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. 2021 Feb 11;10(2):278. doi: 10.3390/antiox10020278

Table 3.

Metabolites putatively identified in the MeOH extract of C. sativa (Marrone di Roccadaspide) burs (CSB) and leaves (CSL).

N. Compound Rt (min) a Molecular
Formula		 [M-H]− a [M-2H]2− a [(M+FA)-H]− a Delta (ppm) a Product ions (m/z) a CSB CSL
1 Sucrose 5.10 C12H22O11 341.1083 387.1137 1.38 179, 161 X X
2 Sorbitol/glucitol 5.22 C6H14O6 227.0766 2.05 181 X -
3 Monogalloyl glucose 6.44 C13H16O10 331.0665 1.59 313, 271, 211, 193, 169, 125 X X
4 NHTP-glucose (vescalin) 7.20 C27H20O18 631.0561 −0.69 613, 587, 569, 551, 467, 441, 425 X X
5 HHDP-glucose isomer 7.27 C20H18O14 481.0610 −0.61 421, 301, 275 X X
6 HHDP-glucose isomer 7.60 C20H18O14 481.0601 −0.48 421, 301, 275 X -
7 Phenol glucoside (crenatin) # 7.88 C13H18O9 317.0872 1.61 299, 155 X X
8 Digalloyl glucose isomer 8.31 C20H20O14 483.0771 −0.87 465, 331, 313, 169 X X
9 Hexahydroxydiphenic acid 8.55 C14H10O10 337.0192 0.44 293, 249, 169, 167 X -
10 Digalloyl glucose isomer 11.07 C20H20O14 483.0772 0.58 465, 331, 313, 169 X -
11 Digalloyl glucose isomer 12.29 C20H20O14 483.0763 −1.33 465, 331, 313, 169 X -
12 NHTP-valoneoyl-glucose
(castavaloninic acid)		 14.01 C48H30O31 1101.0671 550.0282 −1.44 1057, 933, 931, 631, 587, 449, 441, 425 X -
13 Castacrenin C 14.05 C27H18O17 613.0456 −0.71 595, 493, 301, 299 X -
14 Castacrenin B 14.87 C27H18O17 613.0456 −0.71 595, 493, 301, 299 X -
15 Chebulic acid isomer 14.94 C14H12O11 355.0297 0.45 337, 311, 267, 191 X -
16 Chebulic acid isomer 15.45 C14H12O11 355.0296 0.04 337, 311, 267, 191 X -
17 NHTP-HHDP-glucose
(vescalagin)		 15.67 C41H26O26 933.0611 466.0271 −1.88 915, 631, 613, 587, 569, 551, 467, 441, 425, 301 X -
18 Castamollissin/ maplexin D 15.73 b C20H20O13 467.0821 b 0.28 b 449, 423, 315, 169 - X
19 Castacrenin A 15.97 C27H18O17 613.0453 −1.10 595, 523, 493, 301, 299 X -
20 Bis-HHDP-glucose isomer
(casuariin/pedunculagin isomer)		 16.45 C34H24O22 783.0669 391.0299 −0.88 765, 481, 301, 275 X X
21 Chesnatin 16.68 C27H26O18 637.1030 −0.82 593, 467, 305 X -
22 HHDP-Valoneoyl-glucose isomer (praecoxin A/platycariin isomer) 17.13 C41H28O27 951.0714 475.0315 −2.11 907, 783, 465, 453 X -
23 Galloyl-HHDP-glucose isomer (punicacortein A-B/pterocaryanin B/gemin D) 17.46 C27H22O18 633.0718 316.0328 −0.76 615, 589, 481, 463, 301, 275, 257 X -
24 Bis-HHDP-glucose isomer (pedunculagin/casuariin isomer) 17.56 C34H24O22 783.0672 391.0298 −0.42 765, 721, 481, 301, 275 X -
25 Trigalloyl glucose isomer 17.71 C27H24O18 635.0878 −0.08 483, 465, 331, 313, 271, 211 X -
26 Galloyl-chebuloyl-HHDP-glucose (chebulagic acid) 18.03 C41H30O27 953.0881 476.0402 −1.03 909, 785 X -
27 Isochesnatin 18.05 C27H26O18 637.1030 −0.80 593, 469 X -
28 Digalloyl-HHDP-glucose isomer (1-desgalloyleugeniin isomer) 18.64 C34H26O22 785.0834 392.0372 0.22 633, 615, 483, 313, 301, 275 X X
29 Galloyl-bis-HHDP-glucose (stachyurin) 18.71 C41H28O26 935.0787 467.0347 0.25 917, 783, 633 X -
30 Methylvaloneoyl–NHTP–glucose
(vescavaloninic/castavaloninic acid methyl ester)		 18.86 C49H32O31 1115.0844 −0.01 1053, 933, 569 X -
31 Galloyl phenol glucoside dimer (chestanin) # 19.21 C40H42O26 937.1825 468.0897 −0.59 893, 637, 635, 467, 301 X X
32 Galloyl phenol glucoside
(cretanin) # 		19.22 C20H22O13 469.0974 −0.55 169 X X
33 Galloyl-chebuloyl-HHDP-glucose (chebulagic acid) 19.25 C41H30O27 953.0881 0.98 909, 785 X -
34 Trigalloyl glucose isomer 19.41 C27H24O18 635.0870 −1.34 483, 465, 331, 313, 271, 211 X -
35 Digalloyl-HHDP-glucose isomer (tellimagrandin I isomer) 19.97 C34H26O22 785.0825 392.0377 −0.69 633, 615, 483, 313, 301, 275 X X
36 Trigalloyl glucose isomer 20.20 C20H22O13 635.0873 0.75 483, 465, 313, 271, 211 X X
37 3-O-SSupp-coumaroylquinic acid 20.21 C16H18O8 337.0920 0.55 191, 179 X -
38 Galloyl phenol glucoside 20.58 b C20H22O13 469.0980 b 0.75 b 169 - X
39 coumaroylquinic acid 20.72 C16H18O8 337.0919 0.37 191, 179 X X
40 Galloyl-methylchebuloyl-HHDP-glucose (chebulagic acid methyl ester) 20.74 C42H32O27 967.1033 483.0481 −1.50 785, 765 X X
41 Galloyl phenol glucoside dimer (isochestanin) 20.75 b C40H42O26 937.1877 b −0.40 b 637, 467 - X
42 Ellagic acid pentoside 20.84 C19H14O12 433.0402 0.09 301, 300 X X
43 Euphorbin A/B 21.15 C82H58O53 944.0816 1419, 922, 860, 783, 467, 301 X -
44 Nobotanin A/Malabathrin B/1-Desgalloylrugosin F/Zeylaniin A isomer 21.35 C75H52O48 859.0722 0.41 1417, 1115, 1085, 937, 917, 783, 767, 301 X -
45 Galloyl-methylchebuloyl-HHDP-glucose (chebulagic acid methyl ester) 21.44 C42H32O27 967.1038 483.0478 −0.99 785, 765 X X
46 Rugosin E/Camptothin B 21.56 C75H54O48 860.0796 −1.40 1419, 1089, 953, 937, 935, 917, 909, 785, 767, 699, 615, 597, 465, 301, 275, 249 X -
47 Digalloyl-HHDP-glucose isomer (tellimagrandin I isomer) 21.77 C34H26O22 785.0833 392.0378 0.03 633, 615, 483, 313, 301 X X
48 Quercetin galloyl hexoside 21.99 C28H24O16 615.0969 −1.95 463, 301 X X
49 Valoneic acid dilactone 22.21 C21H10O13 469.0035 −0.55 425, 301, 299, 169 X -
50 Rugosin E/Camptothin B 22.42 C75H54O48 860.0798 1.26 1419, 1089, 953, 937, 935, 917, 909, 785, 767, 699, 615, 597, 465, 301, 275, 249 X -
51 Isorhamnetin deoxyhexose hexoside 22.52 C28H32O16 623.1603 −0.61 315, 300, 271 X X
52 Kaempferol deoxyhexose hexoside 22.57 C27H30O15 593.1500 −0.13 285 X X
53 Methylellagic acid hexoside 22.62 b C21H18O13 477.0662 b −0.24 b 315, 301 - X
54 Quercetin 3-O-β-D-glucopyranoside # 22.74 C21H20O12 463.0869 −0.19 301 X X
55 Quercetin hexuronoside 22.80 C21H18O13 477.0660 −0.75 301 X -
56 Galloyl phenol glucoside gallate (galloyl-cretanin) 22.97 C27H26O17 621.1082 −0.38 577, 469, 451, 317, 313 X X
57 Trigalloyl-HHDP-glucose (Tellimagrandin II) 23.05 C41H30O26 937.0933 468.0430 0.03 MS2 (468): 767, 635, 633, 617, 392 [M−2H−152]2−, 313, 301, 169 X X
58 Tetragalloyl glucose isomer 23.14 C34H28O22 787.0987 393.0453 −0.14 635, 617, 483, 465, 447, 295 X X
59 Kaempferol hexoside (astragalin) 23.97 C21H20O11 447.0922 0.07 327, 285 X X
60 Ellagic acid # 24.37 C14H6O8 300.9989 0.47 284, 257, 229, 201, 185, 145 X X
61 Isorhamnetin 3-O-β-D-glucopyranoside # 24.60 C22H22O12 477.1029 0.33 357, 315, 314 X X
62 Quercetin pentoside 24.68 b C20H18 O11 433.0769 b 0.77 b 301, 300 - X
63 Quercetin 3-O-α-L-rhamnopyranoside # 25.06 b C21H20O11 447.0924 b 0.50 b 301 - X
64 Methyl coumaroyl quinate 25.11 C17H20O8 351.1082 2.29 163 X X
65 Methylellagic acid pentoside 25.51 C20H16O12 447.0553 −1.12 315, 301, 300 X X
66 Isorhamnetin hexuronoside 26.05 C22H20O13 491.0818 −0.40 315, 301 X X
67 Lignan hexoside 27.01 C26H32O11 519.1862 0.14 357 X X
68 Valoneic acid dilactone methyl ester 27.14 C22H12O13 483.01902 −0.53 451, 301 X X
69 Bartogenic acid hexoside 27.33 C36H56O12 679.3693 725.3736 0.67 559, 517, 455 X -
70 Lignan hexoside 27.34 C26H34O11 521.2018 567.2074 0.19 359, 341, 177 X X
71 Dimethylellagic acid pentoside 27.53 C21H18O12 461.0713 −0.35 446, 328, 313, 299, 285, 284 X X
72 Quercetin coumaroyl hexoside 29.43 C30H26O14 609.1234 −0.77 463, 301 X X
73 Dimethylellagic acid deoxyhexoside 29.70 C22H20O12 475.0865 −1.23 460, 328, 313, 299, 275, 217, 193 X X
74 Trimethylellagic acid hexoside 30.74 C23H22O13 505.0981 551.1031 343, 328, 313, 299, 284 X X
75 Kaempferol coumaroyl hexoside 32.45 C30H26O13 593.1285 −0.72 447, 285, 257, 229 X -
76 Kaempferol coumaroyl hexoside 32.87 C30H26O13 593.1285 −0.72 447, 285, 257, 229 X -
77 Kaempferol deoxyhexosyl coumaroyl hexoside 33.27 b C36H36O17 739.1870 b 0.18 b 593, 575, 453, 285 - X
78 Isorhamnetin coumaroyl hexoside 33.29 C31H28O14 623.1394 −0.21 477, 315, 300 X X
79 Kaempferol coumaroyl hexoside 34.02 C30H26O13 593.1284 −0.92 447, 285, 257, 229 X X
80 Castaartancrenoic acid D/E hexoside 34.17 b C36H58O10 649.3951 b 695.3998 b 0.67 b 649, 487 - X
81 Kaempferol coumaroyl hexoside 34.57 C30H26O13 593.1285 −0.82 447, 285, 257, 229 X X
82 Roburgenic acid isomer 35.58 C30H46O8 533.3109 0.03 485, 471, 457, 453 X -
83 Isorhamnetin coumaroyl hexoside 37.04 b C31H28O14 623.1395 b −0.10 b 477, 315, 300 - X
84 Dimethylellagic acid 38.17 C16H10O8 329.0296 1.33 314, 299, 285 X -
85 Trimethylellagic acid deoxyhexoside 38.51 C23H22O12 535.1085 0.43 343, 328, 313, 299 X -
86 l-PI (18:3) 39.28 C27H47O12P 593.2720 −0.18 413, 315, 277, 241 X X
87 Kaempferol acetyl coumaroyl hexoside 39.33 C32H28O14 635.1392 −0.58 575, 489, 285 X X
88 Castaartancrenoic acid B 39.33 C27H44O5 447.31039 −0.25 429, 401, 365 X -
89 Dimethylellagic acid 39.60 C16H10O8 329.0297 1.42 314, 299, 285 X -
90 l-PI (18:2) 40.20 C27H49O12P 595.2876 −0.84 415, 315, 279, 241, 179 X X
91 Quercetin dicoumaroyl hexoside 40.21 C39H32O16 755.1605 −0.19 609, 463, 301 X X
92 SQMG (18:3) 40.32 C27H46O11S 577.2676 −0.22 299, 277, 225 X X
93 l-PI (16:0) 40.43 C25H49O12P 571.2873 −0.77 409, 391, 333, 315, 255, 241, 223, 171 X X
94 Roburgenic acid isomer 40.43 C30H46O8 533.3104 −0.89 485, 471 X -
95 NA-GPE (18:2) 40.45 C23H44O7NP 476.2767 −0.98 415, 279, 214, 196, 153 X X
96 Bartogenic acid # 40.78 C30H46O7 517.3156 −0.72 499, 455, 437 X -
97 SQMG (18:2) 41.37 C27H48O11S 579.2831 −0.48 299, 279, 225 X X
98 SQMG (16:0) 41.55 C25H48O11S 555.2833 −0.05 299, 255, 225 X X
99 Kaempferol dicoumaroyl hexoside 41.81 C39H32O15 739.1650 −1.04 593, 575, 453, 285, X X
100 DGMG (18:3) 42.16 C33H56O14 675.3594 1.19 415, 397 X X
101 l-PG (16:0) 42.29 C22H45O9P 483.2722 0.92 391, 255, 245, 227, 153 X X
102 l-PG (18:1) 43.32 b C24H47O9P 509.2876 b 0.34 b 417, 281, 245, 227, 153 - X
103 l-PA (18:3) 43.78 C21H37O7P 431.2194 0.24 413, 277, 153 X X
104 l-PC (16:0) 44.46 C25H52O9NP 540.3298 0.18 480, 255, 225 X X
105 l-PA (18:2) 44.94 C21H39O7P 433.2350 −1.15 171, 153 X X
106 Kaempferol acetyl dicoumaroyl hexoside 45.04 C41H34O16 781.1753 −0.98 635, 617, 495, 435, 285 X X
107 l-PA (16:0) 45.26 C19H39O7P 409.2354 1.01 391, 255, 153 X X
108 Kaempferol acetyl dicoumaroyl hexoside 45.46 C41H34O16 781.1757 −0.76 635, 617, 495, 435, 285 X X
109 Kaempferol acetyl dicoumaroyl hexoside 45.87 C41H34O16 781.1754 −0.92 635, 617, 495, 435, 285 X X
110 Kaempferol acetyl dicoumaroyl hexoside 46.21 C41H34O16 781.1767 0.18 635, 617, 495, 435, 285 X -
111 l-PA (18:1) 46.36 C21H41O7P 435.2510 0.83 417, 281, 153 X X
112 Trimethylellagic acid 46.43 C17H12O8 343.0452 0.31 328, 313, 299, 297, 284, 275 X -
113 Kaempferol diacetyl dicoumaroyl hexoside 47.87 C43H36O17 823.1856 −1.31 677, 659, 635, 617, 557, 531, 391, 285 X X
114 Kaempferol diacetyl dicoumaroyl hexoside 48.04 C43H36O17 823.1865 −0.50 677, 659, 617, 391, 285 X X
115 Kaempferol diacetyl dicoumaroyl hexoside 48.34 C43H36O17 823.1862 0.83 677, 659, 635, 617, 557, 531, 391, 285 X X
116 Kaempferol diacetyl dicoumaroyl hexoside 48.57 C43H36O17 823.1864 −0.58 677, 659, 617, 557, 531, 391, 285 X -
117 PI (16:0; 18:3) 51.26 C43H77O13P 831.5017 −0.11 575, 553, 413, 391, 277, 255 X X
118 SQDG (16:0; 18:3) 51.58 b C43H76O12S 815.4966 b −0.90 b 559, 537, 277, 255 - X
119 Hederagenin 52.31 C30H40O4 471.3466 −0.50 453, 425, 407 X X
120 2-Pentadecanone 52.72 C16H32O3 271.2270 0.92 225, 209 X -
121 SQDG (16:0; 16:0) 53.21 b C41H78O12S 793.5132 b 0.20 b 537, 255, 225 - X
122 GlyCer (t18:1;h16:0) 54.01 C40H77O10N 730.5461 776.5514 −0.40 568, 550, 326, 271 X X
123 DGDG (18:3; 18:3) 54.94 b C51H84O15 935.5726 b 981.5783 b −0.08 b 657, 397, 341, 323, 277 - X
124 GlyCer (d18:2;h16:0) 55.34 C40H75O9N 712.5351 758.54028 −0.99 550, 532, 312, 296, 271, 253, 225 X X
125 DGDG (18:3, 16:0) 56.40 C49H86O15 913.5881 959.5929 2.03 657, 635, 379, 277 X X
126 DGDG (18:2, 16:0) 57.29 C49H88O15 915.6023 961.6087 −1.81 659, 635, 379 X X
127 Glycerol-ω-hydroxyacid-ferulic acid (22:0) 57.83 C35H58O8 605.4042 −0.92 531, 513, 193, 175 X -
128 GlyCer (t18:1;h22:0) 58.78 b C46H89O10N 814.6398 b −0.62 b 652, 634, 410, 355, 337, 309 - X

a Calculated from the LC-MS analysis of CSB in negative ion mode; b calculated from the LC-MS analysis of CSL in negative ion mode; # the identification of this compound was corroborated by comparison with standards.