New Pyranoanthocyanins Synthesized from Roselle (Hibiscus sabdariffa L.) Anthocyanins
DOI:
https://doi.org/10.29356/jmcs.v60i1.65Keywords:
pyranoanthocyanins, roselle, 4-vinylphenol, acetone, pi-notins, methylpyranoanthocyaninsAbstract
Six new pyranoanthocyanins were synthesized through the reaction between dephinidin-3-sambubioside and cyanidin-3-sam-bubioside, extracted from roselle calyxes, with 4-vinylphenol, acetone and 2-butanone. The reaction products were characterized by liquid chromatography coupled to mass spectrometry (HPLC-TOF-MS), ul-traviolet-visible spectroscopy (UV/Vis) and high-performance liquid chromatography. Those new pigments belong to the families of pino-tins and methylpyranoanthocyanins and show a hypsochromic shift, which results in a more orange colour compared to the red hue of the original anthocyanins. Therefore, these compounds could be used to obtain new colorants more stable against certain factors such as pH.Downloads
References
Aurelio, D.-L.; Edgardo, R. G.; Navarro-Galindo, S. Int. J. Food Sci. Tech. 2008, 43, 322-325. DOI: https://doi.org/10.1111/j.1365-2621.2006.01439.x
D’Heureux-Calyx, F.; Badrie, N. Food Serv. Tech. 2004, 4, 141-148. DOI: https://doi.org/10.1111/j.1471-5740.2004.00100.x
Alobo, A. P.; Offonry, S. U. J. Inst. Brew. 2009, 115, 91-94. DOI: https://doi.org/10.1002/j.2050-0416.2009.tb00351.x
Duangmal, K.; Saicheua, B.; Sueeprasan, S. LTW- Food Sci. Tech-nol. 2008, 41, 1437-1445. DOI: https://doi.org/10.1016/j.lwt.2007.08.014
Carvajal-Zarrabal, O.; Barradas-Dermitz, D. M.; Orta-Flores, Z.; Hayward-Jones, P. M.; Nolasco-Hipólito, C.; Aguilar-Uscanga, M. G.; Miranda-Medina, A.; Bujang, K. B. J. Pharmacol. Exp. 2012, 4, 25-39. DOI: https://doi.org/10.2147/JEP.S27974
Ali, B. H.; Wabel, N. A.; Blunden, G. Phytother. Res. 2005, 19, DOI: https://doi.org/10.1002/ptr.1628
- 375.
Chiou, D.; Langrish, T. A. G. J. Food Eng. 2007, 82, 84-91. DOI: https://doi.org/10.1016/j.jfoodeng.2007.01.021
Rodriguez-Saona, L. E.; Giusti, M. M.; Wrolstad, R. E. J. Food Sci. 1998, 63, 458-465. DOI: https://doi.org/10.1111/j.1365-2621.1998.tb15764.x
Özkan, M. Food Chem. 2002, 78, 499-504. DOI: https://doi.org/10.1016/S0308-8146(02)00165-6
Bakhshayeshi, M. A.; Khayami, M.; Heidari, R.; Jamei, R. Pak. J. Biol. Sci. 2006, 9, 428-433.
Nikkhah, E.; Khayamy, M.; Heidari, R.; Jamee, R. J. Biol. Sci. 2007, 7, 1412-1417. DOI: https://doi.org/10.3923/jbs.2007.1412.1417
Nikkhah, E.; Khayami, M.; Heidari, R.; Bernousi, I. Res. J. Biol. Sci. 2008, 3, 80-84.
Kader, F.; Rovel, B.; Girardin, M.; Metche, M. J. Sci. Food Agric. 1997, 74, 31-34. DOI: https://doi.org/10.1002/(SICI)1097-0010(199705)74:1<31::AID-JSFA764>3.0.CO;2-9
Kader, F.; Irmouli, M.; Nicolas, J. P.; Metche, M. J. Food Sci. 2002, 67, 910-915. DOI: https://doi.org/10.1111/j.1365-2621.2002.tb09427.x
Calderón, A. A.; García-Florenciano, E.; Muñoz, R.; Ros Barceló,
A. Vitis 1992, 31, 139-147. DOI: https://doi.org/10.1016/0304-386X(92)90114-F
Li, J.; Jiang, Y. Molecules 2007, 12, 745-758. DOI: https://doi.org/10.3390/12040745
Wrolstad, R.; Durst, R. W.; Lee, J. Trends Food Sci. Tech. 2005, 16, 423-428. DOI: https://doi.org/10.1016/j.tifs.2005.03.019
Cameira-dos-Santos, P. -J.; Brillouet, J. -M.; Cheynier, V.; Mout-ounet, M. J. Sci. Food Agric. 1996, 70, 204-208. DOI: https://doi.org/10.1002/(SICI)1097-0010(199602)70:2<204::AID-JSFA484>3.3.CO;2-6
Fulcrand, H.; Cameira dos Santos, P. -J.; Sarni-Manchado, P.; Cheynier, V.; Favre-Bonvin, J. J. Chem. Soc., Perkin Trans. 1996, 7, 735-739. DOI: https://doi.org/10.1039/p19960000735
Rentzsch, M.; Schwarz, M.; Winterhalter, P. Trends Food Sci. Tech. 2007, 18, 526-534. DOI: https://doi.org/10.1016/j.tifs.2007.04.014
He, F.; Liang, N. -N.; Mu, L.; Pan, Q. -H.; Wang, J.; Reeves, M. J.; Duan, C. –Q. Molecules 2012, 17, 1483-1519. DOI: https://doi.org/10.3390/molecules17021483
Schwarz, M.; Jerz, G.; Winterhalter, P. Vitis 2003, 42, 105-106.
Wang, H.; Race, E. J.; Shirikhande, A. J. J. Agric. Food Chem. 2003, 51, 7989-7994. DOI: https://doi.org/10.1021/jf034501q
Rentzsch, M.; Schwarz, M.; Winterhalter, P.; Hermosín-Gutiérrez,
I. J. Agric. Food Chem. 2007, 55, 4883-4888. DOI: https://doi.org/10.1021/jf0702491
Vivar-Quintana, A. M.; Santos-Buelga, C.; Rivas-Gonzalo, J. C. Anal. Chim. Acta 2002, 458, 147-155. DOI: https://doi.org/10.1016/S0003-2670(01)01619-1
Hillebrand, S.; Schwarz, M.; Winterhalter, P. J. Agric. Food Chem. 2004, 52, 7331-7338. DOI: https://doi.org/10.1021/jf0487957
Schwarz, M.; Winterhalter, P. Tetrahedron Lett. 2003, 44, 7583-7587. DOI: https://doi.org/10.1016/j.tetlet.2003.08.065
Lu, Y.; Foo, L. Y. Tetrahedron Lett. 2001, 42, 1371-1373. DOI: https://doi.org/10.1016/S0040-4039(00)02246-2
Alcalde-Eon, C.; Escribano-Bailón, M. T.; Santos-Buelga, C.; Ri-vas-Gonzalo, J. C. Anal. Chim. Acta 2006, 563, 238-254. DOI: https://doi.org/10.1016/j.aca.2005.11.028
de Freitas, V.; Mateus, N. Anal. Bioanal. Chem 2011, 401, 1463-1473. DOI: https://doi.org/10.1007/s00216-010-4479-9
Oliveira, J.; Fernandes, V.; Miranda, C.; Santos-Buelga, C.; Silva, A.; de Freitas, V.; Mateus, N. J. Agric. Food Chem. 2006, 54, 6894-6903. DOI: https://doi.org/10.1021/jf061085b
Håkansson, A. E.; Pardon, K.; Hayasaka, Y.; de Sa, M.; Herderich,
M. Tetrahedron Lett. 2003, 44, 4887-4891. DOI: https://doi.org/10.1016/S0040-4039(03)01090-6
Mateus, N.; de Pascual-Teresa, S.; Rivas-Gonzalo, J. C.; San-tos-Buelga, C.; de Freitas, V. Food Chem. 2002, 76, 335-342. DOI: https://doi.org/10.1016/S0308-8146(01)00281-3
Palé, É.; Kouda-Bonafos, M.; Nacro, M. C. R. Chim 2004, 7, 973-980. DOI: https://doi.org/10.1016/j.crci.2003.12.019
Hong, V.; Wrolstad, R. E. J. Agric. Food Chem. 1990, 38, 708-715. DOI: https://doi.org/10.1021/jf00093a026
Bakker, J.; Timberlake, C. F. J. Agric. Food Chem. 1997, 45, 35-43. DOI: https://doi.org/10.1021/jf960252c
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
