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. 2020 Mar 9;25(5):1228. doi: 10.3390/molecules25051228

Table 1.

Tentative characterization of chemical constituents of two species of GRR by UHPLC-LTQ-Orbitrap/MS in negative ion mode.

No Name Formula m/z Adduction Fragment Ion RT Scabra Rigescens
Iridoid
1 Secologanic acid C16H22O10 373.11 [M-H] 179/108/204/282 8.40 +
2 Longanic acid * C16H24O10 375.13 [M-H] 371/179 2.35 +
3 Gentiolactone C10H12O5 211.10 [M-H] 167 7.50 + +
4 Gentiopicroside* C16H20O9 401.11 [M-H+HCOOH] 179/355/149/119 5.22 + +
5 Sweroside * C16H22O9 403.12 [M-H+HCOOH] 357/195/179/125 5.63 + +
6 8-epikingside C17H24O11 403.12 [M-H] 371/223/179 7.49 +
7 Caryptoside C17H26O11 405.14 [M-H+HCOOH] 179 2.26 + +
8 Swertiamarin * C16H22O10 419.12 [M-H+HCOOH] 179/355/211/119 3.85 + +
9 Loganin * C17H26O10 435.22 [M-H+HCOOH] 389.22 7.17 +
10 Secoxyloganin C17H24O11 449.13 [M-H+HCOOH] 179/241/359/403 2.66 +
11 Morroniside C17H26O11 451.14 [M-H+HCOOH] 405/243/179/ 2.94 +
12 2′-O-(2,3-dihyrben)-gentiopicroside C20H28O14 491.14 [M-H] 167/323/459 4.59 + +
13 2′-O-(2,3-dihyben)-swertamairn C23H26O13 509.13 [M-H] 153/297/315/367 10.53 +
14 3′-O-(2,3-dihyben)-swertamairn C23H26O13 509.22 [M-H] 153/517/411/321 6.11 +
15 Deglu-noneacetylate-rindoiside C23H26O13 509.22 [M-H] 153/297/315/367 9.53 +
16 Rigenolide A C25H28O12 519.15 [M-H] 307 11.20 +
17 4-glu+D97RT C26H34O11 521.20 [M-H] 359/329 9.44 +
18 Lacriciresinol C26H34O11 521.20 [M-H] 473/355/375/415 15.26 +
19 6′-O-d-glu swertiamarin C25H28O13 535.14 [M-H] 409/491/153/339 14.39 +
20 6′-O-d-glu-Loganic acid C22H34O15 537.18 [M-H] 213 2.05 + +
21 Dideacetylate-deglu-rindoside C25H28O14 551.14 [M-H] 491/409/509 12.34 +
22 Gentianaside C22H36O13 553.13 [M-H+HCOOH] 507 5.03 +
23 6-O-d-glu-gentiopicroside C22H30O14 563.16 [M-H+HCOOH] 341/517 5.69 + +
24 Tortoside B C28H38O13 581.15 [M-H] 401/357/313/269 1.47 +
25 Gentiabavaroside C26H30O15 581.16 [M-H] 401/357/313/221 1.47 +
26 6-O-d-glu-swertianmarin C22H32O15 581.17 [M-H+HCOOH] 341/535/517/179 2.83 +
27 Deacetylate-deglu-rindoside C27H30O15 593.15 [M-H] 451/531/551 19.54 + +
28 Deglu-trifloroside C29H32O15 619.17 [M-H] 577 24.5 + +
29 Deglu-gelidoside C29H32O16 635.16 [M-H] 551/451/593 23.19 + +
30 Gentiotrifloroside C29H36O17 655.19 [M-H] 315/493/529 7.41 + +
31 Deglu-scabraside C34H34O15 681.18 [M-H] 639/475/153 28.45 + +
32 Gentrigeoside A C36H60O12 683.40 [M-H] 640/622 28.46 +
33 2,3-deacetyl-trifloroside C32H40O17 695.18 [M-H] 315 13.78 +
34 6′-O-ace-3-O-glu-2-hy-sweroside C31H38O18 697.17 [M-H] 315/535/571/315 14.25 +
35 Trideacetylate-trifloroside C31H38O18 697.18 [M-H+HCOOH] 505/651/313/269 8.78 +
36 Scabran G3 C28H40O19 725.21 [M-H] 341/383/503/679 2.55 + +
37 2-deaceyl-trifloroside C33H38O19 737.19 [M-H] 315/575/693 16.1 +
38 Dedihydroxybenzoate-Macrophylloside C33H40O19 739.20 [M-H] 697/577/613/535 15.76 + +
39 Deacetylate-Trifloroside C33H40O19 739.20 [M-H] 697/577/613/535 14.7 + +
40 Deacetylate-Rindoside C33H40O20 755.20 [M-H] 593/315/713 13.92 + +
41 Trifloroside * C35H42O20 781.22 [M-H] 619/739/577/315 18.44 +
42 Dideacetylate-Macophylloside C36H40O20 791.24 [M-H] 521/629/315 15.11 +
43 Rindoside * C35H42O21 797.21 [M-H] 315/493/635/755 17.19 + +
44 Deacetylate-scabraside C38H42O19 801.22 [M-H] 639/597 18.41 +
45 Acetylate-trifloroside C37H44O21 823.23 [M-H] 619/577/781 21.59 +
46 Deacetylatemacrophylloside A C38H42O21 833.21 [M-H] 671/697/535/315 15.33 + +
47 Scabraside C40H44O20 843.24 [M-H] 681/639/315/801 21.66 + +
48 Dideacetylate-4′-glu-trifloroside C37H48O23 859.23 [M-H] 697 19.31 + +
49 Macrophylloside A C40H44O22 875.22 [M-H] 739/577/535 18,74 + +
50 Deacetylate-4′-glu-trifloroside C39H50O24 901.26 [M-H] 577/459/535/859 13.36 +
51 4-O-β-d-trifloroside C41H52O25 943.27 [M-H] 459/619/901/577 16.29 + +
52 Acetylate-4′-glu-scabraside C46H54O25 1005.29 [M-H] 963/681/639/477 20.73 +
53 4″-O-β-d-glucopyranosy1-6′-O-(4-O-β-d-glu-caffeoyl) linearroside C46H56O25 1007.30 [M-H] 845/801/487/639 11.59 +
54 Benzoxy-4″-O-β-d-glucopyranosy1-6′-O-(4-O-β-d-glucopyranosylcaffeoyl)linearroside C53H60O26 1111.33 [M-H] 845/487/639/801 15.03 +
Flavonoids
55 Isovitexin C21H20O10 431.10 [M-H] 9.7 + +
56 Isoorientin(Homoorientin) * C21H20O11 447.15 [M-H] 327/357/429 8.29 + +
57 Isoscoparin C22H22O11 507.17 [M-H+COOH] 461 6.66 +
58 2-glu-isovitexin C27H30O15 593.15 [M-H] 551/451/531/409 19.54 +
59 Isosaponarin C27H30O16 593.15 [M-H] 311/431/473/503 7.68 +
60 Saponarin C27H30O17 593.15 [M-H] 367 11.51 +
61 4′-glu-isoorientin C27H30O16 609.14 [M-H] 447 5.27 +
62 Lutonarin C27H30O16 609.14 [M-H] 447/519/489/327 6.87 +
63 Rutin C27H30O16 609.14 [M-H] 447/519/489/327 6.9 +
64 Keampferol C15H10O6 331.04 [M-H+HCOOH] 285/165 22.50 +
65 7-glu-isopyrenine C29H34O17 653.17 [M-H] 315 10.06 + +
66 Hyperoside C21H20O12 509.22 [M-H+HCOOH] 463 8.95 +
67 Lonicerin C27H30O15 593.19 [M-H] 551/451 17.06 +
Miscellaneous Compounds
68 Caffeic acid C9H8O4 179.03 [M-H] 135/109 9.25 + +
69 Ferulic acid C10H10O4 193.02 [M-H] 149 3.77 +
70 Isoferulic acid C10H10O4 193.02 [M-H] 149 4.01 +
71 Vanilloloside C13H16O9 315.07 [M-H] 153 1.6 + +
72 Glu-2,3-dihydroxybenzoic acid C14H20O8 315.11 [M-H] 187/297/253/145 22.81 +
73 Glu-2-hydro-3-methoben C14H18O9 329.09 [M-H] 167 6.89 + +
74 Methyl-3-(β-d-glucopyranosyl)-2-hydroxybenzoate C14H18O9 329.23 [M-H] 209/311 19.25 +
75 Glu-caffeic acid C15H18O9 341.09 [M-H] 179/135/203/239 1.97 +
76 Syringin C17H24O9 371.10 [M-H] 249 4.7 +
77 3-[(6-O-Arabinopyranosyl)-β-d-glucopyranosyloxy]oct-1-en C19H34O10 421.20 [M-H] 289/133 12.57 +
78 Methyl-3-[(6-O-β-d-glucopyranosyl)-β-d- glucopyranosyloxy]-2-hydroxybenzoate C23H24O12 491.12 [M-H] 153/315/475 12.31 +
79 (+) Syringaresinol C24H30O8 491.14 [M-H+HCOOH] 315/447/153 9.94 +
80 Lonicerin C27H30O15 593.19 [M-H] 551/451/ 16.68 +
Xanthones
81 Mangiferin * C19H18O11 421.08 [M-H] 403/331/301 5.98 +
82 Gentianabavaroside C26H30O15 581.16 [M-H] 401/357/313/ 3.71 +
Triterpenoids
83 Gentrigeoside D C36H60O13 745.40 [M-H+HCOOH] 699 11.99 +
84 Gentrigeoside C C42H70O17 845.24 [M-H] 683/803 21.77 +
85 Glu-Gentigeoside C C46H56O25 1007.31 [M-H] 845/801/639/487 11.52 +
86 Gentrigeoside A (Dammarane) C36H60O12 683.40 [M-H] 640/622 28.46 +
87 Rha-Gentrigeoside C46H54O27 1037.51 [M-H+HCOOH] 991 13.6 +

Annotation: + indicated the compound in the specie; * indicated compound compared with standards; blank indicated without the compound.