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. 2022 May 16;14(5):347. doi: 10.3390/toxins14050347

Table 3.

Metabolites tentatively identified in the 70% ethanol extract of (Mentha pulegium L.) and its fractions methylene chloride (MecH), ethyl acetate (EtOAc), butanol (But) and remaining liquor (Rem. aq.) via UPLC-ESI-TOF-MS in both; negative/positive ESI ionization modes.

Peak # RT.
(min.)		 Metabolite Name Mol. Ion m/z Mass (ppm) Elemental Composition MS2 Ions m/z
(−)/(+)		 Fractions
[M − H]− [M + H]+
Hydroxycinnamic acids and derivatives
1 1.31 Caffeic acid-O-glucuronide 355.0852 −5.2 C15H16O10 193, 161
2 1.33 Caffeic acid 179.0561 0.3 C9H8O4 161 EtOAc, Rem. aq.
3 1.49 Ferulic acid 195.0856 0.8 C10H10O4 177, 109 MecH, Rem. aq
4 1.58 Caffeic acid dimer 341.1071 343.0823 −2.2/3.2 C18H14O7 179, 161/181, 163 EtOAc
5 1.87 Sinapoyl-O-hexoside 387.1408 1.9 C17H22O10 255, 169 Rem. aq
6 1.89 Cinnamic acid 149.0949 4.1 C9H8O2 121, 65
7 5.17 Ethyl caffeate 209.0811 1.4 C11H12O4 191, 166
8 7.26 Salvianolic acid K 557.1252 −6 C27H24O13 363, 345 But.
9 8.82 Caffeoyl-O-sinapoylquinic acid 559.1422 −4.3 C27H28O13 490, 354, 287 MecH, EtOAc
10 8.98 Salvianolic acid F 315.0836 −7.8 C17H14O6 209, 179, 167 Rem. aq
11 12.55 Rosmarinic acid 361.0907 −2.9 C18H16O8 331, 313 MecH, EtOAc
12 13.30 Caftaric acid 313.2372 7.8 C13H12O9 295, 272, 259, 137 EtOAc
13 14.42 Methyl rosmarinate 375.1082 1.9 C19H18O8 360, 345, 197 EtOAc
14 18.03 Rosmarinic acid derivative 379.2811 −2 C23H38O4 361, 319, 165 EtOAc
Flavones and derivatives
15 4.87 Apigenin-6,8-di-C-hexoside 593.1489 3.5 C27H30O15 473, 353 Rem. aq, EtOAc
16 5.18 Penduletin-4′-O- glucuronide 521.1812 −1.5 C24H24O13 503, 345, 327, 253 EtOAc
17 7.15 5-Hydroxy-6,7,4′-trimethoxyflavone (Salvigenin) 327.2178 3.6 C18H16O6 190, 171 MecH
18 7.36 Apigenin-7-O-rutinoside (Isorhoifolin) 577.1605 9.1 C27H30O14 464, 269 But.
19 7.67 Unknown apigenin glycoside 563.1752 −1.3 C27H30O13 401, 383, 271 But.
20 7.79 Diosmetin-7-O-rutinoside (Diosmin) 607.1656 609.1782 −2.4/−0.3 C28H32O15 299/463, 301 But.
21 7.85 Luteolin-7-O-glucuronide 463.0899 6.1 C21H18O12 446, 287
22 8.52 Apigenin-7-O-glucuronide 445.0776 447.0827 −7.3/1.1 C21H18O11 269, 175/271 MecH, But.
23 9.35 Acacetin-7-O-rutinoside (Linarin) 593.1876 1.9 C28H32O14 447, 285 But., Rem. aq
24 10.11 5,6,7-Trihydroxyflavone (Baicalein) 269.0448 1.1 C15H10O5 But., MecH
25 10.32 Pedalitin tetraacetate 483.0909 −2.6 C24H20O11 336, 309 EtOAc
26 10.42 5,7,3′-trihydroxy-4′-methoxyflavone (Diosmetin, 4′-Methylluteolin) 299.0927 301.1382 −1.5/2.1 C16H12O6 284, 151/283 But.
27 13.11 5,7-Dihydroxy-4′,6-dimethoxyflavone (Pectolinarigenin) 315.0857 −2.1 C17H14O6 300, 282, 254 Rem. aq
28 14.02 5,4′-Dihydroxy-3,6,7-trimethoxyflavone (Penduletin) 345.0946 −6.6 C18H16O7 330, 315, 197 MecH
29 14.23 5,7-Dihydroxy-4′-methoxyflavone (Acacetin) 283.0611 285.0753 3.5/−1.5 C16H12O5 268, 151/242, 153 MecH
30 15.33 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (Retusin) 359.1128 0.8 C19H18O7 326, 162 EtOAc, Rem. aq
31 16.41 5-Hydroxy-3,3′,4′,6,7-pentamethoxyflavone (Artemetin) 387.1095 389.1230 5.2/−0.3 C20H20O8 340, 319/359, 341 EtOAc, But., Rem. aq
32 16.88 5-hydroxy-7,4′-dimethoxy-6,8-dimethylflavone (Eucalyptin) 327.1252 8.0 C19H18O5 277, 137 But., Rem. aq
Flavanone and Flavanol derivatives
33 5.07 Naringenin-7-O-glucuronide 449.1112 7.6 C21H20O11 357, 273, 181
34 5.37 Isosakuranetin-O-rutinoside (Didymin) 595.2831 3.6 C28H34O14 577, 457
35 5.93 Hesperetin 301.2005 −1.5 C16H14O6 283, 255 But.
36 8.16 Eriodictyol-7-O-glucuronide 463.0990 3.2 C21H20O12 354, 286, 218 But.
37 13.09 Sakuranetin 285.0781 8 C16H14O5 267, 164 But.
38 15.45 Taxifolin 305.0845 8.3 C15H12O7
39 21.51 Hesperetin-7-O-rutinoside (hesperidin) 611.2864 −7.5 C28H34O15 567, 538
Prenyl flavones
40 5.66 Prenyl pinocembrin 325.1398 1.4 C20H20O4 307, 191
41 7.24 Prenyl kaempferol 353.2329 1.9 C20H18O6 285
42 7.93 7-O-methyl isoxanthohumol 369.1311 −5.9 C22H24O5
43 8.21 7,4′-Di-O-methyl isoxanthohumol 383.184 −3.4 C23H26O5 365, 233
44 10.88 Isoxanthohumol 355.1521 −5.3 C21H22O5 267, 163
45 14.99 Prenyl naringenin 339.216 341.1379 6.5/−1.3 C20H20O5 309, 265
46 21.76 Dorsmanin F 441.1897 −2.5 C25H28O7
Isoflavone
47 4.35 Daidzein-8-C-hexoside 417.1302 −4.6 C21H20O9 267, 255 But., Rem. aq
Flavonols
48 7.35 Myricetin-3-O-glucuronide 495.2094 4.1 C21H18O14 319, 301, 283 EtOAc
49 11.44 3,5,7,3′,4′,5′-Hexahydroxyflavone (Myricetin) 317.0562 319.0758 −2.7/0.6 C15H10O8 225, 164/151
Biflavonoid
50 18.88 Di-O-methylamentoflavone (Ginkgetin) 565.1129 567.1288 0.3/0.3 C32H22O10 297, 283, 165 Rem. aq
51 21.59 Amentoflavone-7,4′,4‴-trimethyl ether (Sciadopitysin) 579.1275 581.1424 −1.8/−3.2 C33H24O10 297 MecH
52 22.62 4′-Monomethylamentoflavone (Bilobetin) 553.2685 −3.6 C31H20O10 335, 473 Rem. aq
53 24.06 Unknown biflavonoid 647.2296 3.2 C39H34O9 629
54 24.98 Isochamaejasmin 543.1318 4.9 C30H22O10 381, 322, 122
Quinones
55 11.49 Przewaquinone C 297.1134 4.1 C18H16O4 279, 261 Rem. aq
56 12.76 Przewaquinone A 311.1283 1.7 C19H18O4 EtOAc, Rem. aq
57 12.78 Tanshinone IIA 295.1339 3.5 C19H18O3 277, 149 MecH, Rem. aq
58 15.07 Przewaquinone F 313.1075 1.5 C18H16O5 277, 259, 149 Rem. aq
Iridoids
59 5.54 Loganic acid 377.1466 6.4 C16H24O10 MecH
60 5.66 Aucubin 347.1309 −6.6 C15H22O9 329, 193
61 9.09 Nepetalactone (Epi-nepetalactone) 165.0916 167.1074 3.8/4.5 C10H14O2 147, 107/149, 121 But.
62 10.61 Dihydronepetalactone 169.1218 −2.9 C10H16O2 151, 123, 83
63 14.97 Kanokoside A 475.1817 1.6 C21H32O12 339, 271 Rem. aq
64 15.80 Loganin 391.1634 8.9 C17H26O10
65 17.77 Patriscabroside I 361.1489 −1.1 C16H26O9 196, 165 But., Rem. aq
66 21.56 Kanokoside C 639.2484 −1.7 C27H42O17 621, 579, 562
67 22.64 Deoxyloganic acid tetraacetate 527.1747 −2.3 C24H32O13 459, 391, 323 But.
68 23.67 Kanokoside D 625.2671 −4.9 C27H44O16 607, 581, 521
Mono and diterpenes
69 13.33 Carnosic acid 333.2042 −5.4 C20H28O4 315, 297
70 13.53 Abienol 291.0687 −0.2 C20H34O 273, 217
71 13.88 Carnosol 331.1913 2.7 C20H26O4 278, 203 Rem. aq, MecH
72 17.08 Ethyl abietic acid 331.1690 −0.8 C23H22O2 183
73 18.28 12-O-Methylcarnosic acid 345.2070 2.9 C21H30O4 299, 277
74 18.93 Taxodione 315.1958 0.9 C20H26O3 177, 123
75 18.94 Coleonol (Forskolin) 409.2562 −5.5 C22H34O7 351, 341
76 19.01 Pachyphyllone 315.1958 317.2122 3.4 C20H28O3 149
77 19.60 Picrocrocin 331.1741 −3.2 C16H26O7 183, 149
78 21.03 Neoandrographolide 481.2781 −3.1 C26H40O8 441, 401
79 21.61 Abietic (Sylvic) acid 303.2223 −3.2 C20H30O2 165
80 22.85 Casearborin E 597.2730 2.8 C33H40O10 579, 553
81 23.82 Casearborin C/D 555.2575 −2.4 C31H38O9 527
82 24.25 Casearborin A 539.2663 4.4 C31H38O8 EtOAc, But., Rem. aq
83 24.91 Dihydrotanshinone I 279.1027 4.2 C18H14O3 149 MecH
Triterpenes
84 16.05 Corosolic acid 473.2323 0.1 C30H48O4 455 MecH
85 17.22 Asiatic acid 489.3607 6.7 C30H48O5 453, 407, 201 MecH, EtOAc
86 19.21 Ursolic acid methyl ester 471.3478 1.8 C31H50O3 425, 407
87 20.87 Melilotoside A 591.4307 8.2 C35H58O7 574, 292, 133
88 21.31 Platanic acid 459.3481 2.7 C29H46O4 442, 316 But.
89 21.92 Orthosiphol D 553.2685 −0.7 C31H36O9 525
90 23.53 Unknown triterpene (Swietmanin I) 567.2609 3.6 C32H38O9
91 22.71 Micromeric acid 455.3526 1.3 C30H46O3 437, 247, 203
92 23.25 Ursolic acid 457.3684 1.6 C30H48O3 439, 411, 393
93 25.26 Conrauidienol 467.3876 −1.7 C32H50O2 450
Fatty acids and esters
94 7.83 Pinellic acid 329.2337 4.2 C18H34O5 211, 171 MecH
95 14.89 16-Hydroxyhexadecanoic acid (Juniperic acid) 271.2267 −0.3 C16H32O3 225 MecH
96 17.56 Myrestic acid 227.2007 0.6 C14H28O2 Rem. aq
97 19.19 Palmitoleic acid 253.2173 4.3 C16H30O2
98 19.31 Hydroxyoctadecatrienoic acid 295.2268 −6.7 C18H30O3 277, 179
99 19.58 Linolenic acid 277.2182 −0.3 C18H30O2
100 22.73 Palmitic acid 255.2318 −0.1 C16H32O2 237
101 23.18 Tetracosanoic (Lignoceric) acid 367.3574 1.0 C24H48O2
102 23.46 Methyl 12,13-epoxystearate 313.2753 5.0 C19H36O3 257, 239, 97 MecH, But.
103 23.52 Glyceryl palmitate 331.2858 4.7 C19H38O4 239
104 23.77 Oleic acid 281.2485 3.6 C18H34O2
105 25.55 Methyl oleate 295.2628 −1.1 C19H36O2
106 26.48 3-Hydroxypropyl oleate 341.3038 −3.6 C21H40O3 95
107 26.66 Eicosadienoic acid 309.2762 −8.2 C20H36O2 291, 109
Aliphatic and Hydroxybenzoic acid derivatives
108 1.18 Tartaric acid 149.0098 −2.0 C4H6O6
109 1.21 Quinic acid 191.0549 −0.5 C7H12O6 111 Rem. aq
110 1.35 3,4-Dihydroxyphenylacetic acid 167.0007 −0.9 C8H8O4 148, 78
111 1.37 2-Isopropylmalic acid 175.0588 8.6 C7H12O5 But.
112 1.38 Galacturonic acid 193.0709 2.0 C6H10O7 MecH
113 1.39 Malic acid 133.0500 −0.9 C4H6O5 Rem. aq, But.
114 1.40 Protocatechuic acid hexoside 315.0716 1.8 C13H16O9 195, 153, 109 But., Rem. aq
115 1.41 Hydroquinone glucuronide 285.0592 −4.5 C12H14O8 165, 152 But.
116 1.48 Hydroxyphenyllactic acid 181.0486 −5.0 C9H9O4 166, 112
117 4.57 Suberic acid 173.1190 0.1 C8H14O4
118 6.39 Tuberonic acid (12-hydroxy-7-isojasmonic acid) 227.1286 3.6 C12H18O4 209, 191, 131
119 6.61 Pinonic acid 183.1021 2.7 C10H16O3 137 But.
120 16.93 Menthyl salicylate 277.1786 −4.3 C17H24O3 231, 137
Others
121 1.26 Valine 118.0862 −3.9 C5H11NO2 58
122 1.68 Niacin (nicotinic acid) 124.0393 1.0 C6H5NO2 106, 80
123 2.12 Proline 116.0706 −7.2 C5H9NO2 84, 70
124 4.25 Oleacein 321.1337 1.2 C17H20O6 149 MecH, EtOAc, But.
125 4.34 Hydroxyquinoline 146.0600 −1.1 C9H7NO 118, 91
126 8.05 Loliolide 197.1166 −3.3 C11H16O3 179, 105
127 10.58 Tryptophol 162.0913 5.8 C10H11NO 146, 118
128 26.89 7-hydroxy-4-methyl-coumarin (Hymecromone) 177.0543 −1.6 C10H8O3 159, 149 But.