CN113648321B - 矢车菊素-3-o-葡萄糖苷及其与丙烯醛加合产物作为丙烯醛抑制剂的应用 - Google Patents
矢车菊素-3-o-葡萄糖苷及其与丙烯醛加合产物作为丙烯醛抑制剂的应用 Download PDFInfo
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Abstract
本发明公开了矢车菊素‑3‑O‑葡萄糖苷或其与丙烯醛加合产物作为丙烯醛抑制剂的应用，本发明公开了矢车菊素‑3‑O‑葡萄糖苷及其与丙烯醛的一加合产物或者二加合产物的一种新应用，即其能够快速有效捕获ACR以控制其含量，避免其与生物大分子内的亲核基团如氨基、巯基、羟基和咪唑基结合，形成交联产物，妨碍机体功能正常行使。本发明的矢车菊素‑3‑O‑葡萄糖苷或其与丙烯醛的加合产物如C3G‑ACR可继续作为ACR的清除剂或者抑制剂，清除或者抑制环境中、食品加工中的丙烯醛，同时可以清除进入体内的外源性ACR或人体内源性产生的ACR，从而控制或缓解由ACR引起的疾病症状。
Description
技术领域
本发明属于花色苷的应用领域，具体涉及矢车菊素-3-O-葡萄糖苷及其与丙烯醛加合产物作为丙烯醛抑制剂的应用。
背景技术
ACR是一种高毒性的不饱和醛，在外部环境中广泛存在，如香烟、石化燃料(汽油或石油)、建筑火灾；其次，也可由食品加工和人体内源性代谢产生。有报道称源于汽车尾气的ACR排放量为1.8吨/年，而商业厨房油烟中ACR 的排放量可高达7.7吨/年。在酒精饮料的酿造过程中，ACR可通过微生物代谢的方式产生，例如成品白酒中ACR的平均浓度可达到72.3μg/L，在威士忌中 ACR浓度范围为700-11100μg/L，作为一种高水溶性的α,β-不饱和醛，ACR可存在水体环境中。
在食品加工过程中，ACR主要通过碳水化合物及氨基酸的热降解、脂肪酸裂解、微生物发酵代谢等方式产生；其中，研究数据表明油炸和烘焙食品中ACR 含量整体较高，范围为0.001-0.9mg/kg。在人体中，ACR可以通过酶介导的多胺或苏氨酸的氧化内源性产生，也可以通过不饱和脂肪酸与活性氧(ROS)的氧化而产生，还可以通过人体肠道中的微生物代谢产生。
作为一种高水溶性的α,β-不饱和醛，ACR可迅速进入生理组织。并因其具有强亲电性，与细胞亲核物质(如蛋白质、DNA、RNA)有很高的反应活性。与蛋白质中的半胱氨酸、组氨酸和赖氨酸残基反应，影响免疫球蛋白抗原识别能力，进而引起自身免疫性疾病(干燥综合征、类风湿性关节炎)；与DNA中的鸟嘌呤碱基反应生成环状加合产物，引起DNA损伤进而致癌和致突变；ACR还可引起氧化应激，导致神经元损伤。
因此，寻找天然、安全、高效的物质捕获ACR，以降低环境或者体内ACR 的水平，并探究其机理是预防环境污染、提高食品安全以及防治慢性疾病的必要手段之一，具有重要的现实意义和理论价值。
矢车菊素-3-O-葡萄糖苷(C3G)为一种花色苷，属于黄酮类化合物，广泛存在于杨梅、黑莓、紫甘蓝、黑米等有色谷物、水果和蔬菜中，水溶性好，具有良好的生理活性，如抗氧化、抗炎、抑菌等，尚未发现其对丙烯醛抑制方面研究。
现有技术公开了矢车菊素-3-O-葡萄糖苷捕获1，2-二羰基化合物(乙二醛， GO)反应机理，其为乙二醛与C3G直接加合，且只能形成二加合产物；但丙烯醛的毒性远远高于乙二醛；因此需要开发全新的丙烯醛抑制剂。
发明内容
发明目的：针对现有技术中存在的问题，本发明提供了矢车菊素-3-O-葡萄糖苷及其与丙烯醛加合产物作为丙烯醛抑制剂的应用，本发明的矢车菊素-3-O- 葡萄糖苷及其与丙烯醛加合产物不仅可抑制自然环境溶液体系中存在的丙烯醛，也可以解决在常温食品加工体系中产生的丙烯醛；同时抑制生物体内的丙烯醛。
本发明还提供矢车菊素-3-O-葡萄糖苷与丙烯醛加合产物、以及环境中或者生物体内丙烯醛抑制剂。
技术方案：为了实现上述目的，本发明所述矢车菊素-3-O-葡萄糖苷及其与丙烯醛加合产物作为丙烯醛抑制剂的应用；所述加合产物包括矢车菊素-3-O-葡萄糖苷与丙烯醛的一加合产物C3G-ACR或者二加合产物C3G-2ACR，其结构分别如下所示：
其中，所述矢车菊素-3-O-葡萄糖苷与丙烯醛加合产物在制备环境中丙烯醛抑制剂中的应用。
进一步地，所述矢车菊素-3-O-葡萄糖苷及其与丙烯醛加合产物能够捕获丙烯醛从而降低丙烯醛含量。
其中，所述矢车菊素-3-O-葡萄糖苷或其与丙烯醛加合产物在制备抑制食品加工中产生的丙烯醛的抑制剂中的应用。在常温食品加工体系中，矢车菊素-3-O- 葡萄糖苷作为食品原料如水果、蔬菜中含有的一种花色苷，可在食品加工过程中捕获丙烯醛形成C3G-ACR，其以加合产物可继续捕获丙烯醛，大大降低了食品中丙烯醛的含量，填补了常温食品体系中如果酒、果冻生产中，丙烯醛抑制剂的空白，如杨梅中就含有大量的C3G，生产杨梅有关产品时，如有丙烯醛产生， C3G可将其捕获。
其中，所述矢车菊素-3-O-葡萄糖苷或其与丙烯醛加合产物在制备抑制生物体内丙烯醛的抑制剂中的应用。
进一步地，所述矢车菊素-3-O-葡萄糖苷或其与丙烯醛加合产物抑制由丙烯醛与亲核生物大分子反应形成的各种有害加合或交联产物在制备环境中、食品加工或者生物体内丙烯醛抑制剂中的应用。
本发明所述矢车菊素-3-O-葡萄糖苷或者矢车菊素-3-O-葡萄糖苷与丙烯醛加合产物在制备预防人体慢性疾病的药物中的应用。
其中，所述人体慢性疾病包括阿尔兹海默症、帕金森症，类风湿性关节炎或者心脑血管疾病。
本发明所述矢车菊素-3-O-葡萄糖苷或其与丙烯醛加合产物可以制备成相关试剂或者药物用于抑制或者清除环境、食品加工或生物体内的丙烯醛。
本发明所述矢车菊素-3-O-葡萄糖苷及其与丙烯醛一加合产物、二加合产物：分别为C3G、C3G-ACR、C3G-2ACR，其结构分别如下所示：
本发明所述环境中或者生物体内丙烯醛抑制剂，所述抑制剂以矢车菊素 -3-O-葡萄糖苷或其与丙烯醛加合产物为唯一的成分，或者作为主要成分，与其他物质复配共同使用，所形成的制剂。
本发明所述杨梅红在制备抑制食品加工中产生的丙烯醛的抑制剂中的应用，所述杨梅红主要成分为矢车菊素-3-O-葡萄糖苷。
其中，所述矢车菊素-3-O-葡萄糖苷为水果、蔬菜中主要的花色苷物质。
本发明所述矢车菊素-3-O-葡萄糖苷其母环结构为2-苯基苯并吡喃阳离子。
本发明针对环境中、食品加工或者生物体内毒性较高的丙烯醛，通过C3G 捕获ACR后形成的一加合产物具有继续捕获ACR活性，且C3G捕获ACR的反应机理为迈克尔加成反应，即C3G与ACR在碱性条件下发生1，4-加成反应后 C3G结构A环上的羟基与丙烯醛上的醛基反应形成半缩醛结构。
本发明通过C3G捕获ACR后形成的加合产物继续捕获ACR活性，C3G与 ACR的一加合产物捕获丙烯醛的活性高于C3G和二加合产物C3G-2ACR。有效填补环境中、市面上常温食品加工体系中、生物体内丙烯醛抑制剂的空白。
有益效果：与现有技术相比，本发明具有如下优点：
本发明首次提出了矢车菊素-3-O-葡萄糖苷或其与丙烯醛加合产物的一种新应用能够有效控制ACR的含量，避免其进一步与亲核生物大分子反应形成的各种不可逆的有害加合或交联产物。矢车菊素-3-O-葡萄糖苷及其与丙烯醛加合产物C3G-ACR可作为ACR的清除剂或者抑制剂，清除环境、食品加工中的丙烯醛、和体内由外源性摄入或内源性产生的ACR，并进一步阻断ACR诱导的有害交联产物形成，预防其对环境和人体造成的危害。
附图说明
图1为在模拟室温条件下矢车菊素-3-O-葡萄糖苷及其加合产物抑制ACR活性比较；
图2为本发明矢车菊素-3-O-葡萄糖苷及其加合产物的化学结构及质谱结果； (图A，图B分别为C3G的ESI-MS1和MS2光谱图；图C，图D分别为C3G-ACR 的ESI-MS1和MS2光谱图；图E，图F分别为C3G-2ACR的ESI-MS1和MS 2光谱图)；
图3为矢车菊素-3-O-葡萄糖苷-丙烯醛一加合产物对丙烯醛的清除机制研究结果；(图A，B分别为C3G-ACR与ACR反应1，5min的液相色谱图)；
图4为杨梅红中的C3G与白酒中丙烯醛反应后的C3G及其与丙烯醛加合产物的液相-质谱图；
图5为矢车菊素-3-O-葡萄糖苷抑制果酒中丙烯醛的活性测定结果(柱形图从左到右依次为C3G、C3G-ACR、C3G-2ACR)。
具体实施方式
实施例中所述实验方法，如无特殊说明，均为常规方法；所述试剂和材料，如无特殊说明，均可从商业途径获得。
实施例1
矢车菊素-3-O-葡萄糖苷与ACR加合产物的纯化和结构研究
(1)实验材料与仪器
聚酰胺树脂100-200目(上海阿拉丁试剂公司)；乙醇(分析纯，上海国药集团化学试剂有限公司)；纯净水(杭州哇哈哈集团有限公司)；盐酸(上海国药集团化学试剂有限公司)。
AVANCE 400MHz核磁共振仪器(布鲁克公司)；1290/6460液相色谱-质谱联用仪(美国安捷伦公司)。
(2)实验步骤
称取134.7mgC3G溶于2mL甲醇溶液中，移取208μLACR原液，加入到1.792 mLPBS(PH＝7.0、0.1mol/L)溶液中，使C3G与ACR的最终摩尔浓度比为1： 10，涡旋混匀后，放入37℃，220rpm的恒温摇床中反应30min.样品取出后冰浴冷却备用。
C3G摩尔浓度不变，使其与ACR摩尔比例为1:3，涡旋混匀后，放入37℃， 220rpm的恒温摇床中反应60min.样品取出后冰浴冷却备用。
将浓缩后的C3G与ACR反应液按照每100g聚酰胺填料1g上样比例上样，上样后水、10％乙醇水(pH＝3)梯度进行洗脱，分步收集器收集洗脱液，并采用聚酰胺薄膜薄层层析跟踪分析每管产物，直至无产物检出，停止洗脱，将Rf 值相同的洗脱组分合并，旋转蒸发浓缩，置于-80℃冰箱贮藏。
通过不同摩尔比研究发现产生的加合产物量不同，按1:3是一加合产物多，按1:10时二加合产物多。
分别采用摩尔比1:3和1:10获得C3G与ACR的一加合产物C3G-ACR，二加合产物C3G-2ACR。LC-MS分析分子量，1D-NMR(1H，13C)，2D-NMR (HMQC，HMBC)进行结构分析。
(3)实验结果
C3G-ACR鉴定
制备的C3G-ACR经液质联用测定，正离子模式下，其母离子质量为m/z 505 [M+H]+，比C3G的母离子质量m/z 449[M+H]+多56(MWACR为56)，并且MS/MS 中其主要碎片离子峰为m/z 343[M+H]+表明丢失了一个葡萄糖分子(m/z 162)，是C3G的碎片离子峰m/z 287加上一分子ACR(MWACR 56)，另一个主要碎片离子峰为m/z299[M+H]+，表明丢失了一个葡萄糖分子(m/z 162)和一个 [-CHOH-CH2-](m/z 44)基团，这可表明C3G-ACR为一分子ACR与C3G的加合产物，C3G-ACR的1H NMR(400Hz)和13C NMR(100MHz)光谱数据详见表1。
表1 C3G与C3G-ACR加合产物的1H NMR(400Hz)和13C NMR(100MHz)光谱数据(氘代甲醇，δ的单位为ppm)
由表1可知，C3G-ACR与C3G具有相同的C环结构。C3G H-6上的氢信号消失，同时C3G-ACR出现了3个新的氢信号δH 2.81(2H,d),δH 2.17(2H,d)和δH 5.82(1H,d)，此外HMBC图谱结果显示(图2)，H-11与δC 152.27(C-7),δC 105.76(C-6),δC 95.36(C-13)和δC 27.58(C-12)均有关联，判断出C3G-ACR中有一个-CHCH2CH2-侧链，与A环相连，在C3G-ACR中，丙烯醛上的羰基与 C-7上的羟基脱水缩合形成了一个半缩醛结构。综合C3G-ACR的HPLC-MS/MS、1H NMR、13C NMR、HMBC、HMQC谱图结果(图2)，最终确定C3G-ACR 的结构，为一种新化合物，其结构为：
C3G-ACR鉴定
制备的C3G-ACR经液质联用测定，在正离子模式ESI-MS(m/z)下准分子离子峰是561[M+H]+，表明其分子量为561，比C3G分子量多了112(2个MWACR)。二级质谱图中有碎片离子峰m/z 399[M-162]+，355[M-162-44]+，311 [M-162-44-44]+分别是由C3G-2ACR丢失一个葡萄糖分子(m/z 162)、一个 [CHOH-CH2-]基团(m/z 44)、两个[CHOH-CH2-]基团形成的。由此推测C3G-2ACR 为C3G与ACR反应的二加合产物。C3G-2ACR的1H NMR(400Hz)和13C NMR(100MHz)光谱数据详见表2。
表2 C3G与C3G-2ACR加合产物的1H NMR(400Hz)和13C NMR(100MHz) 光谱数据(氘代甲醇，δ的单位为ppm)
将C3G-2ACR与C3G的氢谱和碳谱进行对比，C3G-2ACR与C3G具有相同的C环结构。原C3G H-6和H-5’上的氢信号消失，同时出现了6个新的氢信号δH 2.71(H-11，m)、δH 2.16(H-12，d)、δH 5.86(H-13，s)、δH 2.81(H-14，m)、δH2.03(H-15，d)、δH 5.80(H-16，s)，此外HMBC图谱结果显示，H-11与δC 102.58 (C-6)、δC 93.63(C-13)有关联，H-14与δC 112.69(C-5′)，δC25.63(C-15) 和δC 93.59(C-16)相关联，可以推断出C3G-2ACR中有两个-CHCH2CH2-侧链，分别与A环和B环相连，在C3G C-6和C-5′位上分别形成了两个半缩醛结构。综合C3G-2ACR的1H NMR、13C NMR、HMBC、HMQC谱图结果，最终确定 C3G-2ACR的结构式，如下所示：
实施例2
在模拟室温条件下矢车菊素-3-O-葡萄糖苷及其与丙烯醛加合产物抑制ACR 活性测定结果。
(1)实验材料与仪器
矢车菊素-3-O-葡萄糖苷(纯度>85％，成都瑞芬思生物科技有限公司)；2,4- 二硝基苯肼(DNPH·HCl，纯度>98％，Tokyo Chemical Industry)；矢车菊素-3-O- 葡萄糖苷-丙烯醛一加合产物(实施例1制备)；矢车菊素-3-O-葡萄糖苷-丙烯醛二加合产物(实施例1制备)；丙烯醛(ACR，98％水溶液，分析纯，山东西亚化学工业有限公司)；乙腈(色谱纯，上海国药集团化学试剂有限公司)；纯净水 (杭州哇哈哈集团有限公司)；磷酸二氢钠、磷酸氢二钠均为分析纯试剂(上海国药集团化学试剂有限公司)。
高效液相色谱仪：Agilent Technologies 1260(美国安捷伦公司)；ZQTY-70 台式振荡培养箱(上海知楚仪器有限公司)；QL-861涡旋混合仪(江苏海门市其林贝尔仪器制造有限公司)；KQ-300B超声波清洗器(昆山市超声仪器有限公司)； PHS-3C数字式pH计(上海三信仪表厂)；FA2104N电子分析天平(上海精密科学仪器有限公司)；
(2)实验步骤
用0.1mol/L，pH＝7.0的PBS配制ACR溶液，用甲醇配制C3G及C3G-ACR、 C3G-2ACR溶液。在2mL离心管中，分别加入0.5mL 1.0mmol/LACR和0.5mL 3.0 mmol/L C3G或C3G-ACR或C3G-2ACR，涡旋混匀后置于25℃，220rpm摇床中分别反应0、15、30、60、120min，取样后立即冰浴终止反应。空白对照组以相同体积的PBS代替矢车菊素-3-O-葡萄糖苷溶液，同时取500μL反应液进行衍生化，通过HPLC分析计算ACR清除率。每个样品均做3组平行。
HPLC方法：
采用Agilent 1260高效液相色谱仪进行分离检测，选用Kromasil 100-5 C18 色谱柱(250×4.6mm i.d.，5μm)，二极管阵列检测器(Diode array detector，DAD)，进样量20μL，柱温30℃，检测波长372nm，流动相A为乙腈、流动相B为超纯水(含0.1％甲酸)，流速1.0mL/min状态下以70％流动相A等度洗脱7.5min。
(3)实验结果
由图1可以看出，在模拟室温条件下，C3G-ACR对溶液中丙烯醛的抑制活性远远高于C3G抑制ACR的效果，在反应5min时，C3G-ACR对ACR的捕获率已高达66％，而C3G和C3G-2ACR的捕获率几乎为0。反应至30min时， C3G-ACR对ACR的捕获效率仍高于C3G和C3G-2ACR对ACR的捕获效率，继续反应60min后C3G可产生C3G-ACR，产生的C3G-ACR还可继续捕获ACR甚至产生二加合产物C3G-2ACR，因此捕获效率开始上升。
实施例3
矢车菊素-3-O-葡萄糖苷-丙烯醛一加合产物对丙烯醛的清除机制研究
(1)实验材料与仪器
矢车菊素-3-O-葡萄糖苷-丙烯醛一加合产物(实施例1制备)，丙烯醛(ACR， 98％水溶液，分析纯，山东西亚化学工业有限公司)；乙腈(色谱纯，上海国药集团化学试剂有限公司)；纯净水(杭州哇哈哈集团有限公司)；磷酸二氢钠、磷酸氢二钠均为分析纯试剂(上海国药集团化学试剂有限公司)。
高效液相色谱仪：Agilent Technologies 1260(美国安捷伦公司)；ZQTY-70 台式振荡培养箱(上海知楚仪器有限公司)；QL-861涡旋混合仪(江苏海门市其林贝尔仪器制造有限公司)；
(2)实验步骤
用0.1M、pH 7.0的PBS配制ACR溶液(15mM)，甲醇配制成5mM的矢车菊素-3-O-葡萄糖苷-丙烯醛一加合产物(C3G-ACR)；取0.5mL ACR溶液与0.5mL C3G-ACR溶液置于25℃、220rpm台式振荡培养箱中避光孵育1，5 min，进行液相分析。
(3)实验结果
当C3G-ACR与ACR以摩尔比1:3反应1min，如图3所示，体系中便出现C3G-2ACR，说明C3G-ACR可以通过捕获ACR生成加合产物来清除体系中的ACR，且捕获速度十分迅速。反应5min后生成的C3G-2ACR的含量可占整个反应体系的40％。说明一加合产物在C3G-ACR模拟环境溶液体系中对ACR 的捕获活性很好,捕获一分子ACR形成C3G-2ACR，完全明晰了C3G捕获ACR 的机制。
实施例4
杨梅红、矢车菊素-3-O-葡萄糖苷抑制果酒中丙烯醛的活性测定
(1)实验材料与仪器
杨梅红(苏州思源天然产物有限公司)；白酒(江苏桃林酒业有限公司)；XevoTMTQ-XS三重四极杆质谱联用仪(美国沃特世有限公司)。
(2)实验步骤
依据GB 31622-2014《食品安全国家标准食品添加剂杨梅红》，杨梅红可作为一种食品着色剂，其主要成分为矢车菊素-3-O-葡萄糖苷；依据GB 2760-2014《食品安全国家标准食品添加剂使用标准》果酒中杨梅红添加量可至200mg/L。因此，模拟果酒体系，称取2mg杨梅红溶解于10mL白酒中(普通白酒，酒精度为42％)，放置1h、4h、24h、3d和5d，分别测定体系中C3G、 C3G-ACR和C3G-2ACR含量。
UPLC条件：
色谱柱：ACQUITY
BEH C18 column(1.7μm,2.1×50mm,Waters)；柱温：40℃；流动相：0.1％甲酸水溶液(A)，乙腈(B)；梯度洗脱：5％B，0-2 min；5-35％B，2-5min；5-35％B，5-5.1min；95％B 5.1-6min；5％B，6-8min.进样量：10μL,流速：0.4mL/min。
MS/MS条件
使用Waters ACQUITY Xevo TQ-XS UPLC/MS系统，电喷雾离子源(ESI), 正离子模式，毛细管电压：2.5kv，脱溶剂气温度：500℃；选择多反应检测扫描模式(MRM)，三种物质的准分子离子峰、主要子离子碎片峰及其采集参数见表 3。
表3 C3G、C3G-ACR和C3G-2ACR的质谱采集参数
(3)实验结果
杨梅红中主要成分为C3G，如图4所示，在模拟杨梅酒酿造过程中，放置1 h即可捕获酒中的丙烯醛，生成C3G-ACR和C3G-2ACR，并且随着放置时间的延长，加合物的含量不断增高(图5所示)。说明杨梅红不仅可作为着色剂的主要成分用于食品中，还可作为丙烯醛的抑制剂或者清除剂，同时杨梅红中的C3G 不仅可作为着色剂的主要成分用于食品中，也可作为丙烯醛的抑制剂或者清除剂，有利于生态或者人体健康。
Claims (2)
1.矢车菊素-3-O-葡萄糖苷与丙烯醛加合产物的应用，其特征在于，所述矢车菊素-3-O-葡萄糖苷与丙烯醛加合产物作为环境或者食品加工中丙烯醛抑制剂的应用，所述加合产物为矢车菊素-3-O-葡萄糖苷与丙烯醛的一加合产物C3G-ACR，其结构如下所示：
2.根据权利要求1所述的应用，其特征在于，所述矢车菊素-3-0-葡萄糖苷与丙烯醛加合产物通过抑制丙烯醛与亲核生物大分子反应形成的各种有害加合或交联产物，从而作为环境或者食品加工中丙烯醛抑制剂。
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