TABLE 2.
Compound name | Molecular formula | Molecular weight (g/mol) | RT (min) | Mass error (ppm) | Adduct | ID level | a CV for QC (%) | Low vs. high altitude samples | ||
---|---|---|---|---|---|---|---|---|---|---|
b FC | c VIP | d p-value with FDR | ||||||||
Flavonoids | ||||||||||
Luteolin 6-C-glucoside 8-C-arabinoside | C27H30O16 | 610.1534 | 5.17 | 1 | [M-H]− | 2 | 0.64 | 0.67 | 3.26 | 2.41E-02 |
Quercetin 3,7-dirhamnoside | C27H30O15 | 594.1585 | 5.39 | 1 | [M-H]− | 2 | 1.73 | 0.65 | 3.71 | 2.81E-04 |
Kaempferol-3-O-rutinoside | C27H30O15 | 594.1585 | 6.09 | 4 | [M-H]− | 4 | 0.86 | 0.77 | 2.34 | 1.70E-02 |
Vitexin 6''-(3-hydroxy-3-methylglutarate) | C27H28O14 | 576.1479 | 6.86 | 1 | [M-H-H2O]− | 3 | 3.42 | 0.45 | 3.03 | 6.10E-05 |
Maysin | C27H28O14 | 576.1479 | 5.86 | 1 | [M-H]− | 2 | 3.53 | 0.53 | 3.58 | 1.47E-04 |
Cassiaoccidentalin B | C27H28O14 | 576.1479 | 6.72 | 2 | [M-H]− | 2 | 1.76 | 0.58 | 2.70 | 2.91E-04 |
Nicotiflorin | C27H30O15 | 594.1585 | 5.96 | 0 | [M-H]− | 2 | 2.95 | 0.68 | 1.88 | 8.91E-03 |
Scutellarein 4′-methyl ether 7-glucuronide | C22H20O12 | 476.0955 | 6.44 | 1 | [M-H]− | 2 | 1.46 | 0.44 | 2.68 | 3.25E-06 |
Denticulaflavonol | C35H42O6 | 558.2981 | 12.92 | 9 | [M+Cl]− | 2 | 0.94 | 0.26 | 2.03 | 7.02E-12 |
Apigenin 7-[6''-(3-Hydroxy-3-methylglutaryl)glucoside] | C27H28O14 | 576.1479 | 8.29 | 5 | [M-H-H2O]− | 4 | 1.00 | 0.61 | 2.21 | 1.23E-03 |
Quercetin 3-(2″,3″,4″-triacetylgalactoside) | C27H26O15 | 590.1272 | 6.90 | 1 | [M-H-H2O]− | 3 | 0.74 | 0.35 | 2.33 | 5.17E-07 |
Hosloppin | C22H16O7 | 392.0896 | 8.82 | 7 | [M+HCOO-H]− | 2 | 0.62 | 0.68 | 1.54 | 1.25E-03 |
Vitexin 2″-O-rhamnoside* | C27H30O14 | 578.1636 | 5.96 | 3 | [M-H]− | 2 | 0.58 | 0.67 | 1.87 | 1.41E-03 |
Allivicin | C27H30O16 | 610.1534 | 5.81 | 1 | [M-H]− | 2 | 1.38 | 0.75 | 2.35 | 2.99E-02 |
Paniculatin | C27H30O15 | 594.1585 | 6.86 | 0 | [M-H-H2O]− | 4 | 2.88 | 0.50 | 2.42 | 1.24E-03 |
6″-O-(3-Hydroxy-3-methylglutaroyl)astragalin | C27H28O15 | 592.1428 | 6.21 | 1 | [M-H]− | 2 | 1.60 | 0.58 | 1.31 | 3.73E-03 |
Baicalin | C21H18O11 | 446.0849 | 6.18 | 3 | [M-H]− | 4 | 2.31 | 0.47 | 1.59 | 2.05E-03 |
4′-O-Methylneobavaisoflavone 7-O-(2″-p-coumaroylglucoside) | C36H36O11 | 644.2258 | 6.14 | 8 | [M-H]− | 3 | 0.63 | 2.14 | 1.37 | 8.96E-03 |
Apigenin 7-[rhamnosyl-(1->2)-galacturonide] | C27H28O15 | 592.1428 | 6.21 | 2 | [M-H]− | 4 | 2.60 | 0.66 | 1.09 | 2.01E-03 |
Isorhamnetin 3-galactoside-7-rhamnoside | C28H32O16 | 624.1690 | 5.52 | 2 | [M-H]− | 2 | 0.71 | 0.67 | 1.47 | 8.10E-03 |
Violanthin | C27H30O14 | 578.1636 | 6.51 | 4 | [M-H]− | 4 | 1.05 | 0.56 | 1.27 | 2.10E-05 |
Eruberin B | C30H40O15 | 640.2367 | 6.23 | 2 | [M-H]− | 3 | 1.81 | 5.15 | 1.07 | 9.72E-04 |
Kaempferol 7-sophoroside | C27H30O16 | 610.1534 | 5.17 | 6 | [M-H]− | 2 | 0.26 | 0.74 | 2.44 | 4.45E-02 |
Vicenin 2* | C27H30O15 | 594.1585 | 5.96 | 1 | [M-H]− | 2 | 3.76 | 0.74 | 1.74 | 2.13E-02 |
Thonningianin B | C35H30O17 | 722.1483 | 9.07 | 3 | [M+HCOO-H]− | 2 | 0.86 | 0.58 | 1.49 | 1.25E-04 |
Bracteoside | C22H20O12 | 476.0955 | 6.01 | 2 | [M-H]− | 4 | 5.58 | 0.48 | 1.07 | 4.91E-05 |
Orientin 2″-rhamnoside | C27H30O15 | 594.1585 | 6.09 | 1 | [M-H]− | 2 | 0.77 | 0.74 | 2.47 | 6.33E-03 |
7,8,3′,4′-Tetrahydroxyflavanone 7-(2,4,6-triacetylglucoside) | C27H28O14 | 576.1479 | 6.72 | 1 | [M-H]− | 2 | 1.66 | 0.57 | 2.72 | 2.80E-04 |
Epigallocatechin 3-gallate | C22H18O11 | 458.0849 | 7.93 | 2 | [M-H]− | 2 | 2.83 | 0.45 | 1.15 | 3.29E-06 |
Glychalcone A | C22H22O5 | 366.1467 | 1.34 | 4 | [M-H]− | 4 | 1.85 | 0.48 | 1.29 | 6.72E-08 |
Quercetin 3-(3″,6″-diacetylgalactoside) | C25H24O14 | 548.1166 | 6.94 | 6 | [M-H-H2O]− | 3 | 1.39 | 0.52 | 1.06 | 9.13E-05 |
2″,4″-Diacetylafzelin | C25H24O12 | 516.1268 | 6.79 | 1 | [M-H]− | 3 | 0.39 | 0.73 | 2.54 | 3.65E-03 |
Epigallocatechin 3-O-caffeate | C24H20O10 | 468.1057 | 8.30 | 5 | [M+HCOO-H]− | 3 | 1.06 | 0.48 | 1.16 | 1.05E-06 |
Cyanidin 3-rutinoside | C27H31O15 | 595.1663 | 6.72 | 8 | [M-H-H2O]− | 4 | 1.72 | 0.73 | 1.29 | 1.24E-02 |
5,7,3′,4′-Tetrahydroxyflavanone 7-alpha-L-arabinofuranosyl-(1->6)-glucoside | C26H30O15 | 582.1585 | 5.17 | 2 | [M+HCOO-H]− | 4 | 0.24 | 0.63 | 2.60 | 2.76E-03 |
Isoorientin 2″-O-rhamnoside | C27H30O15 | 594.1585 | 5.86 | 2 | [M-H]− | 4 | 1.15 | 0.60 | 2.82 | 1.20E-03 |
Neosaponarin | C27H30O15 | 594.1585 | 6.72 | 2 | [M-H]− | 4 | 0.99 | 0.64 | 2.92 | 1.85E-03 |
Chamaemeloside | C27H28O14 | 576.1479 | 6.08 | 1 | [M-H]− | 2 | 1.39 | 0.59 | 1.68 | 3.16E-05 |
5′,5‴,8,8″-Tetrahydroxy-3′,3‴,4′,4‴,7′,7″-hexamethoxy-5,5″-biflavan | C36H38O12 | 662.2363 | 5.90 | 8 | [M-H-H2O]− | 3 | 0.33 | 0.61 | 1.45 | 1.39E-05 |
Kaempferol 7-neohesperidoside | C27H30O15 | 594.1585 | 6.09 | 1 | [M-H]− | 2 | 0.85 | 0.72 | 2.56 | 4.44E-03 |
Saponarin* | C27H30O15 | 594.1585 | 5.40 | 2 | [M-H]− | 2 | 1.32 | 0.69 | 2.78 | 7.22E-04 |
Astragalin 7-rhamnoside | C27H30O15 | 594.1585 | 6.54 | 1 | [M-H-H2O]− | 3 | 1.66 | 0.51 | 1.61 | 5.64E-05 |
Apigenin 7-glucuronide-4′-rhamnoside | C27H28O15 | 592.1428 | 6.54 | 1 | [M-H-H2O]− | 3 | 1.95 | 0.50 | 1.64 | 5.20E-05 |
Fatty acids | ||||||||||
TriHODE | C18H32O5 | 328.2250 | 8.07 | 1 | [M-H]− | 4 | 0.36 | 0.65 | 3.90 | 2.34E-08 |
Sativic acid | C18H36O6 | 348.2512 | 8.45 | 1 | [M-H-H2O]− | 4 | 0.26 | 0.61 | 3.96 | 4.91E-13 |
Coriolic acid | C18H32O3 | 296.2351 | 11.70 | 1 | [M-H]− | 2 | 0.75 | 0.35 | 2.40 | 7.02E-12 |
HoTrE | C18H30O3 | 294.2195 | 11.20 | 1 | [M-H]− | 2 | 0.76 | 0.33 | 2.44 | 1.84E-12 |
Dodecanedioic acid | C12H22O4 | 230.1518 | 6.43 | 0 | [M-H]− | 2 | 0.45 | 0.67 | 1.88 | 1.95E-04 |
TriHOME | C18H34O5 | 330.2406 | 8.88 | 2 | [M-H]− | 4 | 1.37 | 0.48 | 1.30 | 3.66E-07 |
Lauric acid | C12H22O3 | 214.1569 | 8.39 | 1 | [M-H]− | 2 | 0.64 | 0.43 | 1.14 | 2.13E-07 |
Undecylenic acid | C11H20O2 | 184.1463 | 6.70 | 1 | [M+HCOO-H]− | 4 | 0.61 | 0.68 | 1.26 | 1.89E-03 |
HpODE | C18H32O4 | 312.2301 | 10.50 | 1 | [M-H]- | 4 | 1.25 | 0.46 | 1.02 | 1.74E-07 |
HpOTrE | C18H30O4 | 310.2144 | 10.09 | 1 | [M-H]− | 4 | 1.74 | 0.41 | 1.03 | 2.56E-07 |
Undecenoic acid | C11H20O2 | 184.1463 | 8.07 | 1 | [M+HCOO-H]− | 4 | 0.87 | 0.65 | 1.23 | 3.88E-07 |
Cascarillic acid | C11H20O2 | 184.1463 | 8.45 | 1 | [M+HCOO-H]− | 4 | 0.88 | 0.53 | 1.43 | 5.49E-12 |
Sorbic acid | C6H8O2 | 112.0524 | 3.33 | 1 | [M-H-H2O]− | 3 | 1.11 | 0.61 | 1.24 | 9.88E-07 |
Malyngic acid | C18H32O5 | 328.2250 | 9.08 | 2 | [M-H]− | 4 | 9.26 | 0.60 | 1.36 | 9.87E-07 |
Fulgidic acid | C18H32O5 | 328.2250 | 8.55 | 1 | [M-H]− | 4 | 1.53 | 0.56 | 1.01 | 1.06E-05 |
Hydroxyjasmonic acid | C12H18O4 | 226.1205 | 7.50 | 1 | [M-H]− | 2 | 0.83 | 0.61 | 1.04 | 3.25E-06 |
Norlinolenic acid | C17H28O2 | 264.2089 | 9.08 | 2 | [M+HCOO-H]− | 4 | 0.89 | 0.41 | 1.72 | 7.02E-12 |
Cinnamic acid derivatives | ||||||||||
O-Caffeoylquinic acid | C25H24O12 | 516.1268 | 6.79 | 5 | [M-H]− | 2 | 0.26 | 0.77 | 2.16 | 5.80E-03 |
p-Coumaroylquinic acid | C16H18O8 | 338.1002 | 4.97 | 2 | [M-H]− | 4 | 1.22 | 4.38 | 1.15 | 2.61E-06 |
O-Feruloyl-beta-D-glucose | C16H20O9 | 356.1107 | 4.24 | 1 | [M-H-H2O]− | 4 | 1.39 | 2.39 | 1.14 | 2.12E-03 |
Dihydrocaffeic acid 3-O-glucuronide | C15H18O10 | 358.0900 | 5.12 | 7 | [M+HCOO-H]− | 2 | 0.60 | 0.73 | 1.37 | 1.12E-02 |
O-Feruloylgalactarate | C16H18O11 | 386.0849 | 5.83 | 7 | [M+HCOO-H]− | 2 | 0.45 | 0.62 | 2.09 | 1.80E-06 |
Caffeic acid 3-glucoside | C15H18O9 | 342.0951 | 7.31 | 8 | [M+HCOO-H]− | 4 | 1.05 | 0.66 | 1.49 | 3.44E-03 |
Dihydroferulic acid 4-O-glucuronide | C16H20O10 | 372.1056 | 5.30 | 1 | [M-H]− | 4 | 0.83 | 2.96 | 1.51 | 3.60E-07 |
1-Caffeoyl-4-deoxyquinic acid | C16H18O8 | 338.1002 | 5.28 | 1 | [M-H]− | 4 | 9.71 | 2.79 | 1.04 | 1.32E-02 |
Quinic acid | C7H12O6 | 192.0634 | 4.73 | 2 | [M-H]− | 2 | 0.91 | 5.05 | 1.42 | 3.14E-03 |
1-O-Sinapoylglucose | C17H22O10 | 386.1213 | 5.48 | 1 | [M-H]− | 4 | 0.88 | 6.16 | 1.24 | 8.80E-09 |
Unknowns | ||||||||||
Unknown 1 (396.036@4.25) | — | — | 4.25 | — | — | 5 | 1.89 | 0.32 | 2.27 | 1.54E-07 |
Unknown 2 (586.0623@8.9) | — | — | 8.90 | — | — | 5 | 1.77 | 0.67 | 1.49 | 4.69E-04 |
Unknown 3 (572.0832@8.44) | — | — | 8.44 | — | — | 5 | 0.45 | 0.79 | 1.02 | 1.65E-02 |
Unknown 4 (255.989@8.9) | — | — | 8.90 | — | — | 5 | 1.36 | 0.66 | 1.11 | 8.14E-05 |
Unknown 5 | C27H36O12 | — | 6.14 | — | — | 4 | 0.88 | 2.10 | 1.36 | 1.02E-02 |
Unknown 6 | C27H36O12 | — | 5.90 | — | — | 4 | 0.39 | 0.61 | 1.80 | 2.56E-05 |
Peptides | ||||||||||
Tripeptide 1 | C19H25N3O7 | 407.1692 | 4.65 | 6 | [M-H]− | 3 | 1.16 | 9.13 | 1.62 | 2.22E-09 |
Tripeptide 2 | C19H25N3O7 | 407.1692 | 4.55 | 7 | [M-H]− | 3 | 1.46 | 10.31 | 1.61 | 1.56E-10 |
Tripeptide 3 | C15H20N4O6 | 352.1383 | 4.81 | 5 | [M-H]− | 4 | 1.09 | 4.36 | 1.89 | 1.84E-12 |
Glycosylated lignans | ||||||||||
Prupaside | C27H36O12 | 552.2207 | 5.90 | 1 | [M+HCOO-H]− | 3 | 0.40 | 0.61 | 1.88 | 2.37E-05 |
Citrusin B | C27H36O13 | 568.2156 | 6.27 | 2 | [M+HCOO-H]− | 4 | 1.00 | 0.58 | 1.02 | 6.10E-05 |
Alkaloids | ||||||||||
2′-Norberbamunine | C35H38N2O6 | 582.2730 | 8.51 | 5 | [M+HCOO-H]− | 4 | 1.30 | 0.39 | 1.07 | 4.43E-12 |
Vomilenine | C21H22N2O3 | 350.1630 | 4.88 | 8 | [M+Cl]− | 4 | 0.50 | 1.36 | 1.44 | 1.04E-02 |
Carboxylic acids | ||||||||||
3,4,5-trihydroxy-6-(2-hydroxy-6-methoxyphenoxy)oxane-2-carboxylic acid | C13H16O9 | 316.0794 | 2.06 | 2 | [M-H]− | 4 | 0.88 | 2.14 | 1.54 | 5.09E-04 |
Phenols | ||||||||||
Phenol glucuronide | C12H14O7 | 270.0740 | 2.06 | 0 | [M+HCOO-H]− | 4 | 0.90 | 2.14 | 1.54 | 5.10E-04 |
Carbohydrates | ||||||||||
Ribulose | C5H10O5 | 150.0528 | 0.60 | 0 | [M-H]− | 4 | 0.76 | 0.75 | 1.14 | 1.21E-03 |
Steroids | ||||||||||
Physalin L | C28H32O10 | 528.1995 | 1.54 | 3 | [M-H]− | 2 | 1.11 | 0.40 | 1.08 | 1.07E-07 |
Glycosylated stilbenes | ||||||||||
Piceatannol 4′-galloylglucoside | C27H26O13 | 558.1373 | 7.69 | 2 | [M-H]− | 3 | 2.60 | 0.36 | 1.23 | 2.24E-05 |
Prenolipids | ||||||||||
Auxin b | C18H30O4 | 310.2144 | 9.08 | 1 | [M-H]− | 4 | 1.13 | 0.41 | 1.81 | 7.07E-12 |
CV, coefficient of variation in the metabolites in the QC samples.
FC, fold change in the comparison (average in low altitude/average in high altitude).
VIP, variable importance in projection.
p-value corresponding to the p values calculated by the Benjamini–Hochberg false discovery rate post hoc correction (FDR <0.05); *Metabolites annotated with GNPS. RT: retention time; Confidence levels in annotation were as following: Level 1: Confirmed structure, Level 2: Probable structure, Level 3: Tentative candidate(s), Level 4: Unequivocal molecular formula, Level 5: Exact mass (Schymanski et al., 2014).