Study of β-cyclodextrin differential encapsulation of essential oil components by using mixture design and NIR: Encapsulation of α-pinene, myrcene, and 3-carene as an example

doi:10.5246/jcps.2021.06.041

Abstract

Abstract:

The encapsulation of essential oil components in cyclodextrins (CDs) to form inclusion complexes (ICs) is an effective strategy for improving their stability and bioaccessibility. The aim of the present study was to obtain a deeper understanding of the encapsulation behavior of multi-components in β-CD. Guest molecules of α-pinene, myrcene, and 3-carene, having the same molecular weight, formed ICs with β-CD by a freeze-drying method. A simplex lattice mixture design with 28 experiments was carried out. Statistical analysis was applied to analyze the encapsulation behavior of guest components, and quantitative models of guest components in ICs were constructed by coupling with near-infrared (NIR) spectroscopy and chemometrics analysis. Besides, the molecular docking technique was used to obtain the optimal conformation and explain the binding behavior of inclusion. The results suggested that the spatial structure and ratio of guest molecules were the key factors affecting the encapsulation effect. A non-destructive and rapid NIR analytical model for the guest component in ICs could be obtained by second derivative (2nd der) pretreatment. Collectively, the encapsulation of guest components in β-CD was differentiated, and NIR could be used as a rapid and non-destructive tool for quantitative analysis of ICs.

Key words: Inclusion complexes, Cyclodextrin, Differential encapsulation, NIR spectroscopy, Molecular docking

Supporting:

Zhe Li, Yuan Ding, Hao Huang, Kexin Wang, Jiayi Wu, Lin Zhu, Zhenggen Liao, Liangshan Ming. Study of β-cyclodextrin differential encapsulation of essential oil components by using mixture design and NIR: Encapsulation of α-pinene, myrcene, and 3-carene as an example[J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(6): 524-537.

Figures/Tables 9

Table 1. Formulation and evaluation of batches in a Simplex Lattice design.

Table 2. Estimated regression coefficients for the polynomial model and the analysis of variance for the encapsulation efficacies of α-pinene, myrcene, and 3-carene from ICs.

Table 3. Parameters of PLS regression models for the determination of α-pinene, myrcene, and 3-carene in the IC.

References 38

[1]	Rattanathada, T.; Plengsuriyakarn, T.; Asasujarit, R.; Cheoymang, A.; Karbwang, J.; Bangchang, K. Development of oral pharmaceutical formulation of standardized crude ethanolic extract of Atractylodes lancea (Thunb) DC. J. Chin. Pharm. Sci. 2020, 29, 280–293.
[2]	Ming, L.S.; Huang, H.; Jiang, Y.M.; Cheng, G.; Zhang, D.Y.; Li, Z. Quickly identifying high-risk variables of ultrasonic extraction oil from multi-dimensional risk variable patterns and a comparative evaluation of different extraction methods on the quality of forsythia suspensa seed oil. Molecules. 2019, 24, 3445.
[3]	Cui, H.Y.; Zhang, C.H.; Li, C.Z.; Lin, L. Antimicrobial mechanism of clove oil on Listeria monocytogenes. Food Control. 2018, 94, 140–146.
[4]	Yin, Y. Effects and mechanisms of Artemisia argyi essential oil on monocrotaline-induced pulmonary hypertension in rats. J. Chin. Pharm. Sci. 2018, 27, 183–192.
[5]	Rakmai, J.; Cheirsilp, B.; Mejuto, J.C.; Simal-Gándara, J.; Torrado-Agrasar, A. Antioxidant and antimicrobial properties of encapsulated guava leaf oil in hydroxypropyl-beta-cyclodextrin. Ind. Crop. Prod. 2018, 111, 219–225.
[6]	Yuan, W.Q.; Teo, C.H.M.; Yuk, H.G. Combined antibacterial activities of essential oil compounds against Escherichia coli O157: H7 and their application potential on fresh-cut lettuce. Food Control. 2019, 96, 112–118.
[7]	Karimirad, R.; Behnamian, M.; Dezhsetan, S. Bitter orange oil incorporated into chitosan nanoparticles: Preparation, characterization and their potential application on antioxidant and antimicrobial characteristics of white button mushroom. Food Hydrocoll. 2020, 100, 105387.
[8]	Ma, W.N.; Gu, F.G. Complexation of poorly aqueous soluble drug risperidone with hydroxypropyl-β-cyclodextrin enhances its dissolution. J. Chin. Pharm. Sci. 2015, 24, 47–53.
[9]	Garcia-Sotelo, D.; Silva-Espinoza, B.; Perez-Tello, M.; Olivas, I.; Alvarez-Parrilla, E.; González-Aguilar, G.A.; Ayala-Zavala, J.F. Antimicrobial activity and thermal stability of rosemary essential oil: β–cyclodextrin capsules applied in tomato juice. LWT. 2019, 111, 837–845.
[10]	Shan, X.Y.; Jiang, K.Y.; Li, J.C.; Song, Y.; Han, J.; Hu, Y. Preparation of β-cyclodextrin inclusion complex and its application as an intumescent flame retardant for epoxy. Polymers. 2019, 11, 71..
[11]	Xiao, Z.B.; Liu, Y.F.; Niu, Y.W.; Kou, X.R. Cyclodextrin supermolecules as excellent stabilizers for Pickering nanoemulsions. Colloids Surf. A Physicochem. Eng. Aspects. 2020, 588, 124367.
[12]	Wang, J.; Cao, Y.P.; Sun, B.G.; Wang, C.T. Physicochemical and release characterisation of garlic oil-β-cyclodextrin inclusion complexes. Food Chem. 2011, 127, 1680–1685.
[13]	Rakmai, J.; Cheirsilp, B.; Mejuto, J.C.; Torrado-Agrasar, A.; Simal-Gándara, J. Physico-chemical characterization and evaluation of bio-efficacies of black pepper essential oil encapsulated in hydroxypropyl-beta-cyclodextrin. Food Hydrocoll. 2017, 65, 157–164.
[14]	Szente, L.; Szejtli, J. Cyclodextrins as food ingredients. Trends Food Sci. Technol. 2004, 15, 137–142.
[15]	Qiu, N.; Zhao, X.; Liu, Q.M.; Shen, B.; Liu, J.D.; Li, X.B.; An, L.Y. Inclusion complex of emodin with hydroxypropyl-β-cyclodextrin: Preparation, physicochemical and biological properties. J. Mol. Liq. 2019, 289, 111151.
[16]	Abarca, R.L.; Rodríguez, F.J.; Guarda, A.; Galotto, M.J.; Bruna, J.E. Characterization of beta-cyclodextrin inclusion complexes containing an essential oil component. Food Chem. 2016, 196, 968–975.
[17]	Hill, L.E.; Gomes, C.; Taylor, T.M. Characterization of beta-cyclodextrin inclusion complexes containing essential oils (trans-cinnamaldehyde, eugenol, cinnamon bark, and clove bud extracts) for antimicrobial delivery applications. LWT - Food Sci. Technol. 2013, 51, 86–93.
[18]	Hadidi, M.; Pouramin, S.; Adinepour, F.; Haghani, S.; Jafari, S.M. Chitosan nanoparticles loaded with clove essential oil: Characterization, antioxidant and antibacterial activities. Carbohydr. Polym. 2020, 236, 116075.
[19]	Wilde, A.S.; Haughey, S.A.; Galvin-King, P.; Elliott, C.T. The feasibility of applying NIR and FT-IR fingerprinting to detect adulteration in black pepper. Food Control. 2019, 100, 1–7.
[20]	Yağmur, N.; Şahin, S. Encapsulation of ellagic acid from pomegranate peels in microalgae optimized by response surface methodology and an investigation of its controlled released under simulated gastrointestinal studies. J. Food Sci. 2020, 85, 998–1006.
[21]	Baj, T.; Baryluk, A.; Sieniawska, E. Application of mixture design for optimum antioxidant activity of mixtures of essential oils from Ocimum basilicum L., Origanum Majorana L. and Rosmarinus officinalis L. Ind. Crop. Prod. 2018, 115, 52–61.
[22]	Ortega-Zúñiga, C.; La Rosa, C.P.D.; Román-Ospino, A.D.; Serrano-Vargas, A.; Romañach, R.J.; Méndez, R. Development of near infrared spectroscopic calibration models for in-line determination of low drug concentration, bulk density, and relative specific void volume within a feed frame. J. Pharm. Biomed. Anal. 2019, 164, 211–222.
[23]	Ming, L.S.; Li, Z.; Wu, F.; Du, R.F.; Feng, Y. A two-step approach for fluidized bed granulation in pharmaceutical processing: Assessing different models for design and control. PLoS One. 2017, 12, e0180209.
[24]	Wan, H.D.; Ni, Y.; Li, D. Preparation, characterization and evaluation of an inclusion complex of steviolbioside with γ-cyclodextrin. Food Biosci. 2018, 26, 65–72.
[25]	Cui, H.Y.; Siva, S.; Lin, L. Ultrasound processed cuminaldehyde/2-hydroxypropyl-β-cyclodextrin inclusion complex: Preparation, characterization and antibacterial activity. Ultrason. Sonochem. 2019, 56, 84–93.
[26]	Wadhwa, G.; Kumar, S.; Chhabra, L.; Mahant, S.; Rao, R. Essential oil–cyclodextrin complexes: an updated review. J. Inclusion Phenom. Macrocycl. Chem. 2017, 89, 39–58.
[27]	Marques, C.S.; Carvalho, S.G.; Bertoli, L.D.; Villanova, J.C.O.; Pinheiro, P.F.; dos Santos, D.C.M.; Yoshida, M.I.; de Freitas, J.C.C.; Cipriano, D.F.; Bernardes, P.C. Β-Cyclodextrin inclusion complexes with essential oils: Obtention, characterization, antimicrobial activity and potential application for food preservative sachets. Food Res. Int. 2019, 119, 499–509.
[28]	Costa, P.; Medronho, B.; Gonçalves, S.; Romano, A. Cyclodextrins enhance the antioxidant activity of essential oils from three Lamiaceae species. Ind. Crop. Prod. 2015, 70, 341–346.
[29]	Badaró, A.T.; Morimitsu, F.L.; Ferreira, A.R.; Clerici, M.T.P.S.; Fernandes Barbin, D. Identification of fiber added to semolina by near infrared (NIR) spectral techniques. Food Chem. 2019, 289, 195–203.
[30]	Sampaio, P.S.; Soares, A.; Castanho, A.; Almeida, A.S.; Oliveira, J.; Brites, C. Optimization of rice amylose determination by NIR-spectroscopy using PLS chemometrics algorithms. Food Chem. 2018, 242, 196–204.
[31]	Sirisomboon, P.; Posom, J. On-line measurement of activation energy of ground bamboo using near infrared spectroscopy. Renew. Energy. 2019, 133, 480–488.
[32]	Ferreiro-González, M.; Espada-Bellido, E.; Guillén-Cueto, L.; Palma, M.; Barroso, C.G.; Barbero, G.F. Rapid quantification of honey adulteration by visible-near infrared spectroscopy combined with chemometrics. Talanta. 2018, 188, 288–292.
[33]	Shawky, E.; Abu El-Khair, R.M.; Selim, D.A. NIR spectroscopy-multivariate analysis for rapid authentication, detection and quantification of common plant adulterants in saffron (Crocus sativus L.) stigmas. LWT. 2020, 122, 109032.
[34]	Costa, M.C.A.; Morgano, M.A.; Ferreira, M.M.C.; Milani, R.F. Quantification of mineral composition of Brazilian bee pollen by near infrared spectroscopy and PLS regression. Food Chem. 2019, 273, 85–90.
[35]	Pu, H.Y.; Sun, Q.M.; Tang, P.X.; Zhao, L.D.; Li, Q.; Liu, Y.Y.; Li, H. Characterization and antioxidant activity of the complexes of tertiary butylhydroquinone with β-cyclodextrin and its derivatives. Food Chem. 2018, 260, 183–192.
[36]	Gursul, S.; Karabulut, I.; Durmaz, G. Antioxidant efficacy of thymol and carvacrol in microencapsulated walnut oil triacylglycerols. Food Chem. 2019, 278, 805–810.
[37]	Yuan, C.; Wang, Y.L.; Liu, Y.W.; Cui, B. Physicochemical characterization and antibacterial activity assessment of lavender essential oil encapsulated in hydroxypropyl-beta-cyclodextrin. Ind. Crop. Prod. 2019, 130, 104–110.
[38]	Zhang, J.Q.; Wu, D.; Jiang, K.M.; Zhang, D.; Zheng, X.; Wan, C.P.; Zhu, H.Y.; Xie, X.G.; Jin, Y.; Lin, J. Preparation, spectroscopy and molecular modelling studies of the inclusion complex of cordycepin with cyclodextrins. Carbohyd. Res. 2015, 406, 55–64.