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. 2022 Mar 25;12(4):288. doi: 10.3390/metabo12040288

Table 2.

List of annotated OPLS-DA candidates; compounds written in italics were isolated from L. hypoglauca, and their structures were elucidated fully or partially by NMR spectroscopy (Section 2.4); priority: deduced from S-plots of respective OPLS-DA models; low number represents high priority; numbers written in gray represent candidates with low levels of reliability (jackknife-based confidence interval, including 0); annotation: phospholipid and sphingolipid nomenclature, see Reference [18], fragmentation patterns and identification sources and Supplementary Table S4. ID level ([19,20]): 0, isolated pure compound, unambiguous 3D structure; 1, confident 2D structure, identified by reference standard match (retention time and MS/MS); 2, tentative annotation by comparison of structural formula and MS/MS fragmentation pattern with data from databases or literature. 3, no data available in literature or databases; compound tentatively assigned on the basis of the MS/MS fragmentation pattern (theoretical interpretation and/or comparison to related compounds).

Nr Monoisotopic Mass (Calculated) RT (min) m/z (Experimental) Molecular Formula ∆ (ppm) IL-8 Priority NFκB Priority NO Priority Annotation ID level Compound Class
1 180.042 10.71 179.033 C9H8O4 −3.5 8 caffeic acid 2 hydroxycinnamic acid derivative
2 338.100 12.63 337.092 C16H18O8 1.7 12 coumaroylquinic acid 2 hydroxycinnamic acid derivative
3 338.100 13.42 337.093 C16H18O8 2.2 20 coumaroylquinic acid 2 hydroxycinnamic acid derivative
4 404.132 15.62 403.124 C17H24O11 1.5 9 Secoxyloganin 1 iridoid glycoside
5 610.153 18.27 609.145 C27H30O16 0.7 30 luteolin-dihexoside 2 flavonoid-O-glycoside
6 580.143 19.99 579.134 C26H28O15 1.7 10 13 luteolin-hexoside-pentoside 2 flavonoid-O-glycoside
7 448.101 20.91 447.092 C21H20O11 −0.9 27 luteolin-7-O-glucoside 1 flavonoid-O-glycoside
8 594.159 21.59 593.150 C27H30O15 0.0 15 2 kaempferol-3-hexoside-7-deoxyhexoside 2 flavonoid-O-glycoside
9 478.111 21.99 477.104 C22H22O12 1.7 26 isorhamnetin-7-O-hexoside 2 flavonoid-O-glycoside
10 594.159 22.00 593.150 C27H30O15 −0.3 25 lonicerin (luteolin hexoside deoxyhexoside) isomer 2 flavonoid-O-glycoside
11 516.127 22.19 515.189 C25H24O12 0.1 24 dicaffeoylquinic acid 2 hydroxycinnamic acid derivative
12 516.127 24.18 515.118 C25H24O12 −1.5 11 dicaffeoylquinic acid 2 hydroxycinnamic acid derivative
13 448.101 25.16 447.092 C21H20O11 0.6 2 kaempferol-3-hexoside (astragalin isomer) 2 flavonoid-O-glycoside
14 478.111 25.50 477.104 C22H22O12 1.6 30 isorhamnetin-3-O-hexoside 2 flavonoid-O-glycoside
15 484.137 26.69 483.129 C25H24O10 1.8 22 3,5-di-O-p-coumaroylquinic acid 2 hydroxycinnamic acid derivative
16 610.132 28.94 609.124 C30H26O14 0.8 29 luteolin-O-caffeoyl-O-hexoside 3 flavonoid-O-glycoside derivative
17 484.137 29.84 483.129 C25H24O10 0.8 16 4,5-di-O-p-coumaroylquinic acid 2 hydroxycinnamic acid derivative
18 286.048 30.06 285.040 C15H10O6 2.3 28 3 luteolin 1 flavonoid aglycone
19 316.058 30.89 315.050 C16H12O7 2.1 39 21 isorhamnetin 2 flavonoid aglycone
20 594.137 31.73 593.129 C30H26O13 0.7 27 luteolin-O-coumaroyl-O-hexoside 3 flavonoid-O-glycoside derivative
21 270.053 32.50 269.045 C15H10O5 2.7 25 apigenin 1 flavonoid aglycone
22 358.105 32.64 357.098 C19H18O7 3.0 8 7 7-hydroxy-5,3′,4′,5′-tetramethoxyflavone0 flavonoid aglycone
23 300.063 32.79 299.056 C16H12O6 1.6 26 diosmetin/chrysoeriol 2 flavonoid aglycone
24 328.225 33.76 327.217 C18H32O5 −0.7 23 trihydroxyoctadecadienoic acid isomer I 2 fatty acid
25 328.225 33.98 327.217 C18H32O5 −0.8 19 1 trihydroxyoctadecadienoic acid isomer II 2 fatty acid
26 538.090 35.07 537.083 C30H18O10 1.6 17 1 cupressuflavone 0 biflavonoid
27 568.101 35.29 567.093 C31H20O11 1.1 6 14 6 3′-methoxycupressuflavone0 biflavonoid
28 330.241 35.42 329.233 C18H34O5 −0.9 32 trihydroxyoctadecenoic acid 2 fatty acid
29 598.111 35.51 597.104 C32H22O12 1.5 36 20 10 3′,3′′-dimethoxy-cupressuflavone0 biflavonoid
30 928.503 36.92 973.502 [M+HCOO]- C47H76O18 1.4 2 Akebia saponin D 2 triterpene glycoside
31 444.205 36.99 443.197 C27H28O4N2 −0.5 9 aurantiamide acetate 2 alkaloid
32 538.090 37.24 537.082 C30H18O10 −0.9 4 31 amentoflavone 1 biflavonoid
33 552.106 40.28 551.098 C31H20O10 −0.5 18 25 podocarpusflavone A 1 biflavonoid
34 538.0900 40.96 537.081 C30H18O10 −2.5 12 hinokiflavone 2/ochnaflavone 2 biflavonoid
35 538.09 41.43 537.082 C30H18O10 −0.4 29 hinokiflavone 2/ochnaflavone 2 biflavonoid
36 294.430 41.93 293.212 C18H30O3 2.8 5 oxo-octadecadienoic acid 2 fatty acid
37 766.450 41.95 765.440 C41H66O13 −2.8 34 Akebia saponin C 2 triterpene glycoside
38 604.398 42.77 603.389 C35H56O8 −2.0 16 Akebia saponin PA 2 triterpene glycoside
39 676.367 43.50 721.363 [M+HCOO]− C33H56O14 −0.7 26 gingerglycolipid A isomer 2 glycolipid
40 517.317 44.07 562.314 [M+HCOO]− C26H48NO7P −1.6 23 LPC 18:3 2 phospholipid
41 602.476 47.19 601.468 C34H66O8 0.3 5 14 4 trihydroxy-monoacetoxy-dotriacontanoic acid I 3 fatty acid
42 602.476 47.55 601.468 C34H66O8 0.4 15 13 trihydroxy-monoacetoxy-dotriacontanoic acid II 3 fatty acid
43 644.486 47.96 643.469 C36H68O9 0.6 6 22 5 trihydroxy-diacetoxy-dotriacontanoic acid I 2 fatty acid
44 644.486 48.24 643.479 C36H68O9 0.4 17 31 9 trihydroxy-diacetoxy-dotriacontanoic acid II 2 fatty acid
45 482.265 48.42 481.256 C22H43O9P −0.4 35 LPG 16:1 2 phospholipid
46 644.486 48.45 643.479 C36H68O9 0.1 11 6 3 trihydroxy-diacetoxy-dotriacontanoic acid III 2 fatty acid
47 630.507 48.60 629.499 C36H70O8 1.2 32 14 tetrahydroxy-monoacetoxy-tetratriacontanoic acid I 3 fatty acid
48 556.291 48.91 555.283 C25H48O11S −0.7 21 palmitoyl-sulfoquinovosyl-glycerol 2 glycolipid
49 630.507 48.96 629.499 C36H70O8 1.1 13 11 tetrahydroxy-monoacetoxy-tetratriacontanoic acid II 3 fatty acid
50 686.497 49.16 685.489 C38H70O10 1.3 40 18 dihydroxy-triacetoxy-dotriacontanoic acid 3 fatty acid
51 672.518 49.24 671.510 C36H72O9 0.6 17 trihydroxy-diacetoxy- tetratriacontanoic acid I 3 fatty acid
52 592.269 49.32 591.260 C35H36N4O5 −0.0 7 pheophorbide A 1 chlorophyll breakdown product
53 672.518 49.52 671.510 C38H72O9 1.5 31 15 trihydroxy-diacetoxy-tetratriacontanoic acid II 3 fatty acid
54 672.518 49.75 671.510 C38H72O9 1.3 10 6 trihydroxy-diacetoxy-tetratriacontanoic acid III 2 fatty acid
55 484.280 49.77 483.272 C22H45O9P 0.5 7 LPG 16:0 2 phospholipid
56 714.528 50.34 713.521 C40H74O10 1.4 24 dihydroxy-triacetoxy-tetratriacontanoic acid 3 fatty acid
57 713.544 51.99 712.535 C40H75O9N −2.0 21 soyacerebroside isomer (HexCer 18:2;O2/16:0;O) 2 glucocerebroside
58 384.360 52.47 383.354 C24H48O3 1.4 19 hydroxytetracosanoic acid 2 fatty acid
59 669.591 54.33 668.582 C40H79O6N −0.8 39 Cer 18:1;O3/22:0;O2 2 ceramide
60 653.596 55.44 652.587 C40H79O5N −1.1 14 Cer 18:1;O3/22:0;O 2 ceramide
61 697.622 55.60 696.613 C42H83O6N −1.1 4 16 Cer 18:1;O3/24:0;O2 2 ceramide
62 667.612 56.15 780.595 [M+CF3COO]− C41H81O5N −1.1 30 Cer 18:1;O3/23:0;O 2 ceramide
63 681.627 56.95 680.618 C42H83O5N −1.1 1 Cer 18:1;O3/24:0;O 2 ceramide
64 683.643 57.83 796.627 [M+CF3COO]− C42H85O5N −0.4 20 Cer 18:0;O3/24:0;O 2 ceramide
65 709.659 58.85 822.642 [M+CF3COO]− C44H87O5N −1.5 37 Cer 18:1;O3/26:0;O 2 ceramide