Abstract
By-products (silk, cob, and husk) from purple corn processing are rich in anthocyanins, which can be used as natural antioxidants. In this work, the polyphenol and anthocyanin content and the chemical composition of solvent extracts from silk, cob, and husk were examined separately. The total anthocyanin (TAC) and polyphenols (TPC) content of purple corn silk is higher than the cob and husk. Ethanol can significantly improve the TAC in various purple corn extracts. Anthocyanins were identified using high-performance liquid chromatography coupled with an electrospray ionization mass spectrometer (HPLC-ESI-MS), and their composition was quantified using a diode matrix detector (DAD) coupled HPLC. The results of the quantitative analysis demonstrated that cyanidin derivatives were the main components of purple corn extracts, regardless of the solvent used. The selection of solvent and acidifier had a significant effect on the composition of anthocyanins. Ethanol and water can promote the dissolution of cyanidin derivatives, while methanol provides a solid incentive to extract peonidin derivatives. Formic acid may favor the production of malonyl anthocyanin, whereas hydrochloric acid may favor the production of succinyl anthocyanin. The results of the correlation analysis showed that the TAC primarily determined the antioxidant capacity of the purple maize extract in different extracts. The predictive evaluation of the VIP analysis shows that the higher relative concentration of C3dM, C3M, Pg3dM, and Pg3M in the water extract may contribute to its higher antioxidant power.
Similar content being viewed by others
Abbreviations
- HPLC:
-
High-performance liquid chromatography
- DAD:
-
Diode array detector
- rpm:
-
Round per minute
- DPPH:
-
1,1-Diphenyl-2-picrylhydrazyl radical
- ABTS:
-
2,2′-Azino-bis (3-ethylben-zothiazolin-6-sulfonate) diammonium salt
- TPTZ:
-
2,4,6-Tri(2-pyridyl)-s-triazine
- FRAP:
-
Ferric ion reducing antioxidant power
- TAC:
-
Total anthocyanin content
- TPC:
-
Total polyphenol content
- EAC:
-
Equivalent antioxidant capacities
- PCA:
-
Principal component analysis
- HCA:
-
Hierarchical cluster analysis
- PLS-DA:
-
Partial least square discriminant analysis
- OPLS-DA:
-
Positive cross-partial least squares discriminant analysis
- VIP:
-
Variables in the predicted
- C3G:
-
Cyanidin-3-glucoside
- Pg3G:
-
Pelargonidin-3-glucoside
- P3G:
-
Peonidin-3-glucoside
- C3M:
-
Cyanidin-3-(6″-malonyl)-glucoside
- C3S:
-
Cyanidin-3-(6″-succinyl)-glucoside
- Pg3M:
-
Pelargonidin-3-(6″-malonyl)-glucoside
- C3dM:
-
Cyanidin-3-(3″,6″-dimalonyl)-glucoside
- P3M:
-
Peonidin-3-(6″-malonyl)-glucoside
- Pg3dM:
-
Pelargonidin-3-(3″,6″-dimalonyl)-glucoside
- C3E:
-
Cyanidin-3-(6″-ethyl-malonyl)-glucoside
- C3dS:
-
Cyanidin-3-(6″-disuccinyl)-glucoside
- P3dS:
-
Peonidin-3-(6″-disuccinyl)-glucoside
- CD:
-
Cyanidin derivative
- CEM(FA):
-
Cob extracted with methanol (added by formic acid)
- CEE:
-
Cob extracted with ethanol
- CEW:
-
Cob extracted with water
- CEM:
-
Cob extracted with methanol
- HEM(FA):
-
Husk extracted with methanol (added formic acid)
- HEE:
-
Husk extracted with ethanol
- HEW:
-
Husk extracted with water
- HEM:
-
Husk extracted with methanol
- SEM(FA):
-
Silk extracted with methanol (added by formic acid)
- SEE:
-
Silk extracted with ethanol
- SEW:
-
Silk extracted with water
- SEM:
-
Silk extracted with methanol
References
Abdel-Aal ESM, Akhtar H, Rabalski I, Bryan M (2014) Accelerated, microwave-assisted, and conventional solvent extraction methods affect anthocyanin composition from colored grains. J Food Sci 79(2):C138–C146. https://doi.org/10.1111/1750-3841.12346
Arunachalam K, Parimelazhagan T (2014) Evaluation of nutritional composition and antioxidant properties of underutilized Ficus talboti King fruit for nutraceuticals and food supplements. J Food Sci Technol 51(7):1260–1268
Aruoma OI (1998) Free radicals, oxidative stress, and antioxidants in human health and disease. J Am Oil Chem Soc 75(2):199–212
Cevallos-Casals BA, Cisneros-Zevallos L (2004) Stability of anthocyanin-based aqueous extracts of Andean purple corn and red-fleshed sweet potato compared to synthetic and natural colorants. Food Chem 86(1):69–77. https://doi.org/10.1016/j.foodchem.2003.08.011
Charepalli V, Reddivari L, Vadde R, Walia S, Radhakrishnan S, Vanamala J (2016) Eugenia jambolana (Java plum) fruit extract exhibits anti-cancer activity against early stage human HCT-116 colon cancer cells and colon cancer stem cells. Cancers 8(3):29
Chatham LA, West L, Berhow MA, Vermillion KE, Juvik JA (2018) Unique flavanol-anthocyanin condensed forms in Apache red purple corn. J Agric Food Chem 66(41):10844–10854
Chen C, Somavat P, Singh V, de Mejia EG (2017) Chemical characterization of proanthocyanidins in purple, blue, and red maize coproducts from different milling processes and their anti-inflammatory properties. Ind Crops Prod 109:464–475. https://doi.org/10.1016/j.indcrop.2017.08.046
Colombo R, Ferron L, Papetti A (2021) Colored corn: an up-date on metabolites extraction, health implication, and potential use. Molecules 26(1):199
Cristianini M, Guillén Sánchez JS (2020) Extraction of bioactive compounds from purple corn using emerging technologies: a review. J Food Sci 85(4):862–869
Fukamachi K, Imada T, Ohshima Y, Xu J, Tsuda H (2008) Purple corn color suppresses Ras protein level and inhibits 7,12-dimethylbenz a anthracene-induced mammary carcinogenesis in the rat. Cancer Sci 99(9):1841–1846. https://doi.org/10.1111/j.1349-7006.2008.00895.x
Gallegos SR, Arrunátegui GT, Valenzuela R, Rincón-Cervera MÁ, Espinoza MEV (2018) Adding a purple corn extract in rats supplemented with chia oil decreases gene expression of SREBP-1c and retains Δ5 and Δ6 hepatic desaturase activity, unmodified the hepatic lipid profile. Prostaglandins Leukot Essent Fatty Acids 132:1–7
Gk A, Jw B, Rk B, Up B (2021) Evaluation of glycerol usage for the extraction of anthocyanins from black chokeberry and elderberry fruits. J Appl Res Med Aromat Plants 22:100296
Hagiwara A, Miyashita K, Nakanishi T, Sano M, Tamano S, Kadota T, Koda T, Nakamura M, Imaida K, Ito N, Shirai T (2001) Pronounced inhibition by a natural anthocyanin, purple corn color, of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-associated colorectal carcinogenesis in male F344 rats pretreated with 1,2-dimethylhydrazine. Cancer Lett 171(1):17–25. https://doi.org/10.1016/S0304-3835(01)00510-9
Han J, Wei FX (2010) Determination of Polyphenols in Apple Pomace by Folin-Ciocalteu Colorimetry[J]. Food Scie 31(4):179–182
Harakotr B, Suriharn B, Scott MP, Lertrat K (2015) Genotypic variability in anthocyanins, total phenolics, and antioxidant activity among diverse waxy corn germplasm. Euphytica 203(2):237–248. https://doi.org/10.1007/s10681-014-1240-z
Hassani D, Liu H, Chen Y, Wan Z, Zhuge Q, Li S (2015) Analysis of biochemical compounds and differentially expressed genes of the anthocyanin biosynthetic pathway in variegated peach flowers. Genet Mol Res 14(4):13425–13426
Herrera-Sotero MY, Cruz-Hernández CD, Oliart-Ros RM, Chávez-Servia JL, Guzmán-Gerónimo RI, González-Covarrubias V, Cruz-Burgos M, Rodríguez-Dorantes M (2020) Anthocyanins of blue corn and tortilla arrest cell cycle and induce apoptosis on breast and prostate cancer cells. Nutr Cancer 72(5):768–777
Hong HT, Netzel ME, O’Hare TJ (2020) Optimisation of extraction procedure and development of LC–DAD–MS methodology for anthocyanin analysis in anthocyanin-pigmented corn kernels. Food Chem 319(1):126515
Hong SH, Heo JI, Kim JH, Kwon SO, Yeo KM, Bakowska-Barczak AM, Kolodziejczyk P, Ryu OH, Choi MK, Kang YH, Lim SS, Suh HW, Huh SO, Lee JY (2013) Antidiabetic and beta cell-protection activities of purple corn anthocyanins. Biomol Ther 21(4):284–289. https://doi.org/10.4062/biomolther.2013.016
Huang B, Wang Z, Park JH, Ryu OH, Choi MK, Lee J-Y, Kang Y-H, Lim SS (2015) Anti-diabetic effect of purple corn extract on C57BL/KsJ db/db mice. Nurs Res Pract 9(1):22–29
Jomova K, Hudecova L, Lauro P, Simunková M, Barbierikova Z, Malcek M, Alwasel SH, Alhazza IM, Rhodes CJ, Valko M (2022) The effect of luteolin on DNA damage mediated by a copper catalyzed Fenton reaction. J Inorg Biochem 226:111635
Khamphasan P, Lomthaisong K, Harakotr B, Ketthaisong D, Scott MP, Lertrat K, Suriharn B (2018) Genotypic variation in anthocyanins, phenolic compounds, and antioxidant activity in cob and husk of purple field corn. Agronomy 8(11):271
Lao F, Giusti MM (2016) Quantification of purple corn (Zea mays L.) anthocyanins using spectrophotometric and HPLC approaches: method comparison and correlation. Food Anal Methods 9(5):1367–1380
Lao F, Giusti MM (2018) Extraction of purple corn (Zea mays L.) cob pigments and phenolic compounds using food-friendly solvents. J Cereal Sci 80:87–93
Lech K, Jarosz M (2011) Novel methodology for the extraction and identification of natural dyestuffs in historical textiles by HPLC–UV–Vis–ESI MS. Case study: chasubles from the Wawel Cathedral collection. Anal Bioanal Chem 399(9):3241–3251
Li A-N, Li S, Zhang Y-J, Xu X-R, Chen Y-M, Li H-B (2014) Resources and biological activities of natural polyphenols. Nutrients 6(12):6020–6047
Li C-Y, Kim H-W, Won SR, Min H-K, Park K-J, Park J-Y, Ahn M-S, Rhee H-I (2008) Corn husk as a potential source of anthocyanins. J Agric Food Chem 56(23):11413–11416
Li J, Li X-D, Zhang Y, Zheng Z-D, Qu Z-Y, Liu M, Zhu S-H, Liu S, Wang M, Qu L (2013a) Identification and thermal stability of purple-fleshed sweet potato anthocyanins in aqueous solutions with various pH values and fruit juices. Food Chem 136(3):1429–1434
Li J, Li XD, Zhang Y, Zheng ZD, Qu ZY, Liu M, Zhu SH, Liu S, Wang M, Qu L (2013b) Identification and thermal stability of purple-fleshed sweet potato anthocyanins in aqueous solutions with various pH values and fruit juices. Food Chem 136(3–4):1429–1434. https://doi.org/10.1016/j.foodchem.2012.09.054
Liang XL, Wang XL, Li Z, Hao QH, Wang SY (2010) Improved in vitro assays of superoxide anion and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity of isoflavones and isoflavone metabolites. J Agric Food Chem 58(22):11548
Lim KT, Son YO, Lee JC, Lim JC, Chung Y (2002) Effects of Glycoprotein from Ulmus Davidiana Nakai on hydroxyl radical induced-cytotoxicity, and on activation of nuclear factor-kappa B and activator protein-1 in cultured mouse primary thymocytes. Food Sci Biotechnol 11:172–178
Liu H, Wang X, Warburton ML, Wen W, Jin M, Deng M, Liu J, Tong H, Pan Q, Yang X (2015) Genomic, transcriptomic, and phenomic variation reveals the complex adaptation of modern maize breeding. Mol Plant 8(6):871–884
Long N, Suzuki S, Sato S, Naiki-Ito A, Sakatani K, Shirai T, Takahashi S (2013) Purple corn color inhibition of prostate carcinogenesis by targeting cell growth pathways. Cancer Sci 104(3):298–303. https://doi.org/10.1111/cas.12078
Lopez-Martinez LX, Oliart-Ros RM, Valerio-Alfaro G, Lee CH, Parkin KL, Garcia HS (2009) Antioxidant activity, phenolic compounds and anthocyanins content of eighteen strains of Mexican maize. LWT-Food Sci Technol 42(6):1187–1192. https://doi.org/10.1016/j.lwt.2008.10.010
Lopez-Martinez LX, Parkin KL, Garcia HS (2014) Antioxidant and quinone reductase inducing activities of ethanolic fractions from purple maize. LWT-Food Sci Technol 59(1):270–275
Luna-Vital DA, Weiss M, De Mejia EG (2017) Comparative effect of an anthocyanin-rich extract from purple corn and pure anthocyanins on 3T3-L1 adipocytes under different physiological conditions. FASEB J 31:2
Matsuoka Y, Vigouroux Y, Goodman MM, Sanchez J, Buckler E, Doebley J (2002) A single domestication for maize shown by multilocus microsatellite genotyping. Proc Natl Acad Sci 99(9):6080–6084
Mazewski C, Liang K, de Mejia EG (2017) Inhibitory potential of anthocyanin-rich purple and red corn extracts on human colorectal cancer cell proliferation in vitro. J Funct Foods 34:254–265. https://doi.org/10.1016/j.jff.2017.04.038
Mohamed G, Lertrat K, Suriharn B (2017) Phenolic compound, anthocyanin content, and antioxidant activity in some parts of purple waxy corn across maturity stages and locations. Int Food Res J 24(2):490
Moure A, Cruz JM, Franco D, Domı́nguez JM, Sineiro J, Domı́nguez H, Núñez M, Parajó J (2001) Natural antioxidants from residual sources. Food Chem 72(2):145–171
Muangrat R, Williams PT, Saengcharoenrat P (2017) Subcritical solvent extraction of total anthocyanins from dried purple waxy corn: influence of process conditions. J Food Process Preserv 41(6):e13252
Naczk M, Shahidi F (2006) Phenolics in cereals, fruits and vegetables: occurrence, extraction and analysis. J Pharm Biomed Anal 41(5):1523–1542
Nankar AN, Dungan B, Paz N, Sudasinghe N, Schaub T, Holguin FO, Pratt RC (2016) Quantitative and qualitative evaluation of kernel anthocyanins from southwestern United States blue corn. J Sci Food Agric 96(13):4542–4552
Nazareth TDM, Luz C, Torrijos R, Quiles JM, Luciano FB, Mañes J, Meca G (2019) Potential application of lactic acid bacteria to reduce aflatoxin B1 and fumonisin B1 occurrence on corn kernels and corn ears. Toxins 12(1):21
Ono K, Sugihara N, Hirose Y, Katagiri K (2002) An examination of optimal extraction solvents for anthocyanin pigments from black rice produced in Gifu. Gifu City Womens Coll Res Bull 52:135–138
Ozgen M, Reese RN, Tulio AZ, Scheerens JC, Miller AR (2006) Modified 2,2-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method to measure antioxidant capacity of selected small fruits and comparison to ferric reducing antioxidant power (FRAP) and 2,2’-diphenyl-1-picrylhydrazyl (DPPH) methods. J Agric Food Chem 54(4):1151
Paucar-Menacho LM, Martinez-Villaluenga C, Duenas M, Frias J, Penas E (2017) Optimization of germination time and temperature to maximize the content of bioactive compounds and the antioxidant activity of purple corn (Zea mays L.) by response surface methodology. LWT-Food Sci Technol 76:236–244
Peniche-Pavía HA, Tiessen A (2020) Anthocyanin profiling of maize grains using DIESI-MSQD reveals that cyanidin-based derivatives predominate in purple corn, whereas pelargonidin-based molecules occur in red-pink varieties from Mexico. J Agric Food Chem 68(21):5980–5994. https://doi.org/10.1021/acs.jafc.9b06336
Pérez-Jiménez J, Arranz S, Tabernero M, Díaz-Rubio M, Serrano J, Goñi I, Saura-Calixto F (2008) Updated methodology to determine antioxidant capacity in plant foods, oils and beverages: extraction, measurement and expression of results. Food Res Int 41(3):274–285
Petroni K, Trinei M, Fornari M, Calvenzani V, Marinelli A, Micheli L, Pilu R, Matros A, Mock H-P, Tonelli C (2017) Dietary cyanidin 3-glucoside from purple corn ameliorates doxorubicin-induced cardiotoxicity in mice. Nutr Metab Cardiovasc Dis 27(5):462–469
Ramos-Escudero F, Muñoz AM, Alvarado-Ortíz C, Alvarado Á, Yáñez J (2012) Purple corn (Zea mays L.) phenolic compounds profile and its assessment as an agent against oxidative stress in isolated mouse organs. J Med Food 15(2):206–215
Ranum P, Peña-Rosas JP, Garcia-Casal MN (2014) Global maize production, utilization, and consumption. Ann N Y Acad Sci 1312(1):105–112
Serna-Saldivar SO, Carrillo EP (2019) Chapter 16—food uses of whole corn and dry-milled fractions. In: Serna-Saldivar SO (ed) Corn, 3rd edn. AACC International Press, Oxford, pp 435–467
Shen S, Wang J, Zhuo Q, Chen X, Liu T, Zhang S-Q (2018) Quantitative and discriminative evaluation of contents of phenolic and flavonoid and antioxidant competence for Chinese honeys from different botanical origins. Molecules 23(5):1110
Simunkova M, Barbierikova Z, Jomova K, Hudecova L, Lauro P, Alwasel SH, Alhazza I, Rhodes CJ, Valko M (2021) Antioxidant vs. prooxidant properties of the flavonoid, kaempferol, in the presence of cu (ii) ions: a ros-scavenging activity, fenton reaction and dna damage study. Int J Mol Sci 22(4):1619
Siyuan S, Tong L, Liu R (2018) Corn phytochemicals and their health benefits. Food Sci Human Wellness 7(3):185–195
Sulaiman SF, Sajak A, Ooi KL, Seow EM (2011) Effect of solvents in extracting polyphenols and antioxidants of selected raw vegetables. J Food Compos Anal 24(4–5):506–515
Tangwongchai R, Lertrat K, Saikaew K (2018) Influence of variety and maturity on bioactive compounds and antioxidant activity of purple waxy corn (Zea mays L. var. ceratina). Int Food Res J 25(5):1985–1995
Van Heerwaarden J, Doebley J, Briggs WH, Glaubitz JC, Goodman MM, Gonzalez JDJS, Ross-Ibarra J (2011) Genetic signals of origin, spread, and introgression in a large sample of maize landraces. Proc Natl Acad Sci 108(3):1088–1092
Volden J, Bengtsson GB, Wicklund T (2009) Glucosinolates, l-ascorbic acid, total phenols, anthocyanins, antioxidant capacities and colour in cauliflower (Brassica oleracea L. ssp. botrytis); effects of long-term freezer storage. Food Chem 112(4):967–976
Wang D, Lei Y, Ma Y, Zhang L, Zhao X (2014) Inhibition of ALV-A-induced apoptosis in DF-1 cells via inactivation of nuclear transcription factor κB by anthocyanins from purple corn (Zea mays L.). J Funct Foods 10:274–282
Warburton ML, Wilkes G, Taba S, Charcosset A, Mir C, Dumas F, Madur D, Dreisigacker S, Bedoya C, Prasanna B (2011) Gene flow among different teosinte taxa and into the domesticated maize gene pool. Genet Resour Crop Evol 58(8):1243–1261
Won JY, Son SY, Lee S, Singh D, Lee S, Lee JS, Lee CH (2018) Strategy for screening of antioxidant compounds from two Ulmaceae species based on liquid chromatography-mass spectrometry. Molecules 23(7):1830
Wrolstad RE, Durst RW, Giusti MM, Rodriguez-Saona LE (2002) Analysis of anthocyanins in nutraceuticals. ACS Publications
Yang Z, Zhai W (2010a) Identification and antioxidant activity of anthocyanins extracted from the seed and cob of purple corn (Zea mays L.). Innov Food Sci Emerg Technol 11(1):169–176
Yang ZD, Zhai WW (2010b) Identification and antioxidant activity of anthocyanins extracted from the seed and cob of purple corn (Zea mays L.). Innov Food Sci Emerg Technol 11(1):169–176. https://doi.org/10.1016/j.ifset.2009.08.012
Zhang C, Ma Y, Zhao XY, Wang F (2011) Effect of drying treatments on anthocyanin, fumonisin B-1, aflatoxin B-1 content of anthocyanin extract from purple corn (Zea may L.) in north China. In: Kim YH, Yarlagadda P, Zhang XD, Ai ZJ (eds) Advanced materials and structures, pts 1 and 2, vol 335–336. Trans Tech Publications Ltd, Stafa-Zurich, pp 1396–1401
Zhao X, Corrales M, Zhang C, Hu X, Ma Y, Tauscher B (2008a) Composition and thermal stability of anthocyanins from Chinese purple corn (Zea mays L.). J Agric Food Chem 56(22):10761–10766. https://doi.org/10.1021/jf8025056
Zhao X, Zhang C, Guigas C, Ma Y, Corrales M, Tauscher B, Hu X (2009a) Composition, antimicrobial activity, and antiproliferative capacity of anthocyanin extracts of purple corn (Zea mays L.) from China. Eur Food Res Technol 228(5):759–765
Zhu M, Shi ZS, Li FH (2014) Correlation between anthocyanins, total phenolics content and antioxidant activity of purple corn (Zea mays L.). In: Liu HW, Wang G, Zhang GW (eds) Material science, civil engineering and architecture science, mechanical engineering and manufacturing technology II, vol 651–653. Trans Tech Publications Ltd, Stafa-Zurich, pp 220–226
Acknowledgements
This work was supported by Shanxi Province 1331 engineering advantages of the characteristic subject chemistry construction project (2019-64), Xinzhou Normal University College Student Science and Technology Innovation Project (2021).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Hao, R., Zhang, H., Feng, Y. et al. The effect of different solvents and acidifying reagents on the anthocyanin profiles and antioxidant capacity of purple corn. Chem. Pap. 76, 4691–4704 (2022). https://doi.org/10.1007/s11696-022-02195-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-022-02195-z