Skip to main content
. 2019 Apr 22;24(8):1585. doi: 10.3390/molecules24081585

Table 1.

Compounds identified from fruits, leaves and root barks of L. barbarum by UPLC-Q-Orbitrap-MS/MS.

No RT 1 Formula [M + H]+ [M − H]− ppm MS/MS Fragments 2 Identification Ref. 3 F 4 L 5 R 6
A1 8.70 C21H29O13 487.1485 1.78 324.8671; 303.7701; 163.0403; 145.0296; 119.0503 Lycibarbarphenylpropanoid A isomer [28] ✓
A2 9.72 C21H29O13 487.1492 1.22 398.1759; 229.0514; 163.0381; 145.0275; 119.0503 Lycibarbarphenylpropanoid A isomer [28] ✓
A3 10.44 C22H30O14 517.1583 0.72 334.8634; 235.0619; 193.0510; 175.0403; 160.0169; 134.0375 Lycibarbarphenylpropanoid C isomer [28] ✓
A4 10.47 C15H16O8 325.0937 0.23 298.8872; 163.0398; 145.0276; 119.0497 p-coumaric acid O-glycosides [16] ✓ ✓
A5 15.45 C16H18O9 355.1050 353.0854 1.34 308.9027; 285.0117; 181.0513; 163.0402; 145.0296; chlorogenic acid isomer [28] ✓
A6 16.16 C22H30O14 517.1594 1.58 354.5810; 259.0620; 193.0510; 175.0403; 160.0169; 134.0375 Lycibarbarphenylpropanoid C isomer [28] ✓
A7 16.88 C16H18O9 355.1050 353.0854 1.55 163.0395; 145.0289; 135.0445; 117.0339; 89.0390; chlorogenic acid * ✓
A8 17.32 C23H32O13 515.1417 1.00 395.0988; 353.0877; 274.9858; 191.0557; 161.0242 Lycibarbarphenylpropanoid F isomer [28] ✓ ✓
A9 18.78 C23H32O13 515.1422 1.24 323.0873; 274.9858; 191.0539; 161.0225 Lycibarbarphenylpropanoid F isomer [28] ✓ ✓
A10 18.87 C16H18O9 355.1008 353.0855 1.42 303.0228; 193.0512; 178.0276; 134.0375 Scopolin * ✓
A11 18.92 C27H36O18 647.1873 1.34 485.2170; 323.1666; 191.0319; 176.0087; 161.0431; 148.0142 lycibarbarcoumarin A [28] ✓
A12 20.42 C16H18O9 355.1047 353.0854 1.34 285.0116; 193.0510; 163.0403; 145.0295; 123.1177 chlorogenic acid isomer [28] ✓
A13 30.04 C17H22O10 385.1140 1.29 326.9597; 185.0199; 163.0381; 119.0486 sinapate 4-O-β-glucopyranoside [29] ✓ ✓
B1 17.87 C28H42O6N4 531.3170 529.3001 1.41 513.3074; 367.2724; 293.1855; 222.1123; 165.0546 kukoamine B ismoer [30] ✓
B2 18.48 C40H62O16N4 855.4222 853.4034 1.38 693.3734; 529.3273; 455.2405; 384.1668; 293.1871; 222.1121; 165.0545 2Glu-[kukoamine] ismoer ✓
B3 19.30 C40H62O16N4 855.4222 853.4034 1.38 693.3693; 531.3206; 455.2379; 384.1668; 293.1853; 222.1121; 165.0545 2Glu-[kukoamine] ismoer ✓
B4 19.48 C46H72O21N4 1017.4749 1015.4559 1.31 855.4216; 617.2904; 455.2379; 384.1645; 222.1122; 165.0557 3Glu-[kukoamine] ismoer ✓
B5 19.50 C28H42O6N4 531.3213 529.3011 1.41 513.3074; 367.2728; 293.1855; 222.1123; 165.0546 kukoamine B ismoer ✓
B6 19.59 C34H52O11N4 693.3698 691.3521 1.05 531.3168; 367.2730; 293.1855; 222.1122; 165.0560; 123.0440 Glu-[kukoamine] ismoer ✓
B7 20.28 C28H42O6N4 531.3165 529.3001 1.41 513.3103; 447.8046; 376.2692; 293.1879; 222.1140; 165.8764 kukoamine A [30] ✓
B8 20.60 C46H72O21N4 1017.4747 1015.4559 1.49 855.4216; 617.2901; 455.2379; 384.1642; 222.1121; 165.0552 3Glu-[kukoamine] ismoer ✓
B9 20.65 C28H42O6N4 531.3220 529.3001 1.41 513.3074; 367.2712; 310.2152; 293.1855; 222.1123; 165.0545 kukoamine B * ✓
B10 21.02 C28H42O6N4 531.3199 529.3003 1. 40 402.9773; 367.2716; 293.1880; 222.1141; 193.0510; 165.0553; 129.1395 kukoamine B ismoer [30] ✓
B11 21.73 C28H40O6N4 529.3059 527.2831 1.13 472.2346; 367.2725; 293.1877; 222.1140; 163.0402 Dihydrocaffeoyl quinonespermine ismoer 7 [31] ✓
B12 23.31 C28H40O6N4 529.3012 527.2847 1.72 511.2894; 455.2384; 384.1648; 293.1855; 220.0986; 163.0406 Dihydrocaffeoyl quinonespermine ismoer [31] ✓ ✓
B13 23.83 C43H63O21N3 958.4016 956.3817 1.18 796.3486; 634.2960; 472.2396; 310.2119; 220.0966; 163.0388 Glu-[lycibarbarspermidine F] isomer ✓
B14 24.41 C37H51O16N3 794.3339 792.3145 0.36 632.2804; 470.2540; 382.1489; 220.0965; 163.0388 [lycibarbarspermidine O] isomer [32] ✓
B15 24.41 C43H65O21N3 960.4161 958.3975 2.28 798.3622; 636.3112; 474.2588; 384.1645; 222.1122; 163.0402 Glu-[lycibarbarspermidine M]ismoer ✓
B16 24.75 C37H55O16N3 798.3640 796.3453 1.80 636.3071; 474.2589; 384.1644; 220.0965; 163.0388 [lycibarbarspermidine M] isomer [32] ✓
B17 24.78 C37H53O16N3 796.3492 794.3301 180 634.2957; 472.2431; 310.2126; 220.0965; 163.0398 [lycibarbarspermidine F] isomer [32] ✓
B18 24.80 C31H43O11N3 634.2959 632.2784 1.31 472.2431; 310.2122; 220.0966; 163.0390 lycibarbarspermidine B isomer [32] ✓
B19 24.94 C43H63O21N3 958.4267 956.3817 1.82 796.3481; 634.2957; 472.2414; 310.2119; 220.0964; 163.0388 Glu-[lycibarbarspermidine F] isomer ✓
B20 25.17 C37H55O16N3 798.3640 796.3453 1.89 636.3117; 474.2589; 384.1644; 222.1121; 165.0545 [lycibarbarspermidine M] isomer [32] ✓
B21 25.62 C28H42O5N4 515.3267 7.61 498.2995; 367.2717; 293.7878; 277.1928; 222.1139; 165.0556; 129.1395 Dihydrocaffeoyl spermine derivative ✓
B22 25.72 C28H40O6N4 529.3054 527.2847 7.16 458.2317; 367.2724; 291.1721; 220.0988; 163.0401 Dihydrocaffeoyl quinonespermine ismoer [31] ✓ ✓
B23 25.72 C28H40O6N4 529.3059 527.2847 1.72 511.2894; 393.2533; 384.1649; 291.1745; 220.2846; 163.0422 Dihydrocaffeoyl quinonespermine ismoer [31] ✓
B24 25.77 C43H63O21N3 958.4016 956.3817 1.69 796.3489; 634.2968; 472.2392; 310.2118; 220.09656; 163.0383 Glu-[lycibarbarspermidine F] isomer ✓
B25 26.02 C37H55O16N3 798.3626 796.3453 3.63 636.3112; 474.2581; 384.1645; 222.1128; 165.0544 [lycibarbarspermidine M] isomer [32] ✓
B26 26.10 C37H53O16N3 796.3409 794.3301 1.92 634.2957; 472.2431; 310.2121; 220.0965; 163.0390 [lycibarbarspermidine F] isomer [32] ✓
B27 26.36 C43H65O21N3 960.4125 958.3969 3.30 798.3621; 636.3112; 474.2590; 384.1646; 222.1121; 163.0404 Glu-[lycibarbarspermidine M]ismoer ✓
B28 26.41 C43H63O21N3 958.4011 956.3817 1.63 796.3483; 634.2957; 472.2428; 398.1824; 310.2119; 220.0965; 163.0388 Glu-[lycibarbarspermidine F] isomer ✓
B29 26.44 C37H55O16N3 798.3609 796.3453 1.58 636.3071; 474.2585; 384.16455; 222.1122; 163.0385 [lycibarbarspermidine M] isomer ✓
B30 26.79 C43H63O21N3 958.4009 956.3817 1.82 796.3530; 634.2994; 472.2431; 382.1511; 310.2120; 220.0978; 163.0398 Glu-[lycibarbarspermidine F] isomer ✓
B31 27.02 C31H43O11N3 634.2964 632.2784 1.03 472.24500; 310.21201; 220.09660; 163.03981 lycibarbarspermidine B isomer [32] ✓
B32 27.03 C31H41O11N3 632.2814 630.2632 0.07 470.2284; 382.1489; 308.1962; 220.0965; 163.0388 lycibarbarspermidine N isomer [32] ✓
B33 27.23 C43H63O21N3 958.3870 956.3817 1.80 796.34717; 634.29457; 472.2424; 310.2124; 220.0964; 163.0383 Glu-[lycibarbarspermidine F] isomer ✓
B34 27.42 C43H65O21N3 960.4155 958.3969 9.00 798.3629; 636.3112; 474.2588; 384.1645; 222.1121; 165.0404 Glu-[lycibarbarspermidine M] ismoer ✓
B35 27.51 C31H45O11N3 636.3115 634.2941 2.00 474.2589; 384.1649; 222.1121; 165.0544 lycibarbarspermidine J ✓
B36 27.73 C31H41O11N3 632.2811 630.2632 0.50 470.2276; 382.1480; 308.1962; 220.0963; 163.0388 lycibarbarspermidine N isomer ✓
B37 27.85 C37H51O16N3 794.3337 792.3145 0.67 632.28010; 470.2540; 382.1489; 220.0965; 163.0388 [lycibarbarspermidine O] isomer ✓
B38 27.91 C43H63O21N3 958.3870 956.3817 1.22 796.3475; 634.2955; 472.2420; 310.2120; 220.09654; 163.0388 Glu-[lycibarbarspermidine F] isomer ✓
B39 28.04 C37H53O16N3 796.3495 794.3301 1.39 634.2959; 472.2431; 310.2122; 220.0966; 163.0391 [lycibarbarspermidine F] isomer [32] ✓
B40 28.16 C43H61O21N3 956.3857 954.3660 1.48 794.3328; 632.2972; 470.2267; 220.0965; 163.0387 Glu-[lycibarbarspermidine O] ismoer ✓
B41 28.30 C43H65O21N3 960.4146 958.3969 3.39 798.3626; 636.3109; 474.2587; 384.1645; 222.1122; 165.0404 Glu-[lycibarbarspermidine M]ismoer ✓
B42 28.57 C31H43O11N3 634.2960 632.2784 1.69 472.2424; 382.1488; 310.2118; 220.0969; 163.0388 lycibarbarspermidine B isomer [32] ✓
B43 28.64 C29H44O6N4 545.3377 543.3162 7.85 527.3255; 432.0255; 322.2652; 293.1878; 236.1295; 222.1139; 129.1396 Dihydrocaffeoyl spermine derivative ✓
B44 28.77 C41H57O20N3 912.3596 910.3403 1.38 750.3066; 634.2957; 472.2431; 310.2121; 220.0965; 163.0398 Dihydrocaffeoyl spermidine derivative ✓
B45 28.83 C29H44O6N4 545.3377 543.3162 7.97 527.3264; 381.2884; 307.4034; 293.1878; 222.1139; 165.14386; 129.1396 Dihydrocaffeoyl spermine derivative ✓
B46 29.06 C49H73O26N3 1120.4537 1118.4336 1.58 958.3557; 796.3481; 634.2957; 310.2118; 220.0965; 163.0402 2Glu-[lycibarbarspermidine F] ismoer ✓
B47 29.11 C41H57O20N3 912.3597 910.3403 1.25 750.3068; 634.2960; 472.2431; 310.2121; 220.0965; 163.0398 Dihydrocaffeoyl spermidine derivative ✓
B48 29.16 C31H43O11N3 634.2959 632.2780 1.79 617.2727; 558.1018; 472.2414; 310.2120; 220.0966; 163.0388 lycibarbarspermidine B isomer [32] ✓ ✓
B49 29.23 C31H41O11N3 632.2813 630.2630 0.12 604.2890; 587.2619; 470.2543; 382.1489; 308.1963; 220.0965; 163.0388 lycibarbarspermidine N isomer ✓
B50 29.29 C49H73O26N3 1120.4536 1118.4336 1.69 958.3558; 796.34814; 634.2957; 472.2396; 310.2118; 220.0965; 163.0412 2Glu-[lycibarbarspermidine F] ismoer ✓
B51 29.32 C37H51O16N3 794.3336 792.3145 0.82 632.2830; 470.2540; 382.1489; 220.0966; 163.0389 [lycibarbarspermidine O] isomer ✓
B52 29.40 C25H35O6N3 474.2585 472.2435 2.79 457.2319; 310.2120; 222.1121; 165.0544; 123.0438 N1-N10dihydrocaffeoyl spermidine [31,33] ✓ ✓ ✓
B53 29.44 C41H57O20N3 912.3593 910.3403 1.71 750.3066; 634.2957; 498.1598; 310.2121; 220.0965; 163.0398 Dihydrocaffeoyl spermidine derivative ✓
B54 29.58 C49H73O26N3 1120.4535 1118.4336 1.80 958.3557; 796.3481; 634.2957; 310.2115; 220.0965; 163.0412 2Glu-[lycibarbarspermidine F] ismoer ✓
B55 29.59 C31H43O11N3 634.2960 632.2784 1.70 513.0655; 472.2426; 310.2116; 222.1120; 163.0388 lycibarbarspermidine B isomer ✓
B56 29.60 C31H41O11N3 632.2805 630.2630 1.42 496.2304; 470.2259; 382.1489; 308.1962; 220.0965; 163.0388 lycibarbarspermidine N isomer ✓
B57 29.64 C41H57O20N3 912.3593 910.3403 1.71 750.3065; 588.2751; 382.1488; 310.2121; 220.0964; 163.0398 Dihydrocaffeoyl spermidine derivative ✓
B58 29.71 C37H53O16N3 796.3480 794.3300 2.31 634.2957; 472.2431; 310.2121; 220.0965; 163.0390 [lycibarbarspermidine F] isomer ✓
B59 29.71 C37H51O16N3 794.3331 792.3145 1.44 632.2804; 470.2540; 308.1962; 220.0964; 163.0388 [lycibarbarspermidine O] isomer ✓
B60 29.74 C35H47O15N3 750.3065 748.2889 1.11 588.2747; 472.2429; 310.2117; 220.0964; 163.0387 Glu-[lycibarbarspermidine B] ismoer ✓
B61 29.74 C49H71O26N3 1118.4481 1116.4180 1.45 956.3852; 794.3327; 632.3016; 470.2233; 220.0965; 163.0388 2Glu-[lycibarbarspermidine O] isomer ✓
B62 29.88 C35H49O15N3 750.3069 748.2889 1.48 588.2748; 472.2429; 310.2118; 220.0965; 163.0389 Glu-[lycibarbarspermidine B] ismoer ✓
B63 30.03 C25H33O6N3 472.2389 470.2264 1.64 455.2168; 310.2119; 220.0965; 163.0388; 112.1121 N1–caffeoyl, N3-dihydrocaffeoyl spermidine [34] ✓ ✓ ✓
B64 30.13 C31H41O11N3 632.2804 630.2628 1.57 470.2497; 382.1489; 308.1962; 220.0965; 163.0388 lycibarbarspermidine N isomer ✓
B65 30.14 C28H41O8N3 548.3005 7.11 530.2393; 474.2629; 293.1877; 222.1940; 165.0555; 128.1080 Dihydrocaffeoyl spermidine derivative ✓
B66 30.14 C34H28O12N4 705.3398 7.98 687.3212; 531.3211; 467.2042; 310.2160; 293.1826; 222.1139; 165.0559 Dihydrocaffeoyl spermine derivative ✓
B67 30.14 C37H51O16N3 794.3336 792.3145 0.76 632.2804; 470.2540; 308.1963; 220.0965; 163.0388 [lycibarbarspermidine O] isomer ✓
B68 30.19 C30H46O6N4 559.3531 1.89 395.2663; 307.2033; 236.1295; 222.123; 165.0561 Dihydrocaffeoyl spermine derivative ✓
B69 30.19 C28H40O7N3 530.2891 528.2696 1.68 474.2629; 310.2142; 293.1877; 222.1140; 165.0558 Propionyl-dihydrocaffeoyl spermidine ✓
B70 30.56 C25H31O6N3 470.2278 468.2115 1.54 308.1962; 291.1698; 234.1121; 220.0965; 163.0388 N, N′-dicaffeoylspermidine [33] ✓ ✓
B71 30.82 C34H46O11N4 687.3308 685.3051 7.59 670.3035; 523.2778; 449.1942; 293.1878; 222.1139 Dihydrocaffeoyl spermine derivative ✓
B72 31.45 C37H50O9N4 695.3701 693.3464 1.28 678.3438; 531.3215; 457.2365; 293.1879; 222.1140; 165.0559 N1,N4,N12-tris(dihydrocaffeoyl)spermine [35] ✓
B73 30.71 C46H46O18N4 963.4437 961.4240 0.87 945.4429; 621.3273; 455.2382; 384.1644; 293.1882; 222.1121; 165.0557 Ddihydrocaffeoyl spermine derivative ✓
B74 31.79 C30H45O8N3 576.3314 574.3247 1.45 544.3050; 512.2786; 412.2842; 293.1877; 222.1139; 165.0558 Ddihydrocaffeoyl spermidine derivative ✓
C1 8.30 C13H18O3N2 251.1409 249.1227 1.41 234.0990; 163.0697; 144.0616; 126.0558; 115.0591 N-caffeoylputrescine isomer [36] ✓ ✓ ✓
C2 10.26 C13H18O3N2 251.1410 1.69 234.1142; 163.0402; 145.0296; 115.0876 N-caffeoylputrescine isomer [36] ✓ ✓
C3 16.49 C15H22O4N2 295.1674 1.20 278.1412; 207.0670; 175.0409; 147.0453; 129.1394 coumaroyl amide derivative [37] ✓
C4 23.48 C15H22O4N2 295.1673 1.17 278.1405; 222.1142; 207.0666; 175.0412; 147.0451 coumaroyl amide derivative [37] ✓
C5 30.22 C21H29O9N 476.1905 474.2481 2.14 314.1381; 222.1119; 177.0545; 145.0284; 121.0648 N-feruloyl-3-O-glucopyranosyl-tyramine ismoer [38] ✓
C6 30.42 C32H45O11N3 648.3118 646.2941 1.32 486.2590; 310.2119; 234.1121; 177.0544; 145.0291 feruloyl-tyramine derivatives ✓
C7 31.30 C17H18O4N 302.1412 300.1221 1.46 286.0265; 245.8081; 165.0556; 138.0924; 121.0657 A4 (caffeoyl-tyramine derivatives) [32] ✓
C8 31.34 C14H14O5N2 486.2587 484.2422 1.07 469.2316; 310.2118; 234.1120; 177.0544; 145.0283; 121.0649 feruloyl-tyramine derivatives ✓
C9 31.83 C21H29O9N 476.1905 474.2481 2.07 314.1381; 222.1118; 177.0545; 145.0284; 121.0648 N-feruloyl-4-O-glucopyranosyl-tyramine [38] ✓
C10 32.09 C36H36O8N2 625.2537 623.1578 1.73 462.1902; 351.0856; 293.08033; 201.0544; 175.0402; 149.0609; 121.0648 Lyciumamide A [39] ✓
C11 32.22 C36H49O16N3 498.2592 498.2576 1.41 480.2489; 322.2119; 234.1126; 177.0545; 145.0284 feruloyl-tyramine derivatives ✓
C12 32.57 C17H19O4N 300.1256 298.1066 0.48 253.8823; 163.0402; 121.0658 A5 (caffeoyl-tyramine derivatives) [32] ✓
C13 32.98 C17H17O3N 284.1275 282.1116 2.29 261.0436; 164.0705; 147.0439; 121.0648 N-p-cis-Coumaroyl tyramine [40] ✓ ✓
C14 33.33 C18H19O4N 314.1382 312.1221 1.67 274.8365; 243.1029; 220.0979; 195.0847; 177.0551; 145.0289; 121.0653 N-cis-feruloyl-tyramine [8] ✓ ✓
C15 33.47 C17H17O3N 284.1275 282.1116 2.29 261.0436; 164.0705; 147.0439; 121.0648 N-p-trans-Coumaroyl tyramine * ✓ ✓
C16 33.62 C28H31O8N 510.2116 508.1944 1.36 462.1963; 325.1065; 210.0545; 177.0546; 121.0648 canabisine-H [36] ✓
C17 33.81 C18H19O4N 314.1382 312.1221 1.51 244.0981; 220.0979; 194.0822; 177.0555; 145.0292; 121.0653 N-trans-feruloyl-tyramine [8] ✓ ✓ ✓
C18 34.02 C19H19O5N 344.1520 342.1323 1.25 282.3545; 177.0559; 145.0295 A12 (feruloyl-tyramine derivatives) [32] ✓
C19 34.98 C36H37O9N2 643.2638 641.2465 1.89 462.1903; 325.1063; 201.0544; 177.0545; 121.0648 feruloyl-tyramine derivatives ✓
C20 35.07 C28H29O7N 492.2010 490.1842 1.46 462.1909; 325.1066; 293.0805; 201.0546; 175.0769; 121.0649 Lyciumamide C [39] ✓
C21 36.57 C54H53O12N3 936.3691 1.20 771.2914; 634.20612; 471.1429; 375.0859; 263.0896; 203.5736; 121.0659 melongenamide D isomer [41] ✓
D1 24.74 C33H40O21 773.2195 771.1937 1.21 611.140; 464.0762; 303.0325; 163.0399; Quercetin-3-O-Glu-7-O-Rha isomer [42] ✓
D2 26.89 C27H30O17 627.1610 625.1376 1.66 585.6912; 303.0520; 285.0409; 257.043; 243.5646; 201.4349; 129.02379 Quercetin-3,7-O-diGlu [42] ✓ ✓
D3 26.98 C33H40O21 773.2195 771.1940 1.84 726.3508; 559.7092; 465.1061; 303.0521; 228.4964; 129.0548 Quercetin-3-O-Soph-7-O-Rha [42] ✓
D4 27.74 C33H40O21 773.2127 771.1940 1.08 611.3322; 472.2473; 303.0492; 220.0965; 163.0399; 129.0541 Quercetin-3-O-Rut-7-O-Glu [42] ✓ ✓
D5 31.39 C27H30O16 611.1600 609.1417 1.03 449.1113; 465.1061; 303.0492; 285.0413; 257.046; 201.0561129.05449 Rutin * ✓ ✓
D6 31.98 C27H30O15 595.1703 593.1472 1.63 465.5521; 329.0679; 287.0529; 258.2196; 243.5895; 230.3383; 129.0553 Kaempferol-3-O-Glu-7-O-Rha [42] ✓ ✓
E1 33.67 C45H72O17 885.4835 0.87 867.4724; 415.3229; 299.2362; 271.2052; 253.1947; 215.1792; 157.1011 Gracillin [43] ✓
E2 33.72 C45H73O16N 884.5084 882.4800 1.13 866.4896; 720.4325; 576.3898; 414.3403; 396.3259; 271.2054; 253.1949 Solasonine * ✓
E3 33.77 C51H84O22 1049.5518 0.90 887.4990; 743.3851; 417.3355; 273.2207; 255.2107 parillin [44] ✓
E4 33.87 C45H75O16N 886.5152 884.4957 0.75 868.5034; 722.4475; 416.356; 398.3409; 273.2205; 255.2102; 173.1323 5,6-dihydrosolasonine * ✓
E5 33.92 C45H73O18 903.5006 1.21 741.4469; 597.3309; 417.3389; 273.2230; 255.2124; 145.0506 Timosaponin BIII [45] ✓
E6 34.49 C47H77O17N 928.5253 1.25 458.3620; 273.2207; 255.2102; 161.1323 Lycioside B [1] ✓
F1 3.93 C9H11O2N 166.0867 1.10 153.0416; 142.9681; 120.0814; 103.0548 Phenylalanine isomer [1] ✓ ✓ ✓
F2 5.51 C9H11O3N 166.0877 1.13 142.9681; 138.0554; 120.0812; 103.0548 Phenylalanine isomer ✓ ✓ ✓
F3 9.95 C11H9O2N 188.0721 1.95 170.0613; 146.0412; 118.0611 3-amino-2-naphthoic acid [46] ✓ ✓ ✓
F4 10.44 371.0991 0.11 205.0506; 163.0398; 145.9288; 119.0498 ✓
F5 31.16 568.3110 539.2707; 363.2378; 268.0598; 135.0436 ✓
F6 31.29 748.3361 609.3981; 399.1691; 360.1675; 314.1518; 215.0829; 171.0929; 136.0770 ✓
F7 31.69 630.3469 498.3042; 469.2647; 387.2245; 241.0723; 151.2698 ✓
F8 32.56 298.1066 256.0959; 178.0492; 135.0435 ✓
F9 32.91 647.3257 618.1393; 483.2572; 412.2080; 395.2055; 161.4154 ✓
F10 34.22 897.3956 895.3695 879.3847; 689.3096; 486.2017; 468.1911; 422.583; 395.1742; 159.0929 ✓
F11 34.23 898.4049 690.3203; 527.2580; 387.1645; 203.0810; 153.0655 ✓

1 RT represents retention time (min); 2 MS/MS fragments only show the fragmentation ions in positive ionization mode except that the [M + H]+ ion of the compound was not detected (show the fragmentation ions in negative ionization mode); the number in bold means the most abundant product ion. 3 Ref. represents the references; 4–6 F, L, R represent fruits, leaves and Root barks respectively. * Represents the compounds confirmed by standards.