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. 2023 Jan 29;12(3):579. doi: 10.3390/foods12030579

Table 2.

Metabolites annotated in various orange samples via nLC -ESI-MS/MS using both the positive and negative ionization modes.

No. Rt (min) Compound Name Chemical Class [M−H]−/
[M + H]+ 		Molecular Formula Mass Error MS/MS frag. Ref. AS AU CB FS FU JS JU
1. 5.7 Citric acid Organic acid 191.0189 C6H7O7− 4.3 111, 87 [19] - - ++ + + ++ ++
2. 11.1 Feruloylagmatine Cinnamic acid amide 307.177 C15H23N4O3+ 1.7 264, 177 ++ ++ + + - + +
3. 13.0 Hydroxy-phenyl-valeric acid-O-sulphate Sulphate ester 275.0607 C11H15O6S+ 8.4 195 + - + + ++ + +
4. 13.2 Dihydroxymegastigmadienone -O-hexoside
(Citroside A)		 Terpene 385.1860 C19H29O8− 0.8 223, 153 [22] ++ + + + ++ - -
5. 13.9 Sinapoyl hexoside Phenolic acid 385.1141 C17H21O10− −1.8 223, 190 [19] ++ + + + ++ - -
6. 13.9 Ferulic acid hexoside Phenolic acid 355.1030 C16H19O9− 0.0 193, 175, 160 [19] ++ ++ ++ ++ ++ + ++
7. 13.7 Citropten Coumarin 205.0504 C11H9O4− 1.1 175, 101 [19] + + + + ++ + +
8. 13.9 Sinapic acid pentoside Phenolic acid 355.1037 C16H19O10− −0.7 223, 205 [23] ++ + + ++ + + -
9. 13.9 Methoxycoumarin Coumarin 175.0392 C10H7O3− 0.2 - [24] + + + + + + +
10. 14.0 Sinapic acid Phenolic acid 223.0607 C11H11O5− 0.2 - [19] ++ ++ ++ + ++ + +
11. 14.2 Di-hexosyl-diosmetin Flavone 625.1757 C28H33O16+ −1 - [25] + + + ++ ++ - -
12. 14.3 Naringenin-O-hexoside Flavanone 433.1145 C21H21O10− 1.2 271 [26] ++ ++ - + - - -
13. 14.7 Limononic acid Limonoid degradation 183.1024 C10H15O3− 1.6 - ++ + + + ++ - +
14. 13.2 Methyl epijasmonate Fatty acid degradation 223.1337 C13H19O3− 1.3 - [27] ++ ++ + + ++ + +
15. 16.4 Apigenin-di-C-hexoside Flavone 595.1654 C27H31O15+ 1.5 385 [26] + + + ++ ++ + +
16. 16.5 Apigenin-di-O-hexoside Flavone 593.1502 C27H29O15− 8.6 431, 269 [26] + - + + ++ - -
17. 16.6 Coumaryl alcohol-O-hexoside Cinnamyl alcohol glycoside 311.1139 C15H19O7− 1.1 269, 161 + + + + ++ + +
18. 16.8 Apigenin-C-hexosyl-O-pentoside Flavone 563.1408
565.1550		 C26H27O14−
C26H29O14+ 		0.3
0.3		 311
 [28] - - + + ++ + +
19. 17.5 Naringenin-O-hexosyldeoxyhexoside Flavanone 579.1720
581.1867		 C27H31O14−
C27H33O14+ 		1.0
−0.5		 271
419, 273		 [29] ++ ++ ++ + + + +
20. 17.6 Chrysoeriol-C-hexoside Flavone 463.1238 C22H23O11+ −0.1 343 [26] + + + ++ ++ + +
21. 18.2 Hesperidin (Hesperetin-O-hexosyldeoxyhexoside) Flavanone 609.1833
611.1971		 C28H33O15−
C28H35O15+ 		−2.2
0.1		 301
-		 [29] ++ ++ ++ ++ ++ ++ +
22. 18.3 Limonin-hexoside Limonoid 649.2507 C32H41O14− 0.7 - [30] + + + + + + +
23. 18.7 Hesperetin-O-deoxyhexoside Flavanone 449.1625 C22H25O10+ −0.4 303 [19] ++ + - + + - -
24. 19.1 Azelaic acid Dicarboxylic acid 187.0969 C9H15O4− 2.1 169, 125 + + + + + + +
25. 19.3 Deacetylnomilin Limonoid 473.2167 C26H33O8+ −1.7 455, 411, 161 ++ + + + + + +
26. 19.4 Scopoletin-O-glucuronide Coumarin 367.0668 C16H15O10− −0.1 191 + + + + ++ + +
27. 20.2 Pyridoxamine phosphate Vitamin B6 phosphate 249.0614 C8H14N2O5P+ −8.4 169, 81 [31] + + ++ + + + +
28. 20.3 Unknown Alkaloid 368.1921 C15H30NO9+ −13 - + + - ++ ++ + -
29. 20.4 Decatrienoic acid Fatty acid 165.0913 C10H13O2− −5.0 - + + + + + + +
30. 21.0 Sakuranetin-O-hexosyl-O-deoxyhexoside Flavanone 595.2020 C28H35O14+ −1.2 433, 287 [28] ++ ++ - + + - -
31. 20.7 Hydroxyhexadecanedioic acid Fatty acid 303.2171 C16H31O5− 1.1 259, 214 [32] + - - + ++ - -
32. 20.9 Sakuranetin-O-hexosyl deoxyhexoside Flavanone 593.1835
595.2018		 C28H33O14−
C28H35O14+ 		1.7
−1.5		 285
 + + ++ ++ ++ ++ +
33. 21.1 Nomilin-hexoside Limonoid 693.2723 C34H45O15− 5.9 159 [19] ++ ++ + + + ++ +
34. 21.2 Sakuranetin Flavanone 285.0770
287.1042		 C16H13O5−
C16H15O5+ 		2.5
0.7		 255
237		 [29] ++ ++ + + + + +
35. 22.5 Perilloside A Terpene 313.1651 C16H25O6− −0.3 - [33] ++ + + ++ + + -
36. 23.0 Trihydroxy-octadecadienoic acid (trihydroxy-linoleic acid) Fatty acid 327.2175 C18H31O5− 0.9 - [28] + + + + ++ + +
37. 23.7 Hydroxy-sphingenine Ceramide 316.2827 C18H38NO3+ −6.1 - [34] + + ++ + + + -
38. 23.9 Linoleamide Fatty acid amide 280.2677 C18H34NO+ 1.4 - [35] + - - + - ++ -
39. 24.1 Trihydroxy-octadecenoic acid Fatty acid 329.2333 C18H33O5− 1.5 - + + + + ++ + +
40. 24.2 Demethylnobiletin Methoxy-flavone 389.1234 C20H21O8+ −0.8 - [36] - - - + ++ - -
41. 24.3 Methyl dihydrojasmonate Organic acid 225.1496 C13H21O3− −0.4 - + + + + + + +
42. 17.7 Naringenin Flavanone 271.0606 C15H11O5− 0.0 - [37] + + ++ ++ + ++ ++
43. 26.1 Nobiletin Methoxy-flavone 403.1385 C21H23O8+ −1.2 388, 373, 342 [38] + + + ++ ++ - -
44. 18.5 Hesperetin Flavanone 301.0717 C16H13O6− 0.9 - [29] ++ ++ + + + + +
45. 26.5 Unknown Methoxy-flavone 403.1568 C25H23O5+ 7.4 373 - - + + ++ + +
46. 27.2 Tangeretin Methoxy-flavone 373.1312 C20H21O7+ 6.7 343, 312 [39] + + + + +++ + +
47. 27.7 Methyl-dodecadienoate Fatty acid ester 209.1548 C13H21O2− 2.4 - + + + + + ++ +
48. 27.8 Unknown Alkaloid 272.1862 C14H26NO4+ −1.8 255, 237 ++ + + + + + +
49. 27.9 Dimethylkaempferol Methoxy-flavone 313.0718 C17H13O6− 1.9 163, 117 [40] - + + ++ ++ - -
50. 28.0 γ-Lactone hydroxy-dodecenedioic acid methyl ester Fatty acid ester 253.1443 C18H15O7− 0.0 209 + + + + + + +
51. 28.1 Limonin Limonoid 469.1869
471.2018		 C26H29O8−
C26H31O8+ 		1.5
0.2		 -
453, 161		 [30] ++ + + + + + +
52. 28.3 Methyllimonexic acid Limonoid 515.1925 C27H31O10− 1.6 469, 229 [41] ++ + - + + + +
53. 28.4 Dihydroxytrimethoxyflavone (xanthomicrol) Methoxy-flavone 343.0826 C18H15O7− 0.2 298, 270, 242 + - + ++ ++ - -
54. 29.0 Tetramethoxyflavone (Tetra-O-methylscutellarein) Methoxy-flavone 343.1201 C19H19O6+ 7.2 313, 282 + + + ++ ++ - -
55. 29.2 Gingerol Phenylpropen-oid polyketide 293.1763 C17H25O4− 3.8 193 [20] + ++ + + + ++ +
56. 29.5 Heptamethoxyflavone Methoxy-flavone 455.1313
433.1511		 C22H24O9Na+
C22H25O9+ 		−1.1
−4.1		 433
403		 [42] - - + +++ ++ - -
57. 29.9 Ionone epoxide Terpene 207.1392 C13H19O2− −3.4 - [43] + + + + + + +
58. 28.7 Hydroxy-tetradecatrienoyl glycerol Acylglycerol 311.1857 C17H27O5− −2.2 - + + + + ++ + +
59. 31.6 Dihydroxyoctadecadienoic acid Fatty acid 311.2225 C18H31O4− 1.2 211, 171, 129 + + + ++ ++ + +
60. 32.0 N-Phenylacetylglycine Nitrogenous compound 194.0821 C10H12NO3− 0.8 - + + ++ + + ++ +
61. 32.5 Hydroxy-oxohexadecanoic acid Fatty acid 285.2069 C16H29O4− 0.7 - [44] ++ ++ + + + + +
62. 32.5 Hydroxylinolenic acid Fatty acid 293.2115 C18H29O3− −2.4 275, 235 [45] + + - + ++ - -
63. 34.1 Hydroxyoctadecadienoic acid (Hydroxylinoleic acid) Fatty acid 295.2276 C18H31O3− 1.6 - + + + + ++ + +
64. 35.7 Heptyl caffeate Cinnamic acid ester 301.1421
279.1600		 C16H22O4Na+
C16H23O4+ 		1.7
−3.3		 279
 + + - ++ ++ + ++
65. 39.1 Erucamide (Docosenamide) Fatty acid amide 338.3428 C22H44NO+ −3.1 321 [35] - - + + - ++ -
66. 40.5 Linoleic acid Fatty acid 279.2326 C18H31O2− 1.3 - [45] + ++ + + + + +

AS: Albedo from Spain; AU: Albedo from Uruguay; CB: concentrate from Brazil; FS: Flavedo from Spain; FU: Flavedo from Uruguay; JS: Juice from Spain; JU: Juice from Uruguay. Signs (-, +, ++ and +++) indicate relative semi-quantification of each compound based on the integrated peak areas of the total ion; - = absent, + = present, ++ = present in higher amount, and +++ = present in highest amount.