Quantification of 6-gingerol, metabolomic analysis by paper spray mass spectrometry and determination of antioxidant activity of ginger rhizomes (Zingiber officinale)

Authors

DOI:

https://doi.org/10.33448/rsd-v9i8.4822

Keywords:

Ginger; conventional and organic cultivation; Antioxidant activity; Gingerol; Paper spray.

Abstract

Ginger is a plant whose rhizome has a high therapeutic potential in combating various diseases due to the action of several of its constituents. The 6-gingerol, phenolic compounds and carotenoids, act on macrophage modulation, antiplatelet aggregation and immunosuppressive activity. This work aimed to determine the total antioxidant capacity as well as to evaluate the use of paper spray mass spectrometry to obtain fingerprints of ginger samples of conventional and organic cultivation. The results demonstrated that organic farming samples showed higher levels of fiber and total protein, as well as 6-gingerol. One must still give preference to organic Ginger intake since it presented significant levels of 6-gingerol, fiber and protein. Several chemical classes such as sugars, fatty acids, phenylpropanoids and flavonoids were identified in organic and conventional ginger through paper spray ionization mass spectrometry. This analysis proved to be a very efficient and fast technique for obtaining fingerprints of ginger, allowing the identification of 19 compounds in the positive mode and 28 in the negative mode.

References

Alberti-Dér, Á. (2013). LC-ESI-MS/MS methods in profiling of flavonoid glycosides and phenolic acids in traditional medicinal plants: Sempervivum tectorum L. and Corylus avellana L. [(Ph.D. Dissertation in Pharmaceutical Sciences ) - Semmelweis University]. https://doi.org/10.14753/SE.2014.1933

Amorim, A. C. L., Hovell, A. M. C., Pinto, A. C., Eberlin, M. N., Arruda, N. P., Pereira, E. J., Bizzo, H. R., Catharino, R. R., Morais Filho, Z. B., & Rezende, C. M. (2009). Green and roasted arabica coffees differentiated by ripeness, process and cup quality via electrospray ionization mass spectrometry fingerprinting. Journal of the Brazilian Chemical Society, 20(2), 313–321. https://doi.org/10.1590/S0103-50532009000200017

AOAC, A. of official analytical chemists. (2018). Official Methods of Analysis (AOAC (org.); 19th ed).

Barros, L., Dueñas, M., Dias, M. I., Sousa, M. J., Santos-Buelga, C., & Ferreira, I. C. F. R. (2013). Phenolic profiles of cultivated, in vitro cultured and commercial samples of Melissa officinalis L. infusions. Food Chemistry, 136(1), 1–8. https://doi.org/10.1016/j.foodchem.2012.07.107

Basaiyye, S. S., Naoghare, P. K., Kanojiya, S., Bafana, A., Arrigo, P., Krishnamurthi, K., & Sivanesan, S. (2018). Molecular mechanism of apoptosis induction in Jurkat E6-1 cells by Tribulus terrestris alkaloids extract. Journal of Traditional and Complementary Medicine, 8(3), 410–419. https://doi.org/10.1016/j.jtcme.2017.08.014

Batista, Â. G., da Silva, J. K., Betim Cazarin, C. B., Biasoto, A. C. T., Sawaya, A. C. H. F., Prado, M. A., & Maróstica Júnior, M. R. (2017). Red-jambo (Syzygium malaccense): Bioactive compounds in fruits and leaves. LWT - Food Science and Technology, 76, 284–291. https://doi.org/10.1016/j.lwt.2016.05.013

Benayad, Z., Gómez-Cordovés, C., & Es-Safi, N. (2014). Characterization of Flavonoid Glycosides from Fenugreek (Trigonella foenum-graecum) Crude Seeds by HPLC–DAD–ESI/MS Analysis. International Journal of Molecular Sciences, 15(11), 20668–20685. https://doi.org/10.3390/ijms151120668

Berto, A., Ribeiro, A. B., de Souza, N. E., Fernandes, E., & Chisté, R. C. (2015). Bioactive compounds and scavenging capacity of pulp, peel and seed extracts of the Amazonian fruit Quararibea cordata against ROS and RNS. Food Research International, 77, 236–243. https://doi.org/10.1016/j.foodres.2015.06.018

Bochi, V. C., Godoy, H. T., & Giusti, M. M. (2015). Anthocyanin and other phenolic compounds in Ceylon gooseberry (Dovyalis hebecarpa) fruits. Food Chemistry, 176, 234–243. https://doi.org/10.1016/j.foodchem.2014.12.041

Borges, G. (2008). Characterisation of phenolic antioxidants in fruits and vegetables : bioavailability of raspberry phenolics in humans and rats. (PhD thesis for the degree of Doctor of Phylosophy (PhD))- University of Glasgow.

Campelo, F., Henriques, G., Simeone, M. L., Queiroz, V., Silva, M., Augusti, R., Melo, J., Lacerda, I., & Araújo, R. (2020). Study of Thermoplastic Extrusion and Its Impact on the Chemical and Nutritional Characteristics and Two Sorghum Genotypes SC 319 and BRS 332. Journal of the Brazilian Chemical Society. https://doi.org/10.21577/0103-5053.20190243

Chen, C.-Y., Liu, T.-Z., Liu, Y.-W., Tseng, W.-C., Liu, R. H., Lu, F.-J., Lin, Y.-S., Kuo, S.-H., & Chen, C.-H. (2007). 6-Shogaol (Alkanone from Ginger) Induces Apoptotic Cell Death of Human Hepatoma p53 Mutant Mahlavu Subline via an Oxidative Stress-Mediated Caspase-Dependent Mechanism. Journal of Agricultural and Food Chemistry, 55(3), 948–954. https://doi.org/10.1021/jf0624594

Deng, J., & Yang, Y. (2013). Chemical fingerprint analysis for quality assessment and control of Bansha herbal tea using paper spray mass spectrometry. Analytica Chimica Acta, 785, 82–90. https://doi.org/10.1016/j.aca.2013.04.056

El Sayed, A. M., Ezzat, S. M., El Naggar, M. M., & El Hawary, S. S. (2016). In vivo diabetic wound healing effect and HPLC–DAD–ESI–MS/MS profiling of the methanol extracts of eight Aloe species. Revista Brasileira de Farmacognosia, 26(3), 352–362. https://doi.org/10.1016/j.bjp.2016.01.009

Commission decision 2002/657/EC of 12 August 2002. Implementing Council Directive 96/23/EC concerning performance of analytical methods and the interpretation of results., Official Journal of the European Communities L221/8 (2002).

Faria, A. F., Marques, M. C., & Mercadante, A. Z. (2011). Identification of bioactive compounds from jambolão (Syzygium cumini) and antioxidant capacity evaluation in different pH conditions. Food Chemistry, 126(4), 1571–1578. https://doi.org/10.1016/j.foodchem.2010.12.007

Gan, F.-F., Nagle, A. A., Ang, X., Ho, O. H., Tan, S.-H., Yang, H., Chui, W.-K., & Chew, E.-H. (2011). Shogaols at proapoptotic concentrations induce G2/M arrest and aberrant mitotic cell death associated with tubulin aggregation. Apoptosis, 16(8), 856–867. https://doi.org/10.1007/s10495-011-0611-3

Garrett, R., Rezende, C. M., & Ifa, D. R. (2013). Coffee origin discrimination by paper spray mass spectrometry and direct coffee spray analysis. Analytical Methods, 5(21), 5944. https://doi.org/10.1039/c3ay41247d

Gouvêa, A. C. M. S., Melo, A., Santiago, M. C. P. A., Peixoto, F. M., Freitas, V., Godoy, R. L. O., & Ferreira, I. M. P. L. V. O. (2015). Identification and quantification of anthocyanins in fruits from Neomitranthes obscura (DC.) N. Silveira an endemic specie from Brazil by comparison of chromatographic methodologies. Food Chemistry, 185, 277–283. https://doi.org/10.1016/j.foodchem.2015.02.086

Guo, Y., Gu, Z., Liu, X., Liu, J., Ma, M., Chen, B., & Wang, L. (2017). Rapid Analysis of Corni fructus Using Paper Spray-Mass Spectrometry. Phytochemical Analysis, 28(4), 344–350. https://doi.org/10.1002/pca.2681

Jia, C., Zhu, Y., Zhang, J., Yang, J., Xu, C., & Mao, D. (2017). Identification of Glycoside Compounds from Tobacco by High Performance Liquid Chromatography/Electrospray Ionization Linear Ion-Trap Tandem Mass Spectrometry Coupled with Electrospray Ionization Orbitrap Mass Spectrometry. Journal of the Brazilian Chemical Society. https://doi.org/10.21577/0103-5053.20160211

Jiang, H., Timmermann, B. N., & Gang, D. R. (2007). Characterization and identification of diarylheptanoids in ginger (Zingiber officinale Rosc.) using high-performance liquid chromatography/electrospray ionization mass spectrometry. Rapid Communications in Mass Spectrometry, 21(4), 509–518. https://doi.org/10.1002/rcm.2858

Krüger, S., Bergin, A., & Morlock, G. E. (2018). Effect-directed analysis of ginger ( Zingiber officinale ) and its food products, and quantification of bioactive compounds via high-performance thin-layer chromatography and mass spectrometry. Food Chemistry, 243, 258–268. https://doi.org/10.1016/j.foodchem.2017.09.095

Mariutti, L. R. B., Pereira, D. M., Mercadante, A. Z., Valentão, P., Teixeira, N., & Andrade, P. B. (2012). Further Insights on the Carotenoid Profile of the Echinoderm Marthasterias glacialis L. Marine Drugs, 10(12), 1498–1510. https://doi.org/10.3390/md10071498

Martucci, M. E. P. (2016). Metabolômica e screening de interações ecoquímicas de plantas da subtribo Lychnophorinae (Asteraceae). (Tese de Doutorado em Ciências) - Universidade de São Paulo.

Mazzotti, F., Di Donna, L., Taverna, D., Nardi, M., Aiello, D., Napoli, A., & Sindona, G. (2013). Evaluation of dialdehydic anti-inflammatory active principles in extra-virgin olive oil by reactive paper spray mass spectrometry. International Journal of Mass Spectrometry, 352, 87–91. https://doi.org/10.1016/j.ijms.2013.07.012

Mikulic-Petkovsek, M., Schmitzer, V., Slatnar, A., Stampar, F., & Veberic, R. (2015). A comparison of fruit quality parameters of wild bilberry ( Vaccinium myrtillus L.) growing at different locations. Journal of the Science of Food and Agriculture, 95(4), 776–785. https://doi.org/10.1002/jsfa.6897

Ok, S., & Jeong, W.-S. (2012). Optimization of Extraction Conditions for the 6-Shogaol-rich Extract from Ginger (Zingiber officinale Roscoe). Preventive Nutrition and Food Science, 17(2), 166–171. https://doi.org/10.3746/pnf.2012.17.2.166

Pan, M.-H., Hsieh, M.-C., Kuo, J.-M., Lai, C.-S., Wu, H., Sang, S., & Ho, C.-T. (2008). 6-Shogaol induces apoptosis in human colorectal carcinoma cellsviaROS production, caspase activation, and GADD 153 expression. Molecular Nutrition & Food Research, 52(5), 527–537. https://doi.org/10.1002/mnfr.200700157

Pawar, N., Pai, S., Nimbalkar, M., & Dixit, G. (2011). RP-HPLC analysis of phenolic antioxidant compound 6-gingerol from different ginger cultivars. Food Chemistry, 126(3), 1330–1336. https://doi.org/10.1016/j.foodchem.2010.11.090

Ramos, A. L. C. C., Mendes, D. D., Silva, M. R., Augusti, R., Melo, J. O. F., Araújo, R. L. B. de, & Lacerda, I. C. A. (2020). Chemical profile of Eugenia brasiliensis (Grumixama) pulp by PS/MS paper spray and SPME-GC / MS solid-phase microextraction. Research, Society and Development, 9(7), 318974008. https://doi.org/10.33448/rsd-v9i7.4008

Ramos, A. S., Souza, R. O. S., Boleti, A. P. de A., Bruginski, E. R. D., Lima, E. S., Campos, F. R., & Machado, M. B. (2015). Chemical characterization and antioxidant capacity of the araçá-pera ( Psidium acutangulum ): An exotic Amazon fruit. Food Research International, 75, 315–327. https://doi.org/10.1016/j.foodres.2015.06.026

Roriz, C. L., Barros, L., Carvalho, A. M., Santos-Buelga, C., & Ferreira, I. C. F. R. (2014). Pterospartum tridentatum, Gomphrena globosa and Cymbopogon citratus: A phytochemical study focused on antioxidant compounds. Food Research International, 62, 684–693. https://doi.org/10.1016/j.foodres.2014.04.036

Rufino, M. do S. M., Alves, R. E., de Brito, E. S., Pérez-Jiménez, J., Saura-Calixto, F., & Mancini-Filho, J. (2010). Bioactive compounds and antioxidant capacities of 18 non-traditional tropical fruits from Brazil. Food Chemistry, 121(4), 996–1002. https://doi.org/10.1016/j.foodchem.2010.01.037

Sanwal, S. K., Rai, N., Singh, J., & Buragohain, J. (2010). Antioxidant phytochemicals and gingerol content in diploid and tetraploid clones of ginger (Zingiber officinale Roscoe). Scientia Horticulturae, 124(2), 280–285. https://doi.org/10.1016/j.scienta.2010.01.003

Silva, E., Augusti, R., Melo, J., Takahashi, J., & Araújo, R. (2020). Physicochemical characterization, antioxidant activity and fingerprints of industrialized “detox” mixed beverages by paper spray mass spectrometry. Química Nova. https://doi.org/10.21577/0100-4042.20170490

Silva, M., Freitas, L., Souza, A., Araújo, R., Lacerda, I., Pereira, H., Augusti, R., & Melo, J. (2019). Antioxidant Activity and Metabolomic Analysis of Cagaitas (Eugenia dysenterica) using Paper Spray Mass Spectrometry. Journal of the Brazilian Chemical Society. https://doi.org/10.21577/0103-5053.20190002

Singleton, V. L., Orthofer, R., & Lamuela-Raventós, R. M. (1999). Analysis of total phenols and other oxidation substrates and antioxidants by means of folin-ciocalteu reagent (p. 152–178). https://doi.org/10.1016/S0076-6879(99)99017-1

Wang, H., Liu, J., Cooks, R. G., & Ouyang, Z. (2010). Paper Spray for Direct Analysis of Complex Mixtures Using Mass Spectrometry. Angewandte Chemie International Edition, 49(5), 877–880. https://doi.org/10.1002/anie.200906314

Yu, Y., Huang, T., Yang, B., Liu, X., & Duan, G. (2007). Development of gas chromatography–mass spectrometry with microwave distillation and simultaneous solid-phase microextraction for rapid determination of volatile constituents in ginger. Journal of Pharmaceutical and Biomedical Analysis, 43(1), 24–31. https://doi.org/10.1016/j.jpba.2006.06.037

Downloads

Published

08/07/2020

How to Cite

OLIVEIRA, C. T.; RAMOS, A. L. C. C.; MENDONÇA, H. de O. P.; CONSENZA, G. P.; SILVA, M. R.; FERNANDES, C.; AUGUSTI, R.; MELO, J. O. F.; FERREIRA, A. V. M.; ARAÚJO, R. L. B. de. Quantification of 6-gingerol, metabolomic analysis by paper spray mass spectrometry and determination of antioxidant activity of ginger rhizomes (Zingiber officinale). Research, Society and Development, [S. l.], v. 9, n. 8, p. e366984822, 2020. DOI: 10.33448/rsd-v9i8.4822. Disponível em: https://rsdjournal.org/index.php/rsd/article/view/4822. Acesso em: 30 dec. 2024.

Issue

Section

Agrarian and Biological Sciences