Discriminative Metabolomics Analysis and Cytotoxic Evaluation of Flowers, Leaves, and Roots Extracts of Matthiola longipetala subsp. livida
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals and Reagents
2.2. Plant Material and Preparation of the Extracts
2.3. Sample Preparation for UPLC-HRMS-MS Measurement
2.4. UPLC-HRMS-MS Analysis
2.5. Data Analysis and Preprocessing
2.6. Feature-Based Molecular Networking (FBMN) and Metabolites Dereplication
2.7. Cytotoxic Activity
2.7.1. Cell Lines
2.7.2. Cell Viability by MTT Assay
3. Results and Discussion
3.1. UPLC-HRMS/MS Metabolites Profiling of the Extracts
3.2. UPLC-HRMS/MS Metabolite Annotation Aided with Molecular Networking
3.2.1. Glucosinolates
3.2.2. Phenolics
Phenolic Acids and Derivatives
Flavonoids
3.2.3. Iridoids and Diterpenes
3.2.4. Coumarin
3.2.5. Amino Acids, Organic Acids, and Derivatives
3.2.6. Fatty Acids and Derivatives
3.2.7. Lipids
3.2.8. Peptides
3.3. Cytotoxicity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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No. | Chemical Class (Sub-Class) | RT | (M − H)− | (M + H)+ | MS2 | Root | Leaf | Flower | Tentatively Identification | Molecular Formula (Error in ppm) | Ref. | |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Negative | Positive | |||||||||||
1 | Amino acids | 2.21 | - | 175.1193 | - | 158.0928, 128.0200, 116.0708, 86.9928 70.0651 | + | + | ++ | Arginine | C6H14N4O2 (1.9) | [22] |
2 | Amino acids | 2.41 | - | 116.0713 | - | 70.0660 | + | + | ++ | Proline | C5H9NO2 (5.3) | [22] |
3 | Saccharides | 2.45 | 341.1090 | - | 179.0565, 161.0469, 149.0471, 119.0348, 89.0245 | - | + | + | Dihexoside | C12H22O11 (0.4) | [23] | |
4 | Alkaloids and derivatives (alkaloids) | 2.54 | - | 138.0505 | - | 122.0648, 110.0594, 96.0445 | - | + | - | Trigonelline * | C7H7NO2 (−2.7) | [24] |
5 | Amino acids and derivatives | 2.58 | - | 130.0861 | - | 86.0965, 84.0807, 70.0651 | ++ | + | + | Methyl proline * | C6H11NO2 (1.0) | [22] |
6 | Amino acids and derivatives | 2.59 | - | 144.1019 | - | 130.0502, 104.0294, 98.0602, 86.0965, 84.0807, 70.0651 | + | ++ | + | Dimethyl proline | C7H13NO2 (0.3) | [22] |
7 | Glucosinolates (alkylglucosinolates) | 2.60 | 434.0253 | - | 419.0020, 274.9899, 259.0128, 240.9670, 195.0335, 168.9510, 129.0253, 96.9602, 74.9912 | - | + | + | ++ | Glucoraphenin | C12H21NO10S3 (0.4) | [25] |
8 | Organic acids (hydroxy acids) | 2.70 | 147.0298 | - | 129.0193, 101.0244, 85.0295 | - | t | ++ | ++ | Hydroxyglutaric acid | C5H8O5 (0.6) | [23] |
9 | Flavonoids (flavonol-O-glycoside) | 2.72 | - | 873.2667 | - | 595.1675, 449.1086, 287.0556 | - | + | +++ | Km-O-rhamnosyl-arabinoside-O- rhamnosyl glucoside | C38H48O23 (0.2) | [8] |
10 | Glucosinolates (alkylglucosinolates) | 2.83 | - | 176.0201 | - | 149.0595, 117.0335, 96.0443, 70.9950 | - | + | +++ | Raphenin * | C6H9NOS2 (−1.6) | [26] |
11 | Glucosinolates (alkylglucosinolates) | 2.93 | 418.0299 | - | 259.0127, 224.9726, 176.0208, 96.9601, 74.9911 | - | +++ | + | - | Methylthiobutenyl- glucosinolate | C12H21NO9S3 (0.8) | [27] |
12 | Phenolic acids and derivatives (hydroxycinnamic acid glycosides) | 3.02 | 487.1458 | - | 163.0422, 145.0295 | - | - | - | + | Coumaric acid-O- dihexoside | C21H28O13 (0.4) | [28] |
13 | Organic acids (hydroxy acids) | 3.60 | 133.0143 | - | 115.0039, 72.9935 | - | t | + | +++ | Malic acid | C4H6O5 (0.4) | [29] |
14 | Glucosinolates (alkylglucosinolates) | 3.67 | 434.0254 | - | 419.0020, 274.9899, 259.0129, 240.9671, 195.0333, 168.9509, 129.0251, 96.9602, 74.9912 | - | + | + | ++ | Glucoraphenin isomer | C12H21NO10S3 (0.2) | [30] |
15 | Organic acids (dicarboxylic acids) | 3.75 | - | 131.0342 | - | 116.9329, 108.9868, 85.0282, 71.0153, 62.9826 | + | + | + | Citraconic acid (methyl maleic acid) | C5H6O4 (−2.3) | [31] |
16 | Organic acids (carboxylic acids) | 3.76 | - | 130.0868 | - | 86.0992, 84.0807, 85.0845, 70.0653 | + | + | + | Pipecolic acid | C6H11NO2 (1.9) | [31] |
17 | Amino acids | 3.79 | - | 132.1019 | - | 86.0965, 84.0809, 73.0648, 71.0128, 69.0699 | + | + | + | Leucine/isoleucine | C6H13NO2 (0.1) | [22] |
18 | Glucosinolates (alkylglucosinolates) | 3.92 | 418.0299 | - | 274.9898, 259.0127, 195.0335, 96.9602, 74.9912 | - | + | - | - | Methylthiobutenyl-glucosinolate isomer | C12H21NO9S3 (0.2) | [27] |
19 | Phenolic acids and derivatives (hydroxybenzoic acid glucoside) | 4.21 | 299.0770 | - | 137.0244, 93.0345 | - | + | + | ++ | Hydroxy benzoic acid-O-hexoside | C13H16O8 (0.8) | [31] |
20 | Glucosinolates (alkylglucosinolates) | 4.31 | 374.0582 | - | 259.0134, 195.0338, 96.9601, 74.9909 | - | + | + | ++ | Butyl glucosinolate | C11H21NO9S2 (0.9) | [27] |
21 | Organic acids (cinnamic acids) | 4.36 | - | 149.0600 | 105.0444, 104.0543, 79.0536 | + | + | + | Cinnamic acid | C9H8O2 (−1.8) | [29] | |
22 | Amino acids | 4.37 | 164.0715 | 166.0630 | 147.0457, 103.0558, 72.0092 | 120.080, 103.0543, 93.0699 | + | + | + | Phenylalanine * | C9H11NO2 (0.3) | [22] |
23 | Glucosinolates (alkylglucosinolates) | 4.53 | 418.0299 | - | 274.9805, 259.0129, 224.9700, 195.0330, 176.0207, 96.9602, 74.9911 | - | - | - | + | Methylthio-butenyl-glucosinolate isomer | C12H21NO9S3 (0.1) | [27] |
24 | Organic acids (carboxylic acids) | 4.54 | 218.1036 | 220.1184 | 146.0823, 88.0406, 71.0501 | 202.1084, 184.0974, 172.1327, 158.0603, 142.0860, 124.0760, 98.0238, 72.0443 | + | + | ++ | Pantothenic acid (vitamin B5) | C9H17NO5 (0.7) | [32] |
25 | Phenolic acids and derivatives (hydroxybenzoic acid glycosides) | 4.70 | 315.0716 | - | 153.0186, 152.0113, 109.0297, 108.0225 | - | + | + | + | Dihydroxybenzoic acid-O-hexoside | C13H16O9 (0.8) | [17] |
26 | Phenolic acids and derivatives (hydroxycinnamic acid glycosides) | 4.81 | 517.1558 | - | 397.1158, 193.0508, 175.0401, 119.0345 | - | t | - | + | Ferulic acid-O-dihexoside * | C22H30O14 (0.0) | [33] |
27 | Flavonoids (flavonol-O- glycosides) | 5.01 | - | 773.2147 | - | 611.1624, 449.1084, 287.0555 | t | + | +++ | Km 3-O-sophroside- 7-O-glucoside | C33H40O21 (1.5) | [34] |
28 | Phenols (methoxyphenols) | 5.02 | - | 151.0757 | - | 136.0605, 119.0496, 91.0543, 79.0550, 68.9826 | t | + | +++ | Methoxy- vinylphenol | C9H10O2 (−2.1) | [35] |
29 | Glucosinolates (alkylglucosinolates) | 5.11 | 386.0582 | - | 274.9892, 259.0134, 195.0335, 96.9602, 74.9912 | - | - | + | +++ | Glucobrassicanapin | C12H21NO9S2 (0.5) | [28] |
30 | Iridoids (iridoids-O-glycosides) | 5.13 | 375.1297 | - | 167.0709, 152.077 | - | t | + | +++ | Loganic acid | C16H24O10 (0.1) | [36] |
31 | Amino acids and derivatives | 5.20 | - | 367.1504 | - | 349.1397, 332.1128, 303.1349, 276.1241, 258.1131, 229.0976, 202.064, 188.0713, 146.0603 | + | + | + | Tryptophan N-hexoside | C17H22N2O7 (0.8) | [37] |
32 | Phenolic acids and derivatives (hydroxybenzoic acid glycosides) | 5.30 | 329.0853 | - | 209.0445, 167.0350, 119.0342, 89.0245 | - | t | + | +++ | Vanillic acid- O-hexoside | C14H18O9 (0.2) | [17] |
33 | Flavonoids (flavonol-O- glycosides) | 5.50 | 917.2648 a | - | 871.2510, 709.1991, 563.1405, 431.0940, 285.0369 | - | - | - | + | Km -O-arabinosyl rhamnoside-O- rhamnoside-O- glucoside b | C38H48O23 (0.5) | [8] |
34 | Amino acids | 5.54 | 203.0824 | 205.0975 | 142.0664, 116.0503, 74.0248 | 188.0711, 170.0606, 159.0916, 146.0602, 132.0810, 118.0653 | + | + | + | Tryptophan * | C11H12N2O2 (−0.2) | [22] |
35 | Glucosinolates (alkylglucosinolates) | 5.65 | 418.0299 | 420.0457 | 274.9805, 259.0129, 224.9700, 195.0330, 176.0207, 96.9602, 74.9911 | 178.0360, 130.0324, 85.0282 | + | + | ++ | Methylthio-butenyl-glucosinolate isomer | C12H21NO9S3 (0.6) | [27] |
36 | Phenolic acids and derivatives (hydroxybenzoic acid derivative) | 5.81 | 246.9919 | - | 167.0350, 152.0116, 153.0452, 108.0219 | - | + | + | + | Vanillic acid-sulfate | C8H8O7S (0.5) | |
37 | Phenolic acids and derivatives (hydroxybenzoic acid glycosides) | 5.81 | 285.0614 | - | 153.019, 152.0112, 109.0292, 108.0220 | - | + | + | + | Dihydroxybenzoic acid-O-pentoside | C12H14O8 (0.5) | [38] |
38 | Coumarins and derivatives (hydroxycoumarins) | 5.91 | - | 163.0605 | - | 147.0446, 131.0497, 119.0494, 103.0544, 91.0541 | t | + | +++ | Hydroxycoumarin | C9H6O3 (−2.0) | [31] |
39 | Phenolic acids and derivatives (hydroxycinnamic acid glycosides) | 5.94 | 487.1452 | - | 367.1031, 163.0397, 145.0293 | - | t | + | +++ | Coumaric acid- O-dihexoside | C21H28O13 (0.5) | [28] |
40 | Flavonoids (flavonol-O- glycosides) | 6.10 | 609.1459 | - | 447.0927, 429.0825, 285.0404 | - | t | ++ | ++ | Km 3-O- sophoroside * | C27H30O16 (0.3) | [39] |
41 | Phenolic acids and derivatives | 6.11 | 395.0649 | - | 241.0023, 152.9863, 96.9602 | - | +++ | + | t | Dihydroxyphenylethanol-O-sulfoglucoside | C14H20O11S (0.9) | [40] |
42 | Flavonoids (flavonol-O- glycosides) | 6.14 | - | 757.2199 | - | 449.1087, 287.0557 | t | + | +++ | Km-O-rutinoside- O-glucoside | C33H40O20 (1.1) | [41] |
43 | Phenolic acids and derivatives (hydroxycinnamic acid glycosides) | 6.24 | 517.1556 | - | 397.115, 193.051, 175.039 | - | t | + | +++ | Ferulic acid-O- dihexoside isomer * | C22H30O14 (0.4) | [33] |
44 | Fatty acids | 6.25 | - | 163.0601 | - | 131.0496, 119.0494, 103.0544, 91.0544, 77.0385 | t | + | +++ | Hydroxylhexanedioic acid * (Hydroxyadipic acid) | C6H10O5 (−2.7) | [42] |
45 | Coumarins and derivatives | 6.31 | - | 207.065 | - | 193.0544, 179.0701, 147.0436, 119.0494, 91.0546 | t | + | +++ | Dimethoxycoumarin | C11H10O4 (2.1) | [43] |
46 | Phenolic acids and derivatives (hydroxycinnamic acid glycosides) | 6.31 | 547.167 | - | 427.1245, 223.0618, 205.051, 190.0268, 179.0564 | - | t | + | +++ | Sinapic acid-O- dihexoside * | C23H32O15 (4.5) | [44] |
47 | Flavonoids (flavonol-O- glycosides) | 6.39 | 871.2510 | 873.2667 | 709.1976, 563.1404, 447.0923, 431.0975, 285.105 | 711.1985, 595.1675, 449.1086, 433.1137, 287.0556 | - | + | +++ | Km 3-O-(2″-rhamnosyl)-arab-inoside-7-O-rhamnoside-4′-O-β-glucoside b | C38H48O23 (0.7) | [8] |
48 | Flavonoids (Flavonol-O- glycosides) | 6.39 | 593.1511 | 595.1665 | 285.0397, 284.0323 | 449.1088, 287.0559, 229.0868, 207.0658 | t | + | +++ | Km 3-O- rutinoside | C27H30O15 (0.4) | [31] |
49 | Flavonoids (flavonol-O- glycosides) | 6.40 | - | 727.2088 | - | 449.1093, 287.0559 | - | + | +++ | Km O-arabinosyl rhamnoside-O- glucoside | C32H38O19 (1.1) | [31] |
50 | Flavonoids (flavonol-O- glycosides) | 6.44 | - | 711.2146 | - | 433.1137, 287.0557 | t | + | +++ | Km-O-arabinosyl rhamnoside-O- rhamnoside | C32H38O18 (1.3) | [8] |
51 | Flavonoids (flavonol-O- glycosides) | 6.54 | 741.1881 | 743.2038 | 609.1461, 579.1348, 463.0872, 447.0924, 301.0351 | 611.1608, 465.1035, 303.0504 | t | + | +++ | Qn-O-arabinosyl rhamnoside-O- glucoside | C32H38O20 (1.9) | [45] |
52 | Flavonoids (flavonol-O- glycosides) | 6.74 | 739.2087 | 741.2247 | 593.1511, 447.0923, 431.0952, 285.0397, 284.0323 | 465.1035, 433.1137, 287.0556 | t | + | +++ | Km 3-O-rhamnoside 7-O-rutinoside * | C33H40O19 (0.5) | [46] |
53 | Flavonoids (flavonol-O- glycoside) | 6.83 | - | 757.2199 | - | 479.1195, 463.1243, 317.0661 | - | + | +++ | Is O-arabinosyl rhamnoside-O- glucoside | C33H40O20 (1.8) | [31] |
54 | Phenolic derivatives (benzoyl derivatives) | 6.88 | - | 137.0600 | - | 123.0394, 122.0365, 107.0500, 95.0415, 94.0415, 79.0544, 77.0387 | t | + | +++ | Methoxybenzaldehyde | C8H8O2 (2.5) | [47] |
55 | Flavonoids (flavonol-O- glycoside) | 6.94 | 709.1973 | - | 563.1407, 431.0960, 285.0397, 284.0324 | - | - | - | + | Km-O-rhamnosyl arabinoside-O- rhamnoside | C32H38O18 (0.3) | [8] |
56 | Coumarin and derivatives | 6.98 | - | 207.0657 | - | 193.0544, 179.0710, 147.0447, 119.0494, 91.0543, 83.0495 | t | + | +++ | Dimethoxycoumarin isomer | C11H10O4 (2.0) | [43] |
57 | Phenolic acids and derivatives (hydroxycinnamic acid glycosides) | 6.98 | 385.1141 | - | 223.0617, 205.0505, 190.0271, 179.0715, 164.0478 | - | t | + | +++ | Sinapic acid-O- hexoside * | C17H22O10 (0.1) | [17] |
58 | Flavonoids (flavonol-O- glycosides) | 7.22 | 725.1937 | 727.2094 | 579.1357, 447.0898, 446.0850, 301.035 | 449.1086, 303.0507 | t | t | + | Qn-O-rhamnosyl- arabinoside-O- rhamnoside | C32H38O19 (0.7) | [46] |
59 | Flavonoids (flavonol-O- glycosides) | 7.29 | 609.1464 | 611.1615 | 463.0878, 447.0852, 301.0352, 285.0399 | 303.0505 | t | + | +++ | Qn 3-O-rhamnoside 7-O-glucoside | C27H30O16 (0.5) | [47,48] |
60 | Flavonoids (flavonol-O- glycosides) | 7.41 | 609.1462 | - | 447.0927, 285.0404 | - | t | + | +++ | Km 3,7 di-O-glucoside * | C27H30O16 (0.3) | [39,49] |
61 | Phenolic derivatives (Benzoyl derivatives) | 7.55 | - | 137.0601 | - | 123.0394, 122.0365, 107.0510, 95.0508, 94.0415 | t | + | +++ | Methoxybenzaldehyde isomer | C8H8O2 (−1.9) | [50] |
62 | Flavonoids (flavonol-O- glycosides) | 7.65 | 579.1349 | 581.1510 | 447.0906, 446.0854, 433.0779, 301.0347 | 303.0506 | t | t | +++ | Qn 3-O-rhamnoside 7-O-arabinoside | C26H28O15 (1.3) | [51] |
63 | Flavonoids (flavonol-O- glycosides) | 7.72 | - | 565.1552 | - | 287.0555 | t | + | +++ | Km 3-O-arabinoside-7-O rhamnoside | C26H28O14 (1.4) | [48] |
64 | Flavonoids (flavonol-O- glycosides) | 7.73 | 709.1991 | - | 563.1407, 431.0960, 285.0397 | - | - | - | + | Km O-rhamnosyl arabinoside-O- rhamnoside | C32H38O18 | [8] |
65 | Flavonoids (flavonol-O- glycosides) | 7.71 | 431.0960 | 433.1133 | 285.0397, 284.0324 | 287.0557 | - | + | +++ | Km 7-O- rhamnoside * | C21H20O10 (0.8) | [31] |
66 | Flavonoids (flavonol-O- glycosides) | 7.82 | 709.1992 | 711.2139 | 563.1403, 431.0986, 285.0400 | 433.1138, 287.0556 | t | + | +++ | Km O-arabinosyl rhamnoside-O- rhamnoside b | C32H38O18 (1.3) | [8] |
67 | Phenolic derivatives (Benzoyl derivatives) | 7.86 | 357.1559 | - | 195.1032, 180.0784, 101.0236 | - | t | + | +++ | Trimethoxy benzaldehyde-O- hexoside | C17H26O8 (0.9) | [50] |
68 | Flavonoids (flavonol-O- glycosides) | 7.91 | 739.2094 | 741.2243 | 285.0402 | 287.0557 | t | + | +++ | Km 3-O-(di-O- rhamnosyl) glucoside * | C33H40O19 (0.5) | [51] |
69 | Phenolic derivatives (benzaldehydes) | 7.93 | - | 197.0813 | - | 137.0597, 105.0338, 79.0541 | + | + | ++ | Trimethoxy benzaldehyde | C10H12O4 (−2.6) | [50] |
70 | Fatty acid derivatives (fatty acyl glycosides) | 8.00 | - | 387.2039, 225.1504, 161.0458, 113.0258, 101.0247 | - | t | ++ | ++ | Hydroxyjasmonic acid-O-hexoside (tuberonic acid- O-hexoside) | C18H28 O9 (2.0) | [52] | |
71 | Flavonoids (flavonol-O- glycosides) | 8.04 | 623.1633 | 625.1774 | 477.1031, 461.1071, 315.0510 | 317.0662 | - | - | + | Is 3-O-rhamnoside 7-O-glucoside | C28H32O16 (1.5) | [46] |
72 | Flavonoids (flavonol-O- glycosides) | 8.14 | 563.1398 | - | 431.0903, 417.08, 285.0403 | - | - | t | + | Km 3-O-rhamnoside 7-O-arabinoside | C26H28O14 (0.5) | [48] |
73 | Flavonoids (flavonol-O- glycosides) | 8.19 | 609.1446 | - | 447.0918, 285.0396, 284.0318 | - | - | + | +++ | Km 3-O- gentobiosde | C27H30O16 (0.8) | [39] |
74 | Flavonoids (flavonol-O- glycosides) | 8.39 | 461.1069 | 463.1240 | 315.0509, 314.0429 | 317.0661 | + | + | ++ | Is 7-O- rhamnoside | C22H22O11 (1.8) | [47] |
75 | Benzoic acid | 8.41 | 153.0192 | - | 109.0296, 81.0350 | - | t | + | +++ | Dihydroxybenzoic acid | C7H6O4 (0.9) | [53] |
76 | Flavonoids (flavonol-O- glycosides) | 8.43 | 593.1509 | 595.1663 | 461.1069, 447.0928, 315.0509 | 317.0661 | t | ++ | ++ | Is 3-O-rhamnoside 7-O-arabinoside | C27H30O15 (0.5) | [28] |
77 | Flavonoids (flavonol-O- glycosides) | 8.45 | 609.1468 | 611.1614 | 301.0346 | 303.0511, 287.0552, 229.0500, 129.0554, 85.0289 | t | + | +++ | Qn 3-O-rutinoside (rutin) * | C27H30O16 (0.3) | [46] |
78 | Benzoic acids and derivatives | 8.61 | 223.0246 | - | 179.0354, 135.0461, 109.0297 | - | t | + | +++ | Carboxyvinyl benzoic acid | C10H8O6 (0.9) | [23] |
79 | Coumarins and derivatives | 8.63 | - | 455.1164 | - | 411.1268, 369.1162, 207.0938, 179.0701, 147.0494, 79.0283, 69.0334 | - | + | +++ | Dimethoxycoumarin-O-malonyl glucoside | C20H22O12 (4.4) | [43] |
80 | Phenolic derivatives | 8.92 | 355.1401 | - | 221.0442, 161.0453, 139.0222, 119.0345, 101.0245, 89.0247, 71.0140, 59.0141 | - | - | - | + | Hydroxy phenyl pentanoic acid-O- glucoside | C17H24O8 (0.6) | [54] |
81 | Flavonoids (flavonol-O- glycosides) | 9.02 | 463.0878 | - | 301.0277, 300.0276 | - | t | + | +++ | Qn 3-O- glucoside * | C21H20O12 (0.2) | [34] |
82 | Flavonoids (flavonol-O- glycosides) | 9.08 | 593.1580 | 595.1665 | 285.0396, 284.0325 | 287.0552 | t | +++ | +++ | Km-O- rutinoside * | C27H30O15 (0.6) | [55] |
83 | Flavonoids (flavonol-O- glycosides) | 9.26 | 623.1622 | 625.1770 | 315.0510 | 317.0661 | t | ++ | +++ | Is 3-O- rutinoside * | C28H32O16 (0.7) | [51] |
84 | Phenolic derivatives (Cinnamaldehyde) | 9.4 | 207.0665 | - | 192.0429, 179.0536 | - | t | + | +++ | Sinapaldehyde | C11H12O4 (0.7) | [17] |
85 | Flavonoids (flavonol-O- acylglycosides) | 9.45 | 549.0881 | 551.1040 | 505.0988, 463.0882, 301.0331, 300.0275, 271.0242 | 303.0507 | t | + | +++ | Qn 3-O- malonylglucoside * | C24H22O15 (1.8) | [56] |
86 | Flavonoids (flavonol-O- acylglycosides) | 9.54 | 505.0979 | - | 463.0886, 301.0332, 300.0272, 271.0247, 255.0306 | - | t | + | +++ | Qn 3-O-acetyl- glucoside * | C23H22O13 (1.7) | [57] |
87 | Flavonoids (flavonoid aglycones) | 9.59 | - | 287.0505 | - | 257.0450, 229.0114, 149.0140, 97.0287 | t | ++ | ++ | Km *,b | C15H10O6 (0.2) | [57] |
88 | Flavonoids (flavonol-O- glycosides) | 9.60 | 447.0931 | 449.1083 | 327.0528, 285.0387, 284.0325, 255.0299, 227.0345 | 287.0555 | t | ++ | ++ | Km 3-O-glucoside (astragalin) * | C21H20O11 (0.8) | [47] |
89 | Flavonoids (flavonol-O- glycosides) | 9.71 | 433.0755 | - | 301.0332, 300.0276 | - | t | + | +++ | Qn 3-O- arabinoside | C20H18O11 (0.4) | [58] |
90 | Flavonoids (flavonol-O- glycosides) | 9.83 | 477.1035 | 479.1195 | 315.0481, 314.0430, 299.0199, 285.0397, 271.0249, 243.0299 | 317.0664 | t | - | + | Is 3-O- glucoside * | C22H22O12 (0.8) | [49,58] |
91 | Phenolics and derivatives | 9.92 | 223.0251 | - | 179.0351, 153.0194, 135.0452, 109.0297 | - | t | + | +++ | Carboxyvinyl benzoic acid isomer | C10H8O6 (0.6) | [23] |
92 | Flavonoids (flavone-O- glycosides) | 10.07 | 431.0981 | 433.1128 | 269.0447 | 271.060 | +++ | t | t | Apigenin 7-O- glucoside * | C21H20O10 (0.3) | [52] |
93 | Phenolic acids and derivatives (hydroxycinnamic acids) | 10.11 | 179.0354 | - | 135.0461, 109.0297 | - | t | + | +++ | Caffeic acid * | C9H8O4 (0.4) | [52] |
94 | Flavonoids (flavonol-O- acylglycosides) | 10.15 | 505.0979 | 507.1142 | 463.0886, 301.0332, 300.0275 | 303.0507 | t | + | +++ | Qn 3-O-acetyl glucoside isomer | C23H22O13 (1.7) | [56] |
95 | Flavonoids (flavonol-O- acylglycosides) | 10.25 | 533.0936 | 535.1091 | 285.0385, 284.0323 | 287.0557 | t | ++ | ++ | Km 3-O- malonylglucoside | C24H22O14 (1.6) | [59,60] |
96 | Flavonoids (flavonol-O- acylglycosides) | 10.46 | - | 565.1198 | - | 317.0662 | t | + | - | Is 3-O- malonylglucoside | C25H24O15 (1.8) | [61] |
97 | Flavonoids (flavonol-O- acylglycosides) | 10.47 | 519.1143 | - | 477.0989, 315.0502, 314.0429 | - | t | + | + | Is 3-O-acetyl glucoside | C24H24O13 (2.1) | [62] |
98 | Flavonoids (flavonol-O- acylglycosides) | 10.51 | 505.0979 | 507.1142 | 463.0886, 301.0338, 300.0275 | 303.0505 | t | + | +++ | Qn 3-O-acetyl glucoside isomer | C23H22O13 (1.7) | [56] |
99 | Phenolic derivatives (phenylpropanoid glycosides) | 10.58 | 341.1242 | - | 161.0428, 133.0660, 101.0254 | - | t | + | +++ | Coniferyl alcohol-O- glucoside (coniferin) | C16H22O8 (0.2) | [63] |
100 | Flavonoids (flavonol-O- glycosides) | 10.65 | 447.0925 | - | 315.0477, 314.0430, 299.0209 | - | t | + | +++ | Is 3-O- arabinoside | C21H20O11 (2.2) | [46] |
101 | Phenolic derivatives (phenylpropanoid glycosides) | 10.91 | 371.1350 | - | 209.0441, 163.0767, 148.0531 | - | t | + | +++ | Sinapoyl alcohol-O-glucoside (syringin) | C17H24O9 (−0.6) | [64] |
102 | Flavonoids (flavonol-O- glycosides) | 10.99 | 431.0980 | - | 285.0400, 284.0323, 155.0303, 227.0347 | - | - | + | +++ | Km 3-O- rhamnoside (afzelin) * | C21H19O10 (0.9) | [65] |
103 | Flavonoids (flavonol-O- acylglycosides) | 11.01 | 591.0995 | 593.1148 | 547.1082, 505.0982, 301.0333, 300.0277 | 303.0506 | t | + | +++ | Qn 3-O-X1 acetyl-X2 malonyl glucoside | C26H24O16 (0.3) | |
104 | Flavonoids (flavonol-O- acylglycosides) | 11.11 | 519.1121 | 521.1297 | 477.1016, 315.0428, 314.0430, 299.0192 | 317.0664, 287.0547 | t | ++ | ++ | Is 3-O-acetyl glucoside isomer | C24H24O13 (1.5) | [62] |
105 | Flavonoids (flavonol-O- acylglycosides) | 11.23 | 489.1035 | 491.1192 | 285.0385, 284.0327 | 287.0555 | t | ++ | ++ | Km 3-O-acetyl glucoside | C23H22O12 (0.7) | [56] |
106 | Saccharides | 11.33 | 405.09 | - | 241.0022, 152.9869, 96.9604 | - | + | + | + | Thioglucose-penta acetate | C16H22O10S (1.4) | |
107 | Flavonoids (flavonol-O- acylglycosides) | 11.44 | 521.1296 | 317.0661, 127.0391 | t | ++ | +++ | Is 3-O-acetyl glucoside isomer | C24H25O13 (0.8) | [62] | ||
108 | Flavonoids (flavonol-O- acylglycosides) | 12.01 | 575.1044 | 577.1191 | 531.1144, 489.1029, 285.0385, 284.0321 | 287.0555, 255.0441, 127.0391 | t | ++ | +++ | Km 3-O-X1 acetyl-X2 malonyl glucoside | C26H24O15 (0.5) | |
109 | Flavonoids (flavonol-O- acylglycosides) | 12.02 | 531.1138 | - | 489.1031, 285.0385, 284.325, 255.0295 | - | t | + | +++ | Km 3-O-diacetyl glucoside | C25H24O13 (0.7) | [62] |
110 | Flavonoids (flavonol-O- acylglycosides) | 12.23 | 561.1236 | - | 519.1152, 477.1016 315.0428, 314.0427, 299.0198 | - | t | + | +++ | Is 3-O-diacetyl glucoside | C26H26O14 (0.7) | [62] |
111 | Flavonoids (flavonol-O- glycosides) | 12.31 | 461.1085 | - | 299.0554, 298.0485, 283.0250 | - | + | ++ | + | Rh 3-O- glucoside b | C22H22O11 (1.9) | [8] |
112 | Flavonoids (flavonol-O- acylglycosides) | 12.68 | - | 577.1201 | - | 449.0908, 287.0555 | t | + | +++ | Km 3-O-X1 acetyl-X2 -malonyl glucoside isomer | C26H24O15 (−2.2) | |
113 | Flavonoids (flavonol-O- acylglycosides) | 12.86 | 547.1095 | 549.1246 | 505.0963, 299.0239, 298.0280, 271.0250, 163.0770 | 301.0713, 231.0520, 159.0292, 127.0396 | + | +++ | + | Rh 3-O-malonoyl glucoside | C25H24O14 (−1.5) | [61] |
114 | Flavonoids (flavonol-O- acylglycosides) | 12.88 | - | 607.1295 | - | 317.0662, 302.0427, 287.0546, 255.0512, 231.0500, 127.0392, 109.0287 | t | + | +++ | Is 3-O-X1 acetyl X2 malonyl glucoside | C27H26O16 (0.3) | |
115 | Flavonoids (flavonol-O- acylglycosides) | 12.90 | 561.1223 | - | 519.1147, 477.0989, 315.0502, 314.0430, 299.0205 | - | - | - | + | Is 3-O-diacetyl glucoside (isomer II) | C26H26O14 (0.5) | [62] |
116 | Fatty acid | 13.70 | 327.2178 | - | 291.1951, 229.1452, 211.1384, 171.1026, 85.0297 | - | ++ | + | + | Trihydroxy- octadecadienoic acid * | C18H32O5 (0.8) | [66] |
117 | Fatty acid | 14.64 | 329.2328 | - | 311.2220, 229.1442, 211.1342, 171.1025 | - | +++ | + | + | Trihydroxy- octadecanoic acid* | C18H36O5 (0.4) | [67] |
118 | Flavonoids (flavonoid aglycones) | 15.87 | - | 373.1285 | 358.1051, 343.0819, 329.1048, 315.0864, 229.0576 | - | t | +++ | + | Pentamethoxyflavone (tangeretin) * | C20H20O7 (0.9) | [68] |
119 | Flavonoids (flavonoid aglycones) | 17.21 | - | 373.1287 | 359.1180, 343.0821, 329.1024, 312.1006, 297.0771, 283.0981, 229.0553 | - | t | +++ | + | Pentamethoxyflavone isomer (sinensetin) * | C20H20O7 (1.2) | [68] |
120 | Flavonoids (biflavone) | 17.08 | 551.098 | - | 519.0691, 457.0573, 431.0760, 389.0667 | - | t | +++ | + | Amentoflavone methyl ether | C31H20O10 (0.0) | [69] |
121 | Flavonoids (biflavone) | 18.05 | 551.099 | - | 519.0727, 457.0560, 431.0769, 389.0660 | - | t | +++ | + | Amentoflavone methyl ether isomer | C31H20O10 (0.1) | [69] |
122 | Flavonoids (flavonoid aglycones) | 18.47 | - | 403.1393 | 373.0923, 359.1129, 343.0824, 329.1024, 313.0703 | - | t | +++ | + | Hexamethoxyflavone (Irigenin trimethyl ether) * | C21H22O8 (1.3) | [68] |
123 | Flavonoids (flavonoid aglycones) | 19.29 | - | 433.1492 | 419.1299, 418.1265, 403.1029, 385.0914 | - | t | +++ | + | Heptamethoxyflavone (Nobiletin) * | C22H24O9 (0.8) | [68] |
124 | Flavonoids (flavonoid aglycones) | 19.88 | - | 373.1286 | 358.1057, 343.0822, 325.0715, 312.0995, 271.0609, 211.0249, 183.0300 | - | t | +++ | + | Pentamethoxyflavone * | C20H20O7 (1.1) | [68] |
125 | Phospholipids (lysoglycerophos- phoinositol) | 19.92 | 593.2724 | 595.2888 | 413.2085, 315.0483, 277.2171, 241.0119, 152.9966 | 335.2586, 261.2222, 243.2124, 184.0707, 155.0107, 81.0697 | ++ | + | ++ | Octadecatrienoyl-glycero-phosphoinositol | C27H47O12P (0.4) | [70] |
126 | Phospholipids (lysoglycerophos- phoinositol) | 21.71 | 595.2885 | - | 415.2244, 315.0475, 279.2329, 241.0116, 152.9960 | - | ++ | + | ++ | Linoleoyl- glycero- phosphoinositol | C27H49O12P (0.2) | [70] |
127 | Diterpenes | 21.82 | - | 283.1698 | - | 265.1586, 223.1485, 197.1330, 183.1205 | + | + | ++ | Miltirone * | C19H22O2 (−1.0) | [71] |
128 | Fatty amides | 22.41 | - | 298.346 | - | 281.0533, 245.1075, 227.0968, 74.0965 | t | + | +++ | N-hydroxyoleylamide * | C18H35NO2 (1.6) | |
129 | Phospholipids (lysoglycerophos- phoinositol) | 22.88 | 571.2884 | - | 391.2254, 315.0487, 255.2329, 241.0119, 152.9959 | - | +++ | + | + | Palmitoyl- glycero-phosphoinositol * | C25H49O12P (−1.7) | [70] |
130 | Peptides | 23.12 | - | 643.2734 | - | 586.2621, 583.2526, 529.2143, 523.2311, 381.2094, 311.1647, 293.1540, 265.1591, 247.1489, 205.1966, 182.1016, 147.0811, 133.1029, 89.0603 | + | - | - | Glycyl-glycyl- phenylalanyl- alanyl- glutamyl-tyrosine | C30H38N6O10 (−1.8) | [72] |
131 | Peptides | 23.94 | - | 657.2866 | - | 597.2677, 537.2455, 507.2379, 343.132, 311.1642, 247.1480, 205.1966, 181.1016 166.0754, 147.0811 133.1029 | + | - | - | Serinyl- serinyl- glycyl- tyrosyl- phenylalanyl- proline | C31H40N6O10 (−1.4) | [72] |
132 | Peptides | 24.00 | - | 691.2720 | - | 631.2520, 571.2318, 541.2204, 495.1999, 453.1890, 393.1681, 353.1750, 311.1641, 293.1539, 265.1591, 247.1485, 223.1123, 133.0858, 91.0540 | + | - | - | Serinyl- phenylalanyl- glycyl- glutamyl- aspartyl- histidine | C34H38N6O10 (−1.5) | [72] |
133 | Fatty amides | 24.43 | - | 322.2751 | - | 304.2645, 135.0326, 107.0862, 95.0860 | +++ | t | + | α-Linolenoyl ethanolamide * | C20H35NO2 (0.5) | [73] |
134 | Fatty acids | 24.52 | 297.243 | 279.2334, 183.0120 | - | +++ | t | + | Methyl-oxo-heptadecanoic acid (lichesterylic acid) * | C18H34O3 (0.6) | ||
135 | Peptides | 24.61 | - | 685.29 | - | 625.2624, 565.2402, 353.1726, 293.1542, 247.1489, 181.1005, 182.0998, 147.0851, 119.0874, 106.0743 | + | - | - | Tryptophyl-glutamyl-tyrosyl-serinyl-threonine | C32H40N6O11 (−1.8) | [72] |
136 | Lipid (sulfoglycolipids) | 24.79 | 555.2844 | - | 299.0446, 255.2331, 206.9963, 80.9655 | - | ++ | +++ | + | Hexadecanoyl glycerol-O- sulfo-rhamnoside | C25H48O11S (0.2) | [74] |
137 | Peptides | 24.99 | - | 627.3956 | - | 369.1955, 351.1849, 333.1749, 313.2087, 277.1588, 182.1230, 166.1178, 106.4462, 91.0543, 97.1052, 75.0725 | + | - | - | Tyrosyl-glycyl-glycyl phenylalanyl- serinyl-proline | C30H38N6O9 (−1.6) | [72] |
138 | Fatty acids | 25.05 | 295.2282 | - | 279.2331 | - | +++ | t | t | Hydroxyoctadecadienoic acid * | C18H32O3 (1.0) | |
139 | Phospholipids (lysophosphatidylglycerols) | 25.16 | 481.2568 | - | 253.2174, 245.0430, 227.0324, 152.9959 | - | t | +++ | + | Hexadecenoyl glycero-phospho- sn-glycerol * | C22H43O9P (0.6) | [70] |
140 | Peptides | 25.36 | - | 699.2995 | - | 639.2786, 579.2571, 519.2348, 495.1999, 453.1890, 393.1681, 353.1750, 311.1641 293.1539, 265.1591, 247.1485, 223.1123, 133.0858, 91.0540 | + | - | - | Tyrosyl- threonyl-valinyl-methionyl-tryptophan | C34H46N6O8S (−1.6) | [72] |
141 | Peptides | 25.72 | - | 675.2624 | - | 618.2624, 455.2040, 421.1996, 295.1699, 277.1592, 267.1749, 249.1642, 205.1903, 107.0875, 91.0543 | + | - | - | Glycyl-Serinyl-tyrosyl-tryptophyl-tyrosine | C34H38N6O9 (−1.3) | [72] |
142 | Peptides | 25.75 | - | 593.2754 | - | 397.2016, 355.1903, 295.1695, 277.1592, 267.1747, 249.1640, 207.1173, 165.0915 | + | - | - | Acetyl-tryptophyl-methyl-alanyl-aspartyl-phenylalaninamide | C30H36N6O7 (−1.8) | [72] |
143 | Peptides | 25.82 | - | 641.2942 | - | 581.2734, 521.2517, 461.2302, 313.1501, 295.1700, 277.1592, 249.1640, 173.0965, 106.0743, 91.0543 | + | - | - | Serinyl-serinyl- glycyl-prolinyl- phenylalanyl-phenylalanine | C31H40N6O9 (−1.6) | [72] |
144 | Peptides | 26.03 | - | 633.2679 | - | 576.2636, 523.2266, 437.1942, 377.1728, 267.1752, 253.1588, 239.1456, 107.0864, 91.0544 | + | - | - | Nicotinoyl- alanyl- alanyl tyrosyl- glycyl- phenylalanine | C32H36N6O8 (−1.8) | [72] |
145 | Fatty amides | 26.26 | - | 324.29 | 306.2793, 263.2363 245.2256, 147.1161, 109.1010, 95.0857, 81.0698, 62.0599 | - | +++ | t | + | Linoleoyl ethanolamide * | C20H37NO2 (0.2) | [73] |
146 | Phospholipids (lysophosphatidylglycerols) | 26.60 | 483.2718 | 227.0324, 152.9955 | - | + | + | + | Hexadecanoyl glycerophospho- glycerol | C22H45O9P (0.2) | [70] | |
147 | Peptides | 27.16 | - | 617.2724 | - | 557.2543, 497.298, 421.1988, 361.1785, 321.2406, 297.1849, 279.1747, 251.1804, 209.1325, 91.0538 | + | - | - | Tryptophyl-glutamyl-prolyl-tryptophan | C18H37NO2 (0.5) | [72] |
148 | Fatty amides | 27.70 | - | 300.2902 | 283.2642, 242.2482, 109.1012, 95.0857 85.1013, 71.0855, 67.0545, 62.0598 | - | +++ | t | + | Palmitoyl ethanolamide * | C18H37NO2 (0.5) | [75] |
149 | Fatty acids | 28.07 | - | 347.2610 | - | 275.1620, 235.1318, 195.1004, 179.9946, 95.0865 | t | t | +++ | Hydroxy- docosa-pentaenoic acid * | C22H34O3 (0.5) | [76] |
150 | Fatty acids | 28.34 | - | 326.3796 | - | 308.2959, 107.0847, 95.0857, 81.0889, 62.0599 | +++ | t | + | N-Oleoylethanolamine * | C20H39NO2 (0.2) | [77] |
151 | Fatty acids | 28.68 | - | 347.2560 | - | - | t | t | +++ | Hydroxy- docosa-pentaenoic acid isomer * | C22H34O3 (0.6) | [76] |
152 | Fatty esters | 30.21 | - | 325.274 | - | 265.2527, 247.2421, 135.1169, 121.1013, 109.1013, 95.0856, 81.0700, 67.0540 | t | + | +++ | Octadecenoic acid methyl ethyl ester | C20H36O3 (1.2) | [78] |
153 | Fatty acids | 32.10 | 355.3217 | - | 337.3118, 309.3161, 297.1527 | - | +++ | t | t | Hydroxyl docosanoate | C22H44O3 (0.2) | [79] |
154 | Fatty amides | 33.72 | - | 310.3111 | 293.2853, 275.2741, 97.1015, 83.0857, 69.0700 | - | + | + | + | Dimethyl-octadecenamide | C20H39NO (−2.1) | [77] |
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Marzouk, M.M.; Hegazi, N.M.; El Shabrawy, M.O.A.; Farid, M.M.; Kawashty, S.A.; Hussein, S.R.; Saleh, N.A.M. Discriminative Metabolomics Analysis and Cytotoxic Evaluation of Flowers, Leaves, and Roots Extracts of Matthiola longipetala subsp. livida. Metabolites 2023, 13, 909. https://doi.org/10.3390/metabo13080909
Marzouk MM, Hegazi NM, El Shabrawy MOA, Farid MM, Kawashty SA, Hussein SR, Saleh NAM. Discriminative Metabolomics Analysis and Cytotoxic Evaluation of Flowers, Leaves, and Roots Extracts of Matthiola longipetala subsp. livida. Metabolites. 2023; 13(8):909. https://doi.org/10.3390/metabo13080909
Chicago/Turabian StyleMarzouk, Mona M., Nesrine M. Hegazi, Mona O. A. El Shabrawy, Mai M. Farid, Salwa A. Kawashty, Sameh R. Hussein, and Nabiel A. M. Saleh. 2023. "Discriminative Metabolomics Analysis and Cytotoxic Evaluation of Flowers, Leaves, and Roots Extracts of Matthiola longipetala subsp. livida" Metabolites 13, no. 8: 909. https://doi.org/10.3390/metabo13080909