Effects of Different Drying Methods on Amino Acid Metabolite Content and Quality of Ophiocordyceps sinensis by LC-MS/MS Combined with Multivariate Statistical Methods
Abstract
:1. Introduction
2. Materials and Procedures
2.1. Source of Materials
2.2. Metabolite Extraction
2.3. Analysis Using LC-MS/MS
2.4. Data Processing
2.5. Preparation and Calculation of Amino Acid Metabolites Content Standard Curve
3. Results
3.1. Characterization of Amino Acid Metabolic Profiles
3.2. Principal Component Analysis (PCA) and Hierarchical Cluster Analysis (HCA)
3.3. Calculation of Amino Acid Metabolites
Difference Analysis of Essential Amino Acid Metabolites and Delicious Amino Acids Metabolites Content
3.4. Screening of Differential Amino Acid Metabolites (DAMs)
3.5. KEGG Analysis
3.6. DAMs Analysis in Critical Paths
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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No. | Compounds | Q1 (Da) | Q3 (Da) | Molecular Weight | Formula | RT | DG | HG | YG | CK |
---|---|---|---|---|---|---|---|---|---|---|
1 | Ethanolamine | 62 | 44 | 61.08 | C2H7NO | 4.73 | 52,263.13 | 30,905.25 | 27,724.37 | 34,209.60 |
2 | Phosphorylethanolamine | 142.026 | 44.049 | 141.06 | C2H8NO4P | N/A | N/A | N/A | N/A | N/A |
3 | Anserine | 241 | 170 | 240.26 | C10H16N4O3 | 10.47 | 2791.09 | 3269.22 | 2023.59 | 3102.44 |
4 | (5-L-Glutamyl)-L-Alanine | 219.09 | 202 | 218.09 | C8H14N2O5 | 9.84 | 59,690.84 | 152,090.55 | 70,597.08 | 174,067.24 |
5 | O-Phospho-L-Serine | 186 | 88.2 | 185.01 | C3H8NO6P | 10.92 | 5014.20 | 10,415.13 | 5146.75 | 9795.23 |
6 | N-Acetylaspartate | 176 | 134 | 175.05 | C6H9NO5 | 4.76 | 18,063.90 | 20,873.08 | 12,980.58 | 8152.68 |
7 | N-Acetyl-L-Tyrosine | 224 | 136 | 223.09 | C11H13NO4 | 1.74 | 680.43 | 1210.69 | 630.95 | 1665.39 |
8 | L-tyrosine methyl ester | 196.2 | 136.3 | 195.09 | C10H13NO3 | 1.52 | 409.23 | 434.79 | 281.85 | 437.05 |
9 | L-Cystathionine | 223.07 | 134 | 222.07 | C7H14N2O4S | 10.86 | 409,853.38 | 386,011.47 | 265,291.90 | 383,347.89 |
10 | Homoserine | 120.065 | 74.06 | 119.12 | C4H9NO3 | 8.57 | 963,95.82 | 160,750.02 | 85,718.14 | 181,130.92 |
11 | D-Alanyl-D-Alanine | 161.09 | 44.04 | 160.09 | C6H12N2O3 | 8.76 | 3157.84 | 7888.17 | 3684.92 | 3824.47 |
12 | S-(5-Adenosyl)-L-Homocysteine | 385 | 136.06 | 384.12 | C14H20N6O5S | 9.37 | 115,970.38 | 835,272.49 | 317,084.08 | 224,819.03 |
13 | 3-Iodo-L-Tyrosine | 308.2 | 261.97 | 306.97 | C9H10INO3 | 4.75 | 37.26 | 66.00 | 36.00 | 42.47 |
14 | glycylphenylalanine | 223.2 | 120.2 | 222.1 | C11H14N2O3 | 7.17 | 881.62 | 7363.57 | 2750.79 | 417.58 |
15 | L-Valine | 118.1 | 72.1 | 117.08 | C5H11NO2 | 6.14 | 405,663.10 | 512,162.35 | 305,943.86 | 389,962.93 |
16 | L-Tyrosine | 182.08 | 136.07 | 181.19 | C9H11NO3 | 6.67 | 808,353.61 | 869,834.54 | 559,398.27 | 872,333.69 |
17 | L-Tryptophan | 205.1 | 118.06 | 204.09 | C11H12N2O2 | 4.46 | 101,179.10 | 151,314.67 | 84,166.08 | 86,786.14 |
18 | Trans-4-Hydroxy-L-Proline | 132.058 | 86 | 131.06 | C5H9NO3 | 8.05 | 98,744.37 | 156,291.27 | 85,014.56 | 191,836.09 |
19 | Glutathione Oxidized | 613.152 | 484 | 612.15 | C20H32N6O12S2 | 11.31 | 7,287,906.55 | 8,895,298.80 | 5,394,405.55 | 8,784,995.30 |
20 | argininosuccinic acid | 291.5 | 176.1 | 290.27 | C10H18N4O6 | 10.99 | 2,964,334.61 | 3,027,278.70 | 1,997,208.10 | 1,930,567.70 |
21 | D-Homocysteine | 136 | 90.036 | 135.04 | C4H9NO2S | 6.14 | 464.30 | 486.99 | 319.14 | 452.44 |
22 | L-Cystine | 239 | 120 | 240.02 | C6H12N2O4S2 | 10.91 | 401.06 | 594.09 | 335.35 | N/A |
23 | Nicotinuric Acid | 181.1 | 135 | 180.05 | C8H8N2O3 | 3.55 | N/A | N/A | N/A | N/A |
24 | N8-Acetylspermidine | 190.18 | 173.15 | 189.18 | C9H23N3O | 9.72 | N/A | N/A | N/A | N/A |
25 | N-Propionylglycine | 130.1 | 74 | 131.06 | C5H9NO3 | 2.14 | N/A | N/A | N/A | N/A |
26 | L-Cysteine | 122.02 | 59 | 121.02 | C3H7NO2S | 7.13 | N/A | N/A | N/A | N/A |
27 | 3-Chloro-L-Tyrosine | 216.1 | 170.1 | 215.04 | C9H10ClNO3 | 5.33 | N/A | N/A | N/A | N/A |
28 | 5-Hydroxy-Tryptamine | 177.1 | 160 | 176.21 | C10H12N20 | 2.55 | N/A | N/A | N/A | N/A |
29 | Nα-Acetyl-L-glutamine | 189.1 | 130.1 | 188.18 | C7H12N2O4 | 6.39 | N/A | N/A | N/A | N/A |
30 | L-Threonine | 120.06 | 74 | 119.06 | C4H9NO3 | 8.38 | 1,590,252.44 | 1,797,878.87 | 1,129,379.90 | 1,226,147.51 |
31 | N,N-Dimethylglycine | 104 | 58 | 103.06 | C4H9NO2 | 5.91 | N/A | N/A | N/A | 566.57 |
32 | L-Homocystine | 269 | 136 | 268.06 | C8H16N2O4S2 | 10.50 | N/A | 3648.26 | N/A | N/A |
33 | Trimethylamine N-Oxide | 76 | 58.1 | 75.07 | C3H9NO | 2.94 | N/A | 3.87 | N/A | 13.15 |
34 | N-Isovaleroylglycine | 158.1 | 74 | 159.09 | C7H13NO3 | 1.32 | N/A | N/A | N/A | N/A |
35 | S-Sulfo-L-Cysteine | 201.98 | 120 | 200.98 | C3H7NO5S2 | 7.86 | N/A | 1428.78 | N/A | N/A |
36 | N-Acetylneuraminic Acid | 310.11 | 274.09 | 309.11 | C11H19NO9 | 9.57 | N/A | 130,727.88 | N/A | 22,726.06 |
37 | γ-Glutamate-Cysteine | 251.07 | 130.05 | 250.06 | C8H14N2O5S | 9.84 | 207,439.45 | 215,940.92 | 141,130.07 | 244,866.08 |
38 | 5-Hydroxy-tryptophan | 219.1 | 74 | 220.22 | C11H12N2O3 | 6.69 | 15,855.02 | 13,153.19 | 9671.64 | 16,623.56 |
39 | L-Theanine | 175 | 158 | 174.1 | C7H14N2O3 | 7.14 | 2049.75 | 1054.52 | 1037.14 | N/A |
40 | L-Tryptophyl-L-glutamic acid | 334 | 159 | 333.13 | C16H19N3O5 | 8.19 | 52,085.37 | 235,428.36 | 95,840.64 | 34,439.12 |
41 | Urea | 61 | 44 | 60.03 | CH4N2O | 1.46 | 73,727.18 | 380,087.66 | 151,272.10 | 304,614.48 |
42 | L-Serine | 106.04 | 60 | 105.04 | C3H7NO3 | 9.03 | 590,199.33 | 684,869.12 | 425,025.83 | 474,754.60 |
43 | L-Histidine | 156.07 | 110.07 | 155.07 | C6H9N3O2 | 10.06 | 1,405,379.02 | 1,404,476.98 | 936,622.02 | 1,071,662.56 |
44 | Glycyl-L-Proline | 173.1 | 116.071 | 172.09 | C7H12N2O3 | 9.10 | 788.76 | 1743.52 | 847.13 | 285.07 |
45 | Glycine | 76.03 | 30 | 75.03 | C2H5NO2 | 8.6 | 403,027.10 | 553,800.33 | 318,945.34 | 282,386.73 |
46 | Succinic Acid | 117.03 | 99 | 118.03 | C4H6O4 | 1.36 | 1,299,153.87 | 1,491,250.31 | 930,135.18 | 730,942.74 |
47 | L-Glutamine | 147.069 | 84 | 146.07 | C5H10N2O3 | 8.98 | 9,799,945.11 | 11,662,924.50 | 7,154,292.86 | 11,198,431.33 |
48 | Beta-Alanine | 90.2 | 30 | 89.05 | C3H7NO2 | 8.05 | 43,449.96 | 60,525.95 | 34,661.32 | 54,251.24 |
49 | L-α-Aspartyl-L-phenylalanine | 281.3 | 166 | 280.11 | C13H16N2O5 | 8.73 | 3981.51 | 5021.82 | 3004.02 | 3711.77 |
50 | L-Aspartate | 134.04 | 74 | 133.1 | C4H7NO4 | 9.93 | 3,544,943.12 | 3,319,674.22 | 2,288,209.09 | 2,792,831.29 |
51 | L-Asparagine Anhydrous | 133.06 | 74 | 132.05 | C4H8N2O3 | 9.13 | 895,965.13 | 974,125.64 | 623,366.63 | 815,367.47 |
52 | L-Arginine | 175.1 | 70.06 | 174.11 | C6H14N4O2 | 10.28 | 1,231,313.96 | 1,537,085.89 | 922,803.38 | 1,047,209.36 |
53 | L-Alanine | 90.05 | 44.05 | 89.05 | C3H7NO2 | 8.07 | 866,190.62 | 1,556,109.93 | 807,436.21 | 1,313,825.59 |
54 | 5-Hydroxylysine | 163.1 | 128.07 | 162.18 | C6H14N2O3 | 10.76 | 13,266.38 | 14,017.87 | 9098.34 | 12,117.00 |
55 | 3-N-Methyl-L-Histidine | 170 | 96 | 169.18 | C7H11N3O2 | 10.19 | 31,543.58 | 32,713.75 | 21,422.51 | 30,344.09 |
56 | 3-Aminoisobutanoic Acid | 104.07 | 86.05 | 103.06 | C4H9NO2 | 6.92 | 165,603.26 | 257,073.67 | 140,894.62 | 232,608.79 |
57 | 1-Methylhistidine | 170.1 | 124 | 169.09 | C7H11N3O2 | 9.40 | 224,915.30 | 237,642.61 | 154,189.10 | 220,762.47 |
58 | Homo-L-arginine | 189 | 144 | 188.13 | C7H16N4O2 | 10.14 | 399,822.88 | 407,488.07 | 269,107.03 | 329,249.02 |
59 | L-Isoleucine | 132.1 | 86.1 | 131.1 | C6H13NO2 | 4.67 | 220,177.26 | 229,017.66 | 149,733.20 | 167,765.33 |
60 | L-Glutamic acid | 148.06 | 84 | 147.05 | C5H9NO4 | 9.39 | 14,736,617.03 | 17,017,140.07 | 10,584,588.83 | 17,347,695.43 |
61 | L-Citrulline | 176.1 | 113 | 175.1 | C6H13N3O3 | 9.37 | 210,279.70 | 144,586.95 | 118,292.00 | 103,110.97 |
62 | L-Proline | 116.1 | 70.1 | 115.06 | C5H9NO2 | 6.20 | 1,026,738.00 | 1,117,680.18 | 714,808.13 | 1,002,877.35 |
63 | L-Phenylalanine | 166.1 | 120.08 | 165.08 | C9H11NO2 | 4.29 | 212,228.29 | 147,826.34 | 120,019.64 | 139,718.17 |
64 | Nα-Acetyl-L-Arginine | 217.1 | 158 | 216.12 | C8H16N4O3 | 8.40 | 4080.90 | 3937.66 | 2675.65 | 4013.49 |
65 | L-Carnosine | 227.2 | 156 | 226.11 | C9H14N4O3 | 10.00 | 7058.33 | 16,999.45 | 8022.59 | 11,899.32 |
66 | N-Glycyl-L-Leucine | 189.1 | 86 | 188.12 | C8H16N2O3 | 7.12 | 3348.98 | 23,136.08 | 8830.73 | 1577.20 |
67 | Methionine Sulfoxide | 166 | 74 | 165.05 | C5H11NO3S | 8.95 | 2511.90 | 3535.30 | 2018.72 | 1485.36 |
68 | L-Methionine | 150.05 | 104 | 149.05 | C5H11NO2S | 5.49 | 12,821.99 | 21,771.01 | 11,532.83 | 7682.36 |
69 | L-Lysine | 147.069 | 84 | 146.11 | C6H14N2O2 | 10.45 | 1,016,825.72 | 1,230,450.69 | 749,095.62 | 1,073,002.26 |
70 | N6-Acetyl-L-Lysine | 189.1 | 126 | 188.12 | C8H16N2O3 | 8.32 | 142,014.00 | 207,737.40 | 116,586.57 | 252,095.63 |
71 | Sarcosine | 90.2 | 44.1 | 89.05 | C3H7NO2 | 7.51 | N/A | N/A | N/A | N/A |
72 | L-Leucine | 132.1 | 86.1 | 131.1 | C6H13NO2 | 4.37 | 371,341.70 | 383,117.21 | 251,487.76 | 307,224.27 |
73 | L-Pipecolic Acid | 130 | 84 | 129.08 | C6H11NO2 | 6.58 | 10,013.19 | 13,560.04 | 7859.94 | 13,645.17 |
74 | L-Ornithine | 133.09 | 70 | 132.16 | C5H13ClN2O2 | 10.50 | 6,438,468.41 | 5,370,492.12 | 3,936,323.68 | 6,452,913.39 |
75 | L-Homocitrulline | 190.1 | 127 | 189.11 | C7H15N3O3 | 9.14 | 8630.02 | 20,657.64 | 9765.60 | 8303.07 |
76 | (S)-β-Aminoisobutyric Acid | 104.07 | 57.03 | 103.06 | C4H9NO2 | 6.92 | 142,049.24 | 232,551.66 | 124,869.27 | 207,825.77 |
77 | 1,3-Dimethyluric Acid | 195 | 180 | 196.06 | C7H8N4O3 | 1.53 | 945.92 | 1515.58 | 821.01 | 1196.77 |
78 | Kynurenic Acid | 190.043 | 144 | 189.04 | C10H7NO3 | 3.02 | 70.73 | 86.35 | 53.37 | 102.69 |
79 | N’-Formylkynurenine | 237.1 | 146.06 | 236.08 | C11H12N2O4 | 5.47 | N/A | N/A | N/A | N/A |
80 | Guanidinoethyl Sulfonate | 168.04 | 151.01 | 167.04 | C3H9N3O3S | 6.37 | N/A | N/A | N/A | N/A |
81 | 2-Aminobutyric acid | 104.1 | 58.14 | 103.12 | C4H9NO2 | 7.25 | 217,013.31 | 413,898.45 | 210,306.34 | 403,754.53 |
82 | Creatine Phosphate | 212.04 | 114.06 | 211.11 | C4H8N3Na2O5P | N/A | N/A | N/A | N/A | N/A |
83 | 6-Aminocaproic Acid | 132.095 | 69 | 131.1 | C6H13NO2 | 3.76 | N/A | N/A | N/A | N/A |
84 | 5-Aminovaleric Acid | 118.2 | 55 | 117.08 | C5H11NO2 | 4.68 | 29,796.26 | 40,011.34 | 23,270.76 | 35,215.87 |
85 | 3,7-Dimethyluric Acid | 195 | 180 | 196.06 | C7H8N4O3 | 1.65 | N/A | N/A | N/A | N/A |
86 | Creatine | 132.1 | 90 | 131.07 | C4H9N3O2 | 8.09 | 2174.93 | 4947.67 | 2376.90 | 2622.21 |
87 | 3-Hydroxyhippuric Acid | 196.05 | 121 | 195.05 | C9H9NO4 | 1.98 | N/A | N/A | N/A | N/A |
88 | P-Aminohippuric Acid | 195.069 | 120 | 194.07 | C9H10N2O3 | 1.93 | 97.15 | 460.48 | 186.52 | 200.29 |
89 | 4-Acetamidobutyric Acid | 146.074 | 86 | 145.07 | C6H11NO3 | 1.17 | 1560.37 | 3167.75 | 1576.43 | 2300.27 |
90 | γ-Aminobutyric Acid | 104.06 | 68.8 | 103.06 | C4H9NO2 | 6.56 | 3,866,168.03 | 3,234,742.41 | 2,366,972.33 | 484,156.29 |
91 | kynurenine | 209.1 | 146 | 208.09 | C10H12N2O3 | 4.48 | 148.87 | 595.04 | 249.46 | 80.48 |
92 | α-Aminoadipic acid | 162.07 | 98.06 | 161.16 | C6H11NO4 | 8.97 | 360,464.64 | 460,812.56 | 273,762.06 | 508,061.11 |
93 | 2-Aminoethanesulfonic Acid | 124 | 80 | 125.15 | C2H7NO3S | 6.49 | 26,317.34 | 37,667.76 | 21,330.53 | 41,370.20 |
94 | 1,3,7-Trimethyluric Acid | 211.08 | 154.06 | 210.08 | C8H10N4O3 | 1.09 | N/A | N/A | N/A | N/A |
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Xiao, M.; Wang, T.; Tang, C.; He, M.; Li, Y.; Li, X. Effects of Different Drying Methods on Amino Acid Metabolite Content and Quality of Ophiocordyceps sinensis by LC-MS/MS Combined with Multivariate Statistical Methods. Metabolites 2024, 14, 459. https://doi.org/10.3390/metabo14080459
Xiao M, Wang T, Tang C, He M, Li Y, Li X. Effects of Different Drying Methods on Amino Acid Metabolite Content and Quality of Ophiocordyceps sinensis by LC-MS/MS Combined with Multivariate Statistical Methods. Metabolites. 2024; 14(8):459. https://doi.org/10.3390/metabo14080459
Chicago/Turabian StyleXiao, Mengjun, Tao Wang, Chuyu Tang, Min He, Yuling Li, and Xiuzhang Li. 2024. "Effects of Different Drying Methods on Amino Acid Metabolite Content and Quality of Ophiocordyceps sinensis by LC-MS/MS Combined with Multivariate Statistical Methods" Metabolites 14, no. 8: 459. https://doi.org/10.3390/metabo14080459