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Article

Nutritional Value and Volatile Compounds of Black Cherry (Prunus serotina) Seeds

by
Leticia García-Aguilar
1,2,
Alejandra Rojas-Molina
2,*,
César Ibarra-Alvarado
2,
Juana I. Rojas-Molina
2,
Pedro A. Vázquez-Landaverde
3,
Francisco J. Luna-Vázquez
2 and
Miguel A. Zavala-Sánchez
4
1
Doctorado en Ciencias Biológicas y de la Salud, Universidad Autónoma Metropolitana, Unidad Xochimilco, Mexico, D.F. 04960, Mexico
2
Laboratorio de Investigación Química y Farmacológica de Productos Naturales, Facultad de Química, Universidad Autónoma de Querétaro, Querétaro, Qro. 76010, Mexico
3
Centro de Investigación en Ciencia Aplicada y Tecnología Avanzada del Instituto Politécnico Nacional, Unidad Querétaro. Cerro Blanco No. 141. Col. Colinas del Cimatario, Querétaro, Qro. 76090, Mexico
4
Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana, Unidad Xochimilco, México, D.F. A.P. 23-181, Mexico
*
Author to whom correspondence should be addressed.
Molecules 2015, 20(2), 3479-3495; https://doi.org/10.3390/molecules20023479
Submission received: 4 January 2015 / Revised: 10 February 2015 / Accepted: 11 February 2015 / Published: 17 February 2015
(This article belongs to the Collection Recent Advances in Flavors and Fragrances)
Versions Notes

Abstract

:
Prunus serotina (black cherry), commonly known in Mexico as capulín, is used in Mexican traditional medicine for the treatment of cardiovascular, respiratory, and gastrointestinal diseases. Particularly, P. serotina seeds, consumed in Mexico as snacks, are used for treating cough. In the present study, nutritional and volatile analyses of black cherry seeds were carried out to determine their nutraceutical potential. Proximate analysis indicated that P. serotina raw and toasted seeds contain mostly fat, followed by protein, fiber, carbohydrates, and ash. The potassium content in black cherry raw and toasted seeds is high, and their protein digestibility-corrected amino acid scores suggest that they might represent a complementary source of proteins. Solid phase microextraction and gas chromatography/flame ionization detection/mass spectrometry analysis allowed identification of 59 and 99 volatile compounds in the raw and toasted seeds, respectively. The major volatile compounds identified in raw and toasted seeds were 2,3-butanediol and benzaldehyde, which contribute to the flavor and odor of the toasted seeds. Moreover, it has been previously demonstrated that benzaldehyde possesses a significant vasodilator effect, therefore, the presence of this compound along with oleic, linoleic, and α-eleostearic fatty acids indicate that black cherry seeds consumption might have beneficial effects on the cardiovascular system.

1. Introduction

Prunus serotina Ehrh (American black cherry), commonly called “capulín” in Mexico, is a native North American tree that belongs to the family Rosaceae [1]. It grows wildly or under cultivated conditions in Mexican highlands and in some regions of Guatemala, Colombia, and Venezuela [2]. In recent times, it has spread widely in some European countries, like Belgium, the Netherlands, and Germany [3]. P. serotina is a very fast-growing tree which has an oval silhouette, its low branches normally droop and touch the ground, the leaves are dark green and shiny; the fruit is a little juice drupe about 1 cm long with a stone which contains a seed [4].
In Mexico, P. serotina has been used since colonial times for nourishment and medicinal purposes. The fruit is commonly consumed fresh, as jam, liquors or syrups, and the seeds are consumed roasted and salted as snacks [2]. In Mexican traditional medicine, teas and syrups prepared from the leaves and fruits are highly appreciated for treating hypertension, stomach upsets, mouth infections, diarrhea, malaria, bronchitis, and cough [5,6], and the seeds are used in decoction for the treatment of cough [5]. Black cherry bark has been used by the Iroquois, Ojibwa, Malecite, and Delaware indigenous people from the North American boreal forest regions of Canada for treating diabetes-related symptoms [7].
Recently, our research group carried out chemical and pharmacological studies of the leaves, fruits and seeds of P. serotine. A bio-directed phytochemical study of the methanolic extract of the leaves led to the isolation of hyperoside and ursolic acid as the main vasodilator compounds. It was also found that benzyl alcohol, benzaldehyde, cinnamyl alcohol, and cinnamaldehyde were the major constituents of the essential oil obtained from the leaves, these compounds promoted vascular smooth muscle relaxation [8]. Regarding P. serotina fruits, we found that they have a high content of phenolic compounds such as chlorogenic acid, gallic acid, caffeic acid, catechin, epicatechin, quercetin, and kaempferol glycosides, which are directly related to the high antioxidant capacity and significant vasodilatory effect of the aqueous extract of the fruits [9]. Additionally, physicochemical and chemical characterization of black cherry seed oil demonstrated that it is mainly composed of polyunsaturated fatty acids, including oleic, linoleic, and α-eleostearic acids [10]. These results support the potential therapeutic significance of P. serotina seed oil, since it has been extensively demonstrated that consumption of unsaturated fatty acids reduce plasma lipids and reduce atherogenesis by decreasing inflammation of macrophages and vascular endothelial cells [11,12]. Moreover, it has been reported that α-eleostearic acid is effective in suppressing growth in cancer cells, and it has been proposed as a chemotherapeutic agent against breast cancer [13].
Although black cherry seeds contain cyanogenic glycosides [14], there are no reports of human intoxication related to their intake, since they are consumed toasted, which indicates that the toasting process decreases the content of these compounds [15]. Heat treatment also provokes emission of volatile compounds contained in the seeds, which undoubtedly contribute to their pleasant and characteristic flavor. These volatile components might also possess pharmacological activity [16].
Currently, the nutritional value of black cherry seeds and their volatile components have not been investigated. Therefore, in the present study the proximate composition, vitamin and mineral content of these seeds were determined in order to assess their nutritional value. In addition, the volatile compounds present in the seeds were analyzed by gas chromatography coupled to mass spectrometry.

2. Results and Discussion

2.1. Proximate Composition

Proximate compositions of raw and toasted black cherry seeds, Prunus dulcis (almonds) and Arachis hypogaea (peanuts) are shown in Table 1. There were no significant differences between protein, ash, crude fiber or carbohydrate contents of the raw and roasted seeds, suggesting that the toasting process does not affect the proximate composition. The mean values of protein content were 37.95% ± 0.16% and 36.55% ± 0.22% for raw and toasted seeds, respectively. These values were significantly higher than those of almonds (19.91%), and peanuts (22.82%), whose protein content is consistent with earlier reports [17,18]. P. serotine seeds possess a protein content which is comparable to that of seeds of other Prunus species, including apricots (P. armeniaca L., 37.4%), sweet cherries (P. avium L. 31.7%), sour cherries (P. cerasus L., 31.7%), nectarines (P. persica ar. nectarina (Aiton) Maxim, 38.7%), peaches (P. persica (L.) Batsch var. persica, 33.4%), and plums (P. domestica L., 35.9%) [19].
Table
Table 1. Proximate composition of raw and toasted black cherry seeds, almond, and peanut.
Table 1. Proximate composition of raw and toasted black cherry seeds, almond, and peanut.
Component (% Dry Basis)Raw Black Cherry SeedsToasted Black Cherry SeedsAlmondsPeanuts
Moisture8.92 ± 0.42 a10.75 ± 0.35 a6.08 ± 0.4 b5.45 ± 0.38 c
Fat40.37 ± 0.73 a39.97 ± 0.20 a49.64 ± 0.42 b41.12 ± 1.51 a
Protein37.95 ± 0.16 a36.55 ± 0.22 a19.91 ± 0.01 b22.82 ± 0.01 c
Ash3.19 ± 0.18 a2.72 ± 0.21 a3.18 ± 0.21 a2.41 ± 0.19 a
Crude Fiber10.73 ± 1.49 a12.12 ± 4.06 a10.91 ± 1.45 a9.21 ± 1.59 a
Carbohydrates7.76 ± 2.24 a8.65 ± 4.28 a10.26 ± 1.98 b18.95 ± 2.68 c
Notes: Data are given as mean ± standard deviation (n = 3 independent experiments performed in different samples). a, b and c: Values in the same row followed by the same superscript letter are not significantly different (p > 0.05).
Lipid content of P. serotina raw (40.37% ± 0.73%) and toasted seeds (39.97% ± 0.20%) was not significantly different from that of peanuts (41.12% ± 1.51%). However, it was significantly lower than almonds lipid content (49.64% ± 0.42%). It is well known that seed oils are mainly composed by mono- and polyunsaturated fatty acids, thus oleic (61%) and linoleic (29%) acids are the main fatty acids contained in almond; oleic acid (81%) is abundant in peanut oil [20], whereas, black cherry seed oil is rich in oleic (35%), linoleic (27%) and α-eleostearic (27%) acids [10].
These findings indicate that P. serotina edible seeds are a good source of unsatured fatty acids with potential health benefits [21]. The mean values of ash and crude fiber of raw and toasted P. serotina seeds, almonds and peanuts did not differ significantly. The crude fiber content was similar to that of other seeds and nuts that represent a complementary source of fiber, like hazelnut (9%–13%) or pumpkin seeds (12.1%) [22,23]. Adequate intake fiber is related to the obesity prevention and better glycemic control in patients with type 2 diabetes mellitus [24,25].

2.2. Minerals

The mineral composition (Ca, Fe, Mg, P, K, Zn and Na) of raw and toasted black cherry seeds, almonds and peanuts are presented in Table 2. The Mg content of raw and toasted black cherry seeds was unaffected by heat processing, but the Ca, Fe, P, K, Zn, and Na content diminished after the toasting process. Usually, nuts and seeds are consumed toasted and salted, and toasting might have an important influence on their nutrimental quality. Chitra et al. [26] and Gamel et al. [27] have pointed out that Ca and Fe content significantly reduced after toasting or autoclaving seeds of soybean and pigeon peas.
Table
Table 2. Mineral composition of raw and toasted black cherry seeds, almond and peanut.
Table 2. Mineral composition of raw and toasted black cherry seeds, almond and peanut.
Mineral (Dry Basis) mg/100 gRaw Black Cherry SeedsToasted Black Cherry SeedsAlmondsPeanuts
Ca192.30 ± 0.58 a127.11 ± 17.51 b305.43 ± 1.88 c91.43 ± 0.05 d
Fe9.49 ± 0.3 a1.21 ± 0.003 b6.08 ± 0.01 c8.31 ± 0.02 d
Mg249.15 ± 0.34 a216.68 ± 18.75 a282.09 ± 0.32 b172.75 ± 0.77 c
P439.0 ± 0.16 a323.40 ± 0.14 b387.03 ± 0.7 c347.41 ± 0.07 d
K873.22 ± 12.64 a454.82 ± 0.41 b656.25 ± 23.80 c571.57 ± 10.03 d
Zn3.40 ± 0.10 a2.96 ± 0.24 b4.48 ± 0.17 c3.92 ± 0.10 d
Na82.98 ± 0.90 a23.59 ± 0.8 b76.57 ± 0.38 a62.99 ± 0.65 c
Notes: Data are given as mean ± standard deviation (n = 3 independent experiments performed in different samples). a, b, c and d: Values in the same row followed by the same superscript letter are not significantly different (p > 0.05).
Raw black cherry seeds possess a higher content of Ca, Fe, Mg, K and Na than that found in peanuts. On the other hand, Fe, K, and Na content is greater than that of almonds. Interestingly, the K content in black cherry seeds (873.22 ± 12.64 mg/100 g) is significantly higher than that of almonds and peanuts, suggesting that P. serotina seeds represent a good complementary source of this mineral.

2.3. Vitamins

Vitamin analysis showed that raw and toasted P. serotina seeds do not contain vitamins A and C. Vitamin E or α-tocopherol was detected at a concentration of 3.916 mg/100 g in raw seeds, while in toasted seed it was absent. This lost may be associated with vitamin degradation due to temperature exposure [27]. Our results are in agreement with previous studies carried out on other seeds and nuts, such as pumpkin seeds, walnuts and peanuts, which do not contain detectable values of vitamins A and C [28,29]. Vitamin E content of black cherry seeds is similar to that of pine nuts (4.1 mg/100 g) and peanuts (6.1 mg/100 g), however it is lower than that of almonds and hazelnuts (24.2 mg/ 100 g and 31.4 mg/ 100 g, respectively) [28].

2.4. Protein Nutritional Quality

Since black cherry seeds contain higher levels of protein (37.95% ± 0.16%) than other seeds, their protein nutritional quality was assessed. Amino acid composition data are presented in Table 3. It is important to mention that in this experiment tryptophan was not determined.
Table
Table 3. Protein amino acids composition of raw and toasted black cherry seeds.
Table 3. Protein amino acids composition of raw and toasted black cherry seeds.
Amino AcidRaw Seeds mg/g ProteinToasted Seeds mg/g Protein
Asp112.29116.97
Glu256.84273.73
Ser32.8442.11
His21.6021.29
Gly37.4338.82
Thr52.8559.16
Arg84.2487.42
Ala41.4744.06
Tyr48.7560.99
Met8.939.83
Val45.4845.62
Phe48.6452.00
Ile39.1740.33
Leu75.1082.11
Lys8.8511.17
Another protein quality measure is digestibility. Differences among the in vitro protein digestibility values of raw and toasted black cherry seeds were not significant (88.12% ± 0.72% and 89.40% ± 1.32%, respectively). These values were similar to that of almonds (90.15% ± 0.85%), however they were lower than those of peanuts (94.06% ± 0.78%) and casein (98.51% ± 0.82%), which was used as control. It has been reported that in vitro protein digestibility values greater than 80% are related to an efficient amino acid bioavailability [27]. Therefore, these results suggest that black cherry seed proteins are highly bioavailable.
Considering these findings, the protein digestibility-corrected amino acid score (PDCAAS) was determined. This method is accepted as the most recognized approach for assessing the protein quality of foods [30]. Every essential amino acid receives a score, but the final PDCAAS value corresponds to that of the limiting amino acid. The highest PDCAAS value for a given protein is 1.0, which indicates that a protein provides adequate amounts of all the essential amino acids [31]. Table 4 shows that lysine is the limiting amino acid in P. serotina seeds, therefore, PDCAAS values for raw and toasted black cherry seeds protein are 0.13 and 0.18, respectively. These values are lower than those reported for almonds (0.23) [17] and peanuts (0.69) [32]. These results suggest that black cherry seeds could be a complementary source of proteins.
Table
Table 4. Black cherry seeds amino acid score (AAS).
Table 4. Black cherry seeds amino acid score (AAS).
AAFAO Reference PatternAAS *AAS *
Raw SeedsToasted Seeds
His191.371.12
Thr341.551.74
Met250.360.39
Val351.301.33
Phe630.770.82
Ile281.401.44
Leu661.381.24
Lys **580.150.19
Notes: * Amino acid score (AAS) = AA content of test protein/reference AA pattern, where reference AA pattern is the amino acid requirement for a preschool child (2–5 years) [30]. ** Limiting amino acid.

2.5. Volatile Compounds

Volatile compounds of raw and toasted black cherry seeds were extracted by head space solid phase micro extraction and analyzed by gas chromatography-mass spectrometry, using DB-5 and Wax capillary columns in order to detect a wide range of polar and non-polar compounds. A total of 59 and 99 volatile compounds were identified in the raw and toasted P. serotina seeds, respectively (Table 5). The identified volatile compounds comprise aldehydes, alcohols, ketones, carboxylic acids, esters, hydrocarbons, and pyrazines.
The predominant aldehyde identified in raw and toasted seeds was benzaldehyde. This compound has a characteristic pleasant almond-taste and aroma [33] and has been identified in bitter and sweet almonds [34], hazelnuts [33], and seeds of other species of the genus Prunus [35,36]. Benzaldehyde is produced by enzymatic degradation of the cyanogenic glycosides amygdalin and prunasin [35,37,38]. Considering on one hand that benzaldehyde content in toasted seeds was higher than that in raw seeds, and on the other, that bitterness attributed to the presence of amygdalin [39,40] diminished in toasted seeds, it is very likely that the toasting process may induce benzaldehyde formation from cyanogenic glycosides. Benzaldehyde might also be generated from phenylalanine during heating processes [41,42] as was demonstrated by Alasalvar et al. [33] in hazelnuts, pumpkin seeds [43], and peanuts [44]. It is worth noting that we have previously identified benzaldehyde as one of the major components in black cherry leaves essential oil, we also proved that this compound induces a significant concentration-dependent vasodilator effect [8]. Therefore, the presence of this compound along with oleic, linoleic, and α-eleostearic fatty acids indicate that black cherry seeds consumption might have beneficial effects on the cardiovascular system.
Table
Table 5. Volatile compounds on raw and toasted black cherry seeds.
Table 5. Volatile compounds on raw and toasted black cherry seeds.
RI
Calculated a		RI
Literature b		CompoundRaw cToasted cID e
DB5WAXDB5WAX(ppm d)(ppm d)
Aldehydes
573805 801Propanal, 2-methyl- 0.604MS, RI
638 640 2-Butenal 0.180MS, RI
642908642 Butanal, 3-methyl- 1.095MS, RI
652910653 Butanal, 2-methyl- 1.419MS, RI
695965695970Pentanal 2.065MS, RI
740 740 2-Butenal, 2-methyl- 0.500MS, RI
1074 1078Hexanal 0.096MS, RI
83414408351443Furfural 2.609MS, RI
902 905 Heptanal 0.084MS, RI
908 909 Propanal, 3-(methylthio)- 0.041MS, RI
1199 11962-Hexenal, (E)- 0.014MS, RI
964 963 2-Furancarboxaldehyde, 5-methyl- 0.112MS, RI
96715089691508Benzaldehyde1.3717.597MS, RI
1053 1053 Benzeneacetaldehyde 0.411MS, RI
1106 1108 Nonanal0.0560.201MS, RI
1443 14553-Furaldehyde0.090 MS, RI
12211697122116972,4-Nonadienal, (E,E)- 0.091MS, RI
1279193012791933Benzeneacetaldehyde, alpha.-ethylidene- 0.045MS, RI
Ketones
707130370813012-Butanone, 3-hydroxy-0.3290.361MS, RI
986 986 3-Octanone0.055 MS, RI
1027 1043 1,2-Cyclopentanedione, 3-methyl- 0.221MS
1067195810671957Ethanone, 1-(1H-pyrrol-2-yl)- 0.233MS,RI
1071 1071.6 Acetophenone 0.051MS,RI
1114 1117 1,7-Octadien-3-one, 2-methyl-6-methylene-0.037 MS,RI
1448 Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S-trans)-0.037 MS
1486 1489Ethanone, 1-(2-furanyl)- 0.119MS, RI
1487 1-(3H-Imidazol-4-yl)-ethanone 0.226MS
1151 1151 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- 0.107MS, RI
1569 15732-Cyclopentene-1,4-dione 1.536MS, RI
1588 1587Ethanone, 1-(2-pyridinyl)- 0.526MS, RI
1814 1,2-Cyclopentanedione, 3-methyl- 0.134MS
2012 2(3H)-Furanone, dihydro-3-hydroxy-4,4-dimethyl- 0.101MS
Carboxylic acids
61314156101415Acetic acid2.1635.939MS, RI
1608 Benzoic acid, hydrazide0.040 MS
1616 Butanoic acid, 4-hydroxy-0.1840.656MS
1829 1827Hexanoic acid0.2820.089MS, RI
2028 2030Octanoic Acid0.1100.209MS, RI
Esters
719972720971Butanoic acid, methyl ester0.019 MS, RI
77410077761007Acetic acid, 2-methylpropyl ester0.1910.096MS, RI
82610768251075Pentanoic acid, methyl ester0.166 MS, RI
878111587711151-Butanol, 3-methyl-, acetate0.2820.404MS, RI
880 880 1-Butanol, 2-methyl-, acetate 0.260MS, RI
91216169121617Butyrolactone0.297 MS, RI
925 926 Hexanoic acid, methyl ester0.120 MS, RI
1320 1317Heptanoic acid, ethyl ester0.061 MS, RI
1045 Pantolactone 0.192MS
1099160711001605Benzoic acid, methyl ester0.162 MS,RI
1167 1165 Acetic acid, phenylmethyl ester 0.096MS,RI
Alcohols
615108561810861-Propanol, 2-methyl-0.3890.229MS, RI
918 920Isopropyl Alcohol0.080 MS, RI
734118973011901-Butanol, 3-methyl-0.173 MS, RI
7381189 1-Butanol, 2-methyl-, (+/−)-0.381 MS
767123176612321-Pentanol0.5950.536MS, RI
797158480015832,3-Butanediol [R-(R*,R*)]-17.03917.448MS, RI
1088 1,2-Cyclopentanediol, trans- 0.030MS
1136 11361-Butanol0.0500.062MS, RI
858163585816382-Furanmethanol 0.747MS, RI
9551700953 2-Furanmethanol, 5-methyl- 0.096MS, RI
1334 13351-Hexanol0.201 MS, RI
1039186610391866Benzyl alcohol0.3321.019MS, RI
1051 3-Octen-1-ol0.069 MS
1379 1379Ethanol, 2-butoxy-0.063 MS, RI
1580 Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1α, 2β, 5α)- 0.743MS
1885 3,6,9,12-Tetraoxatetradecan-1-ol0.008 MS
1903 1905Phenylethyl Alcohol0.0650.166MS, RI
1684 2,6-Bis(1,1-dimethylethyl)-4-(1-oxopropyl)phenol0.0100.014MS
Hydrocarbons
647923648924Benzene0.0430.086MS, RI
76510297651029Toluene0.0520.110MS, RI
1094 Undecane0.030 MS
1126 1123Benzene, 1,3-dimethyl-0.050 MS, RI
862 863 Ethylbenzene0.022 MS, RI
872 Cyclopropane, propyl- 0.324MS
1166 1164p-Xylene0.010 MS, RI
89312378941236Styrene0.1080.084MS, RI
899 Nonane0.0200.074MS
931 2,4-Octadiene 0.057MS
1238 12641,3,5,7-Cyclooctatetraene 0.300MS
996 996 Benzene, 1,3,5-trimethyl-0.040 MS, RI
999997 Decane0.0960.089MS
103310791030 D-Limonene0.0250.048MS, RI
1412 Benzene, 2-ethyl-1,4-dimethyl-0.011 MS
1413 Benzene, 1-ethyl-2,3-dimethyl-0.027 MS
1125 1120 Benzene, 1,2,3,4-tetramethyl-0.040 MS, RI
1303 1300 Tridecane0.0150.027MS, RI
1399 1400 Tetradecane0.0150.040MS, RI
2056 1,4,7,10,13,16-Hexaoxacyclooctadecane0.029 MS
Pyrazines
82612478271247Pyrazine, methyl- 3.745MS, RI
8961487 14912,3,5-Trimethyl-6-ethylpyrazine 0.221MS, RI
91513069151308Pyrazine, 2,5-dimethyl- 7.344MS, RI
1312 1314Pyrazine, 2,6-dimethyl- 1.297MS, RI
99813659981367Pyrazine, 2-ethyl-6-methyl- 0.701MS, RI
1002138410051381Pyrazine, trimethyl- 1.685MS, RI
1330 1326Pyrazine, 2,3-dimethyl- 0.287MS, RI
1371 1367Pyrazine, 2-ethyl-5-methyl- 1.494MS, RI
1078142510781430Pyrazine, 3-ethyl-2,5-dimethyl- 1.907MS, RI
1085 1085 Pyrazine, 2-ethyl-3,5-dimethyl- 0.143MS, RI
1086145810881457Pyrazine, tetramethyl-0.1060.597MS, RI
1411 1415Pyrazine, 2,6-diethyl- 0.066MS, RI
1094 1091 Pyrazine, 2,5-diethyl- 0.106MS, RI
1472 1485Pyrazine, 2-ethenyl-6-methyl- 0.105MS, RI
11471609 16055H-5-Methyl-6,7-dihydrocyclopentapyrazine 0.500MS, RI
1153147511561478Pyrazine, 2,3-diethyl-5-methyl- 0.130MS, RI
1157 1156 Pyrazine, 3,5-diethyl-2-methyl- 0.245MS, RI
1161 1357 2,5-Dimethyl-3-n-pentylpyrazine 0.021MS
1683 16791-(6-Methyl-2-pyrazinyl)-1-ethanone 0.146MS, RI
1318 1254 Pyrazine, 2-butyl-3,5-dimethyl- 0.019MS
1705 1740Pyrazinamide 0.208MS
Pyrroles and Furans
811116581111681H-Pyrrole, 1-ethyl- 0.144MS, RI
847 841 1H-Pyrrole, 3-methyl- 0.082MS, RI
948 1H-Pyrrole, 1-butyl- 0.021MS
8911122892.111232-n-Butylfuran 0.707MS, RI
99112119911213Furan, 2-pentyl-0.0770.236MS, RI
1037 2,3-Dihydrofuran 0.008MS
10162004101620061H-Pyrrole-2-carboxaldehyde 0.114MS, RI
10762020107620202-Pyrrolidinone 0.477MS, RI
1675 16782-Pyrrolidinone, 1-methyl- 0.057MS, RI
Miscellaneous
632 643Methanethiol 0.046MS
559701 Dimethyl sulfide0.0520.071MS
567 531 Methylene chloride0.8440.474MS
61210096151010Trichloromethane0.0590.028MS, RI
724 Propanamide, N,N-dimethyl-0.025 MS
850 850 Oxazole, trimethyl- 0.034MS, RI
1020 1020 Benzene, 1,4-dichloro-0.4500.253MS, RI
1419 Benzene, 1,2-dichloro- 0.450MS
1710 6-Aminoindoline 0.136MS
1923 1912Benzonitrile, 2-methyl- 0.060MS
1537 N-(2-Benzoyl-4-nitrophenyl)-4-tert-butylbenzamide 0.041MS
2051 Octaethylene glycol0.007 MS
Notes: a Calculated Kovats retention index on DB-5 or Wax column using a n-alkanes series; b Reported Kovats retention index on library NIST; c Average of 3 replicates. Coefficient of variation < 9.2%; d Semi-quantitative values. e MS = tentative identification by comparison to mass spectra in NIST library, RI = identification by comparison of calculated Kovats retention index to that reported in literature.
The most abundant alcohol identified in P. serotina seeds was 2,3-butanediol, which was also the major volatile compound in raw (17.03 ppm) and toasted seeds (17.44 ppm). This alcohol is the major volatile component of sweet kernels and has been associated to their characteristic taste [34]. 2,3-butanediol is also found in cheeses [45] and honey [46]. Recently, it has been reported that this metabolite is abundant in roasted Trichosanthes kirilowii seeds, however it was absent in the raw seeds, which suggests that 2,3-butanediol was generated during the toasting process [47]. In contrast, our results indicated that 2,3-butanediol levels in black cherry seeds were not significantly different before and after toasting. Benzyl alcohol, predominantly found in toasted seeds, imparts a sharp, burning taste and a faint aroma in toasted almonds [48]. This compound was previously detected as one of the major volatiles of black cherry leaves and also displays a vasodilator effect [8]. Regarding 1-pentanol, detected in both raw and toasted seeds, it has been proposed that it derives from the oxidation of linoleic acid, and its concentration increases with storage time in almonds [49].
Acetic acid was the main volatile carboxylic acid found in raw and toasted P serotina seeds. This carboxylic acid can be regarded as a result of long-chain fatty acids degradation and it is often related to a strong sour odor [50]. Esters were detected in lesser quantities, some of them, such as methyl esters of short chain fatty acids, were found in raw seeds, but not in toasted seeds. Hydrocarbons and ketones were minor compounds in both raw and toasted seeds.
Pyrazines and pyrroles were other major volatiles identified exclusively in toasted black cherry seeds. These compounds are produced during the toasting process from free amino acids and monosaccharides by the Maillard reaction through Strecker degradation [33], particularly, ethyl-methyl‑, ethyldimethyl-, and diethylmethylpyrazines, are formed in the reaction of glucose and fructose with alanine and glycine [51]. The most abundant pyrazine in black cherry toasted seeds was 2,5-dimethylpyrazine, followed by methylpyrazine, 3-ethyl-2,5-dimethylpyrazine and trimethylpyrazine. The first one has been previously reported as a major pyrazine in roasted hazelnuts [33] and toasted almonds [48]. Pyrazines contribute to the characteristic toasted aroma in chesnuts [52], and peanuts [53], almonds [54], and pyrroles significantly are responsible for the characteristic toasted aroma of different thermal treated foods [44].

3. Experimental Section

Reagents and standards were purchased from Sigma-Aldrich (St. Louis, MO, USA), unless otherwise noted. Solvents were purchased from Baker-Mallincrodt (JT Baker, Mallinckrodt Baker Inc., Phillipsburg, NJ, USA).

3.1. Samples

Ripe black cherry fruits were cultivated in Huejotzingo, Puebla (México) and harvested in May of 2011. Subsequently, the seeds were removed from the pulp with plastic knives, washed and allowed to dry at 25 °C during 48 h. Finally, the seeds were stored at −70 °C until analysis.
All the analyses were carried out on raw and toasted seeds. Toasting was performed in a comal (traditional Mexican iron griddle) during 20 min at 125 °C. Then, the seeds were rotated frequently to avoid overheating and to obtain homogenous toasting. Raw and toasted seeds were cracked and opened with pliers to get the kernel.
Taking into account that black cherry toasted seeds are consumed by Mexican people as snacks, almonds (Prunus dulcis) and peanuts (Arachis hypogaea) samples were analyzed for comparative purposes. Both seeds were purchased in a local market in the city of Queretaro, Queretaro (México).

3.2. Chemical Proximate Analysis

Chemical proximate analysis was carried out on raw and toasted black cherry seeds, almonds and peanuts by using AOAC methods (AOAC, 2000). Moisture, protein, fat, ash, crude fiber and carbohydrates contents were determined by methods 950.46, 928.08, 960.39, 920.153 and 985.29, respectively. Total carbohydrate content (on dry weight basis) was calculated by difference [100 − (protein + lipids + ash + crude fiber)].

3.3. Determination of Vitamins A, C, and E

Vitamins and carotenes were determined by using AOAC methods (2000) for vitamin A (960.46), vitamin C (967.22), and vitamin E (992.03).

3.4. Mineral Content

Sodium, potassium, calcium, magnesium and iron content of samples was determined by method 985.35 described in Association of Official Analytical Chemists (AOAC, 2000). Phosphorous was determined according to method 965.17 (AOAC, 2000).

3.5. In Vitro Protein Digestibility

The in vitro protein digestibility of dry samples was estimated by using the methodology of Hsu et al. [55] and applying the equation Y = 234.84 − 22.56X, where Y is the in vitro protein digestibility (%) and X is the pH of the protein sample suspension, after proteolysis with a multienzyme system consisting of porcine pancreatic trypsin type IX, bovine pancreatic chymotrypsin type II, and porcine intestinal peptidase grade III. The average value of three replicates is reported.

3.6. Amino Acid Analysis

Proteins were hydrolyzed in hydrochloric acid (JT Baker) and amino acids were analyzed using a HPLC autoanalyzer (Waters 2487, Millipore, MA, USA), according to Bidlingmeyer et al. [56].

3.7. Nutritional Quality of Proteins

For predicting dietary protein quality, the in vitro protein digestibility and amino acid composition were used to calculate PDCAAS (protein digestibility corrected amino acid score) according to the FAO/WHO [30] prescribed formula:
PDCAAS = Amino acid score (of the most limiting AA) × Digestibility

3.8. Volatile Compounds Analysis

Extraction conditions were based on previously published work of Krist et al. [52] and Agila et al. [54] with some modifications. Fresh seeds (15 g) were blended in an electric blender (model O-20, OsterizerTM, Boca Raton, FL, USA) for 15 s. The ground seeds (1 g) were transferred into a 20 mL vial, along with 7 µg of a menthol solution (0.01% w/w) as an internal standard and sealed with a Nickel-aluminum crimp cap provided with a needle-pierceable polytetrafluroethylene/silicone septum. Vials were pre-equilibrated for 60 min at 50 °C. Solid-phase microextraction (SPME) was performed with a 75 mm divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/PDMS) fiber (Supelco Co, Bellefonte, PA, USA). Extractions and injections were performed using a MPS2 autosampler (Gerstel, Linthicum-Baltimore City, MD, USA) fitted with a vial heater. The fiber was exposed for 10 min in the head space of the vial for analytes adsorption. Subsequently, the fiber was removed from the vial and placed into the chromatograph injection port for desorption.
Gas chromatography separation and quantification was carried out using an Agilent GC 7890A series intrumenbt (Agilent Technologies, Inc., Santa Clara, CA, USA) equipped with a flame ionization detector (GC-FID). Injection port and detector temperature was 230 °C. The injector was operated in the splitless mode. The capillary columns used were an HP-5 60 m × 0.32 mm i.d., 0.32 µm film thickness; Agilent Technologies, Inc.) and a DB-Wax (60 m × 0.32 mm i.d., 0.32 µm film thickness; Agilent Technologies, Inc.). Oven temperature was programmed at initial temperature of 40 °C for 5 min, then raised at 5 °C/min to 230 °C and hold for 15 min. Helium was used as the carrier gas at a constant flow rate of 1 mL/min. A semi-quantitative evaluation was achieved by comparing individual peak area from GC-FID response to that of the internal standard. Each tabulated value corresponds to the average of 3 extraction replicates.
Gas Chromatography Mass Spectrometry (GC/MS) analysis was carried out using an Agilent GC 7890A series equipped with an Agilent 5975C Mass Spectrometer in electron impact mode (EI) and a quadrupole analyzer. The temperatures of ion source and quadrupole were 230 and 250 °C respectively. Transfer line was set at 280 °C. Full scan mode was used in a range of 33–300 uma, at a scan rate of 5.2/s, with an ionization voltage of 70 eV. The same chromatographic conditions as for GC-FID were used. MSD ChemStation E.01.00.237 software (Agilent Technologies, Inc.) was employed for data analysis.
Identification of volatile compounds was performed by comparing their mass spectra with those in the NIST Mass Spectral Library (National Institute of Standards and Technology, Gaithersburg, MD, USA). Retention indices of all the volatile compounds were determined by the modified Kovats method reported by Van den Dool and Kratz [57]. MS identification was confirmed by comparing Kovats retention indices (RI) to RI reported in the literature [58].

3.9. Statistical Analysis

Results of the experiments are expressed as the mean ± standard deviation (SD) from n = 3 experiments. The data were analyzed by a one-way ANOVA and the Tukey test. Differences between the means were considered to be significant when p ˂ 0.05. Statistical treatment of data was performed with the program Prism 4.0 (GraphPad Software, San Diego, CA, USA).

4. Conclusions

This study demonstrates that black cherry seeds have a significant content of minerals, particularly potassium, lipids and proteins. Their PDCAAS values suggest that they might be considered as a complementary source of protein. Additionally, the gas chromatography/mass spectrometry analysis allowed identification of 59 and 99 volatile compounds in the raw and toasted seeds, respectively. The major volatile components identified in raw and toasted P. serotina seeds were 2,3-butanediol and benzaldehyde. The results derived from this study indicate that these seeds have nutraceutical properties attributed to their high protein and potassium content and the presence of bioactive compounds such as benzaldehyde.

Acknowledgments

Leticia García-Aguilar acknowledges Consejo Nacional de Ciencia y Tecnología (CONACYT) for her Ph. D. scholarship. This work was supported by grants (a) FOFI-UAQ-2012 (Project FCQ-2012-25) and (b) INFR-2014-01-226186 from CONACYT assigned to Alejandra Rojas Molina.

Author Contributions

Leticia García-Aguilar extracted and analyzed the volatile compounds and assessed nutritional protein quality as part of her doctoral degree thesis. Alejandra Rojas-Molina designed this project, coordinated all the activities, and supervised the chemical studies. César Ibarra-Alvarado helped in the design of experiments. Pedro A. Vázquez-Landaverde conducted the final identification of volatile compounds. Juana I. Rojas-Molina supervised the nutrimental analysis. Francisco J. Luna-Vázquez was in charge of the fruit collection and identification and revised the manuscript. Miguel A. Zavala-Sánchez contributed with the preparation of manuscript.

Conflicts of Interest

The authors declare no conflict of interest.

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MDPI and ACS Style

García-Aguilar, L.; Rojas-Molina, A.; Ibarra-Alvarado, C.; Rojas-Molina, J.I.; Vázquez-Landaverde, P.A.; Luna-Vázquez, F.J.; Zavala-Sánchez, M.A. Nutritional Value and Volatile Compounds of Black Cherry (Prunus serotina) Seeds. Molecules 2015, 20, 3479-3495. https://doi.org/10.3390/molecules20023479

AMA Style

García-Aguilar L, Rojas-Molina A, Ibarra-Alvarado C, Rojas-Molina JI, Vázquez-Landaverde PA, Luna-Vázquez FJ, Zavala-Sánchez MA. Nutritional Value and Volatile Compounds of Black Cherry (Prunus serotina) Seeds. Molecules. 2015; 20(2):3479-3495. https://doi.org/10.3390/molecules20023479

Chicago/Turabian Style

García-Aguilar, Leticia, Alejandra Rojas-Molina, César Ibarra-Alvarado, Juana I. Rojas-Molina, Pedro A. Vázquez-Landaverde, Francisco J. Luna-Vázquez, and Miguel A. Zavala-Sánchez. 2015. "Nutritional Value and Volatile Compounds of Black Cherry (Prunus serotina) Seeds" Molecules 20, no. 2: 3479-3495. https://doi.org/10.3390/molecules20023479

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