CN114958796A - 一种姜黄素的糖基化方法 - Google Patents
一种姜黄素的糖基化方法 Download PDFInfo
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- CN114958796A CN114958796A CN202210731651.2A CN202210731651A CN114958796A CN 114958796 A CN114958796 A CN 114958796A CN 202210731651 A CN202210731651 A CN 202210731651A CN 114958796 A CN114958796 A CN 114958796A
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Abstract
本发明公开了一种姜黄素的糖基化方法，属于生物技术领域。蔗糖磷酸酶gtfA其氨基酸序列如序列1所示。所述的蔗糖磷酸酶克隆至罗伊氏乳酸杆菌。本发明为提供了一种高效的姜黄糖基化的酶促反应技术。
Description
技术领域
本发明属于生物技术领域，具体的涉及一种姜黄素的糖基化方法。
背景技术
姜黄素(Curcumin，diferuloylmethane)是从传统中药的莪术和姜黄的根茎中提取的一种药食两用的天然多酚植物化合物。在美国，姜黄素也被用于为糕点、芥末、咖喱和乳制品以及米饭、肉类和鱼类菜肴着色。除了这些用途外，姜黄素还具有良好的药理特性，如抗氧化、抗癌、抗炎和抗纤溶作用。因此，它长期以来一直被认为是一种潜在的保健天然化合物，可以预防心脏病，并且具有保肝和肾保护活性。在过去的几十年里，已经有广泛的研究证明了姜黄素的药理机制，如抑制实验性过敏脑脊髓炎治疗多中心性硬化症，并作为肌浆/内质网状钙泵对抗囊性纤维化。
然而，姜黄素的水溶性极低，这导致了其较差的药代动力学/药效学(PK/PD)特性、，以及较低的生物利用度，均阻碍了其进一步的应用。因此，提高姜黄素水溶性成为具有经济价值的中的一个迫切技术问题。现有技术中通过纳米/微胶囊包埋形式，虽然可以提高姜黄素水中含量，但这依托于亲水载体的分散方法，并不能真正解决其生物利用度的问题(DOI:10.1016/j.molstruc.2020.129774)。
现有技术中,糖基化被认为是有效提高姜黄素水溶性及生物利用度的有效手段。因此高效的低成本的糖基化技术手段,是糖基化姜黄素获取的关键性技术。现有技术中GRVijayakumar公开了利用淀粉葡萄糖苷酶对姜黄素糖苷化的技术方案，然而在该酶催化效率较低，糖基化的摩尔转化率(糖基化率)最高仅能到48％ (DOI:10.1108/02632770710753307)。Y Kaminaga则公开了利用长春花根悬浮细胞，生物催化姜黄素糖基化的技术方案，然而姜黄素的糖基化率仅32％，产量仅2.5μmol/g(DOI: 10.1016/S0014-5793(03)01265-1)。
发明内容
本发明的目的是为了提供一种姜黄素的糖基化方法。以解决现有技术的上述问题。
本发明的目的是通过以下技术方案来实现的。
一种可用于姜黄素糖基化的蔗糖磷酸酶gtfA，其氨基酸序列如序列1所示，该酶克隆至罗伊氏乳酸杆菌。
一种糖基化姜黄素的方法，以蔗糖磷酸酶gtfA为催化剂，在糖基供体存在的情况下通过酶促糖基转移反应获得糖基化姜黄素。
进一步的，所述的蔗糖磷酸酶gtfA的氨基酸序列为序列1所示。
进一步的，所述的蔗糖磷酸酶可以由大肠杆菌、毕赤酵母、酿酒酵母、谷氨酸棒状杆菌等表达宿主所表达的重组菌。
进一步的，所述的糖基供体为蔗糖、麦芽糖、1-磷酸-葡萄糖、 6-磷酸-葡萄糖中的一种。
作为优选的，所述的糖基供体为蔗糖或1-磷酸-葡萄糖。
作为优选的，所述的酶促糖基转移反应的反应条件为反应PH 6.0-7.5，温度35-45℃。
进一步的，所述的酶促糖基转移反应的反应条件为加入表面活性剂作为增溶剂。
作为优选的，所述的表面活性剂为槐糖脂。
蔗糖磷酸酶(又称为蔗糖:磷酸α-D葡萄糖基转移酶；EC 2.4.1.7) 催化蔗糖(α-D-吡喃葡萄糖基-1,2-β-D-呋喃果糖苷)和磷酸可逆转化为α-D-吡喃葡萄糖基-1-磷酸酯(Glc1P)和D-果糖。KEGG数据库表明蔗糖磷酸酶参与了蔗糖的分解和合成。现有技术已知蔗糖磷酸化酶可催化磷酸基与葡萄糖基之间的三种类型反应，包括磷酸基的水解和合成、糖基水解和转糖基化反应。砷酸盐可替代磷酸盐作为葡萄糖基受体底物。蔗糖磷酸酶也被报道可以用于多酚类的糖基化，包括儿茶素和(-)-表没食子儿茶素。
本发明提供了一种高效的姜黄糖基化的酶促反应技术。
具体实施方式
下面结合具体实施例进一步阐述本发明的技术特征。
实施例1：重组蔗糖磷酸酶A的表达
将蔗糖磷酸酶A序列1)按照大肠杆菌密码偏好性对其进行密码子优化，优化后的基因序列如序列2所示。该蔗糖磷酸酶来源于罗伊氏乳杆菌(Lactobacillus reuteri)，并做了人工优化。将密码子优化后的蔗糖磷酸酶A基因序列合成并亚克隆至大肠杆菌表达载体 pET30a(+)(基因合成与亚克隆过程委托苏州金唯智公司完成，pET30a (+)为已公开的商品化大肠杆菌表达载体)。由本公司将带有蔗糖磷酸酶A基因的重组质粒pET30a-A转化大肠杆菌BL21(DE3)宿主，在含有氯霉素(34μg/mL)的LB抗性固体培养基上过夜筛选。选择其中的阳性克隆单菌落分别挑选至摇瓶进行重组酶的表达。重组酶的摇瓶诱导表达采用LB培养基(蛋白胨10g/L、酵母粉5g/L、氯化钠 10g/L)，将LB抗性固体培养基收集的阳性克隆株接种摇瓶后，在 37℃培养至浊度OD600为0.6-1.0后，添加IPTG(异丙基硫代半乳糖苷)的诱导重组蔗糖磷酸酶A表达(摇瓶内终浓度为0.4mM)，同时降温至25℃培养8-14h。以蔗糖磷酸合成酶活性检测试剂盒(上海吉至生化科技有限公司生产)，按其说明书检测蔗糖磷酸酶A的酶的活性，选择酶活最高的克隆top1作为重组酶的表达株。
以top1克隆作为表达株，使用10L发酵罐培养产酶。发酵罐培养采用发酵培养基(蛋白胨10g/L、酵母粉5g/L、氯化钠8g/L、甘油10g/L、硫酸镁1g/L、磷酸二氢钾1g/L、磷酸氢二钾2g/L)，补料为30％甘油，氨水控制pH7.0。接种发酵罐后37℃培养5h开始补料，OD600为20时开始诱导，加入终浓度0.4mM的IPTG并降温至25℃培养，发酵22h放罐。之后离心收集菌体作为蔗糖磷酸酶A 粗酶。
实施例2：蔗糖磷酸酶A的表达催化姜黄素糖基化
反应以1μM的磷酸缓冲液作为反应体系，其中含有30mg/mL糖基供体,10mg/mL实施实例1所制备的蔗糖磷酸酶gtfA粗酶，1mg/mL 槐糖脂(波顿(上海)生物技术有限公司)，0.5mmol/L姜黄素，之后于37℃动态振荡催化酶促反应12h。反应中所添加的糖基化供体如表1所示。
反应前后，姜黄素及其糖基化衍生物含量通过HPLC外标法进行检测，HPLC的分析条件为柱子使用Cosmosil 5C18-ARII柱，4.6U150mm，Nacalai Tesque，流动相使用用以下甲醇与水的梯度洗脱：0至14分钟，甲醇比率从40％提至80％；14至15分钟，甲醇比率从80％提高到100％，15至20分钟，维持100％甲醇等度洗脱。流速为1.0毫升/分钟。在DAD检测器于423nm监测洗脱。基于使用各姜黄素糖苷制备的校准曲线计算产物的量。
表1不同糖基供体反应后糖基化姜黄素产物含量
实施例3：其他蔗糖磷酸酶的转糖基
按照实施实例1的步骤，表达了其他菌株来源的蔗糖磷酸酶，包括来自Ruminococcus callidus菌，AmyAc蔗糖磷酸酶(NCBI Reference Sequence:WP_022410484.1)，来自Lactobacillus crispatus菌株的gtfA蔗糖磷酸酶(NCBI ReferenceSequence: WP_060461996.1)，来自于Paenibacillus sp.A3的蔗糖磷酸酶(NCBIReference Sequence:WP_054973973.1)，来自于Marinobacter flavimaris的蔗糖磷酸酶(NCBI Reference Sequence: WP_104270647.1)。所有酶的基因序列及氨基酸序列公众均可以从 NCBI数据库(https://www.ncbi.nlm.nih.gov/)中凭借NCBI Reference Sequence号查询与获取。之后将上述不同来源的蔗糖磷酸酶重组酶，按照实施实例2所述的方法进行姜黄素的转糖基测试，然而，所有4种重组酶均未检出出有Curcumin 4’-O-glucoside或Curcumin 4’4-O-diglucoside或其他糖基姜黄素生成，因此这4种其他菌株来源的糖磷酸酶不具备姜黄素为受体的糖基转移能力。
序列表
<110> 上海龙殷生物科技有限公司
<120> 一种姜黄素的糖基化方法
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Claims (9)
1.一种可用于姜黄素糖基化的蔗糖磷酸酶gtfA，其特征在于：其氨基酸序列如序列1所示。
2.根据权利要求1所述的一种可用于姜黄素糖基化的蔗糖磷酸酶gtfA，其特征在于：所述的蔗糖磷酸酶克隆至罗伊氏乳酸杆菌。
3.一种糖基化姜黄素的方法，其特征在于：以蔗糖磷酸酶gtfA为催化剂，在糖基供体存在的情况下通过酶促糖基转移反应获得糖基化姜黄素。
4.根据权利要求3所述的一种糖基化姜黄素的方法，其特征在于：所述的蔗糖磷酸酶可以由大肠杆菌、毕赤酵母、酿酒酵母、谷氨酸棒状杆菌表达宿主所表达的重组菌。
5.根据权利要求3所述的一种糖基化姜黄素的方法，其特征在于：所述的糖基供体为蔗糖、麦芽糖、1-磷酸-葡萄糖、6-磷酸-葡萄糖中的一种。
6.根据权利要求5所述的一种糖基化姜黄素的方法，其特征在于：所述的糖基供体为蔗糖或1-磷酸-葡萄糖。
7.根据权利要求3所述的一种糖基化姜黄素的方法，其特征在于：所述的酶促糖基转移反应的反应条件为反应PH 6.0-7.5，温度35-45℃。
8.根据权利要求3所述的一种糖基化姜黄素的方法，其特征在于：所述的酶促糖基转移反应的反应条件为加入表面活性剂作为增溶剂。
9.根据权利要求8所述的一种糖基化姜黄素的方法，其特征在于：所述的表面活性剂为槐糖脂。
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