生产与科研应用

β-环糊精与香芹酮形成常数的测定及其包合物的制备及表征

  • 薛硕 ,
  • 董曼 ,
  • 张璐璐 ,
  • 尹凯静 ,
  • 王琳 ,
  • 任婧楠 ,
  • 潘思轶 ,
  • 范刚
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  • 1.华中农业大学 食品科技学院,环境食品学教育部重点实验室,湖北 武汉,430070;
    2湖北省食品质量安全监督检验研究院,湖北 武汉,430075
硕士研究生(范刚教授为通讯作者,E-mail:fangang@mail.hz au.edu.cn)。

收稿日期: 2018-12-16

  修回日期: 2019-01-05

  网络出版日期: 2019-07-16

基金资助

国家重点研发计划专项(项目批号:2017YFD0400101);国家自然科学基金(项目批准号31671824);湖北省重大科技创新计划项目(2015ABA035,2016ABA112)

Formation constant of β-cyclodextrin with carvone and characterization of inclusion complex

  • XUE Shuo ,
  • DONG Man ,
  • ZHANG Lulu ,
  • YIN Kaijing ,
  • WANG Lin ,
  • REN Jingnan ,
  • PAN Siyi ,
  • FAN Gang
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  • 1. College of Food Science and Technology, Huazhong Agricultural University, Key Laboratory of Environment Correlative Dietology, Ministry of Education, Wuhan 430070, China;
    2. Hubei Provincial Institute for Food Supervision and Test, Wuhan 430075, China

Received date: 2018-12-16

  Revised date: 2019-01-05

  Online published: 2019-07-16

摘要

通过固相微萃取-气相色谱-质谱联用(solid phase micro-extraction-gas chromatography-mass spectrometer, SPME-GC-MS)法测定了β-环糊精在溶液中对香芹酮的保留率及两者之间的形成常数,并用冷冻干燥法制备了β-环糊精与香芹酮的包合物,采用扫描电镜(scanning electron microscopy,SEM)、红外光谱(infrared spectrum,IR)、X-衍射(X-ray diffraction,XRD)及热重分析(thermogravimetric analysis,TGA)对包合物进行结构表征。结果表明,香芹酮与β-环糊精在水溶液中形成了1∶1的包合物,且两者之间的形成常数为1 066.7 mol-1。冷冻干燥法制备的包合物的包合率为75.04%,SEM以及XRD分析结果都表明,β-环糊精在包合前后,其晶体形态发生了变化;IR和TG结果证明β-环糊精与香芹酮形成了包合物。由此得出,β-环糊精适合包埋香芹酮,可以提高香芹酮的热稳定性,从而使香芹酮的应用更加广泛。

本文引用格式

薛硕 , 董曼 , 张璐璐 , 尹凯静 , 王琳 , 任婧楠 , 潘思轶 , 范刚 . β-环糊精与香芹酮形成常数的测定及其包合物的制备及表征[J]. 食品与发酵工业, 2019 , 45(12) : 183 -188 . DOI: 10.13995/j.cnki.11-1802/ts.019641

Abstract

The retention rate of carvone in β-cyclodextrin solution and the formation constant between these two compounds were determined by SPME-GC-MS. The inclusion complex of β-cyclodextrin and carvone was prepared by freeze-drying method, and it was characterized by scanning electron microscopy (SEM), infrared spectroscopy (IR), X-ray diffraction (XRD) and thermogravimetric analysis (TGA). The results showed that carvone and β-cyclodextrin formed an inclusion complex in a ratio of 1∶1 in aqueous solution, and the formation constant was 1 066.7 mol-1. Moreover, the encapsulation efficiency of the complex was 75.04%, and SEM and XRD showed that the crystal morphology of β-cyclodextrin changed before and after inclusion. Furthermore, IR and TGA also showed that β-cyclodextrin and carvone formed an inclusion complex. Therefore, it can be concluded that β-cyclodextrin is suitable for embedding carvone to improve its thermal stability, which will be beneficial for broadening the application of carvone.

参考文献

[1] 张谨. 苧烯催化氧化合成香芹酮的研究[D]. 南京:南京师范大学, 2015.
[2] 钟瑞敏, 王羽梅,曾庆孝,等. 芳香精油在食品保藏中的应用性研究进展[J]. 食品与发酵工业, 2005,31(3): 93-98.
[3] GONG L, LI T, CHEN F, et al. An inclusion complex of eugenol into β-cyclodextrin: Preparation, and physicochemical and antifungal characterization[J]. Food Chemistry, 2016, 196: 324-330.
[4] ASTRAY G, MEJUTO J C, MORALES J, et al. Factors controlling flavors binding constants to cyclodextrins and their applications in foods[J]. Food Research International, 2010, 43(4): 1 212-1 218.
[5] CIOBANU A, LANDY D, FOURMENTIN S. Complexation efficiency of cyclodextrins for volatile flavor compounds[J]. Food Research International, 2013, 53(1): 110-114.
[6] KFOURY M, AUEZOVA L, GREGE-GERGES H, et al. Cyclodextrin, an efficient tool for trans-anethole encapsulation: Chromatographic, spectroscopic, thermal and structural studies[J]. Food Chemistry, 2014, 164: 454-461.
[7] DECOCK G, FOURMENTIN S, SURPATEANU G, et al. Experimental and theoretical study on the inclusion compounds of aroma components with β-cyclodextrins[J]. Supramolecular Chemistry, 2006, 18(6): 477-482.
[8] MAZZOBRE F M, DOS SANTOS C I, DEL-PILARBUERA, M. Solubility and stability of β-cyclodextrin-terpineol inclusion complex as affected by water[J]. Food Biophysics, 2011, 6(2): 274-280.
[9] LI Jiajia, MAN Dong, LIU Yanlong, et al. Effect of food emulsifiers on aroma release[J]. Molecules, 2016, 21(4): 511.
[10] LADAA T I, LEE C M, COATES J T, et al. Cosolvent effects of alcohols on the Henry’s law constant and aqueous solubility of tetrachloroethylene[J]. Chemosphere, 2001, 44(5), 1 137-1 143.
[11] BLACH P, FOURMENTIN S, LANDY D, et al. Cyclodextrins: A new efficient absorbent to treat waste gas streams [J]. Chemosphere, 2008, 70(3), 374-380.
[12] FOURMENTIN S, OUTIRITE M, BLACH P, et al. Solubilisation of chlorinated solvents by cyclodextrin derivatives. A study by static headspace gas chromatography and molecular modelling[J]. Journal of Hazardous Materials, 2007,141(1), 92-97.
[13] LANDY D, FOURMENTIN S, SALOME M, et al. Analytical improvement in measuring formation constants of inclusion complexes between β-cyclodextrin and phenolic compounds [J]. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2000, 38(1-4), 187-198.
[14] 张扬, 周裔彬,曹胜男,等. β-和γ-环糊精与丁酸乙酯包合物的制备及结构表征[J]. 食品与发酵工业, 2014, 40(9): 34-38.
[15] 曹胜男. α-、β-环糊精包合丙酸乙酯和戊酸复合物的制备、表征及其释放动力学研究[D]. 合肥:安徽农业大学, 2015.
[16] 王艳丽, 袁超,刘亚伟. 肉桂精油/羟丙基-β-环糊精包合物的表征及成分分析[J]. 中国食品添加剂, 2018(11): 56-61.
[17] 李萍, 舒展,申晓霞,等. 超声波法制备八角茴香油-β-环糊精微胶囊及其表征分析[J]. 食品科学, 2017,38(4): 243-249.
[18] GUIMARES A G, OLIVEIRA M A, DOS-SANTOSALVES R D S, et al. Encapsulation of carvacrol, a monoterpene present in the essential oil of oregano, with β-cyclodextrin, improves the pharmacological response on cancer pain experimental protocols[J]. Chemico-Biological Interactions, 2015, 227: 69-76.
[19] 曹胜男, 张扬,金姗姗,等. β-环糊精丙酸乙酯包合物的制备及表征[J]. 食品工业科技, 2015, 36(20): 124-127; 132.
[20] 张扬. β-、γ-环糊精与丁酸乙酯、己醛、己醇包合物的制备、表征及释放动力学的研究[D]. 合肥:安徽农业大学, 2015.
[21] WANG X, LUO Z, XIAO Z. Preparation, characterization, and thermal stability of β-cyclodextrin/soybean lecithin inclusion complex[J]. Carbohydrate Polymers, 2014, 101: 1 027-1 032.
[22] 马君义, 张继,王宝生,等. 百里香油β-环糊精包合物的制备与表征[J]. 食品与发酵工业, 2012,38(3): 95-99.
[23] MENEZES P P, SERAFINI M R, QUINTANS-JU′NIOR L J, et al. Inclusion complex of (-)-linalool and β-cyclodextrin[J]. Journal of Thermal Analysis and Calorimetry, 2014, 115(3): 2 429-2 437.
[24] YANG Zujin, XIAO Zuobing, JI Hongbing. Solid inclusion complex of terpinen-4-ol/β-cyclodextrin: Kinetic release, mechanism and its antibacterial activity[J]. Flavour and Fragrance Journal, 2015, 30(2): 179-187.
[25] ZHU Xiashi, PING Wenhui. Optimization of β-cyclodextrin cross-linked polymer for monitoring of quercetin[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 132: 38-43.
[26] ABARCA R L, RODRGUEZ F J, GUARDA A, et al. Characterization of beta-cyclodextrin inclusion complexes containing an essential oil component[J]. Food Chemistry, 2016, 196: 968-975.
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