Table 2.
Identification of chemical compounds in A. unedo leaves using the LC-ESI-QTOF-MS technique.
Compound | Rt (min) | Molecular Formula | MH+/ MNa+ | Error (ppm) | Score (%) | MS fragment (m/z) | UV λ (nm) | Fresh Leaves | Dried Leaves | Ref. | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
FL1 | FL2 | FL3 | FL4 | FL5 | DL1 | DL2 | DL3 | DL4 | DL5 | |||||||||
Phenolic acids | ||||||||||||||||||
Anisic acid | 1.4 | C8H8O3Na | 175.0389 | 1.2 | 95 | 283 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [42] | |
Caffeic acid | 5.5 | C9H8O4 | 181.0498 | 0.4 | 100 | 238, 322 | √ | √ | [43] | |||||||||
Ellagic acid | 12.1 | C14H6O8 | 303.0136 | 0.8 | 100 | 255, 365 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [44] | |
Ellagic acid 4-O-β-D-glucopyranoside | 10.1 | C20H16O13 | 465.0659 | 0.7 | 100 | 303.0136 | 256, 348 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [46] |
Ferulic acid | 1.7 | C10H10O4 | 195.0652 | 2.1 | 100 | 325 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [45] | |
Gallic acid | 3.2 | C7H6O5 | 171.0287 | 0.3 | 100 | 217, 271 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [42] | |
Galloyl quinic acid (3-O- or 5-O-) | 3.9 | C14H16O10 | 345.0814 | 0.3 | 98 | Nd | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [36] | |
Quinic acid | 0.9 | C7H12O6 | 193.0706 | 0.5 | 100 | - | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [43] | |
Shikimic acid gallate (3-O- or 5-O-) | 7.1 | C14H14O9 | 327.0711 | 0.7 | 100 | 174.1350 | 215, 277 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [36] |
Syringic acid | 10.6 | C9H10O5 | 199.0601 | 0.1 | 100 | 273 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [44] | |
Flavonoids | ||||||||||||||||||
Afzelin | 14.4 | C21H20O10 | 433.1131 | 0.1 | 100 | 287.0550 | 265, 301, 347 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [44] |
Catechin | 9.4 | C15H14O6 | 291.0866 | 1.2 | 100 | 280 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [47] | |
Isovitexin 7-O-glucoside | 12.9 | C27H30O15 | 595.1658 | 0.1 | 100 | 432.3768 | 265, 330 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [43] |
Kaempferol | 14.2 | C15H10O7 | 287.0550 | 0.1 | 100 | 254, 365 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [35] | |
Kaempferol 3-O-glucoside | 13.2 | C21H20O11 | 449.1077 | 0.3 | 100 | 287.0488 | 264, 347 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [40] |
Myricetin 3-O-xyloside | 12.4 | C20H18O12 | 451.0752 | 0.5 | 100 | 319.0435 | 255, 373 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [47] |
Naringenin 7-O-glucoside | 12.4 | C21H22O10 | 435.1257 | 0.2 | 100 | 273.5640 | 283, 332 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [43] |
Norbergenin | 9.2 | C13H14O9 | 315.0710 | 0.5 | 100 | 222, 289 | √ | √ | [41] | |||||||||
Rutin | 12.4 | C27H30O16 | 611.1612 | 0.2 | 100 | 303.0499 | 253, 352 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [47] |
Hyperoside(*) | 12.8 | C21H20O12 | 465.1031 | 0.8 | 100 | 303.0499 | 254, 353 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [35] |
Isoquercitrin(*) | 12.8 | C21H20O12 | 465.1031 | 0.8 | 100 | 303.0499 | 253, 353 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [35] |
Myricetin | 12.6 | C15H10O8 | 319.0446 | 0.1 | 100 | 255, 375 | √ | √ | √ | [45] | ||||||||
Myricetin 3-O-rhamnopyranoside(*) | 12.7 | C21H20O12 | 465.1031 | 0.4 | 100 | 319.0389 | 253, 365 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [39] |
Quercetin 3-O-arabinoside(**) | 13.4 | C20H18O11 | 435.7749 | 0.3 | 100 | 303.0499 | 253, 353 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [39] |
Quercetin 3-O-xyloside(**) | 13.5 | C20H18O11 | 435.7749 | 0.3 | 100 | 303.0499 | 254, 356 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [47] |
Quercitrin | 13.6 | C21H20O11 | 449.1079 | 0.7 | 100 | 303.0499 | 254, 356 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [35] |
Proanthocyanidins | ||||||||||||||||||
Gallocatechin | 6.8 | C15H14O7 | 307.0811 | 2.9 | 89 | 271 | √ | √ | √ | √ | √ | [47] | ||||||
Epicatechin-4,6-catechin(***) | 9.5 | C30H26O12 | 579.1495 | 0.1 | 100 | 291.0851 | 280 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [47] |
Epicatechin-4,8-epicatechin(***) | 11.8 | C30H26O12 | 579.1492 | 0.3 | 100 | 291.0851 | 280 | √ | √ | √ | √ | √ | √ | √ | √ | √ | √ | [47] |
Iridoids | ||||||||||||||||||
Asperuloside | 1.8 | C18H22O11 | 415.1214 | 4.4 | 84 | 239 | √ | √ | √ | [34] | ||||||||
Gardenoside | 5.9 | C17H24O11 | 405.1391 | 0.5 | 96 | 237 | √ | √ | √ | √ | √ | √ | √ | √ | [34] | |||
Geniposide | 10.5 | C17H24O10 | 389.1447 | 0.8 | 98 | 239 | √ | √ | [34] | |||||||||
Stilbericoside | 15.7 | C14H20O10 | 349.1129 | 0.1 | 99 | Nd | √ | [48] | ||||||||||
Unedide | 1.2 | C16H24O12 | 409.1340 | 0.4 | 100 | Nd | √ | √ | √ | √ | √ | √ | [48] | |||||
Unedoside | 11.2 | C14H20O10 | 333.0819 | 0.4 | 95 | Nd | √ | √ | [48] | |||||||||
Phenolic glucosides | ||||||||||||||||||
Arbutin | 1.8 | C12H16O7Na | 295.0793 | 0.8 | 96 | 230, 282 | √ | √ | [44] | |||||||||
p-hydroxybenzoic acid glucuronide | 9.8 | C13H14O9 | 315.0712 | 0.5 | 94 | 253 | √ | √ | √ | √ | √ | √ | √ | √ | √ | [42] |
FL: fresh leaves extracts; DL: dried leaves extracts. 1. Ethanolic maceration; 2. hydroalcoholic maceration; 3. decoction; 4. ethanol extraction Soxhlet apparatus; 5. ethanol ultrasound-assisted extraction. Rt: Retention time. √: presence. Nd: not detected. -: no UV. (*) (**)(***): Interchangeable. Ref.: references.