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. 2020 Feb 1;9(2):123. doi: 10.3390/antiox9020123

Table 1.

Resolution UHPLC-PDA-Q-Orbitrap identification of biomolecules from ZpRe resin.

Peak Retention Time (min) UV Max Tentative Identification Elemental Composition [M − H]− Theoretical Mass (m/z) Measured Mass (m/z) Accuracy(δ ppm) MSnIons
1 1.33 unknown C16H15O5 85.00343
2 2.77 279 Naringenin a C15H11O5 271.06110 271.0601 3.67
3 3.35 279–367 Shikoniin a C16H15O5 287.09325 287.0923 3.40
4 3.65 279 Afzelechin a C15H13O5 273.07575 273.0766 3.22
5 4.05 - Calonectrin a C19H25O6 349.16456 349.1654 2.58 85.00342
6 4.18 279 EpiAfzelechin a C15H13O5 273.07575 273.0766 3.10
7 4.28 287 Naringenin enantiomer a C15H11O5 271.06195 271.0611 3.67 151.0394:109.0286
8 4.31 287 3,7-dihydroxiflavanone C15H11O4 255.06519 255.0661 3.67 151.0394:109. 0286
9 4.61 287 7,8-dihydroxiflavone C15H11O4 255.06519 255.0661 3.11 237.0553
10 5.12 287 5-hydroxy-4′,7-dimethoxyflavanone C17H15O5 299.09140 299.0929 2.95 285.0403;179.0345, 135.0444
11 5.38 287 3,7,8-trihydroxydihydroflavanone C15H11O5 271.06010 271.0610 3.33 253.0503;225.0552;
197.0603;151.0029
12 5.67 234-292-325 1-methyl-3-(3′,4′-dihydroxyphenyl)-propyl caffeic acid ester C19H19O6 343.11761 343.1187 2.49 179.0344;161.0236;
135.0443
13 5.88 236-277-312 1-methyl-3-(3′,4′-dihydroxyphenyl)-propyl caffeic acid ester isomer a C19H19O6 343.11761 343.1183 2.22 257.0818;179.0345;
151.0393;135.0444;
107.0494
14 5.88 236-277-312 Guibourtinidol a C15H13O4 257.08084 257.0816 3.10 179.0345;151.0393;
135.0444;107.0494
15 6.14 279–367 1-methyl-3-(3′,4′-dihydroxyphenil)-propyl caffeic acid ester isomer a C19H19O6 343.11853 343.1187 2.66 287.0818;151.0393;
119.0495;107.0494
16 6.14 279–367 Shikoniin isomer a C16H15O5 287.09140 287.0923 3.18 151.0393;119.0495;
107.0494
17 6.27 285 7,4′-dihydroxy-5-methoxy-flavanone C16H13O5 285.07575 285.0766 3.19 149.9952;119.0495
18 6.73 287 Dihydroxyflavanone C15H11O4 255.06519 255.0669 3.05 237.0553;209.0604;
195.0400
19 6.91 251–349 Rhamnetin a C16H11O7 315.04993 315. 0511 3.18 185.0034,146.93796
20 7.18 246-324-237 3,7-dihydroxyflavone C15H9O4 253.05029 253.0495 2.99 208.0524;223.0326;
195.0447; 180.0576
21 7.31 277 314 1-methyl-3-(4′-hydroxyphenil)-propyl caffeic acid ester C19H19O5 327.12357 327.1227 2.64 135.0443
22 7.55 242, 291–324 2-methyl-3-(3-hydroxy-4′-methoxyphenyl)-propyl caffeic acid ester C20H21O6 357.13409 357.1332 2.32 343.1104;193.0500;
179.0343;161.0237;135.0440
23 7.70 249-285-323 1-methyl-3-(4′-hydroxyphenil)-propyl caffeic acid ester isomer a C19H19O5 327.12380 327.1227 3.01 179.0344;163.0394;
135.0443;119.0494
24 8.04 235-343 Pinocembrin C15H11O4 255.06601 255.0651 3.23 227.0907;213.0503;
164.0109;151.0029;
123.0080
25 8.54 239–306 2′hydroxy-4-methoxychalcone a C16H13O3 253.08592 253.0866 3.02
26 9.00 291 Pinocembrin isomer a C15H11O4 255.06599 255.0651 3.17 227.0709;213.0553;
164.0109;145.0642;
123.0080
27 9.14 267-315-360 Galangin(3,5,7-trihydroxyflavone) C15H9O5 269.04579 269.0453 3.22 213.0551;169.0653
28 9.39 242-268-310-357 Caffeic acid phenetyl esther C17H15O14 283.09649 283.0794 3.38
29 9.61 271 4′-terbutyloxyphenyl p-coumaric acid ester C19H19O4 311.12866 311.1286 2.91 163.0394;119.0490
30 9.67 231-308
347		 1-methyl-3-(4′-hydroxyphenyl)-propyl p-coumaric acid ester C19H19O4 311.12779 311.1289 2.91 179.0344;163.0394;
134.0366;119.0490
31 9.88 231-308-347 1-methyl-3-(4′-hydroxyphenyl)-propyl p-coumaric
acid ester isomer a 		C19H19O4 311.12866 311.1289 2.81 179.0344;163.0394;
135.0444;119.0494
32 10.80 277–312 Dunnione a C15H13O3 241.08592 241.0866 2.98
33 10.88 287 Flavanone * C15H11O3 239.07027 239.0709 2.91 197.0603;169.0653;
153.0186;135.0080;
121.0280
34 10.90 232–346 2′,4′-dihydroxychalcone C15H11O3 239.07027 239.0710 197.0603;169.0653;
153.0186;135.0080;
121.0280
35 11.37 232–345 2′,4′-dihydroxy-3′-methoxychalcone C16H13O4 269.08167 269.0808 3.08
36 11.77 285 Blestriarene B a C30H23O6 479.14957 479.14891 1.36
37 11.91 280–323 4′-terbutyloxyphenyl p-coumaric acid ester isomer a C19H19O4 311.12779 311.1286 2.71 179.0344;161.0237;
135.0442
38 12.72 283 Glyvenol a C29H33O6 477.22754 477.2271 0.78
39 12.95 293 1-methyl-3-(3′,4′-dihydroxyphenil)-propyl caffeic acid ester isomer a C19H19O6 343.11761 343.1183 179.0344; 161.0238;
135.0444:
109.0286
40 13.19 280 Vedelianin a C29H35O6 479.24882 479.2433 1.17
41 13.47 280 Hidroxivedelianin a C29H35O7 495.23773 495.2381 0.82 161.0238;135.0443;
109.0286
42 13.93 3,7-dimethyl-2-octaenyl caffeic acid ester C19H21O4 313.14344 313.1443 2.91
43 14.04 267–357 hidroxivedelianin isomer a C29H35O7 495.23785 495.2377 0.25 479.2432;239.0710;
179.0345;161.0238;
135.0442
44 14.42 285 Vedelianin reduced a C29H33O6 477.22717 477.2276 1.10
45 15.26 285–320 3,7-dimethyl-2,6-octadienyl caffeic acid ester (geranyl Caffeate) C19H23O4 315.16993 315.1600 3.10 178.0265;134.0364;
133. 0289
46 16.58 289-320 Lupinifolin C25H25O6 405.16965 405.1754 −1.27
47 16.58 289 Vedelianin isomer a C29H35O6 479.24882 479.2433 1.17
48 16.89 287 Shinflavanone a C25H25O4 389.17474 389.1756 2.37 371.1654
49 17.39 285 Morusin a C25H23O6 419.1502 419.14891 2.21 363.0873;179.0344;
151.0354;109.0286
50 19.23 291 8-C-Prenyl-6″,6″-dimethylpyrano [2″,3″:7,6] flavanone a C25H25O3 373.19782 373.1806 2.09
51 19.68 287 Shinflavanone isomer a C25H25O4 389.17474 389.1757 2.52

a New reports for the species Zuccagnia punctata.