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. 2020 Jun 16;9(6):526. doi: 10.3390/antiox9060526

Table 5.

Chromatographic (tR), mass-spectrometric data (ESI-MS) and presence in organs of compounds 1–146 found in R. rosea.

No. tR, min a ESI-MS, m/z b Group c Compound d Presence (+) in Organs, mg/g ± S.D. e
Roots Rhizome Leaves Flowers Stems
1 1.91 i 331 N GT 1-O-Galloyl glucose S + + + + +
2 2.18 i 331 N GT O-Galloyl glucose L + + + + +
3 2.33 i 331 N GT O-Galloyl glucose L + +
4 2.57 i 331 N GT O-Galloyl glucose L + +
5 2.94 i 169 N GT Gallic acid S [46] [46] + + +
6 4.61 i 483 N GT Di-O-galloyl glucose L +
7 4.78 i 483 N GT 1,6-Di-O-galloyl glucose S + + + + +
8 5.11 i 609 N PC Procyanidin dimer (EGC-EGC) L + + + +
9 5.27 i 305 N CT Gallocatechin S + + +
10 5.52 i 305 N CT Epigallocatechin S [38] +
11 5.76 i 761 N PC Procyanidin dimer (EGC-EGCG) L + [47] +
12 5.85 i 289 N CT Catechin S [38] +
13 6.27 i 635 N GT Tri-O-galloyl glucose L + +
14 6.31 i 913 N PC Procyanidin dimer (EGCG-EGCG) L + [47]
15 6.35 i 913 N PC Procyanidin trimer (EGC-EGC-EGC) L + +
16 6.48 i 1065 N PC Procyanidin trimer (EGC-EGC-EGCG) L + [47]
17 6.54 i 635 N GT 1,3,6-Tri-O-galloyl glucose S + +
18 6.78 i 635 N GT Tri-O-galloyl glucose L + + +
19 6.82 i 1217 N PC Procyanidin trimer (EGC-EGCG-EGCG) L + [47]
20 6.89 i 1369 N PC Procyanidin trimer (EGCG-EGCG-EGCG) L + [47]
21 6.92 i 1369 N PC Procyanidin tetramer (EGC-EGC-EGC-EGCG) L + +
22 7.02 i 289 N CT Epicatechin S [38] +
23 7.12 i 457 N CT Epigallocatechin gallate S [38] +
24 7.22 i 457 N CT Gallocatechin gallate S + +
25 7.41 i 1521 N PC Procyanidin tetramer (EGC-EGC-EGCG-EGCG) L + [47]
26 7.53 i 1673 N PC Procyanidin tetramer (EGC-EGCG-EGCG-EGCG) L + [47]
27 7.55 i 787 N GT Tetra-O-galloyl glucose L +
28 7.63 i 787 N GT 1,2,3,6-Tetra-O-galloyl glucose S + + +
29 7.83 i 787 N GT Tetra-O-galloyl glucose L +
30 8.07 i 441 N CT Epicatechin gallate S [38] +
31 8.14 i 787 N GT Tetra-O-galloyl glucose L +
32 8.26 i 939 N GT Penta-O-galloyl glucose L + + +
33 8.42 i 939 N GT 1,2,3,4,6-Penta-O-galloyl glucose S + + +
34 8.63 i 1091 N GT Hexa-O-galloyl glucose L + + +
35 8.72 i 1091 N GT Hexa-O-galloyl glucose L + + +
36 8.92 i 441 N CT Catechin gallate S + +
37 8.98 i 1243 N GT Hepta-O-galloyl glucose L + + +
38 9.14 i 1243 N GT Hepta-O-galloyl glucose L + + +
39 9.63 i 1395 N GT Octa-O-galloyl glucose L +
40 9.87 i 1395 N GT Octa-O-galloyl glucose L + +
41 10.04 i 1825 N PC Procyanidin tetramer (EGCG-EGCG-EGCG-EGCG) L + [47] + +
42 10.41 i 1673 N PC Procyanidin pentamer (EGC-EGC-EGC-EGC-EGCG) L + + + +
43 11.18 i 1825 N PC Procyanidin pentamer (EGC-EGC-EGC-EGCG-EGCG) L + + +
44 11.43 i 1977 N PC Procyanidin pentamer (EGC-EGC-EGCG-EGCG-EGCG) L + [47] +
45 1.90 ii 403 N PG Hydroquinone O-Hex-O-Pent L + + + + +
46 1.98 ii 271 N PG Hydroquinone O-Glc (=arbutin) S + + + + +
47 2.09 ii 431 N PE Tyrosol O-Hex-O-Pent L + + + + +
48 2.37 ii 299 N PE Tyrosol O-Glc (=salidroside) S [48] [48] + + +
49 4.59 ii 283 N PE Tyrosol O-dHex L + + +
50 4.95 ii 137 N PE Tyrosol (=p-hydroxyphenethyl alcohol) S [48] [48] + + +
51 5.11 ii 401 N PG Benzyl alcohol O-Hex-O-Pent L + + + + +
52 5.23 ii 401 N PG Benzyl alcohol O-Hex-O-Pent L + + + + +
53 5.56 ii 269 N PG Benzyl alcohol O-Hex L + + + + +
54 5.82 ii 443 N HC p-Hydroxycinnamyl alcohol O-Hex-O-Pent L + +
55 6.02 ii 311 N HC p-Hydroxycinnamyl alcohol O-Glc (=triandrin) S [49] [49] + + +
56 6.27 ii 107 N PG Benzyl alcohol S + + + + +
57 6.55 ii 390 N HNG Rhodiocyanoside A/D O-Pent L + +
58 6.76 ii 258 N HNG Rhodiocyanoside D L + + + + +
59 6.97 ii 258 N HNG Rhodiocyanoside A S + + + + +
60 7.18 ii 625 N TG Rosiridol di-O-Hex-O-Pent L + + +
61 7.27 ii 595 N TG Rosiridol O-Hex-di-O-Pent L + + +
62 7.47 ii 595 N TG Rosiridol O-Hex-di-O-Pent L
63 7.52 ii 463 N TG Rosiridol O-Hex-O-Pent L + + + + +
64 7.81 ii 463 N TG Rosiridol O-Hex-O-Pent L + + + + +
65 8.18 ii 341 N PE Tyrosol O-Hex-O-Ac L + + + + +
66 8.72 ii 341 N PE Tyrosol O-Hex-O-Ac L + + +
67 8.98 ii 383 N PE Tyrosol O-Hex-di-O-Ac L + + +
68 9.02 ii 559 N HC Cinnamyl alcohol O-Hex-di-O-Pent L + +
69 9.26 ii 559 N HC Cinnamyl alcohol O-Hex-di-O-Pent L + +
70 9.57 ii 427 N HC Cinnamyl alcohol O-(6′-O-Araf)-Glc (=rosarin) S [50] [50]
71 9.95 ii 427 N HC Cinnamyl alcohol O-(6′-O-Arap)-Glc (=rosavin) S [50] [50]
72 10.26 ii 427 N HC Cinnamyl alcohol O-Hex-O-Pent L + +
73 10.51 ii 295 N HC Cinnamyl alcohol O-Glc (=rosin) S [50] [50]
74 10.98 ii 331 N TG Rosiridol 1-O-Glc (=rosiridin) S [51] [51] + + +
75 11.27 ii 353 N HC p-Hydroxycinnamyl alcohol O-Hex-O-Ac L + + +
76 11.67 ii 353 N HC p-Hydroxycinnamyl alcohol O-Hex O-Ac L + + +
77 12.14 ii 373 N TG Rosiridol O-Hex-O-Ac L + + +
78 12.48 ii 415 N TG Rosiridol O-Hex-di-O-Ac L + + +
79 12.81 ii 415 N TG Rosiridol O-Hex-di-O-Ac L + + +
80 13.65 ii 457 N HC p-Methoxycinnamyl alcohol O-Hex-O-Pent L + +
81 13.94 ii 457 N HC p-Methoxycinnamyl alcohol O-Hex-O-Pent L + +
82 14.57 ii 325 N HC p-Methoxycinnamyl alcohol O-Glc (=vimalin) S [52] [52]
83 15.06 ii 133 N HC Cinnamyl alcohol S [50] [50]
84 15.47 ii 147 N HC Cinnamic acid S + +
85 16.58 ii 163 N HC p-Methoxycinnamyl alcohol S + +
86 5.02 iii 919 P NFG Kaempferol tri-O-Hex-O-dHex (S37) L +
87 5.41 iii 935 P NFG Herbacetin tri-O-Hex-O-dHex (S78) L + +
88 5.56 iii 789 P NFG Gossypetin di-O-Hex-O-dHex (S78) L + +
89 5.63 iii 773 P NFG Quercetin di-O-Hex-O-dHex (S37) L + +
90 5.97 iii 757 P NFG Kaempferol di-O-Hex-O-dHex (S37) L + + + +
91 6.18 iii 643 P NFG Gossypetin di-O-Hex (S8) L +
92 6.21 iii 773 P NFG Herbacetin di-O-Hex-O-dHex (S78) L + +
93 6.32 iii 643 P NFG Gossypetin di-O-Hex (S38) L +
94 6.43 iii 627 P NFG Gossypetin 7-O-(3″-O-Glc)-Rha (=rhodioflavonoside) S [53] [53] + +
95 6.63 iii 611 P NFG Herbacetin 7-O-(3″-O-Glc)-Rha (=rhodiosin) S + +
96 6.82 iii 627 P NFG Gossypetin 7-O-Rha-8-O-Glc (=rhodiolgidin) S [13] [13] +
97 7.02 iii 595 P NFG Kaempferol O-Hex-O-dHex (S7) L + +
98 7.21 iii 435 P NFG Herbacetin-8-O-Xyl (=rhodalin) S + + [14] [14]
99 7.35 iii 611 P NFG Herbacetin 7-O-Rha-8-O-Glc (=rhodionidin) S + + [14] [14] +
100 7.43 iii 627 P NFG Quercetin 3,7-di-O-Glc S +
101 7.54 iii 611 P NFG Kaempferol 3,7-di-O-Glc S + + [15]
102 7.75 iii 611 P NFG Quercetin 3-O-Glc-7-O-Rha S + +
103 7.97 iii 595 P NFG Kaempferol 3-O-Glc-7-O-Rha S [54] [54] + +
104 8.01 iii 481 P NFG Gossypetin 8-O-Glc (=gossypin) S +
105 8.11 iii 579 P NFG Kaempferol 3,7-di-O-Rha (=kaempferitrin) S +
106 8.41 iii 465 P NFG Gossypetin 7-O-Rha (=rhodiolgin) S [13]
107 8.57 iii 465 P NFG Quercetin 3-O-Glc (=isoquercitrin) S + + + +
108 8.98 iii 449 P NFG Quercetin 3-O-Rha (=quercitrin) S [2] [2] +
109 9.22 iii 465 P NFG Herbacetin 8-O-Glc (=herbacin) S [54] [54] + +
110 9.43 iii 449 P NFG Herbacetin O-dHex (S8) L + + +
111 10.12 iii 433 P NFG Kaempferol 3-O-Rha (=afzelin) S + + +
112 10.46 iii 449 P NFG Herbacetin 7-O-Rha (=rhodionin) S [55] [55] +
113 11.27 iii 449 P NFG Herbacetin O-dHex (S3) L +
114 11.45 iii 433 P NFG Kaempferol 7-O-Rha S [56] [56] +
115 1.97 iv 835 P AFG Hibiscetin di-O-Hex-O-HexA (S38) L + +
116 2.58 iv 819 P AFG Gossypetin di-O-Hex-O-HexA (S378) L + +
117 2.82 iv 861 P AFG Gossypetin O-Ac-di-O-Hex-O-HexA (S378) L + +
118 3.15 iv 861 P AFG Gossypetin O-Ac-di-O-Hex-O-HexA (S378) L + +
119 4.42 iv 803 P AFG Herbacetin di-O-Hex-O-HexA (S38) L + +
120 4.63 iv 803 P AFG Herbacetin di-O-Hex-O-HexA (S378) L + + + +
121 5.02 iv 889 P AFG Herbacetin O-Mal-di-O-Hex-O-HexA (S378) L + + + + +
122 5.27 iv 845 P AFG Herbacetin O-Ac-di-O-Hex-O-HexA (S378) L + +
123 5.52 iv 673 P AFG Hibiscetin O-Hex-O-HexA (S38) L + + + + +
124 6.03 iv 759 P AFG Hibiscetin O-Mal-O-Hex-O-HexA (S38) L + + +
125 6.18 iv 715 P AFG Hibiscetin O-Ac-O-Hex-O-HexA (S38) L + +
126 6.53 iv 657 P AFG Gossypetin 3-O-Glc-8-O-GlcA S + + + + +
127 6.97 iv 699 P AFG Gossypetin 3-O-(3″-O-Ac)-Glc-8-O-GlcA (=rhodiquadrin B) S + + + + +
128 7.27 iv 367 N HC 3-O-Feruloylquinic acid S + + + + +
129 7.51 iv 641 P AFG Herbacetin 8-O-(2″-O-Glc)-GlcA (=rhodiquadrin C) S + + + + +
130 7.62 iv 641 P AFG Herbacetin 3-O-Glc-8-O-GlcA S + + + + +
131 7.90 iv 683 P AFG Herbacetin O-Ac-O-Hex-O-HexA (S3,8) L +
132 8.23 iv 683 P AFG Herbacetin 3-O-(3″-O-Ac)-Glc-8-O-GlcA S + + + + +
133 8.48 iv 741 P AFG Gossypetin di-O-Ac-O-Hex-O-HexA (S3,8) L + + + +
134 8.73 iv 741 P AFG Gossypetin di-O-Ac-O-Hex-O-HexA (S3,8) L + + + + +
135 8.98 iv 683 P AFG Herbacetin O-Ac-O-Hex-O-HexA (S3,8) L + + + + +
136 9.49 iv 683 P AFG Herbacetin O-Ac-O-Hex-O-HexA (S3,8) L + + + + +
137 10.47 iv 725 P AFG Herbacetin di-O-Ac-O-Hex-O-HexA (S3,8) L + + + + +
138 11.25 iv 495 P AFG Gossypetin 8-O-GlcA (=hibifolin) S + +
139 11.59 iv 581 P AFG Gossypetin O-Mal-O-HexA (S8) L + +
140 11.98 iv 581 P AFG Gossypetin O-Mal-O-HexA (S8) L + + +
141 12.26 iv 537 P AFG Gossypetin O-Ac-O-HexA (S8) L + + + +
142 12.61 iv 537 P AFG Gossypetin O-Ac-O-HexA (S8) L + +
143 14.01 iv 479 P AFG Herbacetin 8-O-GlcA (=melocorin) S + + + + +
144 14.50 iv 565 P AFG Herbacetin O-Mal-O-HexA (S8) L + + + +
145 15.37 iv 521 P AFG Herbacetin O-Ac-O-HexA (S8) L + + +
146 16.11 iv 521 P AFG Herbacetin O-Ac-O-HexA (S8) L +
Total compounds found 90 90 87 100 69
Total known compounds found 21 25 3 5 0
Total compounds found for the first time 69 65 84 95 69

a Chromatographic conditions: i—mode 1; ii—mode 2; iii—mode 3; iv—mode 4. b Mass spectrometric data: N—deprotonated ion [M − H]−, negative ionization; P—protonated ion [M + H]+, positive ionization. c Chemical group of compound: AFG—acidic flavonol glycosides; CT—catechins; HC—hydroxycinnamates; HNG—hydroxynitrile glycosides; NFG—neutral flavonol glycosides; PE—phenylethanoids; PG—phenolic glycosides; PC—procyanidins; TG—terpene glycosides. d Compound identification was based on comparison of retention time, UV and MS spectral data with reference standard (S) or interpretation of UV and MS spectral data and comparison with literature data (L). e In square brackets—reference for known data of compound presence in R. rosea organs. Abbreviation used: Ac—acetyl; Araf—arabinofuranose; Arap—arabinopyranose; Glc—glucose; GlcA—glucuronic acid; EGC—epigallocatechin unit; EGCG—epigallocatechin gallate unit; Hex—hexose; HexA—hexuronic acid; Mal—malonyl; Pent—pentose; Rha—rhamnose; Xyl—xylose. Substitution type of flavonol glycoside: S3—3-O-substituted; S8—8-O-substituted; S37—3,7-di-O-substituted; S78—7,8-di-O-substituted; S38—3,8-di-O-substituted; S378—3,7,8-tri-O-substituted.