Gallic Acid/2-Hydroxypropyl-β-cyclodextrin Inclusion Complexes Electrospun Nanofibrous Webs: Fast Dissolution, Improved Aqueous Solubility and Antioxidant Property of Gallic Acid

doi:10.1007/s40242-021-0014-0

Chemical Research in Chinese Universities ›› 2021, Vol. 37 ›› Issue (3): 450-455.doi: 10.1007/s40242-021-0014-0

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Gallic Acid/2-Hydroxypropyl-β-cyclodextrin Inclusion Complexes Electrospun Nanofibrous Webs: Fast Dissolution, Improved Aqueous Solubility and Antioxidant Property of Gallic Acid

SONG Yudong¹, HUANG Hui¹, HE Dayong³, YANG Mei³, WANG Hao³, ZHANG Hao², LI Jiali¹, LI Yongxin², WANG Ce³

1. College of Food Science and Engineering, Jilin University, Changchun 130025, P. R. China;
2. Key Lab of Groundwater Resources and Environment of Ministry of Education, College of New Energy and Environment, Jilin University, Changchun 130021, P. R. China;
3. Alan G. MacDiarmid Institute, College of Chemistry, Jilin University, Changchun 130012, P. R. China

Received:2021-01-09 Revised:2021-02-04 Online:2021-06-01 Published:2021-02-25
Contact: LI Yongxin E-mail:liyongxin@jlu.edu.cn
Supported by:
This work was supported by the Project of the Jilin Province Development and Reform Commission, China(No.2020C023-5) and the National Natural Science Foundation of China(No.31772058).

Abstract

Abstract: Gallic acid(GA) is a kind of natural polyphenolic compound, but its low aqueous solubility restricts its application in the fields of food and medicine. Cyclodextrin can form inclusion complexes with guest molecules(e.g., essential oils, food supplements) through cavities with special properties to improve aqueous solubility, thermal stability, and bioavailability of guest molecules. In this research, gallic acid/2-hydroxypropyl-β-cyclodextrin inclusion complexes(GA/2-HP-β-CD/ICs) were formed in a highly concentrated solution of 2-HP-β-CD. Bead-free and uniform nanofibrous webs(GA/2-HP-β-CD/IC-NWs) were produced successfully by electrospun GA/HP-β-CD/IC aqueous solution. The initial molar ratio(GA:2-HP-β-CD=1:1) of GA/2-HP-β-CD/IC in the solutions was largely maintained in GA/2-HP-β-CD/IC-NW. The aqueous solubility of GA was enhanced and GA/2-HP-β-CD/IC-NW has displayed fast dissolution property. Furthermore, in comparison with GA powder, GA/2-HP-β-CD/IC-NW demonstrated improved antioxidant capacity. The results suggested that GA/2-HP-β-CD/IC-NW have broad application prospects as orally fast dissolution systems for food supplements.

Key words: Gallic acid, 2-Hydroxypropyl-β-cyclodextrin, Inclusion complex, Electrospun, Fast dissolution

SONG Yudong, HUANG Hui, HE Dayong, YANG Mei, WANG Hao, ZHANG Hao, LI Jiali, LI Yongxin, WANG Ce. Gallic Acid/2-Hydroxypropyl-β-cyclodextrin Inclusion Complexes Electrospun Nanofibrous Webs: Fast Dissolution, Improved Aqueous Solubility and Antioxidant Property of Gallic Acid[J]. Chemical Research in Chinese Universities, 2021, 37(3): 450-455.

References 30

[1]	Choubey S., Varughese L. R., Kumar V., Beniwal V., Pharm. Pat. Anal., 2015, 4, 305
[2]	Daneshfar A., Ghaziaskar H. S., Homayoun N., J. Chem. Eng. Data, 2008, 53, 776
[3]	Noubigh A., Jeribi C., Mgaidi A., Abderrabba M., J. Chem. Thermodyn., 2012, 55, 75
[4]	Kurkov S. V., Loftsson T., Int. J. Pharm., 2013, 453, 167
[5]	Topuz F., Uyar T., Pharmaceutics, 2019, 11, 6
[6]	Zhang J., Ma P. X., Adv. Drug Delivery Rev., 2013, 65, 1215
[7]	Celebioglu A., Uyar T., J. Agric. Food Chem., 2019, 67, 13093
[8]	Pinho E., Grootveld M., Soares G., Henriques M., Carbohydr. Polym., 2014, 101, 121
[9]	Celebioglu A., Uyar T., Food Chem., 2020, 317, 126397
[10]	Celebioglu A.,Yildiz Z. I., Uyar T., J. Agric. Food Chem., 2018, 66, 457
[11]	Yildiz Z. I., Celebioglu A., Kilic M. E., Durgun E., Uyar T., J. Food Eng., 2018, 224, 27
[12]	Zhang C., Li Y., Wang P., Zhang H., Compr. Rev. Food Sci. Food Saf., 2020, 19, 479
[13]	Ghorani B.,Tucker N., Food Hydrocolloids, 2015, 51, 227
[14]	Deng L.,Taxipalati M., Zhang A., Que F., We H., Feng F., Zhang H., J. Agric. Food Chem., 2018, 66, 6219
[15]	Alejandra Moreno M., Eugenia Orqueda M., Gomez-Mascaraque L. G., Ines Isla M., Lopez-Rubio A., Food Hydrocolloids, 2019, 95, 496
[16]	Li H., Wang M., Williams G. R., Wu J., Sun X., Lv Y., Zhu L.-M., RSC Adv., 2016, 6, 50267
[17]	Feng K., Huang R.-M., Wu R.-Q., Wei Y.-S., Zong M.-H., Linhardt R. J., Wu H., Food Chem., 2020, 310, 125977
[18]	Wen P., Wen Y., Zong M.-H., Linhardt R. J., Wu H., J. Agric. Food Chem., 2017, 65, 9161
[19]	Yildiz Z. I., Kilic M. E., Durgun E., Uyar T., J. Agric. Food Chem., 2019, 67, 11066
[20]	Aytac Z., Kusku S. I., Durgun E., Uyar T., Mat. Sci. Eng. C:Mater., 2016, 63, 231
[21]	Wutticharoenmongkol P., Hannirojram P., Nuthong P., Polym. Adv. Technol., 2019, 30, 1135
[22]	Celebioglu A., Uyar T., Mol. Pharmaceutics, 2019, 16, 4387
[23]	Aydogdu A., Yildiz E., Aydogdu Y., Sumnu G., Sahin S., Ayhan Z., Food Hydrocolloids, 2019, 95, 245
[24]	Yildiz Z. I., Celebioglu A., Kilic M. E., Durgun E., Uyar T., J. Mater. Sci., 2018, 53, 15837
[25]	Aydogdu A., Sumnu G., Sahin S., Carbohydr. Polym., 2019, 208, 241
[26]	Chunshom N., Chuysinuan P., Thanyacharoen T., Techasakul S., Ummartyotin S., Mater. Chem. Phys., 2019, 232, 294
[27]	Neo Y. P., Ray S., Jin J., Gizdavic-Nikolaidis M., Nieuwoudt M. K., Liu D., Quek S. Y., Food Chem., 2013, 136, 1013
[28]	Liu Z., Ren Z., Zhang J., Chuang C.-C., Kandaswamy E., Zhou T., Zuo L., Front. Physiol., 2018, 9, 477
[29]	Roidoung S., Dolan K. D., Siddiq M., Food Chem., 2016, 210, 422
[30]	Bi Y., Sunada H., Yonezawa Y., Danjo K., Otsuka A., Iida K., Chem. Pharm. Bull., 1996, 44, 212

Gallic Acid/2-Hydroxypropyl-β-cyclodextrin Inclusion Complexes Electrospun Nanofibrous Webs: Fast Dissolution, Improved Aqueous Solubility and Antioxidant Property of Gallic Acid

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