Table 2.
UHPLC-ESI(-)-HRMS/MS characterisation of the main compounds present in the turnip methanol extracts.
| Semisystematic Name (Glucosinolate Group) |
Trivial Name (Abbreviation) |
TR (min) |
Ionic Formula |
[M − H]− (m/z (Δ ppm) |
MS/MS [m/z (Δ ppm) (Attribution)] |
|---|---|---|---|---|---|
| 2(R)-2-Hydroxyl but- -3-enyl (hydroxyalkenyl) |
Progoitrin (PRO) |
1.38 | [C11H19N1O10S2]− | 388.0380; −0.7 | 308.0805; −2.4; (C11H18N1O7S1)− 301.0124; −0.5; (C8H13O8S2)− 274.9904; −1.0; (C6H11O8S2)− 259.0131; −0.6; (C6H11O9S1)− 241.0029; −2.3; (C6H9O8S1)− 195.0334; −0.6; (C6H11O5S1)− 194.9794; −1.3; (C6H7O4S2)−*F2b 179.0560; −0.7; (C5H11O6)− 146.0278; +1.9; (C5H8N1O2S1)−*F1 135.9706; +3.1; (C2H2N1O4S1)− |
| 2-Hydroxypent- -4-enyl (hydroxyalkenyl) |
Gluco- napoleiferin (GNL) |
1.45 | [C12H20N1O10S2]− | 402.0543; −2.3 | 322.0950; −2.4; (C12H20N1O7S1)− 274.9902; −1.9; (C6H11O8S2)− 259.0131; −2.1; (C6H11O9S1)− 208.9952; −2.2; (C6H9O4S2)−*F2b 195.0333; −0.9; (C6H11O5S1)− 160.0437; +0.2; (C6H10N1O2S)−*F1 135.9713; −2.0; (C2H2N1O4S)− |
| But-3-enyl (alkenyl) |
Gluconapin (GNA) |
1.47 | [C11H18N1O9S2]− | 372.0432; −1.0 | 292.0861; −0.4; (C11H18N1O6S)− 274.9905; −1.5; (C6H11O8S2)− 259.0133; −1.3; (C6H11O9S1)− 241.0025; −0.5; (C6H9O8S1)− 195.0333; −0.9; (C6H11O5S1)− 178.9834; −4.4; (C5H7O3S2)−*F2b 130.0334; −1.2; (C5H8NOS)−*F1 |
| 4-Hydroxyindol- -3-ylmethyl (indole) |
4-Hydroxy- glucobrassicin (4-OHGBS) |
1.55 | [C16H19N2O10S2]− | 463.0491; −0.9 | 383.0921; −0.6; (C16H19N2O7S)− 274.9903; −0.4; (C6H11O8S2)− 267.0081; −0.2; (C10H7N2O5S)− *F2a 259.0128; −0.4; (C6H11O9S1)− 221.0390; −0.3; (C10H9N2O2S1)−*F1 |
| Pent-4-enyl (alkenyl) |
Gluco- brassicanapin (GBN) |
2.20 | [C12H20N1O9S2]− | 386.0583; −0.6 | 306.1011; −1.1; (C12H20N1O6S)− 274.9900; −0.3; (C6H11O8S2)− 259.0131; −0.6; (C6H11O9S1)− 241.0021; −1.1; (C6H9O8S1)− 195.0332; −0.4; (C6H11O5S)− 190.0187; −3.8; (C6H8NO4S1)−*F2a 144.0484; −2.9; (C6H10NOS1)−*F1 |
| Hydroxyindol- -3-ylmethyl (indole) |
Hydroxy- glucobrassicin isomer (OHGBS isomer) |
3.02 | [C16H19N2O10S2]− | 463.0493; −1.1 | 383.0917; −0.4; (C16H19N2O7S)− 274.9902; −0.3; (C6H11O8S2)− 267.0092; −4.2; (C10H7N2O5S)−*F2a 259.0131; −0.6; (C6H11O9S1)− 221.0391; −0.4; (C10H9N2O4S1)−*F1 195.0339; −4.4; (C6H11O5S)− |
| 4(Methylsulphanyl)- -butyl (sulphur containing) |
Glucoerucin (GER) |
3.21 | [C12H22N1O9S3]− | 420.0467; −1.2 | 340.0913; −5.4; (C12H22N1O6S2)− 331.0716; −1.4; (C11H22N1O6S2)− 274.9900; −1.5; (C6H11O8S2)− 259.0140; −4.3; (C6H11O9S1)− 226.9884; −3.5; (C6H11O3S3)−*F2b 195.0340; −4.9; (C6H11O5S)− 178.0366; −0.1; (C6H12N1OS2)−*F1 130.0334; −1.2; (C5H8NOS)− |
| Pentenyl (alkenyl) |
Gluco- brassicanapin isomer (GBN isomer) |
3.38 | [C12H20N1O9S2]− | 386.0595; −2.6 | 306.1024; −2.5; (C12H20N1O6S)− 274.9905; −2.6; (C6H11O8S2)− 259.0133; −1.3; (C6H11O9S1)− 241.0035; −2.0; (C6H9O8S1)− 195.0339; −2.5; (C6H11O5S)− 190.0187; −3.8; (C6H8NO4S)−*F2a 144.0487; −0.9; (C6H10NOS)−*F1 |
| Indol-3-ylmethyl (indole) |
Glucobrassicin (GBS) |
3.40 | [C16H19N2O9S2]− | 447.0547; −2.0 | 367.0962; −2.0; (C16H19N2O6S1)−
274.9909; −3.1; (C6H11O8S2)− 259.0138; −3.4; (C6H11O9S1)− 253.9961; −3.9; (C10H8N1O3S2)−*F2b 205.0440; −0.5; (C10H9N2OS)−*F1 172.0223; −2.1; (C10H6N1S1)− |
| 2(R)-Hydroxy- -2-phenylethyl (aromatic) |
Glucobarbarin (GBA) |
3.70 | [C15H20N1O10S2]− | 438.0534; −3.7 | 358.0996; −7.4; (C15H20N1O7S1)− 274.9909; −3.1; (C6H11O8S2)− 259.0140; −4.1; (C6H11O9S1)− 244.9941; −2.8; (C9H9O4S2)−*F2b 196.0442; −2.0; (C9H10NO2S1)−*F1 172.0223; −2.1; (C10H6N1S1)− |
| 5-(Methylsulfanyl)- -pentyl (sulfur containing) |
Glucoberteroin (GOB) |
4.46 | [C13H24N1O9S3]− | 434.0626; −1.7 | 354.1060; −2.8; (C13H24N1O6S2)− 274.9903; −0.7; (C6H11O8S2)− 259.0140; −1.8; (C6H11O9S1)− 241.0035; −1.1; (C7H13O3S3)−*F2b 195.0335; −1.3; (C6H11O5S1)− 192.0524; −1.3; (C7H14N1O1S2)−*F1 |
| 2-Phenylethyl (aromatic) |
Gluconasturtiin (GST) |
4.47 | [C15H20N1O9S2]− | 422.0593; −2.0 | 342.1026; −2.8; (C15H20N1O6S1)− 274.9912; −3.9; (C6H11O8S2)− 259.0295; −3.6; (C6H11O9S1)− 241.0032; −3.5; (C6H9O8S1)− 229.0006; −3.1; (C9H9O3S2)−*F2b 226.0184; −1.8; (C9H8N1O4S1)−*F2a 180.0485; −1.8; (C9H10N1O1S1)−*F1 |
| 4-Methoxyindol- -3-ylmethyl (indole) |
4-methoxy- glucobrassicin (NGBS) |
4.78 | [C17H21N2O10S2]− | 477.0655; −2.5 |
284.0062; −2.0; (C11H10N1O4S2)−*F2b 274.9911; −3.9; (C6H11O8S2)− 259.0138; −0.9; (C6H11O9S1)− 235.0560; −5.8; (C11H11N2O2S1)−*F1 205.0441; −0.2; (C10H9N2O1S1)− 203.0286; −0.5; (C10H7N2O1S1)− |
| 1-Methoxyindol- -3-ylmethyl (indole) |
1-methoxy- -glucobrassicin (NGBS isomer) |
5.62 | [C17H21N2O10S2]− | 477.0664; −3.7 | 446.0480; −4.6; (C16H18N2O9S2)−• 274.9900; −0.9; (C6H11O8S2)− 259.0136; −2.6; (C6H11O9S1)− 235.0559; −5.2; (C11H11N2O2S1)−*F1 205.0437; −1.9; (C10H9N2O1S1)− 195.0344; −6.0; (C6H11O5S)− |
| Hydroxyciannamic acids |
|||||
| Sucrose | 1.13 | [C12H21O11]− | 341.1091; −0.5 | 179.0562; −0.7; (C8H11O6)− | |
| Gentisoyl glucoside |
1.93 | [C13H15O9]− | 315.0726; −1.5 | 153.02187; +4,7; (C7H5O4)− | |
| 1-O-Sinapolyl- glucose |
4.80 | [C17H21O10]− | 385.1139; −0.2 | 205.0510; −1.8; (C11H9O4)− 179.0723; −5.3; (C10H11O3)− 164.0480; −0.4; (C9H8O3)−• |
|
| Sinapic acid | 6.17 | [C11H11O5]− | 223.0612; −1.9 | 208.0375; −0.7; (C10H8O5)−• 179.0708; −7.7; (C10H11O3)− 164.0469; −5.7; (C9H8O3)−• |
|
| 1,2-Disinapoyl-gentiobiose | 6.73 | [C34H41O19]− | 753.2252; −0.5 | 529.1571; −0.8; (C23H29O14)− 223.0615; −1.3; (C11H11O5)− 205.0510; −1.4; (C11H9O4)− |
|
| 1-Feruloyl- -1-sinapoyl- gentiobiose |
6.88 | [C33H39O18]− | 723.2145; −0.4 | 449.1471; −2.7; (C22H27O13)− 223.0615; −3.6; (C11H11O5)− 205.0517; −5.0; (C11H9O4)− 175.0463; −1.6; (C10H7O3)− |
|
| 1,2,2′-Trisinapoyl- Gentiobiose |
7.46 | [C45H51O23]− | 959.2855; −2.5 | 735.2155; −1.0; (C34H39O18)− 529.1578; −2.8; (C23H29O14)− 223.0622; −4.7; (C11H11O5)− 205.0505; −0.5; (C11H9O4)− |
|
| 1,2′-Disinapoyl-2- -feruloyl- Gentiobiose |
8.15 | [C44H49O22]− | 929.2721; −3.8 | 705.2057; −2.9; (C33H37O17)− 529.1575; −2.3; (C23H29O14)− 205.0518; −5.5; (C11H9O4)− |
* Symbols F1 and F2a or F2b indicate fragmentation paths which are specific to each GLS molecular structure (differentiated by the R functional group).