CN106074471B - 一种新型抑菌剂六氢β-酸环糊精包合物的制备方法 - Google Patents
一种新型抑菌剂六氢β-酸环糊精包合物的制备方法 Download PDFInfo
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- CN106074471B CN106074471B CN201610551294.6A CN201610551294A CN106074471B CN 106074471 B CN106074471 B CN 106074471B CN 201610551294 A CN201610551294 A CN 201610551294A CN 106074471 B CN106074471 B CN 106074471B
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- Prior art keywords
- acid
- hexahydro
- cyclodextrin
- inclusion compound
- cyclodextrin inclusion
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- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 42
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Abstract
本发明涉及一种水溶性天然抑菌剂的制备方法，属于天然产物活性成分的应用领域。更具体地，本发明涉及一种以啤酒花中β‑酸的衍生物六氢β‑酸的水溶性环糊精包合物的制备方法。该方法以六氢β‑酸与α‑环糊精、β‑环糊精、γ–环糊精及其衍生物等9种不同的环糊精进行包合，获得能够改善六氢β‑酸水溶性的环糊精包合物，根据需要能够用于食品配料、饮料配料、化妆品、洗护用品、饲料产品中，以提高上述产品的防腐性能和保健功效。
Description
技术领域
本发明涉及一种水溶性抑菌剂的制备方法，属于天然植物活性成分应用领域。更具体地，本发明涉及一种以六氢β-酸与α-环糊精、β-环糊精、γ–环糊精及其衍生物等9种不同的环糊精进行包合，获得能够改善六氢β-酸水溶性的环糊精包合物。该方法所得到六氢β-酸环糊精包合物的水溶性明显改善，能够作为抑菌防腐成分添加于各种饮料、糖果、果冻、饼干、糕点中，也能够用于化妆品、洗护用品和饲料产品中，同时由于六氢β-酸本身具有多种药理活性，还能够将其作为保健品的配料使用。
背景技术
为了防止由微生物引起的腐败变质、延长食品保质期，食品防腐剂在食品加工中一直发挥着重要的作用。但近年来，随着人们对食品安全的关注度越来越高，很多合成防腐剂可能存在的潜在安全问题也已越来越受到重视。天然植物中含有很多重要的功效成分，其中一个重要的作用就是具有抑菌防腐的作用，长期以来在多种食品的加工中都得到广泛应用。啤酒花是这类植物的一个突出代表，在啤酒酿造中添加啤酒花的主要作用就是赋予其抑菌功效以延长啤酒的保质期，啤酒花中的苦味树脂是其中的重要功效成分。啤酒花的树脂类成分主要分为α-酸和β-酸两类，α-酸苦味很强，赋予了啤酒明显的苦味，也限制了其在其它食品中的使用。β-酸本身基本没有苦味，但其氧化产物也具有明显的苦味，也对啤酒苦味承担了一定的补充作用。为了扩大啤酒花β-酸在其它食品中的使用范围，中国专利200610066047.3公开了一种生产六氢蛇麻酮的方法，该方法所提到的具有抑菌作用的六氢蛇麻酮即为六氢β-酸分离提纯后的一个组分。实际上，同β-酸相似，六氢β-酸是主要由六氢蛇麻酮、六氢合蛇麻酮和六氢加蛇麻酮等一组同系物组成的化合物，这些成分都具有非常好的抑菌作用。
六氢β-酸是由啤酒花中软树脂β-酸氢化制备，与啤酒花中的其它活性成分相同，六氢β-酸具有非常强的抑菌、防腐能力，其抗菌能力大于乳酸链球菌素，山梨酸钾及苯甲酸，温度及酸碱对它的抑菌活性影响较小，并且它的保鲜能力优于常用的防腐剂，尤其对致病菌李斯特菌有很强的抑制作用。Thomas E.Stephan等对六氢β-酸体外抗肿瘤细胞增生作用的研究表明，六氢β-酸能够有效的抑制癌细胞的增长，特别是对乳腺癌MCF-7的抑制作用很强。尽管天然来源的六氢β-酸具有高效低毒的特点，但与其前体β-酸相比，六氢β-酸在稳定性明显提高的同时，疏水性也更强，这些都限制了应用范围。环糊精( Cyclodextrin,简称 CD)是淀粉在无水参与的条件下，经葡萄糖基转移酶得到的ɑ-1,4葡萄糖苷键连接的环状低聚糖。具有空腔的环糊精分子可以通过非共价作用与客体分子形成环糊精包合物，这对改善非极性客体分子的水溶性、提高活性化合物分子的稳定性、降低药物分子的毒性和对人体的刺激性、以及增加药物的吸收作用都有重要的意义。因此，环糊精包合技术在食品、香料及药物合成等领域的研究已受到了研究人员的广泛关注。
发明内容
由于天然来源的食品抑菌防腐剂的使用越来越受欢迎，本发明提供了一种新型抑菌剂六氢β-酸环糊精包合物的制备方法，因六氢β-酸尽管有非常好的抑菌作用，但水溶性差，该方法提供了一种采用环糊精包合的办法获得了六氢β-酸环糊精包合物，克服了直接使用六氢β-酸水溶解性差的问题，可拓展这一具有抑菌活性的化合物的使用范围。由于六氢β-酸本身不仅具有非常好的抑菌活性，还有非常强的抗氧化、抗肿瘤等功效，将其作为防腐剂使用不仅可以充分利用啤酒花资源，拓宽啤酒花的应用领域，也为其在饮食中的摄入提供了一个非常好的途径，对改善人体健康可以起到积极的作用。
为了实现上述目的，本发明是采用如下技术方案来予以实现的：
一种新型抑菌剂六氢β-酸环糊精包合物的制备方法，包括如下步骤：
(1) 将六氢β-酸与环糊精以质量比1：10~1：150的比例均匀混合，加入少量水使其润湿成为糊状物，在选定的温度下通过研磨使其反应，经过0.5-3小时的研磨后，置于烘箱中在40~60℃的条件下低温干燥至恒重，获得能够溶解于水的六氢β-酸-环糊精包合物；
(2) 将六氢β-酸与环糊精以质量比1：10~1：150的比例均匀混合，加入相当于环糊精质量5倍~100倍的纯度为50%以上的乙醇溶液，在选定的温度下采用超声波辅助溶解和反应，经过0.5-3小时的反应后，蒸馏除去溶剂乙醇和大部分水，在40~60℃的条件下低温干燥至恒重，获得能够溶解于水的六氢β-酸-环糊精包合物；
(3) 将六氢β-酸与环糊精以质量比1：10~1：150的比例均匀混合，加入相当于环糊精质量5倍~20倍纯度为50%以上的乙醇水溶液，在选定的温度下采用微波辅助溶解和反应，经过30秒~300秒的反应后，蒸馏除去溶剂乙醇和大部分水分，置于烘箱中在40~60℃的条件下低温干燥至恒重，获得能够溶解于水的六氢β-酸-环糊精包合物；
(4) 上述步骤（1）~（3）中所得到的新型抑菌剂六氢β-酸-环糊精包合物能够直接作为食品防腐剂应用于各种饮料、糖果、饼干及各种保健食品、化妆品、洗护用品、饲料产品中，在起到防腐抑菌作用的同时，还具有一定的药理活性。
所述的新型抑菌剂六氢β-酸环糊精包合物的制备方法，其特征在于所述的研磨法生产六氢β-酸与环糊精包合物的方法为不添加任何有机溶剂，直接将六氢β-酸与各种环糊精按比例混合后干法研磨，方法绿色环保，安全可靠。
所述的新型抑菌剂六氢β-酸环糊精包合物的制备方法，其特征在于所述的六氢β-酸与环糊精包合的方法为将六氢β-酸与环糊精按比例混合后，仅采用符合食品安全的水或乙醇作为溶剂，整个操作过程中不添加任何有毒、有害有机溶剂，方法绿色安全无污染；所述的符合食品安全的水为蒸馏水、纯净水和去离子水。
所述的新型抑菌剂六氢β-酸环糊精包合物的制备方法，其特征在于所述的环糊精为α-环糊精、β-环糊精、γ–环糊精、羟丙基-β-环糊精、羟丙基-γ-环糊精、2-甲基-β-环糊精、6-甲基-β-环糊精、2,6-二甲基-β-环糊精和2,3,6-三甲基-β-环糊精中的任意一种，所得到的包合物分别为六氢β-酸-α-环糊精包合物、六氢β-酸-β-环糊精包合物、六氢β-酸-γ–环糊精包合物、六氢β-酸-羟丙基-β-环糊精包合物、六氢β-酸-羟丙基-γ-环糊精包合物、六氢β-酸-2-甲基-β-环糊精包合物、六氢β-酸-6-甲基-β-环糊精包合物、六氢β-酸-2,6-二甲基-β-环糊精包合物和六氢β-酸-2,3,6-三甲基-β-环糊精包合物。
所述的新型抑菌剂六氢β-酸环糊精包合物的制备方法，其特征在于所述的六氢β-酸环糊精包合物优选的为六氢β-酸-γ-环糊精包合物。
所述的新型抑菌剂六氢β-酸环糊精包合物的制备方法，所述的六氢β-酸环糊精包合物优选的为六氢β-酸-2-甲基-β-环糊精包合物。
所述的新型抑菌剂六氢β-酸环糊精包合物的制备方法，其特征在于所述的六氢β-酸与环糊精的优选的质量比为1：20~1：50。
所述的新型抑菌剂六氢β-酸环糊精包合物的制备方法，其特征在于所述的选定的研磨温度范围为20℃~100℃，优选的研磨温度为20℃~50℃。
所述的新型抑菌剂六氢β-酸环糊精包合物，其特征在于所得到的六氢β-酸-环糊精包合物为具有一定水溶性物质，能够作为抑菌防腐成分添加于各种酒精饮料、软饮料、乳饮料、糖果、果冻、饼干、糕点中，也能够用于化妆品、洗护用品和饲料产品中，同时由于六氢β-酸本身具有多种药理活性，还能够将其作为保健品的配料使用。
根据本技术方案所得到的六氢β-酸环糊精包合物，具有非常好的食品安全性，能够明显地改善六氢β-酸。
本发明所取得的有益效果是：
本发明所提供的一种新型抑菌剂六氢β-酸环糊精包合物，可以通过采用α-环糊精、β-环糊精、γ–环糊精、羟丙基-β-环糊精、羟丙基-γ-环糊精、2-甲基-β-环糊精、6-甲基-β-环糊精、2,6-二甲基-β-环糊精和2,3,6-三甲基-β-环糊精中的任意一种与六氢β-酸包合，所获得的任一六氢β-酸环糊精包合物都具有增加六氢β-酸水溶性的功效，其中以六氢β-酸-2-甲基-β-环糊精包合物的增溶效果最好，六氢β-酸-γ-环糊精包合物的增加水溶性效果次之，且上述环糊精都具有非常好的安全性，能够用于各种食品、化妆品和保健品领域。
本发明所采用的包合物的制备工艺简单，生产过程中无有毒有害溶剂，工艺过程安全，包合物的收率和纯度都相对较高，易于实现规模化生产。
本发明所获得六氢β-酸环糊精包合物具有非常好的抑菌活性，包合物的水溶液无色无味，能和各种食品添加剂复配使用，生产过程便于调节控制。
具体实施方式
下面采用具体实施例的方式具体地解释本发明，但本发明不局限于实施例。
实施例1
将0.05g六氢β-酸与2gα-环糊精混合后置于研钵中，加入少量蒸馏水调成糊状，研磨1h后，置于烘箱中于40-60 ℃的条件下低温干燥至恒重，得到六氢β-酸-α-环糊精包合物。经分析，包合物的收率为94.6%，包合率为11.3%。
实施例2
将0.1g六氢β-酸与5gβ-环糊精直接混合均匀后置于研钵中，在不加入任何溶剂的条件下进行干法研磨2h，得到六氢β-酸-β-环糊精包合物，经分析，包合物的收率为96.13%，包合率为17.34%。
实施例3
将0.2g六氢β-酸与8g羟丙基-β-环糊精混合均匀后置于研钵中，加入少量去离子水调成糊状，研磨1.5h ，置于烘箱中于40-60 ℃的条件下低温干燥至恒重，得到六氢β-酸-羟丙基-β-环糊精包合物，经分析，包合物的收率为97.32%，包合率为35.41%。
实施例4
将0.5g六氢β-酸与25g 2-甲基-β-环糊精混合均匀后置于研钵中，加入5mL去离子水将其调成糊状，研磨1.5h，然后将其置于烘箱中于40-60 ℃的条件下低温干燥至恒重，得到六氢β-酸-2-甲基-β-环糊精包合物，经分析，包合物的收率为98.75%，包合率为85.42%。
实施例5
将5g六氢β-酸与200gγ-环糊精混合均匀后置于电动研磨机中，加入50mL蒸馏水，打开电源，研磨2h后，置于烘箱中于40-60 ℃的条件下低温干燥至恒重，得到六氢β-酸-γ-环糊精包合物，经分析，包合物的收率为93.45%，包合率为76.88%。
实施例6
将0.1g六氢β-酸与5g 2,6-二-甲基-β-环糊精混合均匀后置于研钵中，加入5mL去离子水将其调成糊状，研磨1h后，将其置于烘箱中于40-60 ℃的条件下低温干燥至恒重，得到六氢β-酸-2,6-二甲基-β-环糊精包合物，经分析，包合物的收率为98.75%，包合率为45.42%。
实施例7
将0.05g六氢β-酸与3g羟丙基-γ-环糊精混合均匀后置于研钵中，2mL去离子水将其调成糊状，研磨2h后，置于烘箱中于40-60 ℃的条件下低温干燥至恒重，得到六氢β-酸-羟丙基-γ-环糊精包合物，经分析，包合物的收率为93.45%，包合率为33.48%。
实施例8
将0.1g六氢β-酸与5g 2,3,6-三甲基-β-环糊精混合均匀后置于研钵中，加入3mL蒸馏水将其调成糊状，研磨1.5h，然后将其置于烘箱中于40-60 ℃的条件下低温干燥至恒重，得到六氢β-酸-2,3,6-三甲基-β-环糊精包合物，经分析，包合物的收率为95.34%，包合率为42.42%。
实施例9
将0.1g六氢β-酸与4g 6-甲基-β-环糊精混合均匀后置于研钵中，加入3mL去离子水将其调成糊状，研磨1.5h，然后将其置于烘箱中于40-60 ℃的条件下低温干燥至恒重，得到六氢β-酸-6-甲基-β-环糊精包合物，经分析，包合物的收率为96.66%，包合率为52.37%。
实施例10
将0.5g六氢β-酸与25g 2-甲基-β-环糊精混合均匀置于500mL的锥形瓶中，加入250mL50%的乙醇溶液，在40 ℃的温度下采用超声波辅助溶解和反应，经过2h的反应后，蒸馏除去溶剂乙醇和水，在40~60℃的条件下置于烘箱中低温干燥至恒重，得到六氢β-酸-2-甲基-β-环糊精包合物，经分析，包合物的收率为86.45%，包合率为36.88%。
实施例11
将5g六氢β-酸与200gγ-环糊精混合均匀后置于电动研磨机中，加入50mL蒸馏水，打开电源，研磨2h后，置于烘箱中于40-60 ℃的条件下低温干燥至恒重，得到六氢β-酸-γ-环糊精包合物，经分析，包合物的收率为93.51%，包合率为79.87%。
实施例12
将50g六氢β-酸与1000g 2-甲基-β-环糊精混合均匀后置于电动球磨机中，打开电源，调好转速，在不加入任何溶剂的条件下研磨1.0h，得到六氢β-酸-2-甲基-β-环糊精包合物，经分析，包合物的收率为97.95%，包合率为87.26%。
Claims (1)
1.一种新型水溶性抑菌防腐剂六氢β-酸环糊精包合物的制备方法，其特征在于，将0.5g六氢β-酸与25g 2-甲基-β-环糊精混合均匀后置于研钵中，加入5mL去离子水将其调成糊状，研磨1.5h，然后将其置于烘箱中于40~60℃的条件下低温干燥至恒重，得到六氢β-酸-2-甲基-β-环糊精包合物。
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| CN112292039A (zh) * | 2019-05-23 | 2021-01-29 | 广州英赛特生物技术有限公司 | 一种包含六氢-β-酸组分化合物的饲用组合物及其应用 |
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