Comprehensive evaluation of solubilization of flavonoids by various cyclodextrins using high performance liquid chromatography and chemometry

Comprehensive evaluation of solubilization of flavonoids by various cyclodextrins using high performance liquid chromatography and chemometry
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DOI:
10.1016/j.lwt.2018.04.035
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发表时间:
2018-08
期刊:
Lwt
影响因子:
--
通讯作者:
Xiao-Liang Ren
Xiao-Liang Ren
中科院分区:
其他
文献类型:
--
作者:
Guang-Jiao You;Li-Li Sun;Xue-Xiao Cao;Huan-Huan Li;Meng Wang;Ya-Nan Liu;Xiao-Liang Ren

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黄酮类化合物具有多种药理活性,但水溶性较差,利用环糊精(Cyclodextrin, CD)可使黄酮类化合物进入其空腔,从而提高其溶解度。不同cd对黄酮类化合物的增溶作用不同。因此,本研究的目的是利用化学计量学方法(I种天然的环糊精:α-环糊精(α-CD)、β-环糊精(β-CD)和γ-环糊精(γ-CD))评价三种环糊精对黄酮类化合物的增溶作用;II亲水性CD衍生物:甲基-β-环糊精(Me-β-CD)和2-羟丙基-β-环糊精(HP-β-CD);III离子CD衍生物:磺基丁基醚β-环糊精(SBE-β-CD)。所选cd均有显著的增溶作用(P< 0.01)。6种cd对黄酮类化合物的增溶系数分别为α-CD: 41.77、γ-CD: 61.81、β-CD: 143.45、HP-β-CD: 415.43、Me-β-CD: 558.53、SBE-β-CD: 709.56。相溶性研究表明,6种CDs与山奈母烯可形成M比为1:1 的包合物,包合物的缔合常数Ka分别为:山奈母烯-α-CD: 808 L/mol、山奈母烯-β-CD: 1541 L/mol、山奈母烯-γ-CD: 1191 L/mol、山奈母烯- hp -β-CD: 9335 L/mol、山奈母烯- me -β-CD: 10421 L/mol、山奈母烯- sbe -β-CD: 12502 L/mol。研究表明,SBE-β-CD对黄酮类化合物的增溶效果最好,因此,SBE-β-CD可作为黄酮类化合物的增溶剂广泛应用。
Flavonoids have many pharmacological activities, but the water solubility is poor, Cyclodextrin (CD) can be used to increase the solubility of flavonoids through making flavonoids into their cavities. While various CDs have different solubilization effects on flavonoids. Therefore, the purpose of this study was to evaluate the solubilization of flavonoids by three classes of cyclodextrins by Chemometrics (I native CDs: alpha-cyclodextrin (α-CD), beta-cyclodextrin (β-CD) and gamma-cyclodextrin (γ-CD); II hydrophilic CD derivatives: methyl-β-cyclodextrin (Me-β-CD) and 2-hydroxypropyl-β-cyclodextrin (HP-β-CD); III ionic CD derivative: sulfobutyl ether β-cyclodextrin (SBE-β-CD)). All selected CDs had significant solubilization effects (P< 0.01). The solubilization coefficients of six kinds of CDs on flavonoids were α-CD: 41.77, γ-CD: 61.81, β-CD: 143.45, HP-β-CD: 415.43, Me-β-CD: 558.53, SBE-β-CD: 709.56, respectively. Phase solubility study indicated that six kinds of CDs and kaempferide can form inclusion complexes with 1:1 M ratio, association constants (Ka) of inclusion compounds were kaempferide-α-CD: 808 L/mol, kaempferide-β-CD: 1541 L/mol, kaempferide-γ-CD: 1191 L/mol, kaempferide-HP-β-CD: 9335 L/mol, kaempferide-Me-β-CD: 10,421 L/mol, kaempferide-SBE-β-CD: 12,502 L/mol, respectively. The study showed that SBE-β-CD has the best solubilization effect on flavonoids, therefore, SBE-β-CD may be widely used as a solubilizing agent for flavonoids.
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