CN113080382B - 小豆蔻明作为丙烯醛抑制剂的应用 - Google Patents
小豆蔻明作为丙烯醛抑制剂的应用 Download PDFInfo
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Abstract
本发明公开了一种小豆蔻明(CAR)作为丙烯醛(ACR)抑制剂的应用,相较于现有技术,本发明公开了查耳酮类化合物小豆蔻明的一种新应用,即其能够有效捕获ACR以控制其含量,避免其与DNA、RNA、蛋白质等细胞中亲核物质交联导致蛋白质结构、功能的改变及DNA的损伤。小豆蔻明可作为ACR的清除剂,抑制食品加工过程中产生的ACR,从而阻断ACR被人体摄入后产生的一系列慢性病危害,如引起心血管疾病、阿尔兹海默症、糖尿病等。
Description
技术领域
本发明公开了小豆蔻明作为丙烯醛抑制剂的应用,属于香辛料中黄酮类物质的新用途技术领域。
背景技术
活性羰基化合物(RCS)是指一类含有C=O键的化合物,具有极高的亲电性。丙烯醛(ACR)作为RCS中一种最简单的α,β-不饱和醛,为高挥发性无色透明、有恶臭的剧毒液体,其蒸汽有强烈的刺激性、催泪性。ACR因同时出现了两个反应性位点(C=C键和C=O键)而具有极高的活性。ACR能够攻击DNA、RNA和蛋白质等亲核物质引起蛋白质结构、功能的改变及DNA的损伤。长期摄入ACR会导致许多慢性疾病,如心血管疾病、阿尔兹海默病、帕金森症、肌萎缩性侧索硬化症和糖尿病等。ACR的来源主要分为外源性和内源性,其中日常饮食是外源性ACR的主要来源之一。日常食用食物如水果、蔬菜、奶酪、酒精饮料、鸡蛋、鱼类和肉类中均含有一定量的ACR,世界卫生组织建议ACR的口服日耐受量为7.5mg/kg体重,而美国环境保护署建议ACR的口服日耐受量为1.09mg/kg体重,因此,如何有效阻断、调控食品加工过程中ACR的形成,降低外源性ACR的摄入,对提高食品安全性具有重要意义。
小豆蔻明为姜科植物草豆蔻的主要提取物,同时也存于草豆蔻、小豆蔻、草果等天然香辛料中,这些豆蔻多为药食两用植物,可以作为天然香辛料,按照国家食品添加剂要求应用于肉制品加工中,按生产需要适量添加,其常常出现于五香粉、十三香粉的配方中,是肉制品加工中重要的香辛料添加物。
目前国内外对于小豆蔻明的研究主要集中在具有多种生物学活性,如抗炎、抗氧化、抗诱变、抗感染等。尚未发现小豆蔻明及含有小豆蔻明的豆蔻属物质在抑制丙烯醛方面的功效。
发明内容
发明目的:针对上述技术问题,本发明提供了小豆蔻明在食品加工中作为丙烯醛(ACR)抑制剂的应用。
技术方案:为达到上述目的,本发明采用以下技术方案:
本发明提供了小豆蔻明或其加合产物作为ACR抑制剂的应用。
所述小豆蔻明为天然产物中所含的(E)-1-(2,4-二羟基-6-甲氧基苯基)-3-苯基丙-2-烯-1-酮,其化学结构式如下所示:
进一步地,所述小豆蔻明或其加合产物作为食品中丙烯醛抑制剂的应用。
进一步地,所述加合产物为小豆蔻明与丙烯醛的一加合产物,其中,一加合产物的结构式为:
CAR-ACR
进一步地,所述小豆蔻明或其加合产物能够捕获丙烯醛从而降低丙烯醛含量。
进一步地,所述小豆蔻明或其加合产物能够抑抑制由丙烯醛与DNA、RNA、蛋白质等亲核生物大分子反应形成的各种有害加合或交联产物。
进一步地,所述抑制剂中,小豆蔻明或其加合产物为唯一的成分。或者,所述抑制剂中,小豆蔻明或其加和产物作为主要成分,与其他物质复配共同使用,所形成的制剂。
一种含所述小豆蔻明的天然产物在抑制丙烯醛方面的应用。
进一步地,所述天然产物包括草豆蔻、小豆蔻、香豆蔻、草果、白豆蔻和肉豆蔻等香辛料。
有益效果:与现有技术相比,本发明具有如下显著优点:
本发明所述小豆蔻明或其加合产物在清除ACR时,可以直接添加或以草豆蔻、小豆蔻、香豆蔻、草果、白豆蔻和肉豆蔻的形式添加到食品中使用,也可以与其他天然或合成的ACR清除剂复配使用,达到降低ACR含量,减少人体摄入有害物质的目的。相较于现有技术,本发明小豆蔻明的一种新应用能够有效控制ACR的含量,避免其与DNA、RNA、蛋白质等亲核生物大分子反应形成的各种有害加合或交联产物。小豆蔻明及其一加和产物均可作为ACR的抑制剂,有效清除肉制品等食品加工过程中产生的ACR,预防加工食品中ACR通过饮食摄入在体内,给人类健康带来的危害。
附图说明
图1为本发明小豆蔻明及加合产物的化学结构式;
图2为本发明在模拟食品加工蒸煮条件下小豆蔻明及其加和产物对ACR的活性抑制测定结果图;
图3为本发明草豆蔻中主要化合物小豆蔻明抑制煮肉中ACR的活性测定液相图;
图4为本发明草豆蔻中主要化合物小豆蔻明抑制煮肉中ACR的质谱图;
图5为本发明草豆蔻中主要化合物小豆蔻明抑制烤肉中ACR的活性测定总离子流图及质谱分子量表格。
具体实施方式
下面结合附图对本发明的技术方案作进一步说明。
实施例1在模拟食品加工蒸煮条件下小豆蔻明抑制ACR活性测定结果。
(1)实验材料与仪器
小豆蔻明(Cardamonin,>98%,西安天丰生物科技公司);2,4-二硝基苯肼(DNPH·HCl,>98%,Tokyo Chemical Industry);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
使用PBS(0.1mol/L,pH 7)配制ACR溶液,在2mL离心管中,分别加入0.5mL的ACR溶液(0.5mmol/L)和0.5mL的小豆蔻明/CAR-ACR溶液(0.5mmol/L),用DMSO代替小豆蔻明溶液作为空白,涡旋混匀后,置于100℃油浴锅中分别反应0,5,15,30,60,120min,反应结束后,采用HPLC检测ACR含量,计算小豆蔻明/CAR-ACR在模拟蒸煮条件下对ACR的抑制率,每个样品做三组平行。
(3)实验结果
由图2可以看出,在模拟蒸煮条件下,小豆蔻明和CAR-ACR均具有良好的抑制ACR的功能,且随着时间的延长抑制效果显著增加。反应至30min时,小豆蔻明对ACR的捕获效率就超过了50%,当反应至2h时,小豆蔻明对ACR的捕获效率超过了95%,CAR-ACR抑制率略低于小豆蔻明,当反应至60min时,CAR-ACR对ACR的捕获效率也超过了50%。推测为体系中生成的加和产物与小豆蔻明协同抑制ACR。
实施例2小豆蔻明与ACR加合产物的纯化和结构研究
(1)实验材料与仪器
ODS填料(日本YMC公司);硅胶填料(日本富士公司);甲醇(分析纯,上海国药集团化学试剂有限公司);正己烷(分析纯,上海国药集团化学试剂有限公司);乙酸乙酯(分析纯,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449.55mg小豆蔻明溶于5mL DMSO溶液中为A液,吸取409μL的ACR原液使用PBS溶液(0.1mol/L,pH 7.0)定容至5mL为B液,使得小豆蔻明与ACR的最终摩尔比为1:3,将A、B液混合并涡旋混匀后放入100℃油浴锅中反应30min,冷却浓缩,并用大量水洗去DMSO溶剂,旋转蒸发浓缩备用。
采用反相ODS柱层析对小豆蔻明与ACR的加合产物进行分离,以60%甲醇-水溶液平衡ODS柱,将反应液浓缩过滤,缓慢滴加至柱填料上表面,以10%,40%,60%,75%的甲醇-水溶液进行梯度洗脱,收集75%的甲醇洗脱液,浓缩后上样到硅胶柱,使用正己烷/乙酸乙酯(v/v=98:2)洗脱混合物,获得小豆蔻明与ACR的加合产物CAR-ACR,LC-MS分析分子量,1D-NMR(1H,13C),2D-NMR(HMQC和HMBC)进行结构分析。
(3)实验结果
3.1 CAR-ACR鉴定
制备的CAR-ACR经液质联用测定,正离子模式下,m/z是327[M+H]+,比CAR的m/z271[M+H]+多56(MWACR为56),并且MS/MS中327[M+H]+的含有碎片离子峰m/z 167,与CAR m/z271[M+H]+的主要碎片离子峰相同,且MS/MS中还含有碎片离子峰283[M-56-92+H]+,推测为ACR在小豆蔻明的A环上8位相接并与7位成环后,丢失了一个-CH2CHOH-分子形成,因而表明CAR-ACR为一分子ACR与小豆蔻明的加合产物。
表1小豆蔻明(CAR)与CAR-ACR加合产物的1H NMR(400Hz)和13C NMR(100MHz)光谱数据(氘代DMSO,δ的单位为ppm)
由表1可知,CAR-ACR的氢谱与CAR相对比,出现了氢质子δH 6.03(1H,s),而不是CAR氢谱中显示的两个氢质子δH 5.96(1H,d)和δH 6.05(1H,d),这表明ACR在CAR的A环的C-6或C-8位置与CAR共轭。HMBC显示,A环上的唯一质子δH 6.03(1H,s)与δC 161.07(C-5)相关,表明该质子为H-6,因此ACR与A环的C-8位置相接。此外,氢质子还出现在δH 2.55(2H,d)、δH1.86(2H,s)和δH 5.54(1H,m)位置,且HMBC表示δH 2.55(2H,d)处的氢质子与δC 164.49(C-7)、δC 102.98(C-8)、δC 160.55(C-9)、δC27.22(C-13)和δC 93.38(C-14)相关,表明ACR取代了C-8位置的羟基,并接在C-8位上。由于在碳谱中发现的唯一的醛质子信号是C-4的醛基信号,因此可以推测CAR捕获ACR形成了一个半缩醛结构,这也提供了一种ACR的加合途径。
实施例3草豆蔻中主要化合物小豆蔻明抑制煮肉中ACR的活性测定结果
(1)实验材料与仪器
小豆蔻明(Cardamonin,>98%,西安天丰生物科技公司);草豆蔻(市购);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);1290/6460液相色谱质谱联用仪(美国安捷伦公司)。
(2)实验步骤
将采购的生猪排骨切成长、宽、高为3、3、2cm的肉块(湿重30g),加入适量草豆蔻(10g/500g排骨)煮肉,并加入3g盐和1L水,于蒸煮锅内沸水煮制140min,于不同时间点取样,冷却后使用粉碎机粉碎排骨,保存在-80℃中进行进一步分析。
取出保存在-80℃的样本解冻,准确称量5.0g样品,使用5mL乙腈饱和的正己烷进行涡旋萃取,再使用15mL正己烷饱和的乙腈涡旋萃取,重复萃取两次后将乙腈层合并浓缩,同时将草豆蔻使用粉碎机粉碎,并以同样的方法使用乙腈和正己烷进行提取,将乙腈层合并浓缩,五花肉提取液和草豆蔻提取液均使用HPLC-DAD及LC-MS/MS检测。
(3)实验结果
由图3所示,草豆蔻提取液中含有较高含量的CAR,其中,A:草豆蔻提取液;B:煮肉30min时排骨提取液;C:煮肉60min时排骨提取液;D:煮肉120min时排骨提取液;E:煮肉140min时排骨提取液。由图3可知,煮肉体系中,随着煮肉时间的延长,排骨中CAR含量逐渐升高,并在煮至140min时,出现了小豆蔻明与ACR的加合产物CAR-ACR,由图4所示,使用LC-MS/MS进行检测,进一步确认了CAR与其加合产物,由此推测草豆蔻的加入,其所含小豆蔻明在蒸煮过程中可以浸出,并捕获ACR,从而降低了肉品中ACR的含量,提高了加工肉制品的安全性。
实施例4草豆蔻中主要化合物小豆蔻明抑制烤肉中ACR的活性测定结果。
(1)实验材料与仪器
小豆蔻明(Cardamonin,>98%,西安天丰生物科技公司);乙腈(色谱纯,上海国药集团化学试剂有限公司);草豆蔻(市售);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);1290/6460液相色谱-质谱联用仪(美国安捷伦公司)。
(2)实验步骤
市购新鲜的五花肉洗净,沥干水分后切成相同大小的正方形(20g),500g为一组,一组中为25片肉,向其中加入料酒(5g)、盐(5g)、蚝油(10g)、糖(5g)以及草豆蔻(10g),并在4℃中腌制30min。腌制后放入烤箱,在200℃下烘烤20min,每隔10min翻转一次五花肉。待烤制完毕冷却后,将五花肉保存在-80℃以进一步分析。
将五花肉用绞肉机均质化,并使用乙腈和正己烷进行萃取,将乙腈层合并浓缩,使用LC-MS/MS检测。
(3)实验结果
由图5可知,高温烤肉过程中仍然检出小豆蔻明和加合产物CAR-ACR,表明小豆蔻明在高温加工条件下稳定,且仍然保留了捕获ACR的活性,该功能有利于降低加工食品中有害ACR的含量,从而提高食品安全,有利于人体健康。
Claims (6)
1.小豆蔻明或其加合产物作为丙烯醛抑制剂的应用,其特征在于,所述加合产物为小豆蔻明与丙烯醛的一加合产物,其中,一加合产物的结构式为:
。
2.根据权利要求1所述的应用,其特征在于,所述小豆蔻明或其加合产物作为食品中丙烯醛抑制剂的应用。
3.根据权利要求1所述的应用,其特征在于,所述小豆蔻明或其加合产物能够捕获食品中的丙烯醛从而降低食品中丙烯醛的含量。
4.根据权利要求1所述的应用,其特征在于,所述小豆蔻明或其加合产物为抑制剂中唯一的成分。
5.根据权利要求1所述的应用,其特征在于,所述抑制剂中,小豆蔻明或其加合产物作为主要成分,与其他物质复配共同使用。
6.含有权利要求1所述小豆蔻明的草豆蔻在抑制丙烯醛方面的应用。
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