Table 3.
LC-ESI-QTOF-MS/MS analysis of phenolic compounds present in Brazilian red propolis.
| Compound | Putative Compound Name | RT (min) | ProposedFormula | [M–H]−(m/z) | MS/MS Fragments (m/z) |
|---|---|---|---|---|---|
| Flavones | |||||
| 1 | Chrysin | 28.6 | C15H10O4 | 253.0510 | 253.0507; 119.0483; 195.0438; 224.0481; 209.0614 |
| 2 | Tricin | 34.2 | C17H14O7 | 329.0677 | 329.0667; 299.0218; 271.0263; 243.0289 |
| 3 | Genkwanin | 36.2 | C16H12O5 | 283.0624 | 268.0360; 283.0583; 269.0397 |
| 4 | Hispidulin | 37.5 | C16H12O6 | 299.0565 | 284.0331; 227.0354; 255.0301; 212.0483 |
| 5 | 8-Hydroxy-5-methoxyflavanone | 44.2 | C16H14O4 | 269.0831 | 254.0589; 252.0437; 195.0451; 210.0685 |
| 6 | Acacetin | 54.2 | C16H12O5 | 283.0617 | 268.0382; 211.0408; 269.042 |
| Flavanones | |||||
| 7 | Liquiritigenin | 25.1 | C15H12O4 | 255.0667 | 119.0495; 135.0083; 255.0656; 120.0526 |
| 8 | Naringenin * | 32.6 | C15H12O5 | 271.0619 | 119.0487; 151.0029; 254.0596; 271.0609; 165.0207 |
| 9 | Pinocembrin * | 48.6 | C15H12O4 | 255.0668 | 255.0678; 240.0426; 151.0034; 133.0285; 213.0540; |
| 10 | 5,6-Dihydroxy-3′,4′-dimethoxyflavanone | 48.7 | C17H16O6 | 315.0882 | 315.0881;151.0037; 235.0636; 255.1042; 121.0292; |
| 11 | 6-Hydroxyflavanone | 57.3 | C15H12O3 | 239.0722 | 239.0732; 135.0091; 197.0643 |
| Chalcones | |||||
| 12 | Isoliquiritigenin * | 41.1 | C15H12O4 | 255.0676 | 119.0496; 135.0082; 120.0531; 151.0384; 255.0665 |
| 13 | 2′,4′-Dihydroxychalcone | 41.9 | C15H12O3 | 239.0723 | 239.0709; 197.0609; 135.0085; 198.0667 |
| 14 | 7-hydroxyflavanone | 42.2 | C15H12O3 | 239.0719 | 197.0610; 135.0085; 239.0732; 198.0643 |
| 15 | 2′,6′-dihydroxy-4′-methoxydihydrochalcone | 45.2 | C16H16O4 | 271.0990 | 254.0590; 135.0444; 109.0287; |
| 16 | 2′-Hydroxy-4′-methoxychalcone | 49.9 | C16H14O3 | 253.0879 | 237.0552; 255.0665; 253.0872; 136.0169; 161.0239 |
| Isoflavonoids | |||||
| 17 | Daidzein * | 28.7 | C15H10O4 | 253.0511 | 253.0513; 208.0523; 119.0488; 135.0089 |
| 18 | Calycosin | 31.9 | C16H12O5 | 283.0617 | 268.0353; 211.0422; 224.0506; 239.0313; 267.0665 |
| 19 | Dihydrobiochanin A | 34.1 | C16H14O5 | 285.0776 | 270.0541; 109.0289; 161.0242; 285.0767 |
| 20 | Vestitone | 34.5 | C16H14O5 | 285.0776 | 270.0535; 161.0240; 109.0286; 271.0607 |
| 21 | Vestitol | 41.4 | C16H16O4 | 271.0987 | 135.0450; 109.0282; 149.0604; 147.0452; 271.0986; 256.0747 |
| 22 | Neovestitol | 41.8 | C16H16O4 | 271.0990 | 135.0360; 109.0217;256.0555; 197.0482; 212.0707 |
| 23 | Formononetin * | 43.9 | C16H12O4 | 267.0666 | 252.0431; 254.0594; 223.0404; 195.0456; 253.0483 |
| 24 | Demethyl medicarpin | 45.2 | C15H12O4 | 255.0673 | 255.0668; 105.0189; 151.0032; 107.0118; 213.0532 |
| 25 | Medicarpin | 48.6 | C16H14O4 | 269.0827 | 254.0594; 225.0540; 105.0191; 121.0300; 133.0287 |
| 26 | Biochanin A * | 52.0 | C16H12O5 | 283.0619 | 268.0389; 239.0354; 211.0393; 132.0202;195.4450 |
| 27 | 5,4′-Dihydroxy-7-methoxyisoflavone | 53.1 | C16H12O5 | 283.0619 | 268.0383; 211.0422; 223.0402; 224.0506; |
| 28 | 3,9-Dimethoxypterocarpan | 63.0 | C17H16O4 | 283.0988 | 253.0515; 225.0564; 268.0754; 183.0456; 254.0554 |
| Flavonols | |||||
| 29 | 7-Hydroxy-6-methoxydihydroflavonol | 30.9 | C16H14O5 | 285.0743 | 270.0534; 268.0383; 78.9984; 123.0078 |
| Neoflavonoids | |||||
| 30 | Dalbergin | 38.3 | C16H12O4 | 267.0667 | 252.0465; 224.0503; 195.0451; 267.0650; 204.9615 |
| Polyprenylated benzophenones | |||||
| 31 | Guttiferone E/Xanthochymol | 92.2 | C38H50O6 | 601.3567 | 109.0291; 108.0214; 202.9997; 177.0198; 335.1285 |
| 32 | Oblongifolin B | 93.8 | C38H50O6 | 601.3569 | 109.0292; 108.0216; 176.0146; 307.1362 |
Bold values indicate the main fragments; RT = retention time; [M−H]− (negative ionization mode) experimental mass of compound. * As compared to an authentic standard.