Evidence-Based Complementary and Alternative Medicine

Research Article

Phytochemical Analysis Using UPLC-MSn Combined with Network Pharmacology Approaches to Explore the Biomarkers for the Quality Control of the Anticancer Tannin Fraction of Phyllanthus emblica L. Habitat in Nepal

Table 1

The UPLC-MSn data and compound names of the 110 peaks.
Peak no.tR (min)Molecular formula[M−H]−ppmNegative modeIdentification
1d0.75C7H8O7203.0186−0.18MS1 : 203.0186 [M−H]−, MS2 : 159.0324 [M−CO2−H]−2-oxo-3-carboxyadipic acid
2d0.86C6H12O6179.05620.25MS1 : 179.0562 [M−H]−, MS2 : 101.0242 [C4H5O3]−, 89.0242 [C3H5O3]−, 71.01382 [C3H2O2]−Glucose
3a0.89C6H10O8209.03780.33MS1 : 209.0378 [M−H]−, MS2 : 191.0267 [M−H2O−H]−, 147.0304 [M−H2O−CO2−H]−Mucic acid
4a0.93C6H8O7191.0264−0.14MS1 : 191.0264 [M−H]−, 383.0234 [2M−H]− MS2 : 147.0304 [M−CO2−H]−, 119.0221 [M−CO2−CO−H]−Mucic acid lactone
5a0.97C4H6O5133.01310.23MS1 : 133.0131 [M−H]−, MS2 : 115.0321 [M−H2O−H]−Malic acid
6e1.01C13H16O10331.06590.34MS1 : 331.0659 [M−H]−, 663.1325 [2M−H]−, MS2 : 169.0145 [galloyl]6-O-galloylglucose
7a1.05C13H14O12361.04060.22MS1 : 361.0406 [M−H]−, MS2 : 209.0378 [M−galloyl−H]−, 191.0264 [M–galloyl–H2O–H]−Mucic acid 2-O-gallate
8b1.13C14H12O11355.0345−0.55MS1 : 355.0345 [M−H]−, MS2 : 331.0666Chebulic acid
9e1.17C13H16O10331.06590.44MS1 : 331.0659 [M−H]−, 663.1325 [2M−H]−, MS2 : 169.0145 [galloyl]2-O-galloylglucose
10b1.20C20H18O16513.05890.33MS1 : 513.0589 [M−H]−, MS2 : 361.0444 [M−H−galloyl]−, 209.0344 [M−H−2 galloyl]−Mucic acid digallate
11d2.57C6H8O7191.01980.93MS1 : 191.0198 [M−H]−, 383.0234 [2M−H]−, MS2 : 147.1211 [M−CO2−H]−, 129.0392 [M−CO2−H2O−H]−Citric acid
12a1.25C13H12O11343.0305−0.29MS1 : 343.0305 [M−H]−, MS2 : 191.0198 [M−galloyl−H]−Mucic acid lactone gallate
13e1.97C13H16O10331.06590.27MS1 : 331.0659 [M−H]−, 663.1325 [2M−H]−, MS2 : 169.0145 [galloyl]1-O-galloylglucose
14a2.16C13H12O11343.03050.77MS1 : 343.0305 [M−H]−, MS2 : 191.0198 [M−galloyl−H]−Mucic acid lactone gallate
15e2.32C7H6O5169.0122−0.38MS1 : 169.0122 [M−H]−, MS2 : 125.0338 [M−CO2−H]−Gallic acid
16a2.43C14H16O12375.0558−0.72MS1 : 375.0558 [M−H]−, MS2 : 223.0434 [M−galloyl−H]−Mucic acid methyl ester gallate
17b2.50C20H18O16513.05890.66MS1 : 513.0589 [M−H]−, MS2 : 361.0444 [M−H−galloyl]−, 209.0344 [M−H−2 galloyl]−Mucic acid digallate
18a2.57C14H16O12375.05580.90MS1 : 375.0558 [M−H]−, MS2 : 345.0323 [M−H−2CH3]−, 331.0711Mucic acid methyl ester gallate
19b2.69C20H18O16513.0589−0.33MS1 : 513.0589 [M−H]−, MS2 : 361.0444 [M−H−galloyl]−, 209.0344 [M−H−2 galloyl]−Mucic acid digallate
20a2.89C14H16O12375.0558−0.48MS1 : 375.0558 [M−H]−, MS2 : 345.0323 [M−H−2CH3]−, 331.0711Mucic acid methyl ester gallate
21b3.11C20H18O16513.05890.78MS1 : 513.0589 [M−H]−, MS2 : 361.0444 [M−H−galloyl]−, 209.0344 [M−H−2galloyl]−Mucic acid digallate
22a3.24C14H16O12375.05580.92MS1 : 375.0558 [M−H]−, MS2 : 345.0323[M−H−2CH3]−, 331.0711Mucic acid methyl ester gallate
23b4.08C20H16O15495.0405−0.93MS1 : 495.0405 [M−H]−, MS2 : 343.0356 [M−H−galloyl]−, 191.0223 [M−H−2 galloyl]−Mucic acid lactone digallate
24a4.75C15H18O12389.07140.22MS1 : 389.0714 [M−H]−, 779.1529 [2M−H]−, MS2 : 237.0564 [M−H−galloyl]−Mucic acid dimethyl ester gallate
25b5.10C20H18O16513.05890.44MS1 : 513.0589 [M−H]−, MS2 : 361.0444 [M−H−galloyl]−, 209.0344 [M−H−2 galloyl]−Mucic acid digallate
26b5.19C21H20O16527.06670.73MS1 : 527.0667 [M−H]−, MS2 : 375.0557 [M−H−galloyl]−, 223.0448 [M−H−2 galloyl]−Mucic acid methyl ester digallate
27b5.41C20H20O14483.0769−0.92MS1 : 483.0769 [M−H]−, 967.1610 [2M−H]− MS2 : 331.0712 [M−H−galloyl]−, 271.0523, 169.01391, 4-di-O-galloylglucose
28a4.79C11H10O9285.02410.4MS1 : 285.0250 [M−H]−, 571.0583 [2M−H]−, MS2 : 133.0122 [M−H−galloyl]−Malic acid gallate
29e5.89C14H16O10343.06590.38MS1 : 343.0659 [M−H]−, MS2 : 255.0522 [M−H−2CO2]−, 169.01413-Galloylquinic acid
30b6.17C27H26O20669.0933−0.65MS1 : 669.0933 [M−H]−, MS2 : 337.0199 [M−H−galloyl−H2O−Hex]−Phyllanemblinin D
31b6.44C20H20O14483.07690.89MS1 : 483.0769 [M−H]−, 967.1610 [2M−H]−MS2 : 331.0712 [M−H−galloyl]−, 271.0523, 169.01391, 6-di-O-galloylglucose
32b6.52C27H26O20669.0933−0.19MS1 : 669.0933 [M−H]−, MS2 : 337.0199 [M−H−galloyl−H2O−Hex]−Phyllanemblinin E
33e6.77C15H18O9341.0867−0.28MS1 : 341.0867 [M−H]−, MS2 : 297.0989 [M−H−CO2]−, 179.0234 [M−H-glc]−Caffeic acid-3-glucoside
34b6.88C14H14O11357.0452−0.23MS1 : 357.0452 [M−H]−, 715.5998 [2M−H]−, MS2 : 205.0332 [M−H−galloyl]−Mucic acid lactone methyl ester digallate
35b3.84C48H28O301083.05810.99MS1 : 1083.0581 [M−H]−, MS2 : 541.0836 [M−2H]2−, 781.3025 [M−H−HHDP]−, 300.9921Punicalagin A
36b5.90C48H28O301083.05810.34MS1 : 1083.0581 [M−H]−, MS2 : 541.0836 [M−2H]2−, 781.3025 [M−H−HHDP]−, 300.9921Punicalagin B
37b7.36C14H14O11357.04520.92MS1 : 357.0452 [M−H]−, 715.5998 [2M−H]−, MS2 : 205.0433 [M−H−galloyl]−Mucic acid lactone methyl ester digallate
38b7.46C21H20O16527.06670.66MS1 : 527.0667 [M−H]−, MS2 : 375.0557 [M−H−galloyl]−, 223.0448 [M−H−2 galloyl]−Mucic acid methyl ester digallate
39b7.51C33H28O24807.08960.71MS1 : 807.0896 [M−H]−, MS2 : 483.0789 [M−H−Ela]−, 331.0189 [M−H−Ela−galloyl]−, 169.0143Mallonin
40c7.91C15H14O7305.06550.59MS1 : 305.0655 [M−H]−, MS2 : 215.0098Gallocatechin
41b8.00C33H28O24807.08960.49MS1 : 807.0896 [M−H]−, MS2 : 483.0789 [M−H−Ela]−, 331.0189 [M−H−Ela−galloyl]−, 169.0143Mallonin
42b8.03C20H16O15495.04050.88MS1 : 495.0405 [M−H]−, MS2 : 343.0356 [M−H−galloyl]−, 191.0223 [M−H−2 galloyl]−Mucic acid lactone digallate
43e8.34C14H10O9321.0251−0.46MS1 : 321.0251 [M−H]−, MS2 : 169.1144 [galloyl]−Digallate
44b8.37C27H26O20669.09330.81MS1 : 669.0933 [M−H]−, MS2 : 337.0199 [M−H−galloyl−H2O−Hex]−Phyllanemblinin F
45e8.60C10H12O7243.16000.24MS1 : 243.1600 [M−H]−, MS2 : 169.0144 [galloyl]−, 125.02461-O-galloyl-glycerol
46b8.78C20H20O14483.07690.34MS1 : 483.0769 [M−H]−, 967.1610 [2M−H]− MS2 : 331.0712 [M−H−galloyl]−, 271.0523, 169.01393, 6-di-O-galloylglucose
47b8.84C46H36O311083.11560.66MS1 : 1083.1156 [M−H]−, MS2 : 541.0836 [M−2H]2−, 781.0341 [M−H−HHDP]−, 629.0609 [M−H−HHDP−galloyl]−, 301.0115Putranjivain A
48b9.03C21H20O16527.06670.71MS1 : 527.0667 [M−H]−, MS2 : 375.0557 [M−H−galloyl]−, 223.0448 [M−H−2 galloyl]−Mucic acid methyl ester digallate
49b9.46C41H28O27951.07340.26MS1 : 951.0734 [M−H]−, MS2 : 799.0563 [M−H−galloyl]−, 497.0219 [M−H−galloyl−HHDP]−, 301.0113Geraniin
50b9.53C41H30O27969.08390.22MS1 : 969.0839 [M−H]−, MS2 : 817.0783 [M−H−galloyl]−Phyllanemblinin C
51b9.72C41H32O28971.09960.30MS1 : 971.0996 [M−H]−, MS2 : 953.0906 [M−H−H2O]−, 935.0800 [M−H−2H2O]−, 467.0361 [M−2H−H2O]2−, 300.9911Neochebulagic acid
52b9.39C41H30O27953.08900.50MS1 : 953.0890 [M−H]−, MS2 : 476.0412 [M-2H]2−, 300.9983Terchebin
53e10.14C8H8O5183.02590.61MS1 : 183.0259 [M−H]−, MS2 : 169.0064 [M−H−CH3]−Methyl gallate
54b10.25C27H24O19651.08280.11MS1 : 651.0828 [M−H]−, MS2 : 499.0782[M−H−galloyl]−Chebulanin
55b10.33C47H34O321109.09490.03MS1 : 1109.0949 [M−H]−, MS2 : 957.0466 [M−galloyl−H]−, 655.0497 [M−galloyl−HHDP−H]−, 300.9091Elaeocarpusin
56b10.48C27H24O18635.08780.06MS1 : 635.0878 [M−H]−, MS2 : 465.0679 [M−galloyl−H2O−H]−, 313.0560 [M−H−galloyl−galloyl–H2O]−, 169.1045Trigalloylglucose
57b10.64C41H30O26937.09410.09MS1 : 937.0941 [M−H]−, MS2 : 785.0648 [M−galloyl−H]−, 633.0566 [M−2 galloyl−H]−, 331.0516 [M−H−2 galloyl−HHDP−H]−, 300.9416Punicafolin
58b10.56C41H28O26935.07850.31MS1 : 935.0785 [M−H]−, MS2 : 783.0648 [M−galloyl−H]−Casuarinin
59b10.73C27H22O18633.07280.92MS1 : 633.0728 [M−H]−, MS2 : 463.0511 [M−galloyl−H]−, 301.0221Corilagin
60b10.73C27H22O18633.07380.39MS1 : 633.0738 [M−H]−, MS2 : 481.0511 [M−galloyl−H]−, 331.0598 [M−HHDP−H]−, 300.9601Phyllanemblinin B
61b10.73C27H22O18633.07220.34MS1 : 633.0722 [M−H]−, MS2 : 481.0511 [M−galloyl−H]−, 331.0598 [M−HHDP−H]−, 300.9601Isostrictinin
62b11.14C20H16O15495.04050.66MS1 : 495.0405 [M−H]−, MS2 : 343.0356 [M−H−galloyl]−, 191.0223 [M−H−2 galloyl]−Mucic acid lactone digallate
63b11.25C33H26O24805.05640.66MS1 : 805.0564 [M−H]−, MS2 : 653.0432 [M−galloyl−H]−Mallonin
64b11.65C27H24O18635.0878−0.39MS1 : 635.0878 [M−H]−, MS2 : 465.0679 [M−H−galloyl−H2O]−, 313.0560 [M−H−2 galloyl−H2O]−, 169.1045Trigalloylglucose
65b11.88C27H20O17615.06160.09MS1 : 615.0616 [M−H]−, MS2 : 463.0506 [M−H−galloyl]−, 177.0534 [M−H−galloyl−THBDF]−Phyllanemblinin A
66b11.92C34H26O22785.08310.01MS1 : 785.0831 [M−H]−, MS2 : 633.0726 [M−H−galloyl]−, 463.0685 [M−H−2 galloyl−H2O]−, 300.9482Digalloyl-HHDP-glucose
67c12.31C15H14O6289.07080.22MS1 : 289.0708 [M−H]−, MS2 : 275.0192 [M−H−CH2]−, 215.0094Epicatechin
68e12.35C20H16O13463.05070.11MS1 : 463.0507 [M−H]−, 927.1101 [2M−H]−, MS2 : 300.9982 [M−H−Hex]−Ellagic acid hexose
69b12.47C41H30O27953.08900.51MS1 : 953.0890 [M−H]−, MS2 : 476.0412 [M−2H]2−, 300.9983Chebulinic acid
70b12.47C41H30O27953.08900.62MS1 : 953.0890 [M−H]−, MS2 : 476.0412 [M−2H]2−, 300.9983Chebulagic acid
71b12.88C34H26O22785.0831−0.71MS1 : 785.0831 [M−H]−, MS2 : 633.0726 [M−H−galloyl]−, 463.0685 [M−H−2 galloyl−H2O]−, 300.9922Digalloyl-HHDP-glucose
72e13.00C19H14O12433.04010.66MS1 : 433.0401 [M−H]−, 867.0895 [2M−H]−, MS2 : 300.9991 [M−H−pent]−Ellagic acid pentose
73c13.23C15H14O6289.0716−0.11MS1 : 289.0716 [M−H]−, MS2 : 241.0354 [M−H−2CH3−H2O]−, 215.0094Catechin
74b13.73C34H26O22785.08310.19MS1 : 785.0831 [M−H]−, MS2 : 633.0726 [M−H−galloyl]−, 463.0685 [M−H−2 galloyl−H2O]−, 300.9911Digalloyl-HHDP-glucose
75b13.80C34H28O22787.09880.29MS1 : 787.0988 [M−H]−, MS2 : 483.0785 [M−H−2 galloyl]−1, 2, 3, 6-tetra-O-galloylglucose
76b14.03C41H30O26937.0941−0.13MS1 : 937.0941 [M−H]−, MS2 : 785.0848 [M−H−galloyl]−, 633.0737 [M−H−2 galloyl]−, 481.0411[M−H−3 galloyl]−, 468.0442 [M−2H]2−, 300.9991Trigalloyl-HHDP-glucose
77c14.06C28H24O16615.09800.51MS1 : 615.0980 [M−H]−, MS2 : 463.0893 [M−H−galloyl]−2′-O-galloylhyperin
78b14.12C34H22O22781.05180.11MS1 : 781.0518 [M−H]−, MS2 : 629.0521 [M−H−galloyl]−, 477.0443 [M−H−2 galloyl]−, 175.0551 [M−H−2 galloyl−HHDP]−, 300.9559Emblicanin A
79b10.40C48H32O321119.07920.19MS1 : 1119.0792 [M−H]−, MS2 : 967.0893 [M−H−galloyl]−Mallotusinic acid
80e14.53C19H14O12433.04010.17MS1 : 433.0401 [M−H]−, 867.0895 [2M−H]−, MS2 : 300.9991 [M−H−pent]−Ellagic acid pentose
81c17.20C28H24O15599.1046−0.22MS1 : 599.1046 [M−H]−, MS2 : 285.0393 [M−galloylgalactoside−H]−, 153.01813Kaempferol-3-(6″-galloylgalactoside)
82c14.86C15H12O5271.06110.92MS1 : 271.0611 [M−H]−, MS2 : 177.0197 [M−C6H7O−H]−, 151.0035 [M−C6H7O−2CH3−H]−, 119.0012 [M−C6H7O−2CH3−2CH4– H]−Naringenin
83e15.02C20H16O12447.05580.62MS1 : 447.0558 [M−H]−, MS2 : 300.9991Ellagic acid deoxyhexose
84c15.10C21H20O12463.0871−0.15MS1 : 463.0871 [M−H]−, MS2 : 301.0312 [M−H−hexose] −Quercetin hexose
85e15.22C14H6O8300.9978−0.71MS1 : 300.9978 [M−H]−, MS2 : 283.2637 [M−H−H2O]−, 273.0035 [M−H−CO]−, 229.0137 [M−H−CO−CO2]−Ellagic acid
86b15.49C41H26O25917.06790.66MS1 : 917.0679 [ M−H]− MS2 : 765.0313 [M−galloyl−H]−, 463.0335 [M−H−galloyl−HHDP]−, 300.9091Mallotusinin
87c15.97C15H14O5273.07690.92MS1 : 273.0769 [M−H]−, MS2 : 215.0100Epiafzelechin
88b16.17C41H30O26937.0941−0.39MS1 : 937.0941 [M−H]−, MS2 : 785.0848 [M−H−galloyl]−, 633.0737 [M−H−2 galloyl]−, 481.0411 [M−H−3 galloyl]−, 468.0442 [M−2H]2−, 300.9922Trigalloyl-HHDP-glucose
89e16.21C9H10O5197.04440.09MS1 : 197.0444 [M−H]−, MS2 : 153.322 [M−CO2−H]−Vanillylmandelic acid
90c16.24C21H20O11447.09210.01MS1 : 447.0921 [M−H]−, MS2 : 300.9988 [M−H−deoxyhex]−Quercetin deoxyhexose
91c16.24C21H20O11447.09270.44MS1 : 447.0921[M−H]−, MS2 : 287.0545 [M−H−Glc]−Luteolin-7-galactoside
92e16.68C15H8O8315.0147−0.72MS1 : 315.0147 [M−H]−, MS2 : 300.0991 [M−H−CH3]−, 212.9015 [M−H−CH3−2CO2]−3-O-Methylellagic acid
93d16.91C12H20O5243.12270.41MS1 : 243.1227 [M−H]−, MS2 : 225.1125 [M−H−H2O]−, 207.5586 [M−H−2H2O]−, 133.2019 [M−H−2H2O−2CH3−CO2]−Methyl 5, 10-dihydroxy-10-methoxydeca-6, 8-dienoate
94b17.36C29H36O8511.23260.38MS1 : 511.2326 [M−H]−, MS2 : 468.2119 [M−CH3−CO−H]−, 425.1767 [M−2CH3−2CO−H]−Mallotojaponin C
95c17.56C21H20O10431.0983-0.15MS1 : 431.0983 [M−H]−, MS2 : 416.0093 [M−H−CH3]−Vitexin
96e18.50C16H10O8329.0302−0.19MS1 : 329.0302 [M−H]−, MS2 : 255.2328 [M−H−CO2−2CH3]−3, 4-di-O-methylellagic acid
97d18.56C10H18O4201.1132−0.18MS1 : 201.1132 [M−H]−, MS2 : 183.1023 [M−H−H2O]−2-hydroxy-4-oxo-decanoic acid
98c18.80C30H28O13595.1446−0.13MS1 : 595.1446 [M−H]−, MS2 : 287.0382 [M−H−coumaroylhexose]−Eriodictyol coumaroylhexose
99c19.06C30H28O13595.14460.19MS1 : 595.1446 [M−H]−, MS2 : 287.0382 [M−H−coumaroylhexose]−Eriodictyol coumaroylhexose
100d19.20C12H20O4227.12880.14MS1 : 227.1288 [M−H]−, MS2 : 183.0382 [M−H−CO2]−, 157.1079 [M−H−CO2−CH = CH]−Traumatic acid
101b20.25C34H20O22779.03620.01MS1 : 779.0362 [M−H]−, MS2 : 477.0342 [M−H– HHDP]−, 300.9809Emblicanin B
102c20.56C28H24O14583.10820.91MS1 : 583.1082 [M−H]− MS2 : 431.0984 [M−H−galloyl]−, 331.05612″-O-galloylisovitexin
103d22.31C11H20O4215.12770.49MS1 : 215.1277 [M−H]−, MS2 : 197.1181 [M−H−H2O]−, 153.1286 [M−H−H2O−CO2]−5-hydroxy-3-methoxydec-2-enoic acid
104b22.54C25H30O8457.18560.14MS1 : 457.1856 [M−H]−, MS2 : 414.1181 [M−H−CH3CO]−, 371.1286 [M−H−2CH3CO]−Mallotojaponin B
105d25.56C18H28O3291.19540.66MS1 : 291.1954 [M−H]−, MS2 : 247.0332 [M−H−CO2]−Licanic acid
106d26.07C18H36O4315.2535−0.24MS1 : 315.2535 [M−H]−, MS2 : 297.1526 [M−H−H2O]−, 253.1221 [M−H−H2O−CO2]−Dihydroxystearic acid
107d26.24C18H30O3293.2111−0.29MS1 : 293.2111 [M−H]−, MS2 : 275.2159 [M−H−H2O]−, 231.1441 [M−H−H2O−CO2]−9-hydroxyoctadeca-5, 10, 12-trienoic acid
108d27.01C18H36O2283.26410.33MS1 : 283.2641 [M−H]−, MS2 : 265.1576 [M−H−H2O]−, 237.0132 [M−H−H2O−CO]−3-Hydroxyoctadecanal
109d28.73C30H48O3455.35190.29MS1 : 455.3519 [M−H]−, MS2 : 401.0874 [M−H−CO2]−Ursolic acid
110d30.71C16H32O2255.23180.33MS1 : 255.2318 [M−H]−, MS2 : 211.0521 [M−H−CO2]−Palmitic acid
a: mucic acid, b: hydrolysable tannin, c: flavonoids, d: fatty acid, and e: phenolic acids.