Table 1.
Compounds detected in the ethanolic extracts of then Peruvian Mentheae by LC-HRMS.
| No peak | Assignment | Rt | [M–H]− | Experimental mass | Δ (ppm) | Fragments | Detected in* | References |
|---|---|---|---|---|---|---|---|---|
| 1 | Quinic acid | 1.33 | C7H11O6 | 191.0559 | 1.57 | 127.0394 | Cb, So, Mm, Sc, Cr, Cs, Cp | 23 |
| 2 | Malic acid | 1.36 | C4H5O5 | 133.0139 | 1.5 | Ss, Sc, | 23 | |
| 3 | Quinic acid isomer | 1.44 | C7H11O6 | 191.0560 | 2.09 | 127.8695 | Cb, Mm, Cr, Cs, Cp | 23 |
| 4 | Citric acid | 1.77 | C6H7O7 | 191.0196 | 2.09 | 111.0081 | So | 23 |
| 5 | Pyroglutamic acid | 1.87 | C5H6O3N | 128.0348 | 0.00 | Sh | 23 | |
| 6 | Succinic acid | 1.98 | C4H5O4 | 117.0187 | 0.85 | So, Mm, Ss, Sc, Cr, Cs, Sh, Hm | 23 | |
| 7 | Monoacetylglycerol | 2.09 | C5H9O4 | 133.0502 | 0.75 | Ss | ||
| 8 | Mesaconic acid | 2.96 | C5H5O4 | 129.0190 | 1.55 | Cp | ||
| 9 | 3,4-dihydroxyphenyl lactic acid “danshensu” | 4.05 | C9H9O5 | 197.0454 | 2.02 | 123.0445, 135.0446, 179.0346 | So, Cb, So, Mm, Sc, Cr, Cs, Hm, Sh | 24,25 |
| 10 | Protocatechuic acid | 4.64 | C7H5O4 | 153.0190 | 1.31 | 109.0289, 135.0448 | So, Sc, Hm, Cp | 24 |
| 11 | 1-O-Caffeoylquinic acid | 6.39 | C16H17O9 | 353.0883 | 2.83 | 135.0447, 179.0347, 191.0559 | Mm | 58,59,58–60 |
| 12 | Protocatechuic aldehyde | 7.73 | C7H5O3 | 137.0239 | 0.00 | 109.0289 | Cb, So, Mm, Ss, Cr, Cs, Sh, Hm, Cp | 24 |
| 13 | Hydroxyheptandioic acid | 8.78 | C7H11O5 | 175.0611 | 2.28 | So, Ss | ||
| 14 | p-Coumaroyl quinic acid | 8.83 | C16H17O8 | 337.0934 | 2.96 | 119.0496, 163.0398, 173.0453, 191.0559 | Mm | 58,59,58–60 |
| 15 | 3-O-Caffeoylquinic acid | 8.99 | C16H17O9 | 353.0883 | 2.83 | 173.0453, 179.0559, 191.056 | Mm, Cr | 58,59,58–60 |
| 16 | Caffeic acid O-hexoside | 9.02 | C15H17O9 | 341.0883 | 2.93 | 179.0347, 233.0458, 251.0564, 281.0670 | So, Ss, Sc | 60,41 |
| 17 | p-Coumaric acid | 9.28 | C9H7O3 | 163.0399 | 2.45 | 119.0497 | Ss | 38 |
| 18 | 5-O-Caffeoylquinic acid | 9.41 | C16H17O9 | 353.0883 | 2.83 | 135.0446, 179.0346, 191.055 | Cb, So, Mm, Cr, Hm, Cp | 58,59,58–60 |
| 19 | Eucomic acid | 9.54 | C11H11O6 | 239.0561 | 2.09 | 195.0660, 178.0586 | Cb | |
| 20 | Caffeic acid | 9.64 | C9H7O4 | 179.0348 | 1.67 | 135.0446, 161.0446 | So, Mm, Ss, Sc, Cr, Cs, Sh, | 38,39,41 |
| 21 | Caffeic acid O-hexoside | 9.77 | C15H17O9 | 341.088 | 2.05 | 179.0345, 235.0453, 251.0561, 281.0667 | Sc | 60,41 |
| 22 | Tuberonic acid hexoside | 9.86 | C18H27O9 | 387.1665 | 2.58 | 101.5668, 163.0033, 206.9725 | So, Ss, Cr, Sh | 23 |
| 23 | p-Coumaroylquinic acid isomer | 10.1 | C16H17O8 | 337.0934 | 2.97 | 163.0397, 173.0454 | So, Mm | 58,59,61,27 |
| 24 | Salvianic acid C | 10.21 | C18H17O9 | 377.0882 | 2.39 | 161.0240, 179.0347, 359.0776 | Cr | 41 |
| 25 | p-Coumaroyl hexoside | 10.38 | C15H17O8 | 325.0930 | 1.85 | 119.0496, 163.0396 | Sc | 60 |
| 26 | Feruloylquinic acid | 10.38 | C17H19O9 | 367.1040 | 3.0 | 149.0240, 191.0560, 193.0504, 173.0453 | Mm | 20,27 |
| 27 | Quercetin 3,7-di-O-hexoside | 10.43 | C27H29O17 | 625.1407 | 0.32 | 121.0288, 179.0346, 273.0980, 301.0354, 303.1084, 463.0882, | Cs, Cp | 62,29,30 |
| 28 | 4-O-Caffeoylquinic acid | 10.45 | C16H17O9 | 353.0880 | 1.12 | 135.0445, 179.0345, 191.0557 | Sc | 58,59,58–60 |
| 29 | p-Coumaroyl hexoside | 10.59 | C15H17O8 | 325.0930 | 1.85 | 119.0496, 163.0396 | Sc | 60 |
| 30 | Salvianic acid C isomer | 10.67 | C18H17O9 | 377.0881 | 2.12 | 197.0453, 347.1708, 359.0775 | Cr | 41 |
| 31 | Tuberonic acid | 10.67 | C12H17O4 | 225.1132 | 2.22 | 134.8648, 146.9382, 168.8359, 187.9417, 213.0961 | Mm, Sh, | 23 |
| 32 | Quercetin O-rutinoside | 10.78 | C27H29O16 | 609.1458 | 0.33 | 121.0289, 179.0345, 301.0356, 273.0881 | Mm, Cp | 60,29,30,35 |
| 33 | Eriodictyol O-rutinosise | 10.89 | C27H31O15 | 595.1661 | 0.34 | 151.0397, 287.0562 | Cs, Sh, Hm | 42,29,30 |
| 34 | Luteolin O-rutinoside | 11.00 | C27H29O15 | 593.1504 | 0.51 | 285.0403, 447.0928 | Cb, Sc, Cr, Cp | 16,63,26 |
| 35 | Apigenin O-rutinoside | 11.01 | C27H29O14 | 577.1556 | 0.35 | 269.1030 | Sc, Cr | 16,38,63,26 |
| 36 | Kaempferol O-hexoside | 11.02 | C21H19O11 | 447.0936 | 1.78 | 151.0031, 285.0406, | Cb, Ss, Cs | 20,29,30 |
| 37 | Quercetin O-hexoside | 11.02 | C21H19O12 | 463.0886 | 1.94 | 301.0358 | So, Mm, Ss, Sc, Cp | 60,44,29,30 |
| 38 | Quercetin O-glucuronide | 11.09 | C21H17O13 | 477.0679 | 2.1 | 301.0356 | So, Ss | 44,29,30 |
| 39 | Feruloyl hexoside | 11.12 | C16H19O9 | 355.1036 | 1.97 | 149.0240, 193.0502 | Sc | 60 |
| 40 | Pentahydroxy-methoxyflavone hexoside | 11.12 | C22H21O13 | 493.0989 | 1.42 | 162.8387, 163.0397, 331.0827, 315.1089 | Cs | 29,30 |
| 41 | Isorhamnetin O-hexoside | 11.23 | C22H21O12 | 477.1046 | 2.72 | 315.0824, 357.0352, 462.0768 | Ss | 43,29,30 |
| 42 | Naringenin O- rutinoside | 11.33 | C27H31O14 | 579.1714 | 0.00 | 151.0030, 271.0612 | Mm, Cb, Cs, Hm, Cp | 29,30 |
| 43 | Eriodictyol O- rutinoside | 11.4 | C27H31O15 | 595.1665 | 0.34 | 151.0033, 287.0564 | Cs | 29,30 |
| 44 | Luteolin O-glucuronide | 11.56 | C21H17O12 | 461.0729 | 1.95 | 133.0290, 151.0395, 285.0407, | So, Ss, Cr, Sh | 44,29,30 |
| 45 | Luteolin O-hexoside | 11.57 | C21H19O11 | 447.0937 | 2.01 | 151.0398, 241.1084, 285.0407 | Mm, Cr | 60,29,30 |
| 46 | Dihydrobaicalin | 11.57 | C21H19O11 | 447.0936 | 1.79 | 271.0250, 403.1613 | Sc | 62 |
| 47 | Sagerinic acid | 11.58 | C36H31O16 | 719.1600 | 1.67 | 161.0239, 179.0348, 359.0715, 539.1186 | Sc, Cr | 38,39,45–47 |
| 48 | Hesperetin 7-O-rutinoside | 11.64 | C28H33O15 | 609.1819 | 0.16 | 151.0397, 179.0347, 301.0718, 257.1035 | Mm, Cb, Hm, Cp | 29,30,64 |
| 49 | Apigenin O-rutinoside | 11.66 | C27H29O14 | 577.1557 | 0.17 | 225.1129, 269.0453 | Cr | 29,30 |
| 50 | Dimethylrosmarinic acid | 11.67 | C20H19O8 | 387.1091 | 2.84 | 179.0347, 135.0447, 161.0452 | So, Sh | |
| 51 | Isorhamnetin 3-O-glucuronide | 11.7 | C22H19O13 | 491.0834 | 1.62 | 151.0396, 179.0346, 302.0388, 300.0602, 301.0358, 299.0565, 315.0513 | So | 29,30 |
| 52 | Salvianolic acid A isomer | 11.75 | C26H21O10 | 493.1142 | 1.42 | 179.0344, 197.0450, 269.0821, 295.1192, 313.0723, 359.0778 | Cs | 24,25,41,49 |
| 53 | Tetrahydroxy-methoxyflavone O-hexoside | 11.78 | C22H21O12 | 477.1041 | 1.68 | 162.8398, 163.8391, 315.1451 | Cr | 29,30 |
| 54 | Trihydroxymethoxyflavone O-hexoside | 11.89 | C22H21O11 | 461.1093 | 1.95 | 299.0559 | Sh, | 29,30 |
| 55 | Salvianolic acid B isomer | 11.99 | C36H29O16 | 717.1443 | 1.81 | 321.0616, 519.0945 | Cs | 25,40,41,47,48 |
| 56 | Apigenin C-hexoside | 12.01 | C21H19O10 | 431.0984 | 0.00 | 269.0452, 281.1024, 311.1130, 341.1960, 371.1002 | Cr | 20 |
| 57 | Rosmarinic acid | 12.04 | C18H15O8 | 359.0775 | 2.23 | 161.0240, 179.0345, 197.0452 | Cb, So, Mm, Ss, Sc, Cr, Cs, Sh, Hm, Cp | 25,38,39,45,46,48 |
| 58 | Luteolin C-hexoside | 12.07 | C21H19O11 | 447.0934 | 2.91 | 285.0404, 297.1353, 357.1921, 387.1160 | Cr | 20 |
| 59 | Dicaffeoylquinic acid | 12.17 | C25H23O12 | 515.1194 | 0.19 | 135.0444, 161.0238, 179.0345, 353.0881 | Cr | 58,59,58–60 |
| 60 | Salvianolic acid B isomer | 12.53 | C36H29O16 | 717.1443 | 1.81 | 295.0611, 321.0408, 339.0512, 493.1137, 519.0930, 537.1024 | Cb, Ss, Hm | 25,40,41,47,48 |
| 61 | Luteolin O-acetylhexoside | 12.71 | C23H21O12 | 489.1039 | 1.23 | 133.0289, 151.0395, 241.0537, 257.1035, 267.0667, 285.0404, 447.0935 | Cr | 63,26 |
| 62 | Artemetin | 12.8 | C20H19O8 | 387.1089 | 2.32 | 327.1241, 342.1067, 357.0992, 372.1184 | Sh, | 29,30 |
| 63 | Isorinic acid | 12.95 | C18H15O7 | 343.0827 | 2.62 | 161.0241, 327.2181 | Cb, Ss, Sc Hm | 41,65 |
| 64 | Lithospermic acid | 13.03 | C27H21O12 | 537.1038 | 0.93 | 295.0610, 493.1147 | Cs | 24,41 |
| 65 | Isosakuranetin O-rutinoside | 13.15 | C28H33O14 | 593.1874 | 0.51 | 285.0770, 594.1905 | Mm, Cp | 29,30 |
| 66 | Methyl rosmarinate | 13.28 | C19H17O8 | 373.0935 | 2.95 | 179.0347, 194.0540, 359.0778 | Sc | 20,25,38 |
| 67 | Quercetin O-(p-coumaroyl)-hexoside | 13.51 | C30H25O14 | 609.1242 | 0.49 | 301.0719, 447.0940, 462.0747, 594.1343 | Cr | 29,30 |
| 68 | Eriodictyol | 13.6 | C15H11O6 | 287.0563 | 2.44 | 107.0133, 135.0445, 151.0030 | Cb, Cp | 29,30 |
| 69 | Luteolin | 13.62 | C15H9O6 | 285.0408 | 3.16 | 133.0289, 151.0032, 241.1085 | Cb, Hm | 29,30,32 |
| 70 | Dihydrophilonotisflavone | 13.63 | C30H19O12 | 571.0883 | 1.05 | 133.0290, 151.0033, 285.0410, 286.0441 | So, Ss | 29,30 |
| 71 | Ferulic acid | 13.68 | C10H9O4 | 193.0504 | 1.55 | 134.0367, 149.0239, 178.0220 | Sc | 20,25,66 |
| 72 | Salvianolic acid A isomer | 13.87 | C26H21O10 | 493.1141 | 1.22 | 159.8595, 179.0345, 197.0451, 295.0612, 269.0821, 313.0719, 359.0774 | Cs, Cp | 24,25,41,49 |
| 73 | Protocatechuic acid O-(hydroxybenzoyl)hexoside | 13.94 | C20H19O11 | 435.0935 | 1.61 | 137.0239, 153.0191, 297.1346, 315.1452 | Cr | |
| 74 | Trihydroxy-methoxyflavone | 14.00 | C16H11O6 | 299.0565 | 3.01 | 151.0397, 255.0698, 285.0413 | Ss, Sh | 29,30,32,35 |
| 75 | Hesperetin O-hexoside | 14.27 | C22H23O11 | 463.1250 | 2.06 | 151.0395, 179.0347, 301.0720 | Cp | 29,30,34 |
| 76 | Caffeic acid ethyl ester | 14.66 | C11H11O4 | 207.0661 | 1.44 | 179.0347 | Cb, Sc | |
| 77 | Quercetin | 14.97 | C15H9O7 | 301.0356 | 2.33 | 273.0407, 257.8189, 179.0346, 151.0392, 121.0288 | Sc | 67,29,30 |
| 78 | Caffeic acid dimethyl derivative | 15.01 | C11H11O4 | 207.0661 | 1.45 | 16,931.0239, 151.940396, 147.069552 | Cs | |
| 79 | Salvianolic acid F isomer | 15.46 | C17H13O6 | 313.0721 | 2.88 | 269.082196, 15,979.0656 | Sc, Cs | 41 |
| 80 | Dimethylquercetin | 15.49 | C17H13O7 | 329.0673 | 3.34 | 314.0756, 301.0716, 179.0347, 151.0396, 121.0288 | Cb | 29,30 |
| 81 | Trihydroxy-dimethoxyflavone | 15.53 | C17H13O7 | 329.0672 | 3.04 | 151.0398, 201.8020, 257.8197, 283.0612, 299.0201, 313.0722, 314.0754 | Mm | 29,30 |
| 82 | Trihydroxylinoleic acid | 16.03 | C18H31O5 | 327.2183 | 2.75 | 269.0457 | Cb, Mm, Ss, Sc, Hm | |
| 83 | Ethyl caffeate | 16.14 | C11H11O4 | 207.0660 | 0.97 | 179.0346 | Ss | |
| 84 | Apigenin | 16.15 | C15H9O5 | 269.0459 | 3.35 | 151.0396, 117.0187 | Ss, Sc, Cr | 40,67,29,30,32 |
| 85 | Naringenin | 16.39 | C15H11O5 | 271.0616 | 3.32 | 151.0397, 177.0190 | Ss, Cp | 68,29,30 |
| 86 | Salvianolic acid F isomer | 16.87 | C17H13O6 | 313.0719 | 2.23 | 269.0822, 159.0658 | Sc | 41 |
| 87 | Ethyl rosmarinate | 17.23 | C20H19O8 | 387.1088 | 2.07 | 179.0344, 206.9724, 359.0777 | Cb | 20,38,39 |
| 88 | Dimethylquercetin | 17.59 | C17H13O7 | 329.0673 | 3.34 | 121.0291, 151.0397, 179.0350, 301.0715, 314.0756 | Ss, Cp | 66,29,30 |
| 89 | Hesperetin | 17.66 | C16H13O6 | 301.0722 | 3.32 | 151.0032, 179.0343, 286.0495 | Cp | 29,30,34 |
| 90 | Salvianolic acid F isomer | 17.87 | C17H13O6 | 313.0721 | 2.87 | 159.0448, 269.0821 | Cs | 41 |
| 91 | 15,16-epoxi-10S-hidroxicleroda-3,7,13(16),14 tetraeno-17, 12S; 18,19 diolido | 17.94 | C20H19O6 | 355.1190 | 2.25 | 311.1291 | Sh | 55 |
| 92 | Trihydroxyoleic acid | 18.13 | C18H33O5 | 329.2336 | 2.43 | 171.0195, 224.7632, 250.1448 | Mm, Cb Cs | 37 |
| 93 | Hydroxyhexadecandioic acid | 18.63 | C16H29O5 | 301.2025 | 3.32 | Cs | 37 | |
| 94 | Trihydroxy-trimethoxyflavone | 18.73 | C18H15O8 | 359.0766 | 0.28 | 301.6655, 314.2232, 329.0299, 344.0546 | Mm, Cb, Cp | |
| 95 | Trihydroxy-methoxyflavanone (hesperetin isomer) | 19.15 | C16H13O6 | 301.0721 | 2.87 | 161.0240, 139.0032 | Cp | 28,30 |
| 96 | trihydroxymethoxyflavone | 19.23 | C16H11O6 | 299.0565 | 3.01 | 151.0397, 284.0327 | So, Mm, Cr, Sh, Cp, Sd | 69,32 |
| 97 | Cirsimaritin | 19.34 | C17H13O6 | 313.0724 | 3.19 | 298.0488, 283.0249 | Ss, Cr | 70,35 |
| 98 | Isolariciresinol | 19.61 | C20H23O6 | 359.1502 | 1.95 | 345.1346, 344.1582, 313.0714 | Sc | 55,31 |
| 99 | Salvianolic acid F isomer | 19.77 | C7H13O6 | 313.0722 | 3.19 | 269.0459, 159.8597 | Cp | 41 |
| 100 | Rosmadial | 20.03 | C20H23O5 | 343.1552 | 1.75 | 299.1652, 315.1598 | Sc | |
| 101 | Eupatorin | 20.06 | C18H15O7 | 343.0829 | 3.21 | 328.0595, 313.0359, 298.0125 | Cb, Mm, Ss, Cr, Cp | 48,50 |
| 102 | Teucrol | 20.3 | C17H15O6 | 315.0880 | 3.5 | 179.0349, 135.0447, 161.0244 | Ss | 51 |
| 103 | Dihydroxy-methoxyflavone | 20.32 | C16H11O5 | 283.0617 | 3.53 | 268.0386, 151.0034, 107.0327 | Mm, Cp | 29,30 |
| 104 | Dihydroxy-dimethoxyflavanone | 20.36 | C16H13O5 | 285.0773 | 3.51 | 153.0190, 161.0453, 179.0349, 151.0397, 243.0668, 270.0535, 164.0012 | Mm | 29,30 |
| 105 | Genkwanin | 20.47 | C16H11O5 | 283.0616 | 3.18 | 268.0386, 239.0922, 165.0192 | Ss, Cr, Sh | 43 |
| 106 | Sakuranetin | 20.57 | C16H13O5 | 285.0771 | 2.81 | 241.1076, 165.0188, 121.0289 | Cr | 29 |
| 107 | Octadecendioic acid | 20.68 | C18H31O4 | 311.2232 | 2.89 | 310.2107 | So, Sh | 23 |
| 108 | Octadihydroxyoctadecadienoic acid | 21.15 | C18H31O4 | 311.2229 | 1.93 | 197.8076 | Sc | 23 |
| 109 | Carnosol | 22.2 | C20H25O4 | 329.1761 | 2.7 | 285.1861 | Ss, Sc | 38,39,54 |
| 110 | 5-Epi-icetexone | 22.45 | C20H21O5 | 341.1396 | 0.88 | 297.1500, 299.1652 | Sc | 56 |
| 111 | 9,10-Dihydroxystearic acid | 23.47 | C18H35O4 | 315.2547 | 3.47 | Ss | 23 |
*Clinopodium brevicalyx (Cb), Salvia oppositiflora (So), Minthostachys mollis (Mm), Salvia sagittata (Ss), Salvia cuspidate (Sc), Clinopodium revolutum (Cr), Clinopodium sericeum (Cs), Salvia haenkei (Sh), Hedeoma mandoniana (Hm), Clinopodium pulchellum (Cp).