Preparation and Physicochemical Properties of Hawthorn Leaf Extract Phospholipid Complex
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摘要:
目的 优化山楂叶提取物磷脂复合物的制备方法并研究其理化性质。 方法 采用质量权重系数法表征山楂叶提取物黄酮组分的整体性质, 在单因素考察的基础上, 利用正交设计试验, 以组分复合率和质量复合率为指标优化制备方法。利用扫描电镜、紫外光谱、红外光谱和X-衍射进行表征, 同时考察其表观油水分配系数。 结果 山楂叶提取物磷脂复合物的最佳制备方法为以无水乙醇为复合溶剂, 山楂叶提取物的质量浓度为1 mg · mL-1, 药脂比为1 ∶ 4, 在60 ℃下复合1.5 h。扫描电镜、X-衍射分析等验证了山楂叶提取物磷脂复合物的形成, 且不同pH下表观油水分配系数较原料药均有所提高。 结论 山楂叶提取物磷脂复合物制备方法合理可行, 脂溶性得到改善。 Abstract:OBJECTIVE To optimize the preparation method of hawthorn leaf extract phospholipid complex and research its physicochemical properties. METHODS The mass fraction weight coefficient method was used to characterize the overall properties of the flavonoids of the hawthorn leaf extract. On the basis of single factor investigation, the orthogonal design experiment was used to optimize the preparation method, taking the component compound rate and mass compound rate as the index. It was characterized by scanning electron microscopy, UV spectrum, infrared spectrum and X-ray diffraction. While its apparent oil-water partition coefficient was also investigated. RESULTS The best preparation method of hawthorn leaf extract phospholipid complex is to use absolute ethanol as the compound solvent, the mass concentration of hawthorn leaf extract is 1 mg ·mL-1, the drug-to-lipid ratio is 1 ∶ 4, and the reaction is compounded at 60 ℃ for 1.5 h. Scanning electron microscopy, X-ray diffraction analysis, etc. verified the formation of hawthorn leaf extract phospholipid complex, and the apparent oil-water partition coefficient of different pH was improved compared with the crude drug. CONCLUSION The preparation method of hawthorn leaf extract phospholipid complex is reasonable and feasible, and the fat solubility is improved. -
图 1 供试品(A)、混合对照品(B)和大豆磷脂(C)HPLC图
注：1.牡荆素葡萄糖苷; 2.牡荆素鼠李糖苷; 3.牡荆素; 4.芦丁; 5.金丝桃苷
Figure 1. HPLC chart of test sanple(A), mixed reference (B) and soybean phospholipid (C)
图 2 不同样品扫描电镜图
注：A.山楂叶提取物; B.大豆磷脂; C.物理混合物; D.磷脂复合物
Figure 2. Scanning electron micrographs of different samples
图 3 不同样品紫外光谱图
注：A.物理混合物；B.磷脂复合物；C.山楂叶提取物；D.大豆磷脂
Figure 3. UV spectra of different samples
图 4 不同样品红外光谱图
注：A.山楂叶提取物；B.大豆磷脂；C.物理混合物；D.磷脂复合物
Figure 4. Infrared spectra of different samples
图 5 不同样品X-衍射分析图谱
注：A.物理混合物；B.大豆磷脂；C.山楂叶提取物；D.磷脂复合物
Figure 5. X-Diffraction analysis patterns of different samples
图 6 质量权重系数法所得油水分配系数比较
Figure 6. Comparison of oil-water distribution coefficient obtained by mass weight coefficient method
表 1 各成分的回归方程、线性范围及相关系数
Table 1. Regression equation, linear range and correlation coefficient of each component
化合物 回归方程 线性范围/(g·mL-1) R2 牡荆素葡萄糖苷 Y=19 926X+28 209 4.41~141.13 0.999 5 牡荆素鼠李糖苷 Y=16 756X+58 733 9.72~310.92 0.999 4 牡荆素 Y=20 874X+3 342 0.30~9.68 0.999 0 芦丁 Y=9 186X+554 0.34~10.95 0.999 7 金丝桃苷 Y=16 157X+1 192 0.33~10.62 0.999 5 
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表 2 因素水平表
Table 2. Factors and levels
水平 A
药脂比B
复合温度/℃C
药物质量浓度/(mg·mL-1)D
误差列1 1∶3 40 1 - 2 1∶4 50 2 - 3 1∶5 60 3 -
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表 3 正交试验各成分复合率结果(%)
Table 3. The results of the compound rate of each component in the orthogonal test(%)
序号 牡荆素葡萄糖苷 牡荆素鼠李糖苷 牡荆素 芦丁 金丝桃苷 组分 1 55.08 58.59 44.52 47.42 46.62 57.37 2 43.83 50.50 51.92 55.23 49.23 49.25 3 40.37 45.52 45.66 49.72 46.27 44.57 4 52.29 60.40 61.65 67.58 58.92 58.89 5 40.45 44.32 45.97 50.25 47.78 43.70 6 66.94 71.28 64.26 67.82 57.73 70.06 7 42.94 49.45 53.49 55.06 49.59 48.30 8 60.98 70.65 65.31 63.25 63.19 68.46 9 53.67 59.71 61.63 66.18 59.96 58.63
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表 4 正交试验直观分析结果
Table 4. Intuitive analysis results of orthogonal test
序号 A B C D 组分复合率/% 质量复合率/% 综合评分/% 1 1 1 1 1 57.37 74.00 65.69 2 1 2 2 2 49.25 61.24 55.25 3 1 3 3 3 44.57 63.07 53.82 4 2 1 2 3 58.89 69.76 64.32 5 2 2 3 1 43.70 56.95 50.33 6 2 3 1 2 70.06 85.71 77.89 7 3 1 3 2 48.30 57.74 53.02 8 3 2 1 3 68.46 83.17 75.81 9 3 3 2 1 58.63 70.00 64.31 k1 58.253 61.010 73.130 60.110 k2 64.180 60.463 61.293 62.053 k3 64.380 65.340 52.390 64.650 极差 6.127 4.877 20.740 4.540
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表 5 方差分析
Table 5. Variance analysis
因素 离差平方和 自由度 F值 显著性 A 72.701 2 2.335 B 42.830 2 1.376 C 649.524 2 20.864 P < 0.05 D(误差) 31.131 2 1.000 注：F0.05(2, 2)=19.0。
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表 6 正交验证试验复合率结果(%)
Table 6. Compound rate results of orthogonal verification test(%)
序号 组分复合率 质量复合率 1 68.11 85.15 2 68.51 86.41 3 68.35 87.38
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表 7 山楂叶提取物各成分的油水分配系数P(x±s，n=3)
Table 7. Oil-water partition coefficient P of each component of hawthorn leaf extract(x±s, n=3)
pH 牡荆素葡萄糖苷 牡荆素鼠李糖苷 牡荆素 芦丁 金丝桃苷 2.0 0.153 1±0.011 2 0.217 0±0.056 6 0.596 9±0.181 0 1.852 6±0.473 3 1.748 2±0.289 1 5.0 0.107 6±0.018 5 0.189 5±0.007 4 0.708 2±0.210 8 2.414 2±0.313 1 3.280 0±0.597 1 5.8 0.104 8±0.013 6 0.168 5±0.017 1 0.641 8±0.112 3 2.310 6±0.463 1 3.224 7±1.278 2 6.8 0.058 6±0.009 5 0.064 9±0.017 1 0.802 9±0.099 9 1.973 5±0.079 2 3.081 4±1.382 5 7.0 0.083 8±0.038 9 0.085 0±0.022 3 0.694 6±0.226 8 1.459 7±0.332 2 1.827 3±0.358 4 7.8 0.039 7±0.017 5 0.020 0±0.001 0 0.769 4±0.166 8 0.599 5±0.034 3 0.743 6±0.036 5 8.0 0.049 4±0.013 6 0.022 4±0.008 5 0.880 4±0.146 0 1.076 2±0.130 1 1.095 6±0.208 9 水 0.070 1±0.024 7 0.132 6±0.015 8 0.656 2±0.198 9 2.096 5±0.139 2 2.014 6±0.285 2
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表 8 山楂叶提取物磷脂复合物各成分的油水分配系数P (x±s，n=3)
Table 8. Oil-water partition coefficient P of each component of hawthorn leaf extract phospholipid complex (x±s, n=3)
pH 牡荆素葡萄糖苷 牡荆素鼠李糖苷 牡荆素 芦丁 金丝桃苷 2.0 0.082 7±0.021 6 0.210 3±0.021 0 0.788 5±0.042 1 2.173 0±0.045 5 2.017 4±0.774 5 5.0 0.103 8±0.008 0 0.240 1±0.010 7 0.886 7±0.065 6 2.986 0±0.284 5 4.543 3±0.543 5 5.8 0.126 7±0.027 0 0.217 0±0.037 7 0.904 3±0.112 7 3.104 2±0.848 0 6.269 1±0.860 0 6.8 0.094 3±0.008 7 0.141 6±0.020 2 0.922 3±0.172 6 1.638 6±0.073 6 1.892 9±0.148 1 7.0 0.108 6±0.030 5 0.129 9±0.030 2 0.832 4±0.072 7 1.963 6±0.517 3 3.700 5±1.691 5 7.8 0.063 8±0.012 1 0.033 2±0.013 8 1.132 9±0.396 9 0.718 9±0.093 3 0.968 4±0.178 4 8.0 0.077 8±0.015 9 0.051 8±0.020 3 1.000 1±0.044 7 1.210 6±0.247 6 1.987 9±0.849 5 水 0.108 4±0.002 8 0.148 0±0.009 7 0.702 5±0.119 0 2.905 0±0.454 1 5.139 3±2.216 2
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[1] 国家药典委员会. 中华人民共和国药典: 一部[M]. 北京: 中国医药科技出版社, 2015: 32.Chinese Pharmacopoeia Commission. Pharmacopoeia of the People's Republic of China: Ⅰ[M]. Beijing: China medical and technology press, 2015: 32. [2] 杨明宇, 潘伟东, 潘海峰. 山楂叶的化学成分研究[J]. 承德医学院学报, 2015, 32(6): 522-524. https://www.cnki.com.cn/Article/CJFDTOTAL-CDYX201506034.htmYANG MY, PAN WD, PAN HF. Study on chemical constituents of Hawthorn leaves[J]. J Chengde Med Coll, 2015, 32(6): 522-524. https://www.cnki.com.cn/Article/CJFDTOTAL-CDYX201506034.htm [3] 耿慧春, 满莹, 赵智勇. 山楂叶化学成分和药理作用研究进展[J]. 中国现代医生, 2009, 47(26): 12-13. doi: 10.3969/j.issn.1673-9701.2009.26.006GENG HC, MAN Y, ZHAO ZY. Advances in chemical constituents and pharmacological action of Hawthorn leaves[J]. China Mod Dr, 2009, 47(26): 12-13. doi: 10.3969/j.issn.1673-9701.2009.26.006 [4] 李强强, 王凯, 薛晓锋, 等. 黄酮类化合物磷脂复合物的制备与功能活性研究进展[J]. 中国现代应用药学, 2018, 35(1): 132-137. https://www.cnki.com.cn/Article/CJFDTOTAL-XDYD201801031.htmLI QQ, WANG K, XUE XF, et al. Advance of the preparation and biological activity of flavonoid phospholipid complex[J]. Chin J Mod Appl Pharm, 2018, 35(1): 132-137. https://www.cnki.com.cn/Article/CJFDTOTAL-XDYD201801031.htm [5] 刘丹, 贾晓斌, 萧伟. 质量分数权重系数法表征银杏内酯组分溶解性及表观油水分配系数的探讨[J]. 中国中药杂志, 2013, 38(12): 1865-1870. https://www.cnki.com.cn/Article/CJFDTOTAL-ZGZY201312006.htmLIU D, JIA XB, XIAO W. Study on solubility of ginkgolide components with mass fraction weight coefficient method[J]. China J Chin Mater Med, 2013, 38(12): 1865-1870. https://www.cnki.com.cn/Article/CJFDTOTAL-ZGZY201312006.htm [6] 刘丹, 贾晓斌, 萧伟. 质量权重系数整合法表征整体银杏黄酮组分在水中及不同pH磷酸盐缓冲液中的平衡溶解度[J]. 中国中药杂志, 2013, 38(12): 1871-1875. https://www.cnki.com.cn/Article/CJFDTOTAL-ZGZY201312007.htmLIU D, JIA XB, XIAO W. Equilibrium solubility of Ginkgo flavonoid components in water and PBS of different pHs with mass fraction weight coefficient method[J]. China J Chin Mater Med, 2013, 38(12): 1871-1875. https://www.cnki.com.cn/Article/CJFDTOTAL-ZGZY201312007.htm [7] 石森林, 高敏, 童丽姣, 等. 山楂叶总黄酮磷脂复合物的制备工艺[J]. 中华中医药杂志, 2013, 28(1): 243-246. https://www.cnki.com.cn/Article/CJFDTOTAL-BXYY201301071.htmSHI SL, GAO M, TONG LJ, et al. Study on preparation of the total flavonoids of hawhorn leaves-phospholipids complex[J]. China J Tradit Chin Med Pharm, 2013, 28(1): 243-246. https://www.cnki.com.cn/Article/CJFDTOTAL-BXYY201301071.htm [8] 王瑜, 史亚军, 邹俊波, 等. 红花提取物磷脂复合物的制备及其透膜性研究[J]. 中草药, 2019, 50(17): 4084-4090. doi: 10.7501/j.issn.0253-2670.2019.17.012WANG Y, SHI YJ, ZOU JB, et al. Preparation and membrane permeability of phospholipid complex from extract of Carthamus tinctorius[J]. Chin Tradit Herb Drugs, 2019, 50(17): 4084-4090. doi: 10.7501/j.issn.0253-2670.2019.17.012 [9] 熊阳, 盛卫国, 杜佳琦, 等. 山楂叶总黄酮磷脂复合物的研究[J]. 中草药, 2008, 39(3): 353-356. doi: 10.3321/j.issn:0253-2670.2008.03.011XIONG Y, SHENG WG, DU JQ, et al. Total flavonoids of hawthorn leaves-phospholipid complex[J]. Chin Tradit Herb Drugs, 2008, 39(3): 353-356. doi: 10.3321/j.issn:0253-2670.2008.03.011 [10] 侯雪峰, 汪刚, 邱辉辉, 等. 基于高生物利用度的创新组分结构中药制剂技术研究[J]. 中草药, 2017, 48(16): 3280-3287. doi: 10.7501/j.issn.0253-2670.2017.16.004HOU XF, WANG G, QIU HH, et al. Study on technology of innovative component structure in Chinese materia medica preparation based on enhanced bioavailability[J]. Chin Tradit Herb Drugs, 2017, 48(16): 3280-3287. doi: 10.7501/j.issn.0253-2670.2017.16.004 -
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