the same metabolites as were detected after in vitro colonic fermentation of NEPAs suggests that dietary NEPAs would undergo colonic fermentation releasing absorbable metabolites with potential healthy effects.     

Polyphenol and vitamin C contents in European commercial blackcurrant juice products

Vitamin C and polyphenol contents (anthocyanins, proanthocyanidins, phenolic acids and flavonols) were analysed in commercial blackcurrant juice products purchased from various European countries (Finland, Poland, Germany, United Kingdom) using HPLC methods. The aim was to study variation between countries, as well as evaluate the intake of polyphenols from commercial juices. There was significant variation in the contents of polyphenols and vitamin C between countries. Expressed as the ready-to-drink beverages, German, Polish, Finnish and British products averaged anthocyanin contents of 38, 32, 12 and 7.5 mg/2.5 dl, proanthocyanidin contents of 27, 24, 10 and 1.2 mg/2.5 dl, flavonol contents of 16, 15, 5.2 & 1.9 mg/2.5 dl and phenolic acid contents of 12, 8.9, 3.7 and 1.5 mg/2.5 dl, respectively. The mean vitamin C content was highest in British (70 mg/2.5 dl) and lowest in Finnish products (15 mg/2.5 dl). The intake of polyphenols from German and Polish ready-to-drink beverages was clearly higher than that from Finnish, and especially, British beverages.     

One-pot depolymerizative extraction of proanthocyanidins from mangosteen pericarps

Reaction of dried mangosteen pericarps powders with mercaptoacetic acid in the presence of hydrochloric acid in methanol afforded 4β-(carboxymethyl)sulphanyl-(−)-epicatechin methyl ester, 1, in 4.5% yield. The structure of 1 was characterised by ¹H, ¹³C NMR, and mass spectra. Two protons on the prochiral methylene carbon next to sulphur atom give rise to characteristic AB pattern peaks indicating its association to chiral environment as is the case in 1. Compound 1 is a potential synthon towards other epicatechin derivatives due to its labile C–S bond under weakly basic conditions. Reaction 1 with epicatechin gave B2. If 3,5-dimethoxyaniline was used, 4β-(2′-amino-4′,6′-dimethoxyphenyl)epicatechin, 2, was isolated in moderate yield. Reaction of 1 with mercaptoethanol leads to synthesis of 4β-(2-hydroxyethylthio)epicatechin, 3, in good yield. Finally mercaptoacetic acid was used as an alternative for successful determination of mean degree of polymerisation of PAs isolated from pine bark, grape seeds, cocoa bean, and mangosteen.     

纤维素酶法提取葡萄籽中原花青素的研究

研究了葡萄籽中原花青素的酶法提取工艺。以葡萄籽中原花青素的提取率为指标,采用单因素法和正交设计法对纤维素酶解法提取工艺条件进行优选。实验结果表明,影响酶法提取原花青素的因素次序为:酶解温度>酶解浓度>pH值>乙醇浓度,其最佳工艺条件为:酶解浓度为0.10%,酶解温度为50℃,pH值为5.5,乙醇浓度为60%,所得葡萄籽中原花青素的提取率为4.16%。     

原花青素微胶囊释放动力学的研究

研究了原花青素微胶囊释放动力学及释放机制.测定了原花青素微胶囊在不同介质中的释放曲线,并用3种模型方程-零级动力学方程、一级动力学方程、Higuchi模型方程对原花青素微胶囊在正己烷与无水乙醇中的释放曲线进行线性拟合.结果表明,原花青素微胶囊在正己烷与无水乙醇中的释放动力学拟合结果的优劣顺序均为:Higuchi模型方程、一级动力学方程、零级动力学方程.原花青素微胶囊在正己烷与无水乙醇中的释放遵从Higuchi模型方程,为骨架扩散机制.     

Phenolic Profile of Peanut By-products: Antioxidant Potential and Inhibition of Alpha-Glucosidase and Lipase Activities

Free, esterified, etherified and insoluble‐bound phenolics from three samples, namely meal from whole peanuts (MWP), meal from dry‐blanched peanuts (MDBP) and peanut skin (PS) were evaluated for their total phenolic content (TPC), and phenolic profile using HPLC–DAD–ESI–MSⁿ. The TPC was in the order of PS > MWP > MDBP. Among 37 compounds identified 10 were reported for peanuts for the first time. Proanthocyanidins were detected in peanut skin and MWP, but not in MDBP. The presence of peanut skin in MWP rendered up to 9.8‐fold higher scavenging activity towards the DPPH radical as compared with MDBP. Phenolics from all samples and fractions showed inhibition of alpha‐glucosidase and lipase activities, which are key enzymes involved in the absorption of glucose and triacylglycerols, respectively. Therefore, their antioxidant properties as well as their potential role in the management of diabetes and obesity makes them worthy of further consideration as functional food ingredients.     

超声强化亚临界水萃取脱脂葡萄籽中原花青素的动力学研究

根据质量衡算微分模型和运用Fick第一定律,建立了超声强化亚临界水萃取(USWE)和亚临界水萃取(SWE)原花青素的动力学模型,并通过对比这2个模型说明了超声对亚临界水萃取的强化作用。结果表明,Y=5.3974×(1-e~(-0.001 4t))和Y=5.2019×(1-e~(-0.001 2t))分别是USWE和SWE原花青素的动力学模型,并且这2个动力学模型都能很好地模拟萃取的过程;对比这2个模型方程的参数可知,超声能够加快葡萄籽内部原花青素的扩散及促进其解吸,因此能够对SWE起到强化作用。     

Structural features,antioxidant and tyrosinase inhibitory activities of proanthocyanidins in leaves of two tea cultivars

In this study the structural features, antioxidant, and tyrosinase inhibitory activities of proanthocyanidins in leaves of two tea cultivars, namely Huangjingui and Qilan, were investigated. The matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and thiolysis-high performance liquid chromatography-electrospray ionization mass spectrometry analyses confirmed that these proanthocyanidins were built up a mixture of procyanidins, propelargonidins, and prodelphinidins, with the predominance of procyanidins. The proanthocyanidins in leaves of Huangjingui and Qilan cultivars exhibited potent antioxidant activities with IC₅₀ values of 87.36 ± 0.83 and 97.33 ± 0.61 µg/mL in 2,2-diphenyl-1-picrylhydrazyl radical scavenging assay, 43.57 ± 0.25 and 55.01 ± 0.22 µg/mL in 2,2’-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical scavenging assay, and with ferric reducing antioxidant power values of 4.83 ± 0.03 and 3.97 ± 0.02 mmol ascorbic acid equivalent/g in ferric reducing antioxidant power assay. It was also found that these proanthocyanidins had strong inhibition on tyrosinase activity with IC₅₀ values of 54.8 ± 1.27 and 20.0 ± 0.89 µg/mL for Huangjingui and Qilan cultivars, respectively. The results indicated that the proanthocyanidins in leaves of two tea cultivars could be considered as natural antioxidants and tyrosinase inhibitors applied in pharmaceutical and cosmetic industries in the future.     

基于响应面法的马尾松树皮原花青素提取及抗氧化性研究

运用响应面分析法对马尾松树皮原花青素的提取条件进行优化，并测定了马尾松树皮粗原花青素对三种自由基体系的清除能力，以及对油酸体系过氧化的抑制作用。结果表明：响应面法能有效优化提取工艺，所得的马尾松树皮粗原花青素有很好的抗氧化活性。