Enhancing stability and antioxidant efficacy of fisetin by encapsulating as β-cyclodextrin inclusion complex with porous polylactic acid film from breath figure


  • Charasphat PREUKSARATTANAWUT Innovative Metals Research Unit, Department of Metallurgical Engineering, Faculty of Engineering, Chulalongkorn University, Bangkok, Thailand
  • Warinyupa MANGMEE Department of Biochemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Wangmai, Patumwan, Bangkok 10330, Thailand
  • Munchumas PROUSOONTORN Department of Biochemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Wangmai, Patumwan, Bangkok 10330, Thailand
  • Ekasit NISARATTANAPORN Innovative Metals Research Unit, Department of Metallurgical Engineering, Faculty of Engineering, Chulalongkorn University, Bangkok, Thailand
  • Krisana SIRALEARTMUKUL Metallurgy and Materials Science Research Institute, Chulalongkorn University, Phayathai Road, Wangmai, Patumwan, Bangkok 10330, Thailand




Fisetin, Polylactic acid, DPPH assay, Porous film, Food and beverage products packaging


This research aims to investigate the scope of fisetin (FIT)/β-cyclodextrin (β-CD) inclusion complexes with the ratios of 1:2 and 2:1 mole by means of freeze-drying, kneading and physical mixing methods (controlled process). Moreover, the complex compounds are analyzed by Fourier-Transform Infrared Spectroscopy (FTIR) and Differential Scanning Calorimetry (DSC). The results show that the most suitable preparation method of fisetin (FIT)/β-CD complex is the freeze-drying method with the fisetin (FIT) to β-CD ratio at 1:2. The emission of FIT/β-CD was investigated and it is found that the emission rate of freeze-dried FIT/β-CD in 1:2 ratio by freeze-drying method is lower than that by kneading and physical mixing methods. These results lead to an initiation of the innovative active packaging materials with synthetic polylactic acid (PLA) porous film by breath figure (BF) method in order to entrap FIT/β-CD inclusion complex. The honeycomb structure with and without the FIT/β-CD complex were analyzed by Scanning Electron Microscopy (SEM). Thereafter, the effectiveness of Antioxidant Activities (%AA) of the porous PLA films is measured by the anti-oxidation caused by 2,2-diphenyl-1-picrylhydrazyl (DPPH method). The result shows that PLA entrapping complex fisetin is more effective than PLA entrapping pure fisetin, by result of 53.0% and 48.6%, respectively.


Download data is not yet available.


J. Das, R. Singh, S. Ladol, S.K. Nayak, and D. Sharma, "Fisetin prevents the aging-associated decline in relative spectral power of α, β and linked MUA in the cortex and behavioral alterations," Experimental Gerontology, vol. 138, pp. 111006, 2020, https://doi.org/10.1016/j.exger.2020.111006.

M. GÁBor, and E. Eperjessy, "Antibacterial Effect of Fisetin and Fisetinidin," Nature, vol. 212(5067), pp. 1273-1273, 1966, https://doi.org/10.1038/2121273a0.

K. Sundarraj, A. Raghunath, and E. Perumal, "A review on the chemotherapeutic potential of fisetin: In vitro evidences," Biomedicine & Pharmacotherapy, vol. 97, pp. 928-940, 2018, https://doi.org/10.1016/j.biopha.2017.10.164.

M. Imran, F. Saeed, S.A. Gilani, M.A. Shariati, A. Imran, M. Afzaal, M. Atif, T. Tufail, and F.M. Anjum "Fisetin: An anticancer perspective," Food Science & Nutrition, vol. 9(1), 2020, https://doi.org/10.1002/fsn3.1872.

H-H. Park, S. Lee, J-M. Oh, M-S. Lee, K-H. Yoon, B.H. Park, J.W. Kim, H. Song, and S-H. Kim, "Anti-inflammatory activity of fisetin in human mast cells (HMC-1)," Pharmacological Research, vol. 55(1), pp. 31-37, 2007, https://doi.org/10.1016/j.phrs.2006.10.002.

J. Chamcheu, S. Esnault, S. Banang-Mbeumi, T. Roy, and H. Mukhtar, "LB1121 Prodifferentiative and anti-inflammatory effects of fisetin in 2D and 3D human skin model of psoriasis are associated with inhibition of PI3K/Akt/mTOR and MAPK signaling," Journal of Investigative Dermatology, vol. 139(9), pp. B19, 2019, https://doi.org/10.1016/j.jid.2019.06.088.

T.A. Bhat, D. Nambiar, A. Pal, R. Agarwal, and R.P. Singh, "Fisetin inhibits various attributes of angiogenesis in vitro and in vivo--implications for angioprevention," Carcinogenesis, vol. 33(2), pp. 385-393, 2012, https://doi.org/10.1093/carcin/bgr282.

A.F. Naeimi, and M. Alizadeh, "Antioxidant properties of the flavonoid fisetin: An updated review of in vivo and in vitro studies," Trends in Food Science & Technology, vol. 70, pp. 34-44, 2017, https://doi.org/10.1016/j.tifs.2017.10.003.

C.A. Rice-Evans, N.J. Miller, and G. Paganga, "Structure-antioxidant activity relationships of flavonoids and phenolic acids," Free Radical Biology and Medicine, vol. 20(7), pp. 933-956, 1996, https://doi.org/10.1016/0891-5849(95)02227-9.

A. Banerjee, and P. Sengupta, "Encapsulation of 3-Hydroxy-flavone and Fisetin in Beta-Cyclodextrins: Excited State Proton Transfer Fluorescence and Molecular Mechanics Studies," Chemical Physics Letters - CHEM PHYS LETT, vol. 424, pp. 379-386, 2006, https://doi.org/10.1016/j.cplett.2006.05.006.

P. Mehta, A. Pawar, K. Mahadik, and C. Bothiraja, "Emerging novel drug delivery strategies for bioactive flavonol fisetin in biomedicine," Biomedicine & Pharmacotherapy, vol. 106, pp. 1282-1291, 2018, https://doi.org/10.1016/j.biopha.2018.07.079.

J.M. Pais, M.J. Barroca, M.P.M. Marques, F.A. Almeida Paz, and S.S. Braga, "Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound," Beilstein journal of organic chemistry, vol. 13, pp. 2138-2145, 2017, https://doi.org/10.3762/bjoc.13.212.

L. Ai, J. Hu, X. Ji, and H. Zhao, "Structure confirmation and thermal kinetics of the inclusion of cis-jasmone in β-cyclodextrin," RSC Advances, vol. 9(45), pp. 26224-26229, 2019, https://doi.org/10.1039/C9RA03343B.

A.B. Pereira, and S.S. Braga, "Cyclodextrin Inclusion of Nutraceuticals, from the Bench to your Table," in Cyclodextrins : Synthesis, chemical applications and role in drug delivery, Ed. F.G. Ramirez, Nova Science Publishers Inc., 2015, Chapter 6, pp. 195-224.

H.M.C. Marques, "A review on cyclodextrin encapsulation of essential oils and volatiles," Flavour and Fragrance Journal, vol. 25(5), pp. 313-326, 2010, https://doi.org/10.1002/ffj.2019.

C. Feng, X. Yuan, K. Chu, H. Zhang, W. Ji, and M. Rui, "Preparation and optimization of poly (lactic acid) nanoparticles loaded with fisetin to improve anti-cancer therapy," Int J Biol Macromol, vol. 125, pp. 700-710, 2019, https://doi.org/10.1016/j.ijbiomac.2018.12.003.

M. Sechi, D.N. Syed, N. Pala, A. Mariani, S. Marceddu, A. Brunetti, H. Mukhtar, and V. Sanna, "Nanoencapsulation of dietary flavonoid fisetin: Formulation and in vitro antioxidant and α-glucosidase inhibition activities," Materials Science and Engineering: C, vol. 68(1), pp. 594-602, 2016, https://doi.org/10.1016/j.msec.2016.06.042.

V. DeStefano, S. Khan, and A. Tabada, "Applications of PLA in modern medicine," Engineered Regeneration, vol. 1, pp. 76-87, 2020, https://doi.org/10.1016/j.engreg.2020.08.002.

A. Oz, Ö. Süfer, and Y. celebi sezer, "Poly (Lactic Acid) Films in Food Packaging Systems," vol. 2, 2017, https://doi.org/ 10.23880/FSNT-16000131.

C. Preuksarattanawut, E. Nisaratanaporn, and K. Siralertmukul, "Highly ordered porous PLA films prepared by breath figure method," Journal of Metals, Materials and Minerals, vol. 29(4), pp. 106-112, 2019, https://doi.org/10.14456/jmmm.2019.53

C. Huang, and N. L. Thomas, "Fabricating porous poly(lactic acid) fibres via electrospinning," European Polymer Journal, vol. 99, pp. 464-476, 2018, https://doi.org/10.1016/j.eurpolymj.2017.12.025.

P. Escalé, L. Rubatat, L. Billon, and M. Save, "Recent advances in honeycomb-structured porous polymer films prepared via breath figures," European Polymer Journal, vol. 48(6), pp. 1001-1025, 2012, https://doi.org/10.1016/j.eurpolymj.2012.03.001.

S. Azarmi, W. Roa, and R. Löbenberg, "Current perspectives in dissolution testing of conventional and novel dosage forms," International Journal of Pharmaceutics, vol. 328(1), pp. 12-21, 2007, https://doi.org/10.1016/j.ijpharm.2006.10.001.

P.B.E. Pretsch, and C. Affolter, Structure Determination of Organic Compounds: Table of spectral data, in Structure Determination of Organic Compounds , Eds 3rd ,New York: Springer, 2000, pp(421).

Z. Jian-Qiang, J. Kun-Ming, A. Kun, R. Si-Hao, X. Xiao-Guang, J. Yi, and L. Jun, "Novel water-soluble fisetin/cyclodextrins inclusion complexes: Preparation, characterization, molecular docking and bioavailability," Carbohydrate Research, vol. 418, pp. 20-28, 2015, https://doi.org/10.1016/j.carres.2015.09.013.

B. Nutho, W.Khuntawee, C. Rungnim, P. Pongsawasdi, P. Wolschann, A. Karpfen, N. Kungwan, and T. Rungrotmongkol, "Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes," Beilstein Journal of Organic Chemistry, vol. 10, pp. 2789-2799, 2014, https://doi.org/ 10.3762/bjoc.10.296.

A. Kadari, S. Gudem, H. Kulhari, M.M. Bhandi, R.M. Borkar, V.R.M. Kolapalli, and R. Sistla, "Enhanced oral bioavailability and anticancer efficacy of fisetin by encapsulating as inclusion complex with HPβCD in polymeric nanoparticles," Drug Delivery, vol. 24(1), pp. 224-232, 2017, https://doi.org/ 10.1080/10717544.2016.1245366.

P.P. Menezes, M. Serafini, L.J. Quintans-Junior, G.F. Silva, J.F. Oliveira, F.M.S. Carvalho, J.C.C. Souza, J. Matos, P.B. Alves, I. Matos, D.I. Hadaruga, and A.A.S. Araujo, "Inclusion complex of (−)-linalool and β-cyclodextrin," Journal of Thermal Analysis and Calorimetry, vol. 115(3), pp. 2429-2437, 2013, https://doi.org/10.1007/s10973-013-3367-x.




How to Cite

C. PREUKSARATTANAWUT, W. . MANGMEE, M. . PROUSOONTORN, E. . NISARATTANAPORN, and K. SIRALEARTMUKUL, “Enhancing stability and antioxidant efficacy of fisetin by encapsulating as β-cyclodextrin inclusion complex with porous polylactic acid film from breath figure”, J Met Mater Miner, vol. 31, no. 1, Mar. 2021.



Original Research Articles