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. 2020 Feb 18;9(2):166. doi: 10.3390/antiox9020166

Table 1.

LC-MS/MS data and tentative characterization of compounds from Anthyllis vulneraria, Fuchsia magellanica, Fuchsia triphylla and Lysimachia nummularia leaf extracts.

No. tR (min) λmax (nm) [M−H]− (m/z) Fragment ions (m/z) Tentative Characterization a Presence and Relative Abundance (%) of Compounds in the Leaf Extracts b Ref.
AvEc AvWc FmEc FmWc Ft Ec FtWc LnEc LnWc
1 2.0 315 343 179, 135 Caffeic acid derivative 0.1 [39]
2 2.2 306 533, 375, 217, 173, 149 Cinnamoylquinic acid derivative 0.3 [39]
3 2.5 315 341 (683) 179, 149, 135 Caffeoyl-O-hexoside (dimer) 0.2 0.3 0.2 [40]
4 2.6 265, 312 337 267, 191, 163, 149, 135 5-p-Coumaroylquinic acid 0.2 0.1 0.1 [39]
5 3.2 288sh, 311 639, 353 191 Caffeoylquinic acid derivative 0.3 0.9 [39]
6 7.1 272 331 169, 125 Galloyl hexoside 0.2 0.2 [41]
7 9.5 311 355 191 Coumaroyl glucarate isomer 0.1 2.9 [42]
8 10.1 298sh, 320 371 209, 191, 179 Caffeoylquinic acid derivative 0.5 [39]
9 10.5 260 611 305 n.i. 2.0 1.8 -
10 10.5 298, 310 355 209, 191, 163 Coumaroyl glucarate isomer 0.5 1.3 [42]
11 10.6 298, 320 549 387, 369, 267, 249, 137 Cinnamic acid derivative 0.3 [43]
12 10.6 298 331 169, 125 Galloyl hexoside 2.6 [41]
13 10.9 300 301 168, 150, 125 Galloyl pentoside 0.2 [41]
14 11.9 282sh, 307 355 (711) 271, 209, 191 Coumaroyl glucarate isomer (dimer) 3.4 [42]
15 12.6 283sh, 312 355 271, 209, 191 Coumaroyl glucarate isomer 1.9 5.0 6.9 [42]
16 13.0 290, 328sh 297, (595) 179, 161, 135 Caffeic acid derivative (dimer) 2.0 2.4 4.0 [39]
17 13.0 296 575 413, 351, 267, 249, 163, 113 Coumaric acid derivative 0.5 [39]
18 13.1 310 385 209, 191 Feruloyl glucarate 2.2 3.9 [42]
19 13.2 255, 350 787 625, 462, 301, 299 Quercetin 3-O-hexosyl-hexosyl-7-O-hexoside 1.0 [44]
20 13.3 283sh, 312 385 209, 191 Feruloyl glucarate 0.7 3.0 10.2 [42]
21 13.5 265, 349 771 609, 462, 301, 299, 285, 284, 283, 179 Quercetin 3-O-hexosyl-desoxyhexosyl-7-O-hexoside 2.2 1.0 [44]
22 13.8 288sh, 312 385 271, 209, 191, 163, 146, 119 Feruloyl glucarate 3.0 2.3 [42]
23 13.9 265, 349 771 609, 446, 445, 285, 284, 283, 179 Kaempferol 3-O-hexosyl-hexosyl-7-O-hexoside 2.6 0.9 [44]
24 13.9 276 475, 453 - n.i. 2.5 -
25 14.4 264, 351 755 593, 446, 284, 283 Kaempferol 3-O-hexosyl-desoxyhexosyl-7-O-hexoside 2.5 2.9 [45]
26 15.0 272 651 399, 325, 163 n.i. 1.9 2.9 -
27 15.2 256, 354 625 463, 462, 301, 299 Quercetin 3-O-hexosyl-7-O-hexoside 1.6 1.2 [45]
28 15.7 257, 352 595 462, 433, 301, 299, 271 Quercetin 3-O-pentosyl-7-O-hexoside 0.7 1.2 [41]
29 15.8 268 305 225, 147, 135 n.i. 0.8 0.5 0.9 1.3 -
30 16.2 265, 347 609 447, 446, 285, 283 Kaempferol 3-O-hexosyl-7-O-hexoside 1.7 0.5 [41]
31 16.4 278 449 357, 275 n.i. 1.5 0.9 -
32 16.5 288sh, 321 575 443, 267, 249, 193, 175 1,3-O-Diferuloylglycerol pentoside 0.7 [46]
33 16.6 254, 354 639 519, 477, 461, 315, 314, 313, 299, 151 Isorhamnetin 3-O-hexosyl-7-O-hexoside 4.6 1.4 [47]
34 17.2 268, 295sh 693 477, 345, 327, 315, 300, 207, 183, 165 n.i. 1.8 -
35 17.4 252, 269sh, 332 443 267, 249, 193, 175, 149, 134, 113 1,3-O-Diferuloylglycerol 5.1 4.4 [46]
36 17.5 252, 269sh, 352 963 801, 625 Flavonoid 0.6 [43]
37 18.0 260 197 n.i. 3.2 -
38 18.0 268, 350 639 319, 301, 283, 239, 213, 203, 197, 157, 142, 130, 116, 109 Flavonoid 6.2 6.5 [43]
39 18.1 276 521 337, 191, 163 Coumaroylquinic acid derivative 1.2 0.7 [39]
40 18.2 266, 350 625 463, 300, 271, 255, 243, 179 Quercetin 3-O-hexosyl-hexoside 2.9 2.5 [47]
41 19.2 274 387 (775) 169, 151, 124 Gallic acid derivative (dimer) 0.4 0.2 [46]
42 19.3 274 537 271, 211, 169, 151, 124 Gallic acid derivative 0.2 0.1 [46]
43 19.3 266, 357 625 479, 306 Myricetin 3-O-desoxyhexosyl-hexoside 2.3 1.5 [48]
44 19.3 266, 355 609 429, 285, 284, 255, 227 Kaempferol 3-O-hexosyl-hexoside 1.2 2.6 [41]
45 19.4 267, 357 479 316 Myricetin 3-O-hexoside 1.1 0.8 -
46 19.5 262, 355 615 463, 301, 300, 271, 169 Quercetin galloyl hexoside 0.4 0.4 1.8 1.0 [47]
47 19.6 264, 352 639 459, 315, 314, 257 Isorhamnetin 3-O-hexosyl-hexoside 1.9 [49]
48 19.8 266, 331 593 429, 284, 255, 227 Kaempferol 3-O-desoxyhexosyl-hexoside 2.7 1.7 [41]
49 20.2 260, 354 463 317, 316 Myricetin 3-O-desoxyhexoside 22.0 17.2 [50]
50 20.3 255, 293sh, 359 615 301 Quercetin galloyl hexoside 0.1 0.1 [47]
51 20.5 259, 356 477 301, 283, 255, 179, 151, 121 Quercetin glucuronide 0.5 0.2 0.6 0.6 [47]
52 20.6 257, 268sh, 356 433 301, 300 Quercetin 3-O-pentoside 0.1 0.1 [47]
53 20.7 257, 268sh, 356 615 301 Quercetin galloyl hexoside 0.9 0.5 [51]
54 20.7 260, 353 463 317, 316 Myricetin 3-O-desoxyhexoside 2.4 [50]
55 20.8 257, 355 463 301, 300, 271, 255, 243, 179, 163, 151 Quercetin 3-O-hexoside 3.6 4.9 0.1 0.1 0.6 0.5 [41]
56 20.9 266, 350 579 463, 315, 313 Isorhamnetin-3-O-pentosyl-7-O-pentoside 5.0 3.8 [47]
57 20.9 257, 355 609 463, 301, 300, 299 Quercetin 3-O-desoxyhexosyl-7-O-hexoside 0.1 0.1 0.2 0.5 0.8 1.8 [48]
58 21 257, 355 599 447, 313, 285, 169 Kaempferol galloyl hexoside 0.1 0.1 [43]
59 21.3 256, 356 433 300, 271, 255, 151 Quercetin 3-O-pentoside 2.4 2.0 0.2 0.1 0.4 0.4 [47]
60 21.5 254, 368 301 284, 245, 229, 201, 185, 145, 129, 117 Ellagic acid 0.3 0.1 1.1 0.6 [51]
61 21.7 266, 350 447 284, 255, 227, 151 Kaempferol 3-O-hexoside 2.6 2.2 0.2 0.1 [41]
62 21.7 266, 350 447 301, 300, 271, 255, 179, 151 Quercetin 3-O-desoxyhexoside 1.1 1.2 [47]
63 21.8 266, 332 705 437, 407, 325, 245, 231, 199, 163, 121 n.i. 2.4 1.8 -
64 21.8 266, 350 521 331, 271, 211, 169 Galloyl hexoside derivative 0.5 0.3 [41]
65 21.9 517 267, 249, 205, 161, 113 n.i. 2.0 1.2 -
66 22.0 266, 347 447 284, 255, 227 Kaempferol 3-O-hexoside 0.4 0.2 [41]
67 22.0 255, 350 477 315, 314, 285, 271, 257, 243 Isorhamnetin 3-O-hexoside 1.8 4.2 [52]
68 22.0 264, 340 477 331, 317 Myricetin desoxyhexoside derivative 2.8 3.4 [53]
69 22.0 264, 340 447 331, 317 Myricetin derivative 2.5 1.0 [53]
70 22.3 266, 340 639 477, 459, 315, 314, 267 Isorhamnetin 3-O-hexosyl-hexoside 1.1 2.6 [52]
71 22.3 266, 347 417 285, 284, 255, 227 Kaempferol 3-O-pentoside 0.3 0.2 [41]
72 22.4 267, 328 727 551, 491, 415, 267, 249 Ferulic acid derivative 2.0 [54]
73 22.4 623 431, 371, 345, 317, 301, 299 n.i. 0.8 0.5 -
74 22.5 267, 328 727 551, 415, 267, 183 Ferulic acid derivative 1.4 [54]
75 22.8 255, 266sh, 334 447 314, 285, 271, 257, 243 Isorhamnetin 3-O-pentoside 1.3 [52]
76 22.9 266, 351 599 447, 301, 300, 179, 151 Quercetin 3-O-desoxyhexoside derivative 0.1 0.1 [47]
77 23.4 266, 348 623 443, 299, 298, 283, 271 Rhamnocitrin 3-O-dihexozid 3.8 3.2 [54]
78 23.7 268, 339 609 315, 314, 193 Isorhamnetin 3-O-pentosyl-hexoside 0.6 1.5 [52]
79 23.8 268, 329 799 623, 485, 397, 299, 298 n.i. 2.1 0.7 -
80 24.8 477 301, 267, 249, 227, 209, 183, 165, 113 Ellagic acid derivative 0.6 [51]
81 24.9 250, 370 531 301, 300 Quercetin derivative 0.1 0.5 [47]
82 24.9 266, 344 593 413, 299, 298, 283 Rhamnocitrin 3-O-hexosyl-pentoside 1.1 0.7 [54]

a Compound numbers and retention times (tR) refer to UV chromatograms shown in Supplementary Materials (Figures S1–S8). b Relative abundance: area% of the compound calculated from the summarized areas of all compounds detected in the UV (280 nm) chromatogram. c Abbreviations: AvE: Anthyllis vulneraria 50% (v/v) ethanolic extract, AvW: Anthyllis vulneraria aqueous extract, FmE: Fuchsia magellanica 50% (v/v) ethanolic extract, FmW: Fuchsia magellanica aqueous extract, FtE: Fuchsia triphylla ethanolic extract, FtW: Fuchsia triphylla aqueous extract, LnE: Lysimachia nummularia 50% (v/v) ethanolic extract, LnW: Lysimachia nummularia aqueous extract, n.i.: not identified.