Table 2.
Compounds identified in the studied extracts.
| Comp. No | Tentative Identification | R Time | Molecular Mass | [M − H]− | Fragment Ions (m/z) | Extracts |
|---|---|---|---|---|---|---|
| 1 | Quinic acid | 1.91 | 192.0507 | 191.0507 | 173.0464; 111.0437; 93.0318; 85.0262 | 1,2,3 |
| 2 | Citric acid | 2.33 | 192.0180 | 191.0180 | 111.0035; 87.0052 | 1,2,3,4 |
| 3 | Caffeic acid derivative | 3.40 | 242.0302 | 241.0302 | 179.0273; 153.0497; 135.0406; 123.0407; 109.0230 | 4 |
| 4 | Quinic acid derivative | 3.46 | 534.1621 | 533.1621 | 337.0845; 191.0508 | 2 |
| 5 | Quinic acid derivative | 4.04 | 406.0968 | 405.0968 | 213.0351; 191.0511 | 4 |
| 6 | 4-Hydroxy-2-(hydroxymethyl)benzoic acid | 4.09 | 168.0307 | 167.0307 | 149.0234; 123.0429 | 3 |
| 7 | Dihydroxybenzoic acid glucoside derivative | 4.13 | 532.0929 | 531.0929 | 353.0781; 315.0642; 153.0155; 96.9570 | 2 |
| 8 | Quinic acid derivative | 4.22 | 470.0574 | 469.0574 | 435.1422; 371.0962; 191.0423 | 2 |
| 9 | Hydroxycaffeoyl-quinic acid | 4.76 | 372.0900 | 371.0900 | 353.0840; 197.0360; 191.0533; 179.0312; 173.0431;135.0409 | 2 |
| 10 | Glucogallic acid/Glucosyl gallate | 6.32 | 332.0607 | 331.0607 | 169.0124; 151.0003; 125.0211 | 2 |
| 11 | Dihydroxybenzoic acid glucoside derivative | 6.49 | 436.0075 | 435.0075 | 315.0710; 153.0056 | 1 |
| 12 | Dihydro-caffeoyl-quinic acid | 6.56 | 356.0959 | 355.0959 | 191.0522; 181.0167; 173.0451; 137.0164; 111.0044 | 2 |
| 13 | Hydroxybenzoic acid derivative | 6.77 | 432.1224 | 431.1124 | 137.0243; 93.0383 | 3 |
| 14 | Caffeoyl-hydroxybenzoic acid | 7.23 | 300.0717 | 299.07117 | 239.0562; 179.0356; 137.0228 | 4 |
| 15 | Dihydroxybenzoic acid glucoside isomer 1 | 7.487 | 316.0628 | 315.0628 | 153.0134; 152.0105; 108.0213 | 1,2 |
| 16 | Dihydroxybenzoic acid | 7.59 | 154.0143 | 153.0143 | 109.0302; 108.0225 | 1,2,3,4 |
| 17 | Coumaric acid-hexoside-pentoside | 8.48 | 458.0892 | 457.0892 | 325.0865; 163.0347 | 2 |
| 18 | Dihydroxybenzoic acid glucoside isomer 2 | 8.51 | 316.0660 | 315.0660 | 153.0147; 109.0258 | 2 |
| 19 | 3-Hydroxy-4-methoxymandelate glucoside | 8.86 | 360.0924 | 359.0924 | 197.0449; 182.0215; 153.0557; 138.0321; 123.0129 | 3 |
| 20 | Caffeic acid derivative hexoside | 9.06 | 376.0601 | 375.0601; | 341.1069; 213.0650; 201.0144; 179.0316; 135.0409 | 1 |
| 21 | Quinic acid derivative | 9.08 | 372.0868 | 371.0868 | 251.0544; 191.052; 167.0327 | 1 |
| 22 | 2-Isopropylmalic acid | 9.19 | 176.0571 | 175.0571 | 157.0486; 115.0371; 85.0638 | 2 |
| 23 | Hydroxybenzoic acid | 9.29 | 138.0208 | 137.0208 | 108.0231 | 3, 4 |
| 24 | Unidentified | 9.39 | 376.1236 | 375.1236 | 312.0725; 169.0827; 151.0726 | 4 |
| 25 | Hydroxybenzoic acid 4-O-glucoside | 10.17 | 300.0669 | 299.0669 | 137.0203; 93.0315 | 1,2 |
| 26 | 3-O-Caffeoylquinic acid | 10.36 | 354.0782 | 353.0782 | 191.0578; 179.0370; 161.0243; 135.0461 | 1,2,3 |
| 27 | Dihydroxybenzoic acid glucoside isomer 3 | 10.69 | 316.0660 | 315.0660 | 153.0144; 109.0258 | 2 |
| 28 | Caffeic acid glucoside | 10.76 | 342.0825 | 341.0825 | 179.0357; 161.0246; 135.0457 | 4 |
| 29 | Dihydroxybenzoic acid O-glucoside-pentoside | 10.84 | 448.1382 | 447.1382 | 315.1063; 153.0548; 109.0301; 108.0249 | 3 |
| 30 | Hydroxycoumarin | 10.93 | 340.0715 | 339.0715 | 177.0178 | 1 |
| 31 | Methyl gallate | 11.02 | 184.0234 | 183.0234 | 168.0071; 124.0155; 78.0128 | 1 |
| 32 | Hydroxybenzoic acid | 11.13 | 138.0210 | 137.0210 | 109.0209; 108.0308; 93.0345 | 4 |
| 33 | Glucogallic acid/Glucosyl gallate | 11.50 | 332.0607 | 331.0607 | 169.0113;168.0047;125.0225 | 1,2,4 |
| 34 | 3-O-p-Coumaroylquinic acid | 11.30 | 338.0840 | 337.0840 | 191.0540; 163.0384 | 1,2 |
| 35 | Procyanidin B (dimer of (epi)catechin) | 11.62 | 578.1270 | 577.1270 | 451.1080; 425.0892; 407.0834; 289.0734; 245.0811; 125.0239 | 3 |
| 36 | Caffeic and coumaric acid derivative | 12.20 | 542.1494 | 541.1494 | 523.1466; 475.1519; 361.0900; 235.0490; 215.0901; 179.0358; 163.0398; 137.0249 | 4 |
| 37 | 1-O-Coumaroylquinic acid | 12.28 | 338.0840 | 337.0840 | 191.0509; 173.0417; 163.0356 | 1,2 |
| 38 | Glucogallic acid tartaric ester | 12.33 | 464.1040 | 463.1040 | 331.0608; 169.0147; 168.0037; 149.9937; 125.0212 | 3 |
| 39 | Caffeic acid glucoside | 12.34 | 342.0825 | 341.0825 | 179.0344; 161.0230; 135.0440 | 4 |
| 40 | Gallic acid glucoside derivative | 12.55 | 412.0173 | 411.0173 | 367.355; 331.0632; 240.9965; 169.0091; 125.0157 | 2 |
| 41 | Caffeic acid derivative hexoside | 12.63 | 542.1494 | 541.1494 | 379.0983; 179.0323; 161.0220; 135.0425 | 4 |
| 42 | Methyl gallate hexoside-pentoside | 12.70 | 448.1542 | 447.1542 | 345.1151; 183.0660; 168.0382; 161.0437 | 3 |
| 43 | (Epi)gallocatechin | 13.18 | 306.0612 | 305.0612 | 287.0562; 269.0489; 219.0678; 195.0310; 179.0321; 161.0246; 137.0237; 125. 0235 | 3 |
| 44 | 5-O-Caffeoylquinic acid | 13.27 | 354.0811 | 353.0811 | 191.0521; 161.0214; 135.0406 | 1,2,3 |
| 45 | Dihydroxycoumarin | 13.47 | 178.0152 | 177.0152 | 161.0960; 133.0279; 105.0338 | 4 |
| 46 | 3-O-Feruloylquinic acid | 13.66 | 368.0964 | 367.0964 | 193.0481; 173.0430; 134.0355 | 2 |
| 47 | 4-O-Caffeoylquinic acid | 14.32 | 354.0811 | 353.0811 | 191.0516; 179.0306; 173.0412; 135.0414 | 2 |
| 48 | Caffeic acid | 14.41 | 180.0293 | 179.0293 | 135.0451 | 1,4 |
| 49 | Coumaroyltartaric acid isomer 1 | 14.68 | 296.0404 | 295.0404 | 163.0357; 149.0051; 130.9957; 119.0460 | 2 |
| 50 | Tartaric acid | 14.94 | 150.0055 | 149.0055 | 130.9997; 102.9993; 87.0065 | 2 |
| 51 | 4-O-Methylgallocatechin | 15.25 | 320.0763 | 319.0763 | 287.0497; 243.0251; 197.0451; 161.0242; 125.0233 | 3 |
| 52 | Caffeic and hydroxycinnamic acid derivative | 15.39 | 380.0995 | 379.0995 | 369.0971; 251.0590; 217.0658; 179.0345; 161.0261; 135.0426 | 4 |
| 53 | Coumaric acid hexoside derivative | 15.49 | 442.0969 | 441.0969 | 325.0912; 163.0378; 119.0507 | 2 |
| 54 | Coumaric acid | 15.76 | 164.0361 | 163.0361 | 119.0483 | 2 |
| 55 | Coumaroyltartaric acid isomer 2 | 15.82 | 296.0404 | 295.0404 | 163.0363; 149.0056; 130.9944; 119.0472 | 2 |
| 56 | B-type procyanidin trimer | 16.03 | 866.1873 | 865.1873 | 739.1731; 713.1525; 577.1396; 425.0996; 287.0524; 245.0479; 125.0216 | 3 |
| 57 | Caffeic acid pentoside | 16.15 | 312.0340 | 311.0340 | 179.0036; 135.0380 | 2 |
| 58 | 4-O-p-Coumaroylquinic acid | 16.33 | 338.0871 | 337.0871 | 191.0520; 173.0423; 163.0363 | 1,2 |
| 59 | Procyanidin B (dimer of (epi)catechin) | 16.54 | 578.1226 | 577.1226 | 451.0947; 425.0842; 407.0791; 289.0774; 245.0500 | 1,3 |
| 60 | Caffeic acid and hydroxycoumarin derivative | 16.93 | 458.1282 | 457.1282 | 383.0989; 221.0481; 179.0362; 161.0255; 135.0433; 133.0275; 117.0335 | 4 |
| 61 | (Epi)catechin derivative | 17.11 | 326.0425 | 325.0425 | 289.0667; 245.0790; 205.0449; 125.0275 | 3 |
| 62 | Sinapoyl-ferulate | 17.22 | 400.0876 | 399.0876 | 223.0469; 205.0374; 193.0429; 129.0150; 111.0050; 85.0271 | 2 |
| 63 | (Epi)catechin | 17.26 | 290.0637 | 289.0637 | 245.0785; 205.0476; 187.0356; 179.0295; 125.0258 | 1,3 |
| 64 | Ferulic acid pentoside | 18.03 | 326.0500 | 325.0500 | 193.0474; 178.0238; 134.0347 | 2 |
| 65 | Caffeoylshikimic acid | 18.03 | 336.0713 | 335.0713 | 179.0325; 173. 0429; 161.0208; 135.0420 | 2 |
| 66 | 5-O-p-Coumaroylquinic acid | 18.50 | 338.0871 | 337.0871 | 191.0514; 173.0417; 163.0356 | 1,2 |
| 67 | Unidentified | 18.67 | 578.1268 | 577.1268 | 541.1482; 379.0918; 179.0298; 161.0208; 135.0406 | 4 |
| 68 | Caffeoylshikimic acid isomer | 19.17 | 336.0713 | 335.0713 | 179.0302; 173. 0411; 161.0200; 155.0291; 135.0415 | 1, 2 |
| 69 | B-type procyanidin trimer | 19.20 | 866.1873 | 865.1873 | 739.1553; 713.1344; 577.1240; 425.0756; 287.0531; 245.0383; 125.0183 | 3 |
| 70 | 4-O-Feruloylquinic acid | 19.75 | 368.0972 | 367.0972 | 191.0531; 173.0423 | 1,2 |
| 71 | Caffeoylmalic acid | 20.07 | 296.0416 | 295.0416 | 179.0315; 133.115; 115.0010 | 1,2 |
| 72 | Procyanidin B (dimer of (epi)catechin) derivative | 20.07 | 880.1656 | 879.1656 | 727.1275; 577.1073; 439.0638; 407.0538; 287.0468; 245.0405; 125.0207 | 3 |
| 73 | B-type procyanidin trimer | 20.38 | 866.1873 | 865.1873 | 739.1553; 713.1344; 577.1292; 451.0938; 425.0813; 407.0716; 287.0522; 245.0383; 125.0207 | 3 |
| 74 | (Epi)catechin-(epi)gallocatechin | 20.55 | 594.1023 | 593.1223 | 575.1061; 467.1034; 441.0792; 423.0659; 305.0549; 287.0417; 245.0385; 125.0204 | 3 |
| 75 | Procyanidin B (dimer of (epi)catechin) derivative | 20.76 | 721.6486 | 720.6486 | 644.1217; 577.1295; 289.0645; 245.0399; 125.0202 | 3 |
| 76 | Quercetin-O-di-glucoside | 21.27 | 626.1342 | 625.1342 | 463.0867; 301.0301; 300.0238; 178.9961; 151.0005 | 4 |
| 77 | Quercetin-O-di-rhamnosyl-glucoside/galcactoside | 21.28 | 756.1880 | 755.1880 | 609.1432; 300.0275; 271.0254; 178.9947; 151.0029 | 1,2,3 |
| 78 | Unidentified | 21.74 | 536.1387 | 535.1387 | 491.1498; 323.0715; 281.0600; 179.0314; 161.0215 | 4 |
| 79 | Procyanidin dimer monoglycoside | 22.18 | 740.1601 | 739.1601 | 587.1146; 459.0606; 449.0773; 435.0625; 289.062; 245.0766; 125.0214 | 3 |
| 80 | 5,8-Dihydroxy-7-methoxyflavone-O-glucoside-rhamnoside | 22.22 | 592.1811 | 591.1811; | 445.1129 325.0735; 297.0404; 293.0638; 282.0504 | 1 |
| 81 | Quercetin-3-O-arabino-glucoside | 22.24 | 596.1230 | 595.1230 | 301.0279; 300.0229; 271.0219; 255.0251; 178.9902 | 4 |
| 82 | Rutin | 23.06 | 610.1377 | 609.1377 | 301.0285; 300.0216; 271.0215; 178.9902; 150.9959 | 3,4 |
| 83 | Procyanidin B (dimer of (epi)catechin) | 23.25 | 578.1270 | 577.1270 | 451.0997; 425.0849; 407.0722; 289.0671; 125.0228 | 3 |
| 84 | Rutin-O-(p-coumaroyl) malate | 23.32 | 890.1862 | 889.1862 | 609.1328; 300.0192; 271.0182; 178.9951; 163.0345; 150.9965; 133.0093 | 1, 2 |
| 85 | Quercetin derivative hexoside | 23.85 | 566.1131 | 565.1131 | 403.1489; 301.0262; 300.0204; 271.0208; 255.0250; 178.9927; 150.9985 | 4 |
| 86 | Quercetin-O-glucoside | 23.86 | 464.0778 | 463.0778 | 300.0028; 271.0183; 178.9940; 150.9981 | 1,2,3,4 |
| 87 | Kaempferol-O-pentoside-hexoside | 24.08 | 580.1286 | 579.1286 | 447.0887; 285.0334; 284.0273; 255.0245; 227.0320; 150.9995; 133.0083 | 4 |
| 88 | Kaempferol-3-O-rhamnosyl galactoside | 24.21 | 594.1381 | 593.1381 | 285.0311; 257.0382; 255.0197; 229.0456; 187.0403 | 1, 2 |
| 89 | Ferulic acid | 24.26 | 194.0463 | 193.0463 | 178.0225; 149.0556; 134.0330; 117.0299 | 2 |
| 90 | Quercetin-O-(glucosyl-feruloylmalate) | 24.36 | 774.1473 | 773.1473 | 463.0811; 309.0561; 193.0466; 134.0333 | 1,2 |
| 91 | Quercetin-O-pentoside (arabinoside) | 24.75 | 434.0683 | 433.0686 | 301.0267; 300.0213; 271.0193; 255.0248; 227.0281; 150.9994 | 1,2,3 |
| 92 | Kaempferol-C-di-hexoside-O-hexoside | 24.85 | 772.1694 | 771.1694 | 609.1382; 485.1224; 429.0806; 383.0925; 323.0716; 285.0338; 255.0239; 227.0213; 161.0214; 133.0241 | 4 |
| 93 | Luteolin-O-glucuronide | 25.13 | 462.0664 | 461.0664 | 285.0343; 175.0245; 133.0246; | 4 |
| 94 | Kaempferol-O-glucoside | 25.18 | 448.0832 | 447.0832 | 284.0261; 255.0237; 227.0277; 150.9974 | 1 |
| 95 | Quercetin-O-(caffeoyl-di-glucoside) | 25.44 | 788.1650 | 787.1650 | 625.1372; 461.0677; 387.1494; 301.0286; 300.0232; 179.0375; 161.0161 | 4 |
| 96 | Quercetin-O-glucuronide | 25.71 | 478.0832 | 477.0832 | 301.0285; 271.0556; 178.9914; 150.9982 | 1,2,3 |
| 97 | Quercetin-O-arabinoside-di-glucoside | 25.92 | 758.1530 | 757.1530 | 595.1207; 463.0830; 301.0292; 300.0215; 178.9928; 150.9968 | 4 |
| 98 | Quercetin-O-glucoside-arabinoside-glucuronide | 26.21 | 772.1694 | 771.1694 | 595.1243; 301.0275; 300.0228; 271.0201; 178.9963; 150.9999 | 4 |
| 99 | Kaempferol-O-di-pentoside | 26.40 | 550.1142 | 549.1142 | 417.0841; 285.0453 | 1,3 |
| 100 | Kaempferol-O-pentoside | 26.42 | 418.0743 | 417.0743 | 284.0376; 285.0421 | 1,2 |
| 101 | Di-caffeoyl-dihydroxybenzoic acid | 26.60 | 478.0983 | 477.0983 | 433.1033; 315.0667; 179.0321; 161.0204; 153.0140; 152.0098; 135.0443; 109.0295; 108.0158 | 4 |
| 102 | (Epi)-afzelechin-7-O-glucoside | 26.82 | 436.1199 | 435.1199 | 345.0936; 273.0730; 167.0336 | 1 |
| 103 | Kaempferol-O-(caffeoyl-arabinoside-glucoside | 27.09 | 742.1608 | 741.1608 | 579.1326; 455.1050; 429.0733; 285.0349; 284.0270; 255.0312; 227.0223; 179.0308; 161.0221; 135.0376 | 4 |
| 104 | Kaempferol-O-rhamnoside | 27.88 | 432.0906 | 431.0906 | 285.0431; 284.0317; 255.0287; 227.0334 | 1,2 |
| 105 | Quercetin-O-glucoside-arabinoside-glucuronide | 27.99 | 772.1694 | 771.1694 | 595.1228; 301.0258; 300.0216; 271.0204; 255.0185; 178.9945; 150.9824 | 4 |
| 106 | Kaempferol-O-arabinosisde-glucoside-rhamnoside | 29.28 | 726.1658 | 725.1658 | 579.1227; 285.0346; 284.0272; 255.0222; 227.0298 | 4 |
| 107 | Luteolin | 31.09 | 286.0364 | 285.0364 | 175.0368; 133.0300 | 4 |
| 108 | Trihydroxy-octadecadienoic acid | 32.36 | 328.2116 | 327.2116 | 291.1989; 229.1460; 211.1336; 171.1031 | 2,4 |
| 109 | Unidentified | 32.36 | 396.1960 | 395.1960 | 349.2045; 327.2269; 251.1307; 233.1170; 193.0888; 171.1032 | 1, 3 |
| 110 | Trihydroxy-octadecenoic acid | 33.91 | 330.2292 | 329.2292 | 311.2203; 293.1239; 229.1450; 211.1334; 171.1011 | 4 |
| 111 | 12-oxo-10E-dodecenoic acid | 34.01 | 228.1222 | 227.1222 | 209.1179; 183.1395; 165.1298 | 1,2 |
| 112 | Apigenin | 34.28 | 270.0417 | 269.0417 | 227.0349; 151.0027; 117.0349; 107.0126 | 4 |
| 113 | Trihydroxy-octadecenoic acid derivative | 35.261 | 444.1493 | 443.1493 | 329.2280; 309.1244; 293.1891 | 4 |
| 114 | 12-oxo-10E-dodecenoic acid derivative | 43.89 | 722.3519 | 721.3519 | 675.3594; 397.1348; 227.2159 | 1,4 |
| 115 | Hydroxy octadecatrienoic acid | 47.40 | 294.2048 | 293.2048 | 275.2015; 224.1403; 195.1388 | 1,2,4 |
| 116 | Palmitic acid derivative | 47.50 | 700.3671 | 699.3671 | 653.7889; 397.1369; 255.2329 | 1 |
| 117 | Palmitic acid derivative | 48.36 | 541.3192 | 540.3192 | 480.3059; 255.2310 | 1,3,4 |
| 118 | Hydroxy octadecadienoic acid derivative | 49.62 | 366.2055 | 365.2055 | 317.2080; 295.2254; 277.2110 | 1,2 |