Characterization and identification of bioactive compounds in agro-food waste flours

Rodrigues, Camila Gonçalves; Silva, Viviane Dias Medeiros; Loyola, Anna Cláudia de Freitas e; Silva, Mauro Ramalho; Augusti, Rodinei; Melo, Julio Onesio Ferreira; Carlos, Lanamar de Almeida; Fante, Camila Argenta

doi:10.21577/0100-4042.20170853

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Article • Quim. Nova 45 (4) • 2022 • https://doi.org/10.21577/0100-4042.20170853 copy

Characterization and identification of bioactive compounds in agro-food waste flours

Authorship SCIMAGO INSTITUTIONS RANKINGS

One of the recurrent problems of the agroindustry sector is the incorrect disposal of waste because of the complexity of the material, moisture, among other factors. Waste is not used in tonnage, but is systematically used. Examples of residues are malt bagasse and cassava peel, produced in large quantities in the brewing industry and flour production, respectively. In this context, the objective of this study was to evaluate bioactive compounds of flours produced from agroindustry waste to potentiate their use as an ingredient rich in antioxidants. The flours produced from agroindustry waste were evaluated for phenolic compounds, total carotenoids, antioxidant activity, and the attainment of phenolic profiles and fingerprints by paper spray mass spectrometry. It was possible to identify a broad class of compounds in both flours, such as phenolic acids, flavonoids, among others. The flours can be possibly included in food commodities or packaging formulation since they are natural antioxidants, thus adding value to these products and reducing environmental issues. However, further analysis is needed to ensure bioavailability as well as food safety.

Keywords:
waste; fragments; phenolics; cassava peel; malt bagasse

Variables under study	CPF¹ 1 Mean value ± standard deviation. Means followed by equal letters in the same row, for the same parameters, do not differ at 5% significance level by the Student’s t-test.	MBF¹ 1 Mean value ± standard deviation. Means followed by equal letters in the same row, for the same parameters, do not differ at 5% significance level by the Student’s t-test.
T (mg CAT Eq./100g)	1066.98 ±0.06^a	48.67 ±0.21^b
C (µg carotenoid/100g)	161.65 ±44.28^b	333.85 ±15.24^a
P (mg GA Eq/100g)	230.83 ±37.17^b	549.41 ±13.53^a

Method	CPF¹ 1 Average value ± standard deviation. Means followed by equal letters in the same row, for the same parameters, do not differ at 5% significance level by the Student’s t-test.	MBF¹ 1 Average value ± standard deviation. Means followed by equal letters in the same row, for the same parameters, do not differ at 5% significance level by the Student’s t-test.	Green banana peel (Oven 70 ºC)²⁸28 e Loyola, A. C. F.; Silva, V. D.; Silva, M. R.; Rodrigues, C. G.; Dos Santos, A. N.; Melo, J. O.; Fante, C. A.; J. Braz. Chem. Soc. 2021, 32, 953.	Pineapple Residue⁴⁵45 Infante, J.; Selani, M. M.; Toledo, N. M. V.; Silveira-Diniz, M. F.; Alencar, S. M.; Spoto, M. H. F.; Braz. J. Food Nutr. 2013, 24, 87.
ABTS (μM Trolox/g)	26.31 ± 2.68^a	35.73 ± 13.3^a	20.84	Nd
FRAP (μM ferrous sulfate/g)	0.02 ±0.01^b	0.32 ± 0.12^a	Nd	72.63
DPPH (μM Trolox/g)	24.13 ± 0.73^a	4.32 ± 0.64^b	66.61	5.63

Phenolics	CPF¹ 1 Average value ± standard deviation. Means followed by equal letters in the same row, for the same parameters, do not differ at 5% significance level by the Student’s t-test. ND: Not detected.	MBF¹ 1 Average value ± standard deviation. Means followed by equal letters in the same row, for the same parameters, do not differ at 5% significance level by the Student’s t-test. ND: Not detected.
Gallic Acid	270.62 ± 1.13^a	134.73 ± 1.07^b
Catechin	14.87 ± 1.04	ND
Chlorogenic Acid	0.79 ± 0.42	ND
Caffeic Acid	0.19 ± 0.26^a	0.03 ± 0.02^a
Rutin	0.96 ± 0.82	ND
Ellagic Acid	ND	ND
Quercetin	ND	ND

Attempted identification	m/z	MS/MS	Reference	Flour
Attempted identification	m/z	MS/MS	Reference	Cassava	Malt
Organic acids
Malic acid	133	115	Abu-reidah et al,⁵¹51 Abu-Reidah, I. M.; Ali-Shtayeh, M. S.; Jamous, R. A.; ArráezRomán, D.; Segura-Carretero, A.; Food Chem. 2015, 166, 179.	+	-
Citric acid	191	111	Cheikhrouhou and Khemakhem,⁵²52 Abid, M.; Yaich, H.; Cheikhrouhou, S.; Khemakhem, I.; Bouaziz, H. A.; Ayadi, M. A.; J. Food Sci Technol. 2017, 54, 2890. Silva et al.²⁰20 Silva, M.; Freitas, L.; Souza, A.; Araújo, R.; Lacerda, I.; Pereira, H.; Augusti, R.; Melo, J.; J. Braz. Chem. Soc. 2019, 30, 1034.	+	-
Traumatic acid	227	83	Wang et al.⁵³53 Wang, J.; Jia, Z.; Zhang, Z.; Wang, Y.; Liu, X.; Wang, L.; Lin, R.; Molecules 2017, 22, 476.	+	-
Palmitic acid	255	237	Zhang et al.⁵⁴54 Zhang, L.; Zhu, M. T.; Shi, T.; Guo, C.; Huang, Y. S.; Chen, Y.; Xie, M. Y.; Food Funct. 2017, 8, 341.	+	-
Oleic Acid	281	237	Wang et al.⁵³53 Wang, J.; Jia, Z.; Zhang, Z.; Wang, Y.; Liu, X.; Wang, L.; Lin, R.; Molecules 2017, 22, 476.	+	-
Ricinoleic acid	297	183	Zhang et al.⁵⁴54 Zhang, L.; Zhu, M. T.; Shi, T.; Guo, C.; Huang, Y. S.; Chen, Y.; Xie, M. Y.; Food Funct. 2017, 8, 341.	+	-
Octadecanedioic acid	313	295	Zhang et al.⁵⁴54 Zhang, L.; Zhu, M. T.; Shi, T.; Guo, C.; Huang, Y. S.; Chen, Y.; Xie, M. Y.; Food Funct. 2017, 8, 341.	-	+
Phenolic Compounds
Benzoic acids
Gallic acid	170	125	Ee et al.⁵⁵55 Lee, J. H.; Johnson, J. V.; Talcott, S. T.; J. Agric. Food Chem. 2005, 53, 6003.	+	+
Ellagic acid	302	284	Ee et al.⁵⁵55 Lee, J. H.; Johnson, J. V.; Talcott, S. T.; J. Agric. Food Chem. 2005, 53, 6003.	+	-
Cinnamic acids
Caffeic acid	179	135	Kang et al.⁵⁶56 Kang, J.; Price, W. E., Ashton, J.; Tapsell, L. C.; Johnson, S.; Food Chem. 2016, 211, 215.	+	+
Ferulic Acid	193	134	Zhang et al.⁴⁹49 Famacognosia: da planta ao medicamento; Simões, C. M. O., org.; 6th ed., Editora da UFSC e UFRGS: Porto Alegre, 2007.	+	-
1-O-Dihydrocaffeoylglycerol	255	135, 181	Kang et al.⁵⁶56 Kang, J.; Price, W. E., Ashton, J.; Tapsell, L. C.; Johnson, S.; Food Chem. 2016, 211, 215.	+	-
Caffeic acid hexose	341	179	Kang et al.⁵⁶56 Kang, J.; Price, W. E., Ashton, J.; Tapsell, L. C.; Johnson, S.; Food Chem. 2016, 211, 215.	-	+
Ferulic acid glucoside	355	193	Svarc-gaji⁵⁷57 Cvetanovic, A.; Svarc-Gaji, J.; Maskovic, P.; Savic, S.; Nikolic, L.; Ind. Crops Prod. 2015, 65, 582.	+	-
Hydroxycinnamic acid derivative	379	185	Valérie et al.⁵⁸58 Tsamo, C. V. P.; Herent, M.; Tomekpe, K.; Emaga, T. H.; Quetin-Leclerq, J.; Rogez, H.; Larondelle, Y.; Andre, C.; Food Chem. 2015, 167, 197.	-	+
Coumaric acid derivative	487	145	Laura M. et al.⁵⁹59 Bystrom, L. M.; Lewis, B. A.; Brown, D. L.; Rodriguez, E.; Obendorf, R. L.; Food Chem. 2011, 111, 1017.	+	-
Chlorogenic acid	353	179	Ammerer, Arle and Chieber⁶⁰60 Schütz, K.; Kammerer, D.; Carle, R.; Schieber, A.; J. Agric. Food Chem. 2004, 52, 4090.	+	-
Quinones
Spinochrome A	265	235	Abu-reidah et al.⁵¹51 Abu-Reidah, I. M.; Ali-Shtayeh, M. S.; Jamous, R. A.; ArráezRomán, D.; Segura-Carretero, A.; Food Chem. 2015, 166, 179.	+	-
Flavonoids
Catechin	289	245	Valls et al.⁶¹61 Valls, J.; Millán, S.; Martí, M. P.; Borràs, E.; Arola, L.; J. Chromatogr. A 2009, 1216, 7143.	+	-
Quercetin	301	151, 178	Wang et al.⁵³53 Wang, J.; Jia, Z.; Zhang, Z.; Wang, Y.; Liu, X.; Wang, L.; Lin, R.; Molecules 2017, 22, 476.	+	-
Epigallocatechin	305	261, 287	Valls et al.⁶¹61 Valls, J.; Millán, S.; Martí, M. P.; Borràs, E.; Arola, L.; J. Chromatogr. A 2009, 1216, 7143.	+	-
Vitexin	431	311	Simirgiotis et al.⁶²62 Simirgiotis, M. J.; Schmeda-Hirschmann, G.; Bórquez, J.; Kennelly, E. J.; Molecules 2013, 18, 1672.	-	+
Apigenin-7-O-glucoside	431	269	Svarc-gaji⁵⁷57 Cvetanovic, A.; Svarc-Gaji, J.; Maskovic, P.; Savic, S.; Nikolic, L.; Ind. Crops Prod. 2015, 65, 582.	-	+
Apigenin-6-C-glucoside	431	269, 311, 341	Kang et al.⁵⁶56 Kang, J.; Price, W. E., Ashton, J.; Tapsell, L. C.; Johnson, S.; Food Chem. 2016, 211, 215.	-	+
9,10-Dihydro-10-(4-hydroxyphenyl)pyrano[2,3-h]epicatechin-8-on	435	189, 341	Zhang et al.⁵⁴54 Zhang, L.; Zhu, M. T.; Shi, T.; Guo, C.; Huang, Y. S.; Chen, Y.; Xie, M. Y.; Food Funct. 2017, 8, 341.	-	+
Dihydrokaempferol hexoside	449	243, 405	Kang et al.⁵⁶56 Kang, J.; Price, W. E., Ashton, J.; Tapsell, L. C.; Johnson, S.; Food Chem. 2016, 211, 215.	+	-
Procyanidin B	577	451, 425, 407, 289	Svarc-gaji⁵⁷57 Cvetanovic, A.; Svarc-Gaji, J.; Maskovic, P.; Savic, S.; Nikolic, L.; Ind. Crops Prod. 2015, 65, 582.	+	-
Rutin	609	301	Valérie et al.⁵⁸58 Tsamo, C. V. P.; Herent, M.; Tomekpe, K.; Emaga, T. H.; Quetin-Leclerq, J.; Rogez, H.; Larondelle, Y.; Andre, C.; Food Chem. 2015, 167, 197.	+	-
Apigenin-5-O-β-D-glucopyranosyl, 8-C-(6” acetyl)-β-D-glucopyranoside	635	473	Simirgiotis et al.⁶²62 Simirgiotis, M. J.; Schmeda-Hirschmann, G.; Bórquez, J.; Kennelly, E. J.; Molecules 2013, 18, 1672.	+	-
Triterpenoids
Asiatic acid	487	469	Zhang et al.⁵⁴54 Zhang, L.; Zhu, M. T.; Shi, T.; Guo, C.; Huang, Y. S.; Chen, Y.; Xie, M. Y.; Food Funct. 2017, 8, 341.	+	-
Other
9-Hode	295	171, 277	Wang et al.⁵³53 Wang, J.; Jia, Z.; Zhang, Z.; Wang, Y.; Liu, X.; Wang, L.; Lin, R.; Molecules 2017, 22, 476.	-	+

Attempted identification	m/z	MS/MS	Reference	Flour
Attempted identification	m/z	MS/MS	Reference	Cassava	Malt
Amino acids
L-Arginine	175	70	Silva et al.²⁰20 Silva, M.; Freitas, L.; Souza, A.; Araújo, R.; Lacerda, I.; Pereira, H.; Augusti, R.; Melo, J.; J. Braz. Chem. Soc. 2019, 30, 1034.	+	-
Phenolic Compounds (benzoic acid)
Galloyl pyrogallol	279	153	Abu-reidah et al.⁵¹51 Abu-Reidah, I. M.; Ali-Shtayeh, M. S.; Jamous, R. A.; ArráezRomán, D.; Segura-Carretero, A.; Food Chem. 2015, 166, 179.	+	-
Flavonoids
Diosmetin	301	258; 286	Zhang et al.⁵⁴54 Zhang, L.; Zhu, M. T.; Shi, T.; Guo, C.; Huang, Y. S.; Chen, Y.; Xie, M. Y.; Food Funct. 2017, 8, 341.	+	-
Myricetin 3-O-galactoside	481	319	Lin and Harnly⁶³63 De Brito, E. S.; De Araújo, M. C. P.; Lin, L. Z.; Harnly, J.; Food Chem. 2007, 105, 1112.	+	-
Chrysoeriol-hexose	579	301	Abu-reidah et al.⁵¹51 Abu-Reidah, I. M.; Ali-Shtayeh, M. S.; Jamous, R. A.; ArráezRomán, D.; Segura-Carretero, A.; Food Chem. 2015, 166, 179.	+	-
malvidin 3-(malonoyl)glucoside pelargonidin 3-rutinoside	579	433	Rior⁶⁴64 Wu, X.; Prior, R. L.; J. Agric. Food Chem. 2005, 53, 2589.	+	-
cyanidin 3-rutinoside	595	287	Rior⁶⁴64 Wu, X.; Prior, R. L.; J. Agric. Food Chem. 2005, 53, 2589.	+	-
Kaempferol rutinoside	595	287	Abu-reidah et al.⁵¹51 Abu-Reidah, I. M.; Ali-Shtayeh, M. S.; Jamous, R. A.; ArráezRomán, D.; Segura-Carretero, A.; Food Chem. 2015, 166, 179.	+	-
Pelargonidin-3-O-(6caffeoyl-glucoside)	595	433, 313	Wang et al.⁵³53 Wang, J.; Jia, Z.; Zhang, Z.; Wang, Y.; Liu, X.; Wang, L.; Lin, R.; Molecules 2017, 22, 476.	+	-
Tiliroside	595	287	Zhang et al.⁵⁴54 Zhang, L.; Zhu, M. T.; Shi, T.; Guo, C.; Huang, Y. S.; Chen, Y.; Xie, M. Y.; Food Funct. 2017, 8, 341.	+	-
Sugars
Sucrose	381	201, 219	Silva et al.²⁰20 Silva, M.; Freitas, L.; Souza, A.; Araújo, R.; Lacerda, I.; Pereira, H.; Augusti, R.; Melo, J.; J. Braz. Chem. Soc. 2019, 30, 1034.	+	-
Other
Dihydroisovaltrate	424	281, 365	Abu-reidah et al.⁵¹51 Abu-Reidah, I. M.; Ali-Shtayeh, M. S.; Jamous, R. A.; ArráezRomán, D.; Segura-Carretero, A.; Food Chem. 2015, 166, 179.	-	+
Verbonol	453	435	Abu-reidah et al.⁵¹51 Abu-Reidah, I. M.; Ali-Shtayeh, M. S.; Jamous, R. A.; ArráezRomán, D.; Segura-Carretero, A.; Food Chem. 2015, 166, 179.	+	-
Sespendole	520	184	Abu-reidah et al.⁵¹51 Abu-Reidah, I. M.; Ali-Shtayeh, M. S.; Jamous, R. A.; ArráezRomán, D.; Segura-Carretero, A.; Food Chem. 2015, 166, 179.	-	+

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