Direct Acylation of Cyanidin-3-Glucoside with Lauric Acid in Blueberry and Its Stability Analysis

Cyanidin-3-glucoside is an anthocyanin that is abundant in blueberry. Lauric acid was used as the acyl donor in the acylation of cyanidin-3-glucoside. Preparative high performance liquid chromatography was used to separate and purify the acylated cyanidin-3-glucoside, the acylated rate was 30.78%. Fourier transform infrared spectroscopy and liquid chromatography mass spectrometry were used to confirm the basic structure of cyanidin-3-glucoside. Lauric acid was combined with cyanidin-3-glucoside. Lauric acid reacted with the glucoside’s primary hydroxyl group and removed a molecule of water, thereby resulting in the obtained structure. The compositions of the unacylated cyanidin-3-glucoside and acylated cyanidin-3-glucoside were compared under different temperatures and under illumination. The effects of different concentrations of additive compounds on the stability of acylated cyanidin-3-glucoside were compared. Stability of acylated cyanidin-3-glucoside was obviously higher than that of the unacylated cyanidin-3-glucoside because of the higher stability of the ester group than the hydroxyl group. The primary hydroxyl esterification of glucoside improved cyanidin-3-glucoside.     

Apple Anthocyanins: Identification of Cyanidin-7-Arabinoside

SUMMARY— The anthocyanin pigments of Red Delicious apples were isolated and identified from their chromatographic, spectral and chemical properties. The maior pigment was cyanidin-3-galactoside. The minor pigments were cyanidin-3-arabinoside and cyanidin-7-arabinoside. Cyanidin-7-arabino-side was isolated from a natural source for the first time. Three pigments were isolated from 74 varieties of apples, two from six varieties and only one from two varieties.     

高效液相色谱法测定阿萨伊冻干粉中矢车菊素-3-O-葡萄糖苷的含量

目的:建立以HPLC-紫外检测器测定阿萨伊冻干粉中矢车菊素-3-O-葡萄糖苷含量的方法。方法:分别采用水和1%盐酸水溶液为溶剂,使矢车菊素-3-O-葡萄糖苷分别呈中性醌式碱和烊阳离子构型,比较两种构型对测定波长、色谱峰分离度、供试品制备方法、响应因子和标准曲线,以及对含量测定结果的影响。结果:采用烊阳离子构型,即供试品和对照品用1%盐酸水溶液为溶剂,以DIKMA C₁₈(4.6 mm×250 mm×5 μm)柱为分析柱,乙腈-0.5%磷酸溶液(12:88,V/V)为流动相,流速为1 mL/min,检测波长为520 nm。矢车菊素-3-O-葡萄糖苷烊阳离子构型在0.002419~0.077412 mg/mL范围呈线性关系,y=37029.5438x-7.6051(R²=0.9999),回收率为98.31%(RSD%=1.44%),3批阿萨伊冻干粉中矢车菊素-3-O-葡萄糖苷的含量为0.1158~0.1663 mg/g。结论:采用矢车菊素-3-O-葡萄糖烊阳离子构型,以HPLC-紫外检测器测定阿萨伊冻干粉中矢车菊素-3-O-葡萄糖苷含量的方法操作简便、灵敏、结果准确、重复性好。     

HPLC法测定不同产地黑豆皮中矢车菊素-3-O-葡萄糖苷的含量

目的：建立黑豆皮中矢车菊素-3-O-葡萄糖苷的含量测定方法,测定5个不同产地黑豆皮中矢车菊素-3-O-葡萄糖苷的含量。方法：采用HPLC法测定黑豆皮中矢车菊素-3-O-葡萄糖苷的含量,色谱柱采用Phenomenex Luna Su C18 柱 (250mm×4.60mm,5μm);流动相A相为0.5%磷酸溶液,B相为水-乙腈(50:50),进行梯度洗脱;流速0.8mL/min;检测波长520nm;柱温30℃;进样量10μL。结果：矢车菊素-3-O-葡萄糖苷标准曲线回归方程为：Y＝2×107X－33120(r＝0.9998),在 0.1041～1.041μg范围内线性关系良好,平均回收率分别为92.4%、 92.5%和95.5%,不同产地黑豆皮中矢车菊素-3-O-葡萄糖苷含量范围为5.263～12.829mg/g。结论：所用方法简便、准确,可用于不同产地黑豆皮的质量控制。     

肉豆蔻酰矢车菊素-3-O-葡萄糖苷在混合溶剂体系中的酶法合成

为了提高矢车菊素-3-O-葡萄糖苷(C3G,Cyanidin-3-O-glucoside)的稳定性及亲脂性,本研究用固定化脂肪酶Lipozyme 435催化肉豆蔻酸甲酯对C3G进行酰基化修饰.首先分别在单一有机溶剂和混合有机溶剂中进行酰基化反应,然后通过半制备液相色谱对C3G酰基化衍生物进行分离纯化,并通过液质联用和核...     

胎牛血清与矢车菊素-3-葡萄糖苷非共价相互作用机制及对其抗氧化活性的影响

本实验运用超高压高效液相色谱、荧光光谱、圆二色光谱、傅里叶变换红外光谱和抗氧化活性评价等方法,研究矢车菊素-3-葡萄糖苷在不同细胞培养条件下的稳定性,同时探究细胞培养中胎牛血清对矢车菊素-3-葡萄糖苷稳定性影响机制和抗氧化活性的影响.结果 表明:胎牛血清能与矢车菊素-3-葡萄糖苷非共价结合,从而提高矢车菊素-3-葡萄糖...     

矢车菊素-3-O-葡萄糖苷进入巨噬细胞的荧光检测

利用荧光技术探索矢车菊素-3-O-葡萄糖苷（cyanidin 3-O-glucoside,C3G）在体外培养的巨噬细胞中的分布。首先采用荧光分光光度法扫描C3G的特异激发波长和发射波长,再利用激光共聚焦技术探讨C3G进入小鼠和人巨噬细胞的过程以及C3G在细胞中的定位,并分析C3G孵育时间对细胞内荧光强度变化的影响。结果表明：在488 nm和520 nm的激发波长下,C3G孵育15 min的细胞质内开始呈现绿色和红色荧光,并且随着孵育时间的变化,细胞内荧光强度逐渐增强,其中孵育60 min可观察到荧光布满细胞核,其荧光强度是孵育前的6.45 倍。研究表明采用特异波长的激光共聚焦断层扫描技术可示踪到花色苷在干预细胞内的分布,结果显示花色苷C3G可快速穿过巨噬细胞的细胞膜和核膜,直达细胞核。     

Cyanidin-3-glucoside ameliorates CCl4-induced liver injury in mice

The protective effect of cyanidin-3-glucoside (C3G) against carbon tetrachloride (CCl₄)-induced liver injury in mice was investigated. Administration of C3G attenuated the levels of serum aspartate aminotransferase, alanine aminotransferase, and liver lipid peroxidation in CCl₄-treated mice. Histopathological examination of mouse livers showed that C3G reduced the incidence of liver lesions induced by CCl₄. Moreover, C3G prevented DNA damage and decreased the protein levels of γ-H2AX in CCl₄-treated mouse livers. C3G also increased the activity of the antioxidant enzymes superoxide dismutase, catalase, glutathione peroxidase, and glutathione reductase, which were decreased due to CCl₄ administration in CCl₄-treated mouse livers. C3G inhibited the expression levels of IL-6 and iNOS in CCl₄-treated mice. C3G apparently protects the liver from CCl₄-induced hepatic damage through antioxidant and anti-inflammatory mechanisms.     

利用中压制备液相色谱从桑葚中快速制备矢车菊素-3-葡萄糖苷单体

单体花色苷的快速大量制备长久以来是花色苷产业化中的难题,而中压制备液相色谱在产业应用中有着很大的开发空间。选取花色苷组分较单一的桑葚为实验原料,经提取分离总花色苷后使用填装有反相C18填料的耐压玻璃柱作为中压制备液相色谱柱,纯化制备矢车菊素-3-葡萄糖苷单体。结果显示：3 个色谱分离峰中目的峰（峰2）经高效液相色谱和质谱确证为由矢车菊素-3-葡萄糖苷（cyanidin-3-glucoside,C3G）和矢车菊素-3-芸香糖苷（cyanidin-3-rutinoside,C3R）组成,采用峰面积归一化法计算得到C3G纯度为73.56%;通过对峰2采用切割方式进行收集,C3G纯度达到98%以上,单次收集到C3G单体溶液650?mL。中压制备液相色谱法单次上样量大、步骤简洁、成本低廉,可为矢车菊素-3-葡萄糖苷单体的规模化生产提供一定的参考。     

矢车菊素-3-葡萄糖苷与大豆蛋白相互作用的多重光谱分析及分子对接

采用多重光谱技术和分子对接技术，研究矢车菊素-3-葡萄糖苷（cyanidin-3-glucoside，C3G）与β-伴大豆球蛋白和大豆球蛋白的相互作用。结果表明，C3G以静态、动态组合模式强烈的猝灭β-伴大豆球蛋白/大豆球蛋白的内源荧光，且C3G对大豆球蛋白的结合亲和力强于β-伴大豆球蛋白。C3G与β-伴大豆球蛋白/大豆球蛋白结合的主要相互作用力不同，但n（结合位点数）表明C3G和大豆蛋白以物质的量比1∶1形成稳定的复合物。C3G能够诱导大豆蛋白二级结构部分展开，促使部分α-螺旋转变为β-折叠，使大豆蛋白多肽链解折叠；并降低β-伴大豆球蛋白色氨酸残基微环境疏水性，而对大豆球蛋白氨基酸残基微环境没有明显影响。C3G的大部分酚羟基参与成键，其与大豆蛋白的结合依靠疏水作用力和氢键为主导的多种作用力维持。大豆球蛋白对C3G具有更好的稳定、递送性能，但可能不利于C3G生物活性的发挥。     

矢车菊素-3-O-葡萄糖苷保护RAW264.7细胞免受过氧化氢诱导的氧化损伤

本研究旨在探究矢车菊素-3-O-葡萄糖苷（cyanidin-3-O-glucoside,C3G）对H2O2诱导RAW264.7细胞氧化损伤的保护作用及其机制。通过噻唑蓝法测定C3G和过氧化氢分别对RAW264.7细胞存活率的影响;采用酶联免疫吸附测定法检测细胞内超氧化物歧化酶（superoxide dismutase,SOD）和谷胱甘肽过氧化物酶（glutathione peroxidase,GSH-Px）活力以及一氧化氮（nitric oxide,NO）和丙二醛（malondialdehyde,MDA）水平;利用2’,7’-二氯荧光素二乙酸酯活性氧荧光探针检测细胞内活性氧（reactive oxygen species,ROS）水平;通过逆转录定量聚合酶链式反应和Western blot法分别测定相关mRNA和蛋白表达水平。结果表明,C3G（6.25～25.00 μmol/L）能显著抑制H2O2诱导RAW264.7细胞活性降低（P＜0.05）。C3G显著降低H2O2诱导RAW264.7细胞内ROS过表达、MDA水平和NO释放（P＜0.05）,显著增加SOD和GSH-Px活力（P＜0.05）。此外,与空白对照相比,400 μmol/L H2O2处理组中,蛋白激酶Mst1/2和Kelch样环氧氯丙烷相关蛋白Keap1的mRNA及蛋白相对表达水平显著上调（P＜0.05）,而细胞中核因子E2相关因子和下游抗氧化酶HO-1的mRNA及蛋白相对表达水平显著下调（P＜0.05）;而采用C3G干预RAW264.7细胞,上述相关mRNA及蛋白的相对表达水平被逆转。结论：C3G对H2O2诱导RAW264.7细胞氧化损伤保护作用,可能与激活Mst/Nrf2信号通路和提高抗氧化酶活性有关。     

矢车菊素-3-葡萄糖苷与四种乳蛋白相互作用的研究

采用荧光光谱法、傅里叶红外光谱法和圆二色谱法,研究矢车菊素-3-葡萄糖苷(cyanidin 3-O-glucoside,C3G)与α-酪蛋白、β-酪蛋白、乳清蛋白和β-乳球蛋白的相互作用。结果表明,C3G对上述四种乳蛋白都产生了荧光静态猝灭作用,在溶液中C3G与乳蛋白相互结合摩尔比约为1:1,且由热力学参数判定C3G与α-酪蛋白结合的分子间作用力为氢键与范德华力,而与β-酪蛋白、乳清蛋白和β-乳球蛋白结合主要靠静电引力。通过比较C3G与α-酪蛋白、β-酪蛋白、乳清蛋白和β-乳球蛋白相互作用的荧光猝灭率(84%、74%、77%、75%);温度分别为298、318、338 K时的结合常数(423.448、362.994、28.655×10⁴ L/mol;9.524、8.056、8.308×10⁴ L/mol;9.262、6.940、7.889×10⁴ L/mol;30.440、11.830、17.262×10⁴ L/mol);结合距离(2.17、2.66、2.18、2.19 nm),由此得出α-酪蛋白与C3G结合最紧密。傅里叶红外光谱和圆二色谱分析显示,C3G的加入使得α-酪蛋白的α-螺旋增加,β-折叠和转角降低;β-酪蛋白的α-螺旋、β-折叠和转角均增加;乳清蛋白的α-螺旋、β-折叠和转角均无明显变化;β-乳球蛋白的α-螺旋降低,β-折叠和转角增加。C3G对四种乳蛋白均有较强的结合能力,可以使其构象发生变化。     

Cyanidin-3-glucoside,nutritionally important constituents and in vitro antioxidant activities of Santalum album L. berries

Anthocyanins are ubiquitous plant pigments. They are hydrophilic, and have high tinctorial value hence, used as natural food colorant. The main aim of this study was characterization of Santalum album L. berries for its pigment content, nutritionally important phytoconstituents and functional attributes. Major pigment identified was cyanidin-3-glucoside (0.21% FW) as confirmed by spectral characteristics including LC–MS. Nutrients such as total carbohydrates (8.5), proteins (5.8), free amino acids (0.8 g), oil (1.5 g), ascorbic acid (1.5 μg), tocopherols (0.3 mg) and niacin (5.2 mg) per 100 g berries were determined along with total soluble solids (13.4°Brix) and phenols (3.1 mg GAE/g). Reducing power and DPPH· scavenging assays showed highest activity in methanol extract, which also efficiently protected bleaching of β-carotene (EC₅₀ 285 μg/mL) in β-carotene–linoleate model. Pigment rich crude extract was not toxic to HepG2 cells during 24 h exposure, whereas cyanidin-3-glucoside was cytotoxic (IC₅₀ 0.1 μg/mL).     

W/O/W型复乳的制备优化及包埋矢车菊素-3-葡萄糖苷效果分析

研究制备方法和乳化剂对W/O/W型复乳稳定性的影响,优化工艺参数,并研究体系包埋矢车菊素-3-葡萄糖苷（cyanidin-3-glucoside,C-3-G）的效果。得到优化条件：初乳搅拌速率15 500 r/min、复乳搅拌速率7 000 r/min、油相乳化剂聚甘油蓖麻醇酯添加量16%、亲水性乳化剂的亲水亲油平衡值10、亲水性乳化剂添加量10%,优化后离心保留率达到80.25%。利用优化得到的复乳体系包裹C-3-G,发现复乳对C-3-G有良好的包裹能力,复乳对C-3-G的载药量为1 500 mg/L,包封率为98.08%,且C-3-G的包埋提高内水相渗透压和复乳稳定性。     

矢车菊素-3-葡萄糖苷对人巨核细胞株Dami增殖分化的影响

目的：研究植物花色苷单体矢车菊素-3-葡萄糖苷（cyanidin-3-O-β-glucoside,Cy-3-g）对人巨核细胞株Dami的增殖、分化作用。方法：不同浓度的花色苷Cy-3-g（0.05、0.50、5.00、50.00、100.00 mmol/L）与人巨核细胞株Dami细胞共同培养,并将用完全培养基培养的细胞设为对照组。培养结束后,用台盼蓝染色法检测巨核细胞活性、噻唑蓝（methyl thiazolyl tetrazolium,MTT）染色法检测细胞增殖能力,软琼脂细胞集落培养法观察巨核细胞集落生成情况。采用Giemsa染色法观察细胞形态、流式细胞术检测巨核细胞DNA多倍体的生成及细胞表面CD41阳性表达率。结果：与对照组相比,50.00、100.00 mmol/L的Cy-3-g可增强Dami细胞活性,差异具有统计学意义（P＜0.05）;各Cy-3-g剂量组与对照组相比,均可明显增强Dami细胞增殖能力（P＜0.01）;Dami细胞集落数目、DNA多倍体数目以及CD41的阳性表达率在50.00、100.00 mmol/L Cy-3-g作用下明显升高,且与对照组相比均具有统计学差异（P＜0.01）。结论：Cy-3-g能够明显促进人巨核细胞株Dami的增殖、分化,这可以为花色苷促进血小板生成提供可能的理论依据。     

矢车菊-3-O-葡萄糖苷及其代谢物原儿茶酸对杂环胺诱导细胞损伤的修复机制

目的：研究矢车菊-3-O-葡萄糖苷（cyanidin-3-O-glucoside,C3G）及其主要代谢物原儿茶酸（protocatechuic acid,PCA）对杂环胺诱导细胞损伤的修复机制。方法：分别采用2-氨基-3-甲基咪唑并[4,5-f]喹啉（2-amino-3-methylimidazo[4,5-f]quinoline,IQ）和2-氨基-1-甲基-6-苯基-咪唑[4,5-b]吡啶（2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine,PhIP）诱导HepG2细胞损伤,利用细胞毒性实验（cell counting kit-8,CCK-8）、Hoechst33258染色法、流式细胞术和实时荧光定量聚合酶链式反应（quantitative polymerase chain reaction,qPCR）技术,评价C3G和PCA对杂环胺诱导损伤细胞的存活情况、细胞周期以及凋亡和DNA损伤关键基因表达的影响。结果：C3G和PCA能够显著提高杂环胺损伤细胞的存活率（P<0.05）,并使细胞发生S期阻滞。与IQ单独损伤组相比,C3G和PCA均可...     

Effects of high-intensity ultrasound treatment on physiochemical properties of caseins-cyanidin-3-galactoside conjugates

The application of protein-polyphenol complexes is increasing and broadening in recent years. Due to their unique properties, these complexes are attracting increased research interest. In this study, the cyanidin-3-galactoside was grafted to the caseins using free radicles induced by ultrasound. The formation of conjugation between caseins and cyanidin-3-galactoside was confirmed by the decrease in free amino groups and sulfhydryl content. Conjugation with cyanidin-3-galactoside resulted in aggregation of caseins, which also led to increase in particle size, relative fluorescence intensity and random coil. Conjugation also disrupted the hydrogen bonds and decreased the electrostatic repulsion and hydrophobic interactions between caseins. The caseins-cyanidin-3-galactoside conjugate had better emulsifying, gelation properties and lower thermal stability than that of caseins.     

Anthocyanin Pigment Composition of Blackberries

ABSTRACT: The anthocyanin pigments in 51 blackberry samples were isolated and characterized by highperformance liquid chromatography (HPLC) with UV-visible detection, electrospray mass spectroscopy (ESMS), and hydrolysis and saponification reactions. Five pigments were detected: cyanidin-3-glucoside, cyanidin-3-rutinoside, cyanidin-3-xyloside, cyanidin-3-glucoside acylated with malonic acid, and an unidentified acylated derivative of cyanidin-3-glucoside. Four different quantitative patterns were evident among the cultivars and selections. Total anthocyanin content ranged from 70.3 to 201 mg/100 g with a mean of 137 mg/100 g. Ten commercial blackberry juice concentrate samples were analyzed. Total anthocyanin ranged from 12.3 to 107 mg/100 g on a single-strength juice basis, and 1 sample had an atypical profile.     

Effects of pectolytic enzyme treatments on anthocyanins in raspberry juice

Raspberry juices treated with two commercial pectinase preparations lost almost 20% of their total anthocyanin pigments; losses were related to both concentration of enzyme and time of treatment. Analysis of individual anthocyanins showed differences between the enzymes. Ultrazyme reduced all components in similar proportions, whereas Pectinex apparently also converted cyanidin-3-sophoroside and cyanidin-3-glucosylrutinoside into cyanidin-3-glucoside and cyanidin-3-rutinoside respectively, presumably by hydrolysis of β1–2 glucosidic bonds by glucosidase present in the Pectinex.