Enzymatic Conversion of Geniposide to Genipin: A Natural Blue Color Precursor and Biopolymer Film Crosslinker
Corressponding author's email:
tiennv@hcmute.edu.vnDOI:
https://doi.org/10.54644/jte.2024.1584Keywords:
Cellulase, Genipin, Chitosan-genipin, Crosslink, Blue colorantAbstract
The research is motivated by the growing interest in using natural products for biopolymer engineering, particularly in developing bioactive and biocompatible materials. Genipin, a natural blue colorant precursor, has garnered attention due to its unique chemical structure and crosslinking properties with natural polymers. This research focuses on the optimizing conditions for efficient enzymatic conversion of geniposide from Gardenia jasminoides into genipin and its subsequent utilization in producing chitosan-genipin films. Geniposide was extracted using 50% ethanol, and its enzymatic conversion to genipin using commercial cellulase was best at pH 4.5, 0.2 g cellulase per gram of geniposide and 6 h of reaction. The synthesized genipin was used to fabricate chitosan-genipin films, which were tested for various properties. The film with 0.01 w/w genipin/chitosan ratio exhibited the highest UV-vis absorbance at 610 nm, indicating significant crosslinking, and demonstrated the greatest mechanical strength at 19.92 N/mm². Additionally, this film showed a moisture content of only 2.01%, significantly lower than that of the control. Increasing the amount of genipin reacting with chitosan significantly reduced the moisture and swelling degree of the chitosan films, indicating their lower hydrophilicity. These results underscore the effectiveness of genipin as a crosslinking agent in biopolymer applications, suggesting its potential to develop sustainable materials with advanced mechanical and moisture-resistant properties.
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References
A. Das, T. Ringu, S. Ghosh, and N. Pramanik, "A comprehensive review on recent advances in preparation, physicochemical characterization, and bioengineering applications of biopolymers," Polymer Bulletin, vol. 80, no. 7, pp. 7247-7312, 2023. DOI: https://doi.org/10.1007/s00289-022-04443-4
R. Ahmed, N. Ul Ain Hira, M. Wang, S. Iqbal, J. Yi, and Y. Hemar, "Genipin, a natural blue colorant precursor: Source, extraction, properties, and applications," (in English), Food Chem, vol. 434, p. 137498, 2024. DOI: https://doi.org/10.1016/j.foodchem.2023.137498
N. Kildeeva et al., "Influence of genipin crosslinking on the properties of chitosan-based films," Polymers, vol. 12, no. 5, p. 1086, 2020. DOI: https://doi.org/10.3390/polym12051086
L. B. H. Colmenares et al., "New sources of genipin-rich substances for crosslinking future manufactured bio-based materials," RSC Sustainability, vol. 2, no. 1, pp. 125-138, 2024. DOI: https://doi.org/10.1039/D3SU00303E
Z. Wang et al., "Biotransformation of geniposide by Synechocystis sp. PCC 6803 into genipin and its inhibitory effects on BEL-7402, Escherichia coli, and cyanobacteria," Annals of Microbiology, vol. 65, no. 3, pp. 1303-1311, 2015. DOI: https://doi.org/10.1007/s13213-014-0968-y
Y.-S. Yang et al., "Transformation of Geniposide into Genipin by Immobilized β-Glucosidase in a Two-Phase Aqueous-Organic System," Molecules, vol. 16, no. 5, pp. 4295-4304, 2011. DOI: https://doi.org/10.3390/molecules16054295
Y.-J. Fu et al., "Enzyme assisted extraction of luteolin and apigenin from pigeonpea [Cajanuscajan (L.) Millsp.] leaves," Food Chemistry, vol. 111, no. 2, pp. 508-512, 2008. DOI: https://doi.org/10.1016/j.foodchem.2008.04.003
B. Manickam, R. Sreedharan, and M. Elumalai, "‘Genipin’–the natural water soluble cross-linking agent and its importance in the modified drug delivery systems: An overview," Current drug delivery, vol. 11, no. 1, pp. 139-145, 2014. DOI: https://doi.org/10.2174/15672018113106660059
J. Brauch, "Underutilized fruits and vegetables as potential novel pigment sources," in Handbook on natural pigments in food and beverages: Elsevier, 2016, pp. 305-335. DOI: https://doi.org/10.1016/B978-0-08-100371-8.00015-4
L. Li, Y. Guo, L. Zhao, Y. Zu, H. Gu, and L. Yang, "Enzymatic hydrolysis and simultaneous extraction for preparation of genipin from bark of eucommia ulmoides after ultrasound, microwave pretreatment," Molecules, vol. 20, no. 10, pp. 18717-18731, 2015. DOI: https://doi.org/10.3390/molecules201018717
W. Winotapun, P. Opanasopit, T. Ngawhirunpat, and T. Rojanarata, "One-enzyme catalyzed simultaneous plant cell disruption and conversion of released glycoside to aglycone combined with in situ product separation as green one-pot production of genipin from gardenia fruit," Enzyme and microbial technology, vol. 53, no. 2, pp. 92-96, 2013. DOI: https://doi.org/10.1016/j.enzmictec.2013.05.001
D. Yang, M. Zhou, W. Wei, H. Zhu, and X. Fan, "Preparation of a genipin blue from egg protein and genipin," Natural product research, vol. 26, no. 8, pp. 765-769, 2012. DOI: https://doi.org/10.1080/14786419.2010.547859
N. Moritome, Y. Kishi, and S. Fujii, "Properties of red pigments prepared from geniposidic acid and amino acids," Journal of the Science of Food and Agriculture, vol. 79, no. 6, pp. 810-814, 1999. DOI: https://doi.org/10.1002/(SICI)1097-0010(19990501)79:6<810::AID-JSFA288>3.0.CO;2-7
K. Delmar and H. Bianco-Peled, "The dramatic effect of small pH changes on the properties of chitosan hydrogels crosslinked with genipin," Carbohydrate Polymers, vol. 127, pp. 28-37, 2015. DOI: https://doi.org/10.1016/j.carbpol.2015.03.039
M. F. Butler, Y. F. Ng, and P. D. Pudney, "Mechanism and kinetics of the crosslinking reaction between biopolymers containing primary amine groups and genipin," Journal of Polymer Science Part A: Polymer Chemistry, vol. 41, no. 24, pp. 3941-3953, 2003. DOI: https://doi.org/10.1002/pola.10960
F. L. Mi, Y. C. Tan, H. C. Liang, R. N. Huang, and H. W. Sung, "In vitro evaluation of a chitosan membrane cross-linked with genipin," Journal of Biomaterials Science, Polymer Edition, vol. 12, no. 8, pp. 835-850, 2001. DOI: https://doi.org/10.1163/156856201753113051
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