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. 2019 Jan 3;24(1):159. doi: 10.3390/molecules24010159

Table 1.

Characterization of chemical compounds in young pear fruits by ultra-performance liquid chromatography coupled with electrospray ionization triple quadrupole mass spectrometry (UPLC-Q TRAP-MS/MS).

Peak NO. Rt (min) Formula [M − H] (m/z) MS/MS Fragments (m/z) Tentative Identification
Polyphenol
1 0.81 C7H12O6 191.1 172.9[M − H − H2O] Quinic acid a
2 1.76 C9H8O2 147.0 129.0[M − H − H2O] Cinnamic acid isomer
3 2.06 C12H16O7 317.1 # 271.2[M − H], 160.9[M − H − C6H6O2], 109.0[M − H − Glc] Arbutin a
4 2.77 C30H24O12 575.3 449.0[M − H − C6H6O3], 285.2[M − H − C15H14O6] A-type procyanidin dimer
5 3.19 C16H18O9 353.3 191.1[M − H − caffeoyl], 179.2[M − H − quinoyl] 4-O-Caffeoylquinic acid (Cryptochlorogenic acid) a
6 3.37 C15H20O9 343.2 181.0[M − H − hexose] Dihydro-caffeoyl-O-hexoside
7 3.48 C30H26O12 577.3 425.2[M − H − C8H8O3], 288.9[M − H − C15H12O6] B-type procyanidin dimer
8 3.51 C15H20O8 327.2 147.1[M − H − hexose − H2O] Hydroxyphenylpropionic acid-O-hexoside
9 3.76 C15H20O10 359.3 197.1[M − H − hexose] Syringic acid-O-hexoside
10 3.84 C12H14O6 253.1 135.1[M − H − C3H6O2 − CO2] Caffeoylglycerol
11 3.88 C15H20O9 343.2 181.0[M − H − hexose] Dihydro-caffeoyl-O-hexoside
12 4.11 C15H14O6 289.1 245.3[M − H − CO2], 202.9[M − H − H2O − C3O2] (+)-Catechin a
13 4.13 C16H18O9 353.3 191.1[M − H − caffeoyl], 161.1[M − H − quinoyl − H2O] 3-O-Caffeoylquinic acid (Chlorogenic acid) a
14 4.31 C45H38O18 865.3 577.1[M − H − C15H12O6], 407.1[M − H − C15H12O6 − C8H8O3 − H2O], 289.0[M − H − 2C15H12O6] B-type procyanidin trimer
15 4.38 C16H18O9 353.3 191.1[M − H − caffeoyl], 173.0[M − H − caffeoyl − H2O] 5-O-Caffeoylquinic acid (Neochlorogenic acid) a
16 4.64 C22H18O10 441.3 325.1[M − H − C4H4O4], 163.0[M − H − C4H4O4 − caffeoyl], 118.9[p-coumaric acid − H − CO2] p-Coumaroylcaffeoyl malate
17 4.89 C30H26O12 577.3 425.1[M − H − C8H8O3], 407.0[M − H − C8H8O3 − H2O], 339.0[M − H − C8H8O3 − H2O − C3O2], 289.1[M − H − C15H12O6], 245.0[M − H − C15H12O6 − CO2] B-type procyanidin dimer
18 4.98 C45H38O18 865.3 577.0[M − H − C15H12O6], 287.1[M − H − C15H12O6 − C15H14O6] B-type procyanidin trimer
19 5.07 C45H36O18 863.3 573.3[M − H − C15H14O6], 289.2[M − H − C15H12O6 − C15H10O6] A-type procyanidin trimer
20 5.28 C16H18O9 353.3 191.1[M − H − caffeoyl] 1-O-Caffeoylquinic acid
21 5.30 C15H18O9 341.1 178.9[M − H − hexose] Caffeoyl-O-hexoside
22 5.44 C16H16O8 335.3 179.1[M − H − shikimoyl] Caffeoylshikimic acid
23 5.45 C19H30O8 431.2 # 385.0[M − H], 223.1[M − H − Glc] Roseoside
24 5.48 C15H14O6 289.1 245.0[M − H − CO2], 202.9[M − H − H2O − C3O2] (−)-Epicatechin a
25 5.53 C16H18O8 337.3 190.9[M − H − p-coumaroyl], 163.2 [M − H − quinoyl] 4-p-Coumaroylquinic acid
26 5.57 C15H20O10 359.3 197.0[M − H − hexose], 160.9[M − H − hexose − 2H2O] Syringic acid-O-hexoside
27 5.64 C45H36O18 863.3 711.3[M − H − C8H8O3], 573.0[M − H − C15H14O6], 289.0[M − H − C15H12O6 − C15H10O6] A-type procyanidin trimer
28 6.05 C16H16O8 335.3 179.0[M − H − shikimoyl], 135.1 [M − H − shikimoyl − CO2] Caffeoylshikimic acid
29 6.49 C45H36O18 863.3 711.1[M − H − C8H8O3], 573.0[M − H − C15H14O6], 451.2[M − H − C15H12O6 − C7H8O2], 289.2[M − H − C15H12O6 − C15H10O6] A-type procyanidin trimer
30 6.54 C30H24O12 575.3 285.3[M − H − C15H14O6] A-type procyanidin dimer
31 6.69 C17H20O9 367.4 191.0[M − H − feruloyl], 193.2[M − H − quinoyl] 3-O-Feruloylquinic acid
32 6.71 C19H16O12 435.3 273.0[M − H − caffeoyl], 205.0[M − H − caffeoylmalonyl] Caffeoyl-malonyl-methylcitric aci
33 7.01 C45H38O18 865.3 577.1[M − H − C15H12O6], 451.1[M − H − C15H12O6 − C6H6O3], 407.1[M − H − C15H12O6 − C8H8O3 − H2O], 289.0[M − H − 2C15H12O6] B-type procyanidin trimer
34 7.24 C16H18O8 337.3 190.9[M − H − p-coumaroyl], 163.2 [M − H − quinoyl] 5-p-Coumaroylquinic acid
35 7.35 C30H26O12 577.3 289.3[M − H − C15H12O6] B-type procyanidin dimer
36 7.40 C17H20O9 367.4 205.1[M − H − caffeoyl] 4-O-Caffeoylquinic acid methyl ester
37 7.58 C30H24O12 575.3 285.2[M − H − C15H14O6] A-type procyanidin dimer
38 7.61 C32H38O20 741.4 301.1[M − H − Xyl-Rha-Gal] Quercetin-3-O-xylosylrhamnosylglucoside
39 7.84 C21H22O10 433.3 323.0[M − H − C6H6O2], 161.1[M − H − arbutin − H2O] Caffeoylarbutin
40 7.89 C60H50O24 1153.3 739.1[M − H − C15H12O6 − C6H6O2], 449.2[C30H26O12 − H − H2O − C6H6O2], 287.1[C30H26O12 − H − C15H14O6] B-type procyanidin tetramer
41 8.04 C24H24O13 519.4 315.3[M − H − acetyl-hexose] Isorhamnetin-acylated-hexoside
42 8.05 C21H22O10 433.3 323.0[M − H − C6H6O2], 178.9[M − H − arbutin], 160.9[M − H − arbutin − H2O], 133.1[M − H − arbutin − H2O − CO] Caffeoylarbutin
43 8.11 C26H28O16 595.4 301.1[M − H − Ara-Gal] Quercetin-3-O-arabinosylgalactoside
44 8.13 C45H36O18 863.3 573.1[M − H − C15H14O6], 451.1[M − H − C15H12O6 − C7H8O2], 289.2[M − H − C15H12O6 − C15H10O6] A-type procyanidin trimer
45 8.19 C30H24O12 575.3 448.9[M − H − C6H6O3], 285.1[M − H − C15H14O6] A-type procyanidin dimer
46 8.32 C15H20O10 359.3 197.2[M − H − hexose] Syringic acid-O-hexoside
47 8.41 C9H8O3 163.0 118.9[M − H − CO2] Hydroxycinnamic acid
48 8.43 C17H20O9 367.4 205.0[M − H − caffeoyl] 3-O-Caffeoylquinic acid methyl ester
49 8.63 C26H28O16 595.4 301.1[M − H − Ara-Glc] Quercetin-3-O-arabinosylglucoside
50 8.65 C27H30O16 609.4 301.0[M − H − Rha-Gal] Quercetin-3-O-rhamnosylgalactoside
51 8.72 C21H20O11 447.3 285.2[M − H − Glc] Luteolin-7-O-galactoside
52 8.87 C27H30O16 609.4 301.0[M − H − Rut] Rutin a
53 8.91 C45H38O18 865.3 577.1[M − H − C15H12O6], 451.1[M − H − C15H12O6 − C6H6O3], 407.1[M − H − C15H12O6 − C8H8O3 − H2O], 289.0[M − H − 2C15H12O6] B-type procyanidin trimer
54 8.93 C25H24O11 499.4 353.1[M − H − p-coumaroyl], 337.2[M − H − caffeoyl], 191.2[M − H − caffeoyl − p-coumaroyl], 163.1[p-coumaroyl − H] p-Coumaroylcaffeoylquinic acid
55 8.98 C21H20O12 463.2 301.2[M − H − Gal] Quercetin-3-O-galactoside (Hyperoside) a
56 9.01 C27H30O15 593.3 285.1[M − H − Rha-Gal] Kaempferol-3-O-rhamnosylgalactoside
57 9.14 C21H22O10 433.3 323.4[M − H − C6H6O2], 161.2[M − H − arbutin − H2O], 133.2[M − H − arbutin − H2O − CO] Caffeoylarbutin
58 9.15 C25H24O11 499.4 353. 1[M − H − p-coumaroyl], 336.9[M − H − caffeoyl], 191.1[M − H − caffeoyl − p-coumaroyl], 163.0[p-coumaroyl − H] p-Coumaroylcaffeoylquinic acid
59 9.16 C21H20O12 463.2 301.2[M − H − Glc] Quercetin-3-O-glucoside
60 9.17 C30H26O12 577.3 425.1[M − H − C8H8O3], 289.0[M − H − C15H12O6] B-type procyanidin dimer
61 9.25 C25H24O12 515.5 353.1[M − H − caffeoyl], 191.0[M − H − 2caffeoyl] Di-O-caffeoylquinic acid
62 9.26 C21H20O11 447.3 285.0[M − H − Glc] Luteolin-7-O-glucoside (Luteoloside) a
63 9.30 C45H38O18 865.3 577.2[M − H − C15H12O6], 406.9[M − H − C15H12O6 − C8H8O3 − H2O], 289.0[M − H − 2C15H12O6] B-type procyanidin trimer
64 9.38 C27H30O15 593.3 285.1[M − H − Rha-Glc] Kaempferol-3-O-rhamnosylglucoside
65 9.44 C21H18O11 445.3 401.0[M − H − CO2], 357.2[M − H − 2CO2], 313.2[M − H − 3CO2], 225.2[M − H − C6H8O6 − CO2], 181.1[M − H − C6H8O6 − 2CO2] Apigenin-O-glucuronide or isomer
66 9.46 C30H24O12 575.3 539.0[M − H − H2O − H2O], 449.1[M − H − C6H6O3], 407.1[M − H − CO2 − C7H8O2], 285.1[M − H − C15H14O6] A-type procyanidin dimer
67 9.51 C45H34O18 861.3 735.1[M − H − C6H6O3], 693.2[M − H − CO2 − C7H8O2], 571.2[M − H − C15H14O6] A-type procyanidin trimer
68 9.54 C21H22O9 417.2 307.3[M − H − C6H6O2], 163.1[M − H − arbutin], 145.1[M − H − arbutin − H2O] p-Coumaroylarbutin
69 9.65 C17H20O9 367.4 205.0[M − H − caffeoyl], 191.1[M − H − caffeoyl − methyl] 5-O-Caffeoylquinic acid methyl ester
70 9.69 C45H36O18 863.3 575.0[M − H − C15H12O6], 449.0[M − H − C15H12O6 − C6H6O3] A-type procyanidin trimer
71 9.70 C19H16O12 435.3 273.1[M − H − caffeoyl], 205.3[M − H − caffeoylmalonyl], 161.1[M − H − caffeoylmalonyl − CO2] Caffeoyl-malonyl-methylcitric acid
72 9.75 C21H18O11 445.3 401.2[M − H − CO2], 357.2[M − H − 2CO2], 313.1[M − H − 3CO2], 225.1[M − H − C6H8O6 − CO2] Apigenin-O-glucuronide or isomer
73 9.76 C27H30O15 593.3 285.1[M − H − Rut] Kaempferol-3-O-rutinoside a
74 9.78 C23H22O13 505.3 445.2[M − H − CH3COOH], 301.1[M − H − acetyl-Gal] Quercetin-acylated-galactoside
75 9.80 C28H32O16 623.5 315.0[M − H − Gal-Rha] Isorhamnetin-3-O-rhamnosylgalactoside
76 9.87 C25H24O12 515.5 353.0[M − H − caffeoyl] 3,4-O-Dicaffeoylquinic acid (Isochlorogenic acid B) a
77 9.92 C27H30O14 577.3 269.1[M − H − Rut] Apigenin rutinoside
78 9.95 C28H32O16 623.5 315.0[M − H − Rut] Isorhamnetin-3-O-rutinoside a
79 10.07 C21H20O11 447.3 285.0[M − H − Glc] Kaempferol-3-O-galactoside
80 10.09 C23H22O13 505.3 445.1[M − H − CH3COOH], 301.1[M − H − acetyl-Glc] Quercetin-acylated-glucoside
81 10.10 C22H22O12 477.3 315.0[M − H − Gal] Isorhamnetin-3-O-galactoside
82 10.14 C28H32O15 607.4 299.1[M − H − Nhe] Chrysoeriol-7-neohesperidoside
83 10.21 C25H24O12 515.5 353.2[M − H − caffeoyl], 191.0[M − H − 2caffeoyl], 178.9[M − H − caffeoyl-quinoyl] 3,5-O-Dicaffeoylquinic acid (Isochlorogenic acid A) a
84 10.22 C30H24O12 575.3 406.9[M − H − CO2 − C7H8O2] A-type procyanidin dimer
85 10.27 C21H22O9 417.2 307.3[M − H − C6H6O2], 163.0[M − H − arbutin], 145.1[M − H − arbutin − H2O] p-Coumaroylarbutin
86 10.28 C22H22O12 477.3 315.0[M − H − Glc] Isorhamnetin-3-O-glucoside
87 10.31 C21H20O11 447.3 285.0[M − H − hexose] Kaempferol-3-O-glucoside
88 10.34 C21H20O10 431.2 269.1[M − H − hexose] Apigenin-O-hexoside
89 10.38 C25H24O11 499.4 353. 0[M − H − p-coumaroyl], 337.0[M − H − caffeoyl], 191.0[M − H − caffeoyl − p-coumaroyl] p-Coumaroylcaffeoylquinic acid
90 10.58 C22H22O11 461.4 298.9[M − H − Gal] Chrysoeriol-7-O-galactoside
91 10.60 C45H34O18 861.3 735.0[M − H − C6H6O3], 693.1[M − H − CO2 − C7H8O2], 571.1[M − H − C15H14O6], 288.9[M − H − 2C15H10O6] A-type procyanidin trimer
92 10.71 C25H24O12 515.5 353.1[M − H − caffeoyl], 191.1[M − H − 2caffeoyl], 179.0[M − H − caffeoyl-quinoyl] 4,5-O-Dicaffeoylquinic acid (Isochlorogenic acid C) a
93 10.75 C22H22O11 461.4 299.2[M − H − Glc] Chrysoeriol-7-O-glucoside
94 10.80 C23H22O12 489.1 285.1[M − H − acetyl-Gal] Kaempferol-acylated-galactoside
95 10.85 C24H24O13 519.4 315.3[M − H − acetyl-Gal], 299.2[M − H − acetyl-Gal − CH4] Isorhamnetin-acylated-galactoside
96 11.05 C24H24O13 519.5 315.0[M − H − acetyl-Glc], 299.2[M − H − acetyl-Glc − CH4], 271.2[M − H − acetyl-Glc − CH4 − H2O] Isorhamnetin-acylated-glucoside
97 11.30 C25H24O11 499.4 353. 0[M − H − p-coumaroyl], 337.1[M − H − caffeoyl], 190.9[M − H − caffeoyl − p-coumaroyl], 163.0[p−coumaroyl − H] p-Coumaroylcaffeoylquinic acid
98 11.78 C23H22O12 489.1 285.1[M − H − acetyl-Glc] Kaempferol-acylated-glucoside
99 11.80 C17H20O9 367.4 205.1[M − H − caffeoyl], 190.9[M − H − caffeoyl-methyl], 147.0[M − H − caffeoyl-methyl − CO2] 1-O-Caffeoylquinic acid methyl ester
100 12.13 C21H20O11 447.3 295.4[M − H − Galloyl] Galloyl-coumaric acid pentoside
101 12.15 C22H22O12 477.3 273.1[M − H − acetyl-hexose] Phloretin-acylated-hexoside
102 12.38 C21H20O11 447.3 295.1[M − H − Galloyl] Galloyl-coumaric acid pentoside
Triterpenoid
1′ 1.21 C30H48O5 487.3 469.1[M − H − H2O], 425.0[M − H − H2O − CO2] Euscaphic acid
2′ 1.40 C30H48O5 487.3 469.3[M − H − H2O], 425.2[M − H − H2O − CO2] Tormentic acid
3′ 1.59 C30H46O5 485.3 467.1[M − H − H2O], 423.2[M − H − H2O − CO2] Anmurcoic acid
4′ 1.95 C30H48O4 471.3 453.2[M − H − H2O], 407.0[M − H − H2O − CH2O] Pomolic acid isomer
5′ 2.47 C30H46O4 469.3 425.1[M − H − CO2], 407.0[M − H − H2O − CO2] 1-Hydroxy-3-oxours-12-en-28-oic acid or isomer
6′ 2.63 C30H48O4 471.3 453.3[M − H − H2O], 407.1[M − H − H2O − CH2O] Pomolic acid a
7′ 2.89 - 701.5 641.2, 555.1, 540.1, 481.1 Unknown
8′ 3.11 C30H48O4 471.3 453.2[M − H − H2O], 407.1[M − H − H2O − CH2O] Alphitolic acid a
9′ 3.45 C30H48O4 471.3 453.0[M − H − H2O], 407.1[M − H − H2O − CH2O] Maslinic acid a
10′ 3.79 C30H48O4 471.3 453.2[M − H − H2O], 407.3[M − H − H2O − CH2O] Corosolic acid
11′ 4.38 C30H46O4 469.3 425.2[M − H − CO2], 407.1[M − H − CO2 − H2O] 1-Hydroxy-3-oxours-12-en-28-oic acid or isomer
12′ 4.79 C30H46O4 469.3 425.1[M − H − CO2], 407.3[M − H − CO2 − H2O] 1-Hydroxy-3-oxours-12-en-28-oic acid or isomer
13′ 6.89 C30H48O3 455.3 407.4[M − H − H2O − CH2O] Betulinic acid a
14′ 7.44 C30H48O3 455.3 407.4[M − H − H2O − CH2O] Oleanolic acid a
15′ 7.95 C30H48O3 455.3 407.2[M − H − H2O − CH2O] Ursolic acid a
16′ 8.37 - 687.4 627.1, 541.2, 526.2, 467.0 Unknown

Note: # the proposal ion was [M − H + HCOOH]; a identification confirmed by authentic standards.