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. 2022 May 11;7(20):17339–17357. doi: 10.1021/acsomega.2c01342

Table 3. Chemical Profiling of Maca Methanolic Extract Using LC-HR-ESI-MS/MS in Positive and Negative Ionization Modes.

    indicated molecular ion (m/z)
        
peak no. RT (min) (M – H)− (M + H)+ error (ppm) elemental composition identification MS/MS (m/z)
Identified Imidazole Alkaloids
40 7.51   227.1541 –0.9 C15H18N2 lepidiline Ea 174.9840, 135.0920, 113.9641
41 7.57   225.1382 –0.2 C15H16N2 1-dibenzyl-2-propyne-4,5-dimethylimidaziliuma 208.1135, 189.0699, 181.1024, 130.0651, 113.9644, 105.0341
44 8.41   239.1543 0 C16H18N2 1-dibenzyl-2-(1,3-butadiene)-4,5-dimethylimidaziliuma 199.9881, 182.9850, 154.9903, 121.0644
46 9.3   263.1542 –0.4 C18H18N2 1-dibenzyl-2-phenyl-4,5-dimethylimidaziliuma 231.0294, 121.0644
49 10.12   277.1700 [M – Cl]+ 1.8 C19H21N2 lepidiline Aa 185.1062
50 10.51   307.1805 [M – Cl]+ 1.5 C20H23N2O lepidiline Ca 215.1188, 200.1296, 185.1083, 116.0713
51 10.52   291.1855 [M – Cl]+ –0.3 C20H22N2 lepidiline Ba 200.1297, 199.1235
54 10.86   321.1932 [M – Cl]+ 1.8 C21H25N2O lepidiline Da 246.2423, 199.1232, 161.0654
60 12.08   339.1857 0.3 C24H22N2 1,3-dibenzyl-2(1,3-glutaric alkynyl)-4,5-dimethylimidaziliuma 319.2153, 248.1299, 231.0299, 199.1236, 184.0735, 171.0910, 136.0621, 121.0656, 113.9641
62 12.35   353.2012 –0.1 C25H24N2 1,3-dibenzyl-2-phenyl-4,5-dimethylimidaziliuma 262.1461, 226.2162, 184.0734, 171.0910, 136.0620, 121.0643
63 12.43   333.2321 –0.4 C23H28N2 1,3-dibenzyl-2-butyl-4,5-dimethylimidaziliuma 241.1693, 199.1232, 121.0654
67 12.86   347.2482 0 C24H30N2 1,3-dibenzyl-2-pentyl-4,5-dimethylimidaziliuma 294.2201, 255.1865, 199.1233, 136.0620
69 13.00   316.2846 –8.5 C21H35N2 1-dibenzyl-3-cyclohexyl-2-propenyl-4,5-dimethylimidaziliuma 298.243, 280.2643, 262.2515, 245.2466, 184.0738, 109.1016
Identified β-Carboline Alkaloids
27 4.28   233.1284 –0.3 C13H16N2O2 1-methyl tetrahydro-5,6-hydride carboline-3-carboxylic acid isomer Ia 116.0711
29 4.90   217.0972 0.1 C12H12N2O2 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acida 144.0800, 113.9641
30 5.24   233.1288 1.4 C13H16N2O2 1-methyltetrahydro-5,6-hydride carboline-3-carboxylic acid isomer IIa 116.0711
31 5.34   231.1127 –0.6 C13H14N2O2 1-methyltetrahydro-β-carboline-3-carboxylic acida 214.087, 168.0814, 158.0958, 143.0731, 130.0647, 113.9639
34 6.27   273.1596 –0.7 C16H20N2O2 1-butyltetrahydro-β-5,6-hydridecarboline-3-carboxylic acida 251.1186, 231.0293, 187.1239, 121.0644, 113.9641
43 8.02   285.1596 –0.6 C17H20N2O2 1-pentyltetrahydro-β-5,6-carboline-3-carboxylic acida 239.1545, 185.1061, 121.0645
58 11.5   271.1440 –0.5 C16H18N2O2 1-butyltetrahydro-β-5,6-carboline-3-carboxylic acida 121.0656
59 12.03   211.0865 –0.5 C13H10N2O 1-methyl-β-carboline-3-carbaldehydea 193.0765, 184.0733, 169.0757, 121.0655
Identified Macaridines and Common Amide Alkaloids
45 8.44   218.1176 0.1 C13H15NO2 3-benzyl-1,2-dihydro-4-methoxy-N-hydroxypyridinea 200.0005, 187.1241, 174.9839, 162.0914, 140.0699, 121.0644, 146.9619, 113.9641
48 9.71   216.1019 –0.1 C13H13NO2 3-benzyl-1,2-dihydro-4-carbaldehyde-N-hydroxypyridine (macaridine)a 198.0910, 170.0950, 141.0705, 128.0625, 121.0645, 113.9642
21 1.08   136.0755 –0.1 C8H9NO 2-phenylacetamidea 119.0359, 112.0511
25 3.19   166.0861 0.1 C9H11NO2 N-methyl-3-hydroxy-benzeneacetamidea 121.0644
32 5.43   136.0757 –0.1 C8H9NO N-benzylformamidea 113.9643
35 6.45   150.0915 –0.4 C9H11NO N-acetylbenzylaminea 134.0603, 113.9642, 106.0656
55 11.37   241.1334 –0.7 C15H16N2O 1,3-dibenzylureaa 227.1160, 205.1328, 121.0645, 113.9642
57 11.46   212.1068 –0.1 C14H13NO N-benzylbenzamidea 136.0623
89 15.2   280.2634 –0.4 C18H33NO linoleamideb 184.0728
90 15.24   306.2789 –0.9 C20H35NO N-ethyl-12-(2′-4′-)-cyclohexadiene-dodeceneamidea 184.0732
91 15.24   342.3002 –0.3 C20H39NO3 N-cyclohexane-(3′-hydroxyl)-tridecane amidea 184.0732, 109.1013, 104.0706
92 15.25   300.2896 –0.4 C18H37NO2 16-hydroxyl-octadecanamidea 282.1337, 121.0656
96 15.52   256.2633 –0.8 C16H33NO hexadecanamideb 184.0732, 133.0861
101 15.63 360.2912 362.3050 1.2 C23H39NO2 methanandamidea 295.2281, 248.9612, 183.0110, 115.9951
Identified Macamides
61 12.29   382.274 –0.5 C25H35NO2 N-(3-hydroxy-benzyl)-11Z,13Z,15Z,17Z-octadecatetrienamidea 290.2130, 226.2166, 184.0736, 136.0622
80 14.38   366.2791 –0.2 C25H35NO N-benzyl-(9Z,12Z,15Z)-octadecatetraenamidea 307.2653, 184.0730
86 14.97   384.2895 –0.6 C25H37NO2 N-benzyl-5-oxo-6E,8E-octadecadienamidea 144.9823
88 15.14   386.3055 –0.5 C25H39NO2 N-benzyl-9-oxo-12E-octadecenamidea 340.2638, 305.2472, 144.9818, 110.0203
98 15.55   398.3053 –0.2 C26H39NO2 N-(3-methoxybenzyl)-(9Z,12Z,15Z)-octadecatrienamidea 121.0653
99 15.61   368.294 0 C25H37NO N-benzyl-(9Z,12Z,15Z)-octadecatrienamidea 345.2422, 108.0808
100 15.62   308.2945 –1 C20H37NO N-ethyl-(9E,11E)-octadecadienamidea 290.2126, 1791300, 136.0756, 121.0643
104 15.67   318.2791 –0.2 C21H35NO N-benzyl-tetradeceneamidea 184.0733, 115.0752
107 15.81   344.2946 –0.6 C23H37NO N-benzyl-4E-hexadecenamidea 144.9822
108 15.86   400.3210 –0.1 C26H41NO2 N-(3-methoxybenzyl)-(9Z,12Z)-octadecadienamidea 121.0651
110 15.92   370.3104 –0.2 C25H39NO N-benzyl-(9Z,12Z)-octadecadienamidea 108.0808
111 15.96   332.2947 –0.3 C22H37NO N-benzyl pentadecanamidea 317.2027, 284.2940, 184.0733, 108.0807
114 16.14   406.331 –1.5 C25H43NO3 N-(3,4-dimethoxybenzyl) hexadecanamidea 286.2165, 184.0729
115 16.16   376.3206 –0.6 C24H41NO2 N-(3-methoxybenzyl) hexadecanamidea 346.3087, 121.0653
116 16.22   346.3102 –0.8 C23H39NO N-benzyl hexadecanamide (macamide B)a 121.0643
117 16.31   372.326 –0.3 C25H41NO N-benzyl-9Z-octadecenamidea 190.1210, 121.9663, 108.0808
118 16.41   360.326 –0.3 C24H41NO N-benzyl heptadecanamidea 121.9663
119 16.43   404.3157 –0.6 C25H41NO3 N-(3,4-dihydroxybenzyl)-oleamidea 184.0735, 133.0863, 121.9664
120 16.86   374.3417 –0.2 C25H43NO N-benzyl octadecanamidea 144.9821, 121.9664
Identified Macaenes and Fatty Acids
52 10.58 215.1283   –2.6 C11H20O4 undecanedioic acidb 132.8669, 112.9846
56 11.42 329.2332   –0.4 C18H34O5 trihydroxy octadecenoic acidb 293.2127, 248.9610, 29.1443, 211.1336, 171.1024, 139.1126, 112.9846
64 12.5   274.2737 –1.4 C16H35NO2 N-ethyl-tetradecene estera 240.2310, 201.1021, 121.0655
65 12.51 307.1922     C18H28O4 7,12-dioxo-8,10-octadecadienoic acidb 235.1351, 185.1186, 112.9847
66 12.79 331.2494   1.3 C18H36O5 9,10,13-trihydroxy-octadecanoic acidb 253.2176, 223.2058, 152.9950, 112.9846
68 12.95 309.2077   1.9 C18H30O4 7S,8S-dihydroxy-9Z,12Z,15Z-octadecatrienoic acidb 209.1172, 152.9949, 112.9847
70 13.08 311.2229 313.2388 0.4 C18H32O4 9Z-octadecenedioic acidb 223.1709, 152.9950, 112.9847
72 13.76 285.2073   0.7 C16H30O4 hexadecanedioic acidb 265.1495, 223.2056, 152.9945, 112.9845
73 13.86 315.2542   0.4 C18H36O4 9,12-dihydroxy-octadecanoic acid 293.2124, 116.9281
74 13.91 293.2125   1 C18H30O3 5-oxo-6E,8E-octadecadienoic acida 279.2329, 185.1185, 152.9949, 116.928
75 13.98 291.1968   0.9 C18H28O3 5-oxo-6E,8E,10E-Octadecatrienoic acida 277.2170, 152.9949, 112.9846
76 14.13   284.3292 2.5 C18H34O2 (E)-octadec-9-enoic acid (elaidic acid)a 184.0729
77 14.22 295.228   0.5 C18H32O3 hydroxy-linoleic acidb 281.2486, 255.2320, 183.1375, 152.9949, 116.9281
78 14.22   283.2639 2.5 C18H34O2 oleic acida 184.0732
79 14.32 243.1965   –0.2 C14H28O3 hydroxy myristic acidb 183.9133, 130.0507, 110.0234
81 14.50   363.2504 –7.2 C22H34O4 dihydroxy-docosapentaenoic acidb 184.0731, 119.0850
82 14.53   277.2161 –0.5 C18H28O2 stearidonic acidb 184.0736, 107.0860
83 14.53 293.2126 295.2266 1.4 C18H30O3 9-oxo-10E,12E-octadecadienoic acida 279.2331, 235.1693, 183.0106, 152.9949, 116.9281
84 14.53 317.2089   –10.4 C20H30O3 5-oxo-6E,8E,10E,12E-eicosatetraenoic acida 277.2139, 184.0736, 107.0860
85 14.72   297.2423 –0.5 C18H32O3 hydroxy octadecadienoic acidb 184.0732
87 14.98 269.2124   0.8 C16H30O3 hydroxy hexadecenoic acidb 152.9948, 116.9280
93 15.3 271.2267   0.9 C16H32O3 hydroxy hexadecanoic acidb 225.2212, 183.0106, 152.9948, 116.9280
94 15.3 277.2174   0.4 C18H30O2 linolenic acidb 225.2212, 116.9280
95 15.45 349.2387   0.8 C21H34O4 dihydroxy eicosatetraenoic acid methyl esterb 116.928
97 15.55 397.3325   0.5 C24H46O4 tetracosanedioic acidb 281.2484, 116.9280
102 15.64 279.2331   0.6 C18H32O2 octadecadienoic acida 183.0106, 152.9949, 116.9281
103 15.64 369.3013   0.8 C22H42O4 docosanedioic acidb 339.2009, 279.2332, 172.9534, 116.9281
105 15.78   325.2734 –1.1 C20H36O3 5-oxo-6E- eicosanoic acida 307.2625, 279.2319, 144.9822, 110.0202
106 15.79   457.3512 –2.6 C26H48O6 byrsonic acidb 426.2997, 413.3223, 378.2995, 344.2948, 327.1997, 283.1740, 239.1468, 177.1123, 133.0862
109 15.91 299.2594   0.8 C18H36O3 hydroxy-octadecanoic acidb 355.1583, 255.2320, 183.0106, 116.9280
112 16.03 255.233   0.3 C16H32O2 palmitic acida 183.0106, 134.8941, 116.9280, 100.9250
113 16.06 327.2543   0.7 C19H36O4 nonadecandioic acidb 229.1443, 211.1336, 171.1024, 112.9847
Identified Glucosinolates
26 3.92 408.0435   1.7 C14H19O9NS2 benzyl glucosinolate (glucotropaeolin)a 341.1110, 267.9721, 183.9132, 146.9383, 112.9846
Identified Hydantoins and Thiohydantoins
47 9.57 307.0724 309.0869 –0.3 C14H16N2O2S2 (+)-meyeniin Ca 263.0815, 248.9609, 233.0729, 205.0779, 191.0604, 183.9132, 174.9554, 146.9383, 134.8644
53 10.77   261.1234 0 C14H16N2O3 meyeniihydantoin Aa 231.0294, 184.0737, 121.0644
Organic Acids and Miscellaneous Compounds
1 0.57 131.0817   –6.6 C5H12N2O2 ornithineb 112.9846
2 0.57 173.1038 175.1198 –3.9 C6H14N4O2 argeninea 131.082
3 0.57   162.0761 0 C6H11NO4 N-methyl-l-glutamic acidb 116.0712
4 0.58 131.0453   –6.8 C4H8N2O3 asparagineb 101.0232
5 0.59 335.1577   1.5 C12H24N4O7 hexosyl argeninea 115.9201
6 0.6 132.0293   –6.8 C4H7NO4 aspartic acidb 112.0394, 104.0337
7 0.64 195.0505   –2.6 C6H12O7 gluconic acida 152.9950, 129.0188, 118.0503, 101.0233
8 0.64 179.0554   –3.8 C6H12O6 hexosea 129.0188, 118.0503, 101.0233
9 0.64   104.071 3.6 C4H9NO2 4-amino-butanoic acidb 102.0553
10 0.65 113.0233   –9.6 C5H6O3 3-oxo-4-pentenoic acidb 112.9846, 100.9250
11 0.65 193.0349   –2.3 C6H10O7 glucuronic acidb 144.0653, 118.0502
12 0.65   118.0865 1.9 C5H11NO2 l-valineb 104.1068
13 0.69 114.055 116.0713 2.4 C5H9NO2 prolinea 104.0709
14 0.7 172.0607   –4.7 C7H11NO4 carboxy methyl prolineb 121.0287, 112.9847
15 0.7 341.1084   1.1 C12H22O11 dihexosidea 276.1084, 179.0558, 114.0549, 101.0232
16 0.71 133.0135   –3.9 C4H6O5 2-hydroxy succinic acida 128.0347, 116.0706, 103.9192
17 0.71 467.1174   –4.4 C21H24O12 catechin-4-ol 3-O-hexosideb 387.1141, 341.1110, 276.1084, 179.0558, 133.0134, 101.10232
18 0.71 618.2258   1.2 C23H41NO18 proline trihexosidea 341.1108, 276.1083, 179.0557
19 0.73   130.0863 0.9 C6H11NO2 N-methyl prolinea 112.0511
20 1.07 549.1679   1.2 C19H34O18 trihexosidea 341.1109, 179.0558, 114.0549, 101.0232
22 1.4 128.0347 130.0495 –4.6 C5H7NO3 5-oxo-prolinea 116.0707, 103.9193
23 1.67 117.0183   –8.5 C4H6O4 succinic acida 103.9193
24 1.85   132.1021 1.3 C6H13NO2 leucinea 113.9642
28 4.49 143.0342   –5.3 C6H8O4 2,4-dihydroxy-3,5-cyclopentyl dienoic acida 112.9846, 103.9192
33 5.53 210.0767   –1.7 C10H13NO4 3-hydroxy-5-methyl-l-tyrosineb 183.9132, 124.0401
35 6.7 132.0446   –6.5 C8H7NO benzyl isocyanatea 112.9846
36 6.46 150.0552   –5.5 C8H9NO2 phenyl glycineb 112.9846, 109.0157
38 6.78 206.0821   –0.7 C11H13NO3 N-acetyl-l-phenylalanineb 183.9132, 164.0711, 112.9846
39 7.29 237.0408   1.5 C11H10O6 malic acid benzoatea 183.9133, 121.087
42 7.98 187.0972   –1.9 C9H16O4 azelaic acidb 141.0914, 125.0965, 112.9846
71 13.37 194.0817   –2.8 C10H13NO3 l-homotyrosineb 152.9949, 112.9846
a

Compounds were identified by comparison with the literature.2,6,26,35,36,42,44,51,54−58

b

Compounds were identified by comparison with an online database: KEGG, lipid maps, and DNP (2015).