Table 2.
Putatively identified bioactive compounds in optimized Sargassum horneri extract by ESI-MS/MS.
| Group | No | Compound Name | EF | OM m/z’ | CM m/z’ | MS/MS (Negative Mode) | Reference |
|---|---|---|---|---|---|---|---|
| Phenolic compounds | 1. | Ferulic acid | C10H10O4 | 193.0499 | 193.0500 | 177, 149, 133 | [15,16,17,19] |
| 2. | Sinapic acid | C9H8O3 | 163.0393 | 163.0395 | 119 | ||
| 3. | Protocatechuic acid | C7H6O4 | 153.0186 | 153.0186 | 135, 109 | ||
| 4. | Caffeic acid | C9H8O4 | 179.0344 | 179.0344 | 161, 135, 117 | ||
| 5. | Syringic acid | C9H10O5 | 197.0449 | 197.0450 | 181, 153, 125 | ||
| 6. | Salicylic acid | C7H6O3 | 137.0236 | 137.0244 | 93 | ||
| 7. | Cinnamoyl glucose | C15H18O7 | 309.0974 | 309.0962 | 147, 131, 103 | ||
| 8. | p-Hydroxybenzaldehyde | C7H6O2 | 121.0287 | 121.0289 | 92, 77 | ||
| 9. | Hydroxytyrosol 4-O-glucoside # | C14H20O8 | 315.1083 | 315.1079 | 153, 123 | ||
| 10. | 5-(3′,4′-Dihydroxyphenyl)-valeric acid | C11H14O4 | 209.0816 | 209.0813 | 165, 149 | ||
| 11. | 5-(3′,5′-Dihydroxyphenyl)-γ-valerolactone 3-O-glucuronide # | C17H20O10 | 383.0972 | 383.0978 | 205, 191 | ||
| 12. | Quinic acid | C7H12O6 | 191.0560 | 191.0555 | 147, 129 | ||
| 13. | Syringin | C17H24O9 | 371.1356 | 371.1345 | 353, 209, 191 | ||
| 14. | Coumaroylquinic acid # | C16H18O8 | 337.0910 | 337.0965 | 293, 191, 163 | ||
| 15. | 3-Sinapoylquinic acid # | C18H22O10 | 397.1140 | 397.1171 | 381, 191, 129 | [20] | |
| 16. | Hydroxyferulic acid # | C10H10O5 | 209.0456 | 209.0477 | 191, 177 | ||
| 17. | Caffeoyl tartaric acid # | C13H12O9 | 311.0408 | 311.0446 | 293, 267, 179 | ||
| 18. | Vanillic acid 4-sulfate | C8H8O7S | 246.9918 | 246.9904 | 203, 167.03 | [21,22] | |
| 19. | Vanillic acid | C8H8O4 | 167.0343 | 167.0344 | 151, 123.04 | ||
| 20. | 3,4-Dihydroxyphenylglycol | C8H10O4 | 169.0500 | 169.0493 | 151, 123 | ||
| 21. | 2-Hydroxy-2-phenylacetic acid # | C8H8O3 | 151.0401 | 151.0498 | 107 | ||
| 22. | Isopropyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate # | C12H16O5 | 239.0929 | 239.0925 | 173, 123 | ||
| Flavonoids and derivatives | 23. | Epigallocatechin | C15H14O7 | 305.0652 | 305.0636 | 287, 137, 125 | [15,16,23,24,25] |
| 24. | Epicatechin | C15H14O6 | 289.0706 | 289.0715 | 245, 109, 125 | ||
| 25. | Dalbergin | C16H12O4 | 267.0710 | 267.0666 | 251, 223, 197 | ||
| 26. | Catechin | C15H14O6 | 289.0718 | 289.0682 | 245, 205, 139 | ||
| 27. | Dihydrobiochanin A # | C16H14O5 | 285.0817 | 285.0763 | 270 | ||
| 28. | Glycitein 7-O-glucuronide # | C22H20O11 | 459.0927 | 459.0923 | 283, 267 | ||
| Lignans | 29. | Arctigenin | C21H24O6 | 371.1468 | 371.1452 | 355, 327, 311 | [15,16,19] |
| 30. | Isohydroxymatairesinol | C20H21O7 | 373.1264 | 373.1266 | 355, 343, 327, 311 | ||
| 31. | Conidendrin | C20H20O6 | 355.1174 | 355.1200 | 340, 311 | ||
| 32. | Deoxyschisandrin # | C24H32O6 | 415.2127 | 415.2120 | 402, 347, 316, 301 | ||
| 33. | Secoisolariciresinol # | C20H26O6 | 361.1629 | 361.1772 | 343, 331, 315 | ||
| Terpenes | 34. | Carnosol | C20H26O4 | 329.1762 | 329.1749 | 285, 267 | |
| 35. | Carnosic acid | C20H28O4 | 331.1921 | 331.1902 | 287, 269 | ||
| 36. | Loliolide | C11H16O3 | 195.1021 | 195.1021 | 161, 179, 133, 105 | ||
| 37. | Isololiolide | C11H16O3 | 195.1021 | 195.1013 | 161, 179, 133, 105 | ||
| 38. | Sargahydroquinoic acid | C27H38O4 | 425.2680 | 425.2691 | 381 | [15,19,20,27,28] | |
| 39. | Sargaquinoic acid | C27H36O4 | 423.2526 | 423.2579 | 379 | ||
| 40. | Dihydroactinidiolide # | C11H16O2 | 179.1071 | 179.1072 | 135, 121 | ||
| 41. | Humulene epoxide II | C15H24O | 219.1751 | 219.1748 | 201 | ||
| 42. | (−)-Isoamijiol | C20H32O2 | 303.2331 | 303.2319 | 261, 243, 225 | ||
| 43. | 3,5-Dihydroxy-6,7-megastigmadien-9-one # | C13H20O3 | 223.1327 | 223.1334 | 205, 187, 163 | [30,31] | |
| 44. | Mojabanchromanol | C27H36O4 | 423.2558 | 423.2576 | 379 | ||
| 45. | Fallahydroquinone | C27H40O4 | 427.2854 | 427.2878 | 383 | ||
| 46. | Fallaquinone | C27H38O4 | 425.2691 | 425.2740 | 381 | ||
| 47. | 1-H-indol-6-carbaldehde | C9H7NO | 144.0455 | 144.0441 | - | ||
| Tannins | 48. | Trifuhalol-A | C18H14O10 | 389.0513 | 389.0496 | 123, 125, 139, 245, 263, 265, 353 | [15,31] |
| 49. | Phloroglucinol | C6H6O3 | 125.0237 | 125.0238 | 97 | ||
| 50. | Fucophlorethol | C36H26O14 | 680.1154 | 680.1179 | 610,601, 495, 469, 229 | ||
| 51. | Eckol | C18H12O9 | 371.0403 | 371.0403 | 335, 317, 246, 229, 140 | ||
| 52. | 1-O-(11-hexadecenoly)-3-O-(6′-sulpho-α-d-quinovopyranosyl) glycerol | C25H45O11S | 553.2643 | 535.2678 | 317, 299, 253, 225, 207 | [32] | |
| 53. | 1-O-Hexadecanoyl-3-O-(60-sulfo-α-d-quinovopyranosyl) glycerol | C25H47O11S | 555.2824 | 555.2834 | 317, 299, 255, 224, 207 | ||
| 54. | Dioxinodehydroeckol # | C18H10O9 | 369.0249 | 369.0284 | 238,195, 167, 112 | ||
| 55. | Dibenzodioxin-1,3,6,8-tetraol # | C12H7O6 | 246.9919 | 246.9909 | 203, 121 | [15,33] | |
| Sulfolipids and phospholipids | 56. | Sulfolipid # | C25H47O11S | 555.2848 | 555.2822 | 299, 255, 225, 206, 164 | |
| 57. | Sulfolipid (SQMG (14:0) # | C23H43O11S | 527.2535 | 527.2500 | 225 | ||
| 58. | Phospholipid # | C25H44NO7P | 500.2733 | 500. 2701 | 303, 259, 196 | ||
| Carboxylic acids | 59. | Fumaric acid | C4H4O4 | 115.005 | 115.0021 | 71 | [3,15,34,35,36,37,38] |
| 60. | Threonic acid | C4H8O5 | 135.0290 | 135.0299 | 117, 91, 72 | ||
| 61. | Gentisic acid | C7H6O4 | 153.0187 | 153.0178 | 152, 108, 81 | ||
| 62. | Kainic acid | C10H15NO4 | 212.0922 | 212.0916 | 168, 194, 150 | ||
| 63. | Mannuronic acid | C6H10O7 | 193.0353 | 193.0340 | 175, 103, 72 | ||
| 64. | Diethyl phthalate | C12H14O4 | 221.0818 | 221.0843 | 193, 177, 149, 121 | ||
| 65. | Phthalic acid | C8H6O4 | 165.0188 | 165.0178 | 121 26, 119, 58 | ||
| 66. | 3-Oxooctanoic acid | C8H14O3 | 157.0863 | 157.0855 | 139, 113, 97 | ||
| 67. | d-Glucaric acid derivative | C12H14O10 | 317.0544 | 317.0536 | 209 | ||
| 68. | Azelaic acid | C9H16O4 | 187.0969 | 188.0961 | 187, 124, 169, 111 | ||
| Fatty acids | 69. | Caprylic acid | C8H15O2 | 143.1070 | 143.1062 | 125, 99, 59 | |
| 70. | Vaccenic acid | C18H34O2 | 281.2486 | 281.2473 | 263, 223, 163, 71 | ||
| 71. | Palmitic acid | C16H32O2 | 255.2330 | 255.2316 | 237, 211, 197 | ||
| 72. | Myristic acid | C14H28O2 | 227.2015 | 227.2002 | 209, 183,179 | ||
| 73. | Octadecendioic acid | C18H32O4 | 311.223 | 311.2217 | 299, 269, 251, 223 | ||
| 74. | α-Linoleic acid | C18H32O2 | 279.2331 | 279.2315 | 261, 235, 233 | ||
| 75. | 13-keto-9Z,11E-Octadecadienoic acid | C18H30O3 | 293.2125 | 293.2109 | 275, 195, 113 | ||
| 76. | 10-Oxooctadecanoic acid | C18H34O3 | 297.2436 | 297.2420 | 279, 209, 141, 127 | ||
| 77. | 10,16-Dihydroxy-palmitic acid | C16H32O4 | 287.2227 | 287.2213 | 269, 257, 239, 185 | ||
| 78. | 2,4-Decadienal | C10H16O | 151.1119 | 151.1113 | 133, 123, 119, 93 | ||
| 79. | Lauric acid | C12H24O2 | 199.1697 | 199.1689 | 181, 155 | ||
| 80. | Vernolic acid | C18H32O3 | 295.2278 | 295.2263 | 277, 251, 195, 127 | ||
| Sugars | 81. | d-Galactose | C6H12O6 | 179.0568 | 179.0548 | 161, 143, 113, 101 | |
| 82. | Mannitol | C6H14O6 | 181.0712 | 181.0703 | 165, 147, 129, 111 | ||
| 83. | Gluconic acid | C6H12O7 | 195.0517 | 195.0498 | 177, 159, 129, 98 | ||
| Other compounds | 84. | 3,4-Dihydroxybenzaldehyde | C7H6O3 | 137.0237 | 137.0244 | 108 | |
| 85. | 4-Hydroxyphenyl acetate | C8H8O3 | 151.0394 | 151.0401 | 106 | ||
| 86. | PGF2α | C20H34O5 | 353.2335 | 353.2320 | 317, 273, 235, 127 | ||
| 87. | Dinor PGF2α | C18H29O5 | 325.1954 | 325.2007 | 307, 199, 183, 171, 129 | ||
| 88. | Threonyl-histidylglutamic acid | C15H23N5O7 | 384.1518 | 384.1514 | - | ||
| 89. | Dihydroxyphenylalanine | C9H10O7NS | 276.0185 | 276.0172 | 259, 231, 215, 196, 179, 150, 135 |
EF: elemental formula; OM: observed mass; CM: calculated mass; (-): Negative mode; # First-time identification.