Table 1.
Flavonoids annotated from LC-MS data of developing grape berries.
| Candidate number | Deduced structure | RT (min) | [M+H]+ (m/z) | Mass accuracy (ppm) | Export formula | MS/MS (m/z) | References | Annotation level |
|---|---|---|---|---|---|---|---|---|
| 1 | Dp-3, 5-O-diGlc | 9.9 | 627.15536 | −0.21 | C27H31O17 | 465, 303 | Liang et al., 2008; He et al., 2010 | 2 |
| 2 | Cy-3, 5-O-diGlc | 11.5 | 611.16031 | −0.4 | C27H31O16 | 449, 287 | Liang et al., 2008; He et al., 2010 | 2 |
| 3 | Procyanidin B2 | 12.07 | 579.14927 | −0.43 | C30H27O12 | 427, 409, 291, 247 | Monagas et al., 2005 | 1 |
| 4 | Pt-3, 5-O-diGlc | 12.5 | 641.17117 | −0.06 | C28H33O17 | 479, 317 | Liang et al., 2008; He et al., 2010 | 2 |
| 5 | DHQ-3-O-hexoside | 12.5 | 467.11823 | −0.17 | C21H23O12 | 449, 305 | Flamini et al., 2015 | 2 |
| 6 | Pn-3, 5-O-diGlc | 14.25 | 625.17598 | −0.33 | C28H33O16 | 463, 301 | Liang et al., 2008; He et al., 2010 | 2 |
| 7 | Mv-3, 5-O-diGlc | 14.7 | 655.18679 | −0.09 | C29H35O17 | 493, 331 | Liang et al., 2008; He et al., 2010 | 2 |
| 8 | Dp-3-O-Glc | 14.9 | 465.10259 | −0.16 | C21H21O12 | 303 | Liang et al., 2008 | 2 |
| 9 | Procyanidin B like | 15.58 | 579.14934 | −0.37 | C30H27O12 | 427, 289, 291, 409 | Monagas et al., 2005 | 3 |
| 10 | MDHQ-hexoside | 15.91 | 481.13399 | −0.06 | C22H25O12 | 463, 319, 301 | Abu-Reidah et al., 2015 | 3 |
| 11 | Dp-3-O-acetylGlc-5-O-Glc | 16.3 | 669.16632 | 0.18 | C29H33O18 | 507, 303, 465 | He et al., 2010 | 2 |
| 12 | Procyanidin B5 | 16.61 | 579.1494 | −0.31 | C30H27O12 | 427, 409, 291, 247 | Monagas et al., 2005 | 2 |
| 13 | Lut/Kae/Cy-methylGlu-hexoside | 16.7 | 639.15567 | 0.09 | C28H31O17 | 477, 287, 449 | 3 | |
| 14 | Cy-3-O-Glc | 16.88 | 449.10768 | −0.16 | C21H21O11 | 287 | Liang et al., 2008 | 2 |
| 15 | Cy-3-O-acetylGlc-5-O-Glc | 17.73 | 653.17121 | −0.02 | C29H33O17 | 491, 287, 449 | Liang et al., 2008; He et al., 2010 | 2 |
| 16 | Pn-methylGlu-hexoside | 18.46 | 653.17117 | −0.06 | C29H33O17 | 491, 301, 463 | 3 | |
| 17 | Mv-methylGlu-glucoside | 18.46 | 683.18171 | −0.08 | C30H35O18 | 521, 331, 317, 493 | 3 | |
| 18 | Pn-3-O-Glc | 19.65 | 463.12328 | −0.21 | C22H23O11 | 301 | Liang et al., 2008 | 2 |
| 19 | Pn-3-O-acetylGlc-5-O-Glc | 20.32 | 667.18708 | 0.2 | C30H35O17 | 505, 301, 463 | He et al., 2012 | 2 |
| 20 | Myr-3-O-Glu | 22.69 | 495.07682 | −0.11 | C21H19O14 | 319 | Flamini et al., 2015 | 2 |
| 21 | Myr-3-O-Glc | 22.85 | 481.09749 | −0.18 | C21H21O13 | 319 | Flamini et al., 2015 | 2 |
| 22 | Dp-3-O-acetylGlc | 23 | 507.11316 | −0.16 | C23H23O13 | 303 | Liang et al., 2008 | 2 |
| 23 | Lut/Kae/Cy-methylGlu | 23.21 | 477.10265 | −0.21 | C22H21O12 | 287 | 3 | |
| 24 | Lut/Kae/Cy-Cou-hexoside or Lut/Kae/Cy-Caff-Rha | 23.74 | 595.14454 | −0.07 | C30H27O13 | 287 | Liang et al., 2008; He et al., 2010 | 3 |
| 25 | Dp-3-O-CouGlc-5-O-Glc | 24.13 | 773.1922 | −0.16 | C36H37O19 | 611, 303, 465 | Liang et al., 2008; He et al., 2010 | 2 |
| 26 | Lar-3-O-Glu | 24.8 | 509.09238 | −0.2 | C22H21O14 | 319 | Flamini et al., 2015 | 2 |
| 27 | Cy-3-O-acetylGlc | 25.04 | 491.11828 | −0.12 | C23H23O12 | 287 | Liang et al., 2008 | 2 |
| 28 | Epicatechin gallate | 25.17 | 443.09711 | −0.16 | C22H19O10 | 273, 151, 291 | Delcambre and Saucier, 2012 | 2 |
| 29 | Pt-3-O-CouGlc-5-O-Glc | 25.76 | 787.20786 | −0.15 | C37H39O19 | 625, 317, 479 | He et al., 2010 | 2 |
| 30 | Cy-3-O-CouGlc-5-O-Glc | 26.1 | 757.19691 | −0.54 | C36H37O18 | 595, 287, 449 | Liang et al., 2008; He et al., 2010 | 2 |
| 31 | Que-3-O-Glu | 26.4 | 479.08192 | −0.1 | C21H19O13 | 303 | Flamini et al., 2015 | 2 |
| 32 | Mv-3-O-CouGlc-5-O-Glc | 27.84 | 801.22316 | −0.49 | C38H41O19 | 639, 611, 493, 331, 303 | Liang et al., 2008; He et al., 2010 | 2 |
| 33 | Pg-3-O-Cou-Glc-5-O-Glc | 28.11 | 741.20284 | 0.31 | C36H37O17 | 579, 271, 433 | He et al., 2012 | 2 |
| 34 | Pn-3-O-CouGlc-5-O-Glc | 28.37 | 771.21278 | −0.31 | C37H39O18 | 609, 301, 463 | Liang et al., 2008; He et al., 2010 | 2 |
| 35 | Lut/Kae/Cy-(GlcCou)-methylGlu | 28.76 | 785.19222 | −0.14 | C37H37O19 | 287, 477, 595, 623 | 3 | |
| 36 | Isorhamnetin-3-O-Glu | 28.96 | 493.09758 | −0.08 | C22H21O13 | 303 | Flamini et al., 2015 | 2 |
| 37 | Dp-3-O-CouGlc | 29.27 | 611.13932 | −0.21 | C30H27O14 | 303 | He et al., 2010 | 2 |
| 38 | Cinchonain Ia | 29.32 | 453.11789 | −0.24 | C24H21O9 | 343, 313, 301 | Chen et al., 2015 | 2 |
| 39 | Kae-3-O-Glu | 29.42 | 463.08706 | −0.04 | C21H19O12 | 287 | Flamini et al., 2015 | 2 |
| 40 | Pn-(Glc-Cou)-methylGlu | 30.29 | 799.20804 | 0.04 | C38H39O19 | 609, 301, 491, 637 | 3 | |
| 41 | Cy-3-O-CouGlc | 30.67 | 595.14423 | −0.38 | C30H27O13 | 287 | Liang et al., 2008; He et al., 2010 | 2 |
| 42 | Pt-3-O-CouGlc | 30.98 | 625.15504 | −0.14 | C31H29O14 | 317 | Liang et al., 2008; He et al., 2010 | 2 |
| 43 | Isorhramnetin-3-O-Glc | 31.2 | 479.11835 | −0.05 | C22H23O12 | 317 | Flamini et al., 2015 | 2 |
| 44 | Phloretin | 31.38 | 275.09134 | −0.23 | C15H15O5 | 107, 169, 149, 127 | Zhao et al., 2014 | 2 |
| 45 | Cinchonain Ib | 31.52 | 453.11784 | −0.38 | C24H21O9 | 343, 301, 313 | Chen et al., 2015 | 2 |
| 46 | Pg-3-O-Cou-Glc | 31.91 | 579.1496 | −0.1 | C30H27O12 | 271 | Castillo-Munoz et al., 2009 | 2 |
| 47 | Pn-3-O-CouGlc | 32.23 | 609.16016 | −0.11 | C31H29O13 | 301 | Liang et al., 2008; He et al., 2010 | 2 |
| 48 | Mv-3-O-CouGlc | 32.23 | 639.17083 | −0.01 | C32H31O14 | 331 | Liang et al., 2008; He et al., 2010 | 2 |
| 49 | Dihydrokaempferide-3-Glu | 35.83 | 479.11835 | −0.06 | C22H23O12 | 289 | 3 |
Api, Apigenin; Caff, Caffeoyl; Cou, Coumaryl; Cy, Cyanidin; DHQ, Dihydroquercetin (taxifolin); Dp, Delphinidin; Glc, Glucose; Glu, Glucuronide; Kae, Kaempferol; Lar, Laricitrin; Lut, Luteolin; MDHQ, methyldihydroquercetin; Mv, Malvidin; Myr, Myricetin; Pg, Pelargonidin; Pn, Peonidin; Pt, Petunidin; Que, Quercetin; Rha, Rhamnoside; Tri, Tricetin.