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Interciencia ISSN: 0378-1844 ISSN: 2244-7776 [email protected] Asociación Interciencia Venezuela

Barrientos Ramírez, Lucia; Ramírez Salcedo, Hilda E.; Fernández Aulis, María Fernanda; Ruíz López, Mario Alberto; Navarro Ocaña, Arturo; Vargas Radillo, J. Jesús ANTHOCYANINS FROM ROSE MAIZE (Zea mays L.) GRAINS Interciencia, vol. 43, no. 3, 2018, pp. 188-192 Asociación Interciencia Venezuela

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Lucía Barrientos Ramírez, Hilda E. Ramírez Salcedo, María Fernanda Fernández Aulis, Mario Alberto Ruíz López, Arturo Navarro Ocaña and J. Jesús Vargas Radillo

SUMMARY

Here we present the anthocyanin composition of grains of Peonidin, and Pelargonidin, while HPLC profile revealed rose corn (Zea mays L.). Extraction was performed using that the most abundant anthocyanin was Cyanidin-3-(6-mal- methanol:water:HCl in an ultrasound bath for 20min. Antho- onyl-glucoside), a malonic derivative of Cyanidin. The re- cyanins were isolated from maize using the combination of sults increase available data regarding the presence of these column chromatography and HPTLC plates, whereas HPLC- compounds in varieties of pigmented corn grains, and thus UV/Vis and HPLC-MS were used for analysis and identifi- help to promote the consumption of these varieties for their cation. Compounds found include the glycosides Cyanidin, beneficial health effects.

Introduction or more sugar molecules (gly- for cosmetic or pharmaceutical Traditionally, it is used to cosylated type), and may also applications (Ignat et al., make tortillas, pozole, gordi- The immediate predecessor contain acyl radicals in the 2011). They also have func- tas, and sweet atole (Ron of domesticated maize, the form of aliphatic organic acid tional properties, since they Parra et al., 2006). The pres- Teocintle, is considered native derivatives linked to sugar cause a slow digestion of ent study aims to assess the of Mesoamerica and, thus, (acylated type) which show starch that has been associat- types and characteristics of Mexico is considered to be the greater stability at different ed with beneficial health ef- anthocyanin metabolites in this origin of maize (Zea mays L., pH levels (Eng et al., 2017). fects like the control of hun- corn variety, which is abun- Poaceae family). Fifty nine of Moreover, they show substan- ger and an more evenly dant in many regions, with the 220-300 races of maize tial bioactivity, mainly as an- spaced food consumption large availability and interest- found in the American conti- tioxidants (Yang and Shai, (Bello-Pérez et al., 2016). ing biological properties due to nent grow in Mexico (Sánchez 2011). These metabolites ex- Bibliographic reports men- the presence of anthocyanin et al., 2000). In addition to hibit health benefits, promot- tion anthocyanin contents of and other polyphenols. white corn, there are over 45 ing reduction of inflammation 9-15.9mg·kg-1 dry matter (DM) races of pigmented maize (He and Giusti, 2010); with in white corn, 163.9mg·kg-1 Materials and Methods (Salinas-Moreno et al., 2005). properties such as prevention DM pink corn, 342.2 in Annual maize yield in 2014 of the chronic diseases diabe- blue corn, 1270 in red corn, Sample was ~23.27×106t of grain, pro- tes and obesity (Li et al., 1277 in purple corn, and duced on ~7.4×106ha, represent- 2015) and cancer (Chen et al., 5290mg·kg-1 DM in black corn Rose maize (Zea mays L.; ing an average yield of 3.14t·ha- 2015), among other. (Salinas-Moreno et al., 2013; National Registry Nº 05046) 1 (SIAP, 2014). The Mexican The Mexican races of maize Escalante-Aburto et al., 2016). was harvested in the summer state of Jalisco is the second present kernels with white, The rose western corn is a (rainy season) in the period of largest national producer of yellow, pink, red, blue, purple very productive variety, with June-August of 2015 in a corn, and harvested 3.47×106t/ and black coloration (Bello- cobs of 15 to 20cm in length, property located in the town year for a yield of 6.42ton·ha-1, Perez et al., 2016). The color cylindrical shape, and 12 to 14 of Nextipac, Zapopan, Jalisco, constituting 15% of national is related to the amounts and lines. The grain is jagged, Mexico (20º45’51”N; 103º31’ production (SIAP, 2014). types of anthocyanins. The pink or pink-red. This maize 44”W; 1634masl). Maize is Anthocyanins, a water-solu- pigmented maize varieties are is included in the variety of cultivated annually under the ble polyphenol, comprise one desirable as food, as well as cone shaped corn races. environmental conditions that

KEYWORDS / Anthocyanin / Antioxidant Bioactivity / HPTLC / Maize / Natural Pigments / Received: 06/06/2017. Modified: 02/14/2018. Accepted: 02/16/2018.

Lucia Barrientos Ramírez. Doc- María Fernanda Fernández Au- Arturo Navarro Ocaña. Doctor fessor, UdG, Mexico. Address: tor of Science in Biology, lis. Doctoral student in Chemis- in Biotechnology, CCH-UNAM, Departamento de Madera, Universidad de Guadalajara try, Universidad Nacional Autó- Mexico. Professor, UNAM, Celulosa y Papel (DMCyP), (UdeG), Mexico. Professor, noma de México (UNAM). e- Mexico e-mail: arturono@ UdeG. Zapopan, Jalisco, Mé- UdeG, Mexico. e-mail: lba- mail: [email protected] unam.mx xico, CP 45100, tel. (33)- [email protected] Mario Alberto Ruíz López. J. Jesús Vargas Radillo. Doctor 36820110. e-mail: jvargasr@ Hilda E. Ramírez Salcedo. Doc- Doctor of Science in Biolog), in Biosystemtics, Ecology and dmcyp.cucei.udg.mx. toral student, BEMARENA, UNAM, Mexico. Professor, Natural and Agricultueral UdeG, Mexico. e-mail: hildae- UdeG, Mexico. e-mail: mruiz Resources Management (BE- [email protected]. @cucba.udg.mx MARENA), UdeG, Mexico. Pro-

188 0378-1844/14/07/468-08 $ 3.00/0 MARCH 2018 • VOL. 43 Nº 3 ANTOCIANINAS DE GRANOS DE MAIZ (Zea mays L.) ROSA Lucía Barrientos Ramírez, Hilda E. Ramírez Salcedo, María Fernanda Fernández Aulis, Mario Alberto Ruíz López, Arturo Navarro Ocaña y J. Jesús Vargas Radillo RESUMEN Se presenta la composición de antocianinas en granos de ina-3-(6-malonilglucosido), un derivado malónico de la Cianidi- maíz Zea mays L., de la raza elotes occidentales tipo maíz rosa. na, el compuesto más abundante de acuerdo con su perfil cro- La extracción de estas fue con un sistema metanol:agua:HCl, us- matográfico. Estos resultados aumentan el acervo de datos so- ando un baño ultrasonido por 20min, para posteriormente ser bre estos compuestos presentes en las variedades de los granos analizado por HPLC-DAD y HPLC-MS. Se identificaron glucósi- pigmentados, y buscan fomentar el consumo de estas variedades dos de Cianidina, Pelargonidina y Peonidina, siendo la Cianid- por sus efectos benéficos en la salud.

ANTOCIANINAS DE GRÃOS DE MILHO (Zea mays L.) ROSA Lucía Barrientos Ramírez, Hilda E. Ramírez Salcedo, María Fernanda Fernández Aulis, Mario Alberto Ruíz López, Arturo Navarro Ocaña e J. Jesús Vargas Radillo RESUMO Apresenta-se a composição de antocianinas em grãos de mi- na-3-(6-malonilglucosídeo), um derivado malônico da Cianidina, lho Zea mays L., da raça elote ocidental, tipo milho rosa. A ex- o composto mais abundante de acordo com seu perfil cromato- tração destas foi realizada com um sistema metanol:água:HCl, gráfico. Estes resultados aumentam o acervo de dados sobre es- usando um banho ultrassom por 20min, para posteriormente ser tes compostos presentes nas variedades dos grãos pigmentados, analisado por HPLC-DAD e HPLC-MS. Identificaram-se glicosí- e buscam fomentar o consumo destas variedades por seus efei- deos de Cianidina, Pelargonidina e Peonidina, sendo a Cianidi- tos benéficos na saúde.

prevail in the area: average thanol acidified with 0.1% HCl, tially until there was no more UV/Vis detector (520nm) and temperature 20-22ºC; average in an ultrasonic bath (Branson separation of spots on the plate. a Hypersil Gold ODS column rainfall 980mm (Climate-data, model 8892; 42kHz), for (250×4.4mm, 5µm). We used a 2018; Sagarpa, 2015), applying 20min. The extract was filtered HPLC analysis gradient of solvent A (H2O: traditional fertilization consist- and concentrated by rotoevapo- ACN: HCOOH, 87:3:10) and ing of the incorporation of ni- ration at <40ºC and purified Crude extract was filtered solvent B (ACN), with the trogen and phosphorus, on a making use of a column through a 0.45µm membrane following elution program: Regosol type soil (sandy-loam (2.0×60cm) of amberlite (XAD- and analyzed using a Waters 97% A and 3% B from texture). About 30 pieces were 7HP, 20-60 mesh; Sigma- liquid chromatograph equipped 0-45min; 75% A and 25% B sampled, obtaining the grains Aldrich). Amberlite is an acryl- with a 2707 autosampler, a from 45-46min; 70% A and manually. A representative ic resin, nonionic, moderately 1525 binary pump, a 2478 30% B from 46-47min; and sample was evaluated for an- polar material that partially thocyanin content as follows: purified the anthocyanins the corn kernels were manually based on polar/non-polar inter- reeled off and washed, they actions (Wang et al., 2014). were then pulverized in a ham- The column was activated with mer mill (Retsch GmbH) using 250ml of methanol at a flow a screen with 0.5mm perfora- rate of 1ml·min-1 and so tions, and the obtained flour washed with 500ml of distilled was dehydrated to constant water in order to achieve a weight in an oven at 40ºC. greater adsorption of the organic compounds and, then the Extraction and purification by extracts were loaded onto a combined column column and washed with abun- chromatography dant distilled water to remove most of sugars, organic acids, A schematic of the proposed proteins and ions (Wang et al., method is illustrated in Figu- 2014). The anthocyanin pig- re 1. Anthocyanins were ob- ment fraction was recovered tained with the ultrasound as- from amberlite with 300ml of sisted extraction (UAE) proce- methanol:acetic acid (19:1 v/v), dure (Vinatoru, 2001). The concentrated by rotary evapo- flour ground from whole corn rator at <40ºC, dryed (Labkept (10g) was extracted with 100ml in amber flasks at 4ºC. This Figure 1. Isolation and fragmentation scheme of anthocyanins of corn (10:1 w/v) of 80% (v/v) me- procedure was repeated sequen- grains.

MARCH 2018 • VOL. 43 Nº 3 189 97% A and 3% B from 47- the crude extract of pink corn TABLE I Peonidin (m/z 301). On the 56min. The flow rate was was processed by HPLC. Rf VALUES OF SPOTS other hand, glycosides (antho- 1.0ml·min-1, and the injection Figure 3 shows the HPLC OBSERVED IN THE THIN- cyanins) contain mainly glu- volume was 20µl. profile of the corn anthocya- LAYER CHROMATOGRAM cose, or are further acylated nins, which exhibit several sig- Fraction Rf value with malonic acid. MS conditions nals. The eight anthocyanins The identification results are 5 0.878 that were identified in this 6 0.683, 0.816, 0.025, 0.683 presented in Table II. Peak 4 is Mass spectrometry was per- study are numbered, with 7 0.480, 0.496, 0.880 the most abundant, and shows formed using an Agilent peaks 4, 2, 8, 1 predominating 8 0.513, 0.843, 0.565, 0.886 a tR of 18.3min, a molecular Technologies model 6430, se- by their height and area, due 9 0.448, 0.480, 0.520, 0.600 ion [M]+ of 535, and fragments ries 1200, mass spectrometer their greater relative abun- 10-13 0.458 of m/z 449 and 287, corre- equipped with a quadrupole dance. Similar amount of sig- 14-15 0.450 sponding to Cyanidin-3-(6- 16-17 0.420 mass filter and electrospray nals (21 spots or fractions) 20-24 0.432 malonyl-glucoside). Similarly, system ionization (ESI). were obtained by column-TLC, studies of purple corn kernels Sample injection volume was as shown in Figure 4 and Rf: retention/retardation factor have reported that this antho- 10µl; detection 520nm; dry gas Table I, some of them by the cyanin is the most abundant -1 (N2), 12l·min , dry temperature combination of spots with sim- (Salinas-Moreno et al., 2012). 400ºC; capillary voltage 4.5kV. ilar Rf. TLC is an analytical column-TLC were analyzed by Peak 1 (tR 12.6min, m/z Analysis was performed in ion tool, simple, fast, cheap and LC-MS obtaining their frag- 449→287) correspond to positive mode and scanning frequently used as a technique mentation pattern. To identify Cyanidin-3-glucoside, which from 200 m/z to 1000 m/z. for separation in natural prod- the anthocyanins, we compared has been previously reported to ucts and organic chemistry, the peak information to previ- be the most common anthocy- Results and Discussion with low consumption of sol- ously reported data (Montilla anin in maize (Escalante- vents. It allows the simultane- et al., 2011; Salinas-Moreno Aburto et al., 2016). Peak 2 The extracts were evaluated ous analysis of several sam- et al., 2012: Zilic et al., 2012), (tR 14.4min, m/z 433→271) by chromatography. Prelimina- ples, it does not require special including the retention times agrees with Pelargonidin-3- rily by TLC using typical stan- instrumentation, and combined (tR) in HPLC, mass/charge glucoside, peak 3 (tR 16.0min, dards for corn anthocyanin. with mass spectrometry is con- (m/z), and characteristic frag- m/z 463→301) corresponds to Although there was no separa- sidered as useful tool in rou- mentation patterns for each Peonidin-3-glucoside and peak tion of compounds for the pink tine analytical methods (Ignat molecule obtained by LC-ESI- 5 (tR 20.3min, m/z 549→463, corn extract in the thin-film et al., 2011). MS. Known maize aglycones 301) matches Peonidin-3-(6- plate (line 1 in Figure 2), the The purified and recovered include Cyanidin (m/z 287), malonyl-glucoside). Based on spot agrees with the standards anthocyanins obtained from Pelargonidin (m/z 287) and previous reports (Cuevas et al., of Pelargonidin-3-glucoside and 2011) and fragmentation pat- Cyanidin-3- (6-malonyl) gluco- terns, peaks 6, 7 and 8 would side. To achieve a greater elu- correspond, respectively, to cidation of the anthocyanins, doubly acylated Cyanidin, Pelargonidin and Peonidin with malonic acid moiety. The- se anthocyanidin (Cyanidin, Pelargonidin and Peonidin) are characteristic in magenta maize, which is the most stud- ied group of grains, and in- cludes maize with grain colors Figure 3. HPLC chromatogram (UV-detector at 520nm) of crude corn from pink to purple, inclu- anthocyanin extracts obtained with MeOH:H2O:HCl system solvent and ding red corn (Salinas-More- cleaning through amberlite column. AU: absorbance units. no et al., 2012). Hence, the anthocyanins from western race corn variety rose (Table II) are coincident with those found in most of the purple-red maize: Cyanidin-3- glucoside, Pelargonidin-3- glucoside, Peonidin- 3-glucoside, Cyanidin3-(6-malonyl- Figure 2. Crude extract Silica-TLC glucoside), and Cyanidin-3- of pink corn compared with an- (3-6-dimalonyl-glucoside), with thocyanin standards. 1: Rose corn Cyanidin as the main aglycon kernel, 2: purple corn kernel, 3: (Salinas-Moreno 2005; Esca- Cyanidin-3-glucoside standard from lante-Aburto et al., 2016). jaboticaba, 4: Pelargonidin-3-glu- However, in maize with grains coside standard from strawberry, 5: Cyanidin-3-(6 malonyl) glucoside Figure 4. Silica TLC development of extracts from rose corn kernels of rose hue Peonidin is the standard from purple lettuce. visualized with UV light at 325nm. Each spot with different Rf is con- relatively more abundant agly- Elution system: etil acetate: water: sidered as a monomeric anthocyanin. Spots with similar Rf were con, according to the intensity formic acid (75:20:10). combined. of the peaks in Figure 3.

190 MARCH 2018 • VOL. 43 Nº 3 TABLE II Chávez PI, Figueroa-Cárdenas MS AND CHROMATOGRAPHIC CHARACTERISTICS RELATIVE TO RETENTION TIME JdeD, Gutiérrez-Dorado R AND FRAGMENTATION PATTERNS OF ANTHOCYANINS FOUND IN ROSE CORN (2016) Specific anthocyanin contents of whole blue maize KERNELS second-generation snacks: An Peak tR (min) Fragments [M-x]+(m/z) Aglicon [A]+ Compound Molecular formula evaluation using response surfa- 1 12.6 287 287 [Cy]+ Cy-3-Glc C H O ce methodology and lime coo- 21 21 11 king extrusion. J. Chem. 2016: 2 14.4 271 271 [Pg]+ Pg-3-Glc C21H21O10 3 16.0 301 301 [Pn]+ Pn-3-Glc C H O 1-8s. http://dx.doi.org/10.1155/ 22 23 11 2016/5491693 4 18.3 449, 287 287 [Cy]+ Cy-3-(6-Mal-Glc) C24H23O14 5 20.3 463, 301 301 [Pn]+ Pn-3-(6-Mal-Glc) C25H25O14 He J, Giusti MM (2010) Anthoc- yanins: Natural colorants with Cy: Cyanidin, Pg: Pelargonidin, Pn: Peonidin, Glc: glucoside, Mal: malonic acid, tR: rentention time, m/z: health promoting properties. mass-to-charge ratio. Annu. Rev. 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