Table 2.
Retention times, UV, and mass spectral data of xanthones in Hypericum perforatum dark-grown (HR1) and photoperiod-exposed (HR2) hairy root culture extractsa.
| Peak no. |
Compounds | t R (min) | UV (nm) | [M–H]–
(m/z) |
–MS2 [M–H]–
(m/z) |
HR1 (mg·100 g−1 DW ± S.D.) | HR2 (mg·100 g−1 DW ± S.D.) |
|---|---|---|---|---|---|---|---|
| X1 | Mangiferin | 37.3 | 238, 256, 312, 362 | 421 | 331, 301, 258 | 1383.25 ± 88.91 | 669.67 ± 24.12 |
| X2 | Xanthone derivative 1 | 45.8 | 208, 257, 322, 374 | 441 | 423, 397, 373, 305, 257, 229 | 109.47 ± 9.81 | n.d. |
| X3 | Xanthone derivative 2 | 46.2 | 242, 306 | 367 | 287 | 635.06 ± 18.52 | 600.59 ± 39.62 |
| X4 | 1,3,5,6-Tetrahydroxyxanthone dimer | 50.2 | 252, 284, 328 | 517 | 499, 468, 446, 391, 365 | 821.61 ± 28.39 | 692.94 ± 19.28 |
| X5 | 1,3,6,7-Tetrahydroxyxanthone dimer | 53.9 | 238, 254, 312, 364 | 517 | 517, 469, 447, 379, 257 | 522.56 ± 25.44 | 88.31 ± 2.88 |
| X6 | 1,3,5,6-Tetrahydroxyxanthone | 55.4 | 250, 282, 328 | 259 | 229, 213, 187 | 190.17 ± 20.73 | 949.35 ± 51.71 |
| X7 | 1,3,6,7-Tetrahydroxyxanthone | 55.8 | 236, 254, 314, 364 | 259 | 231, 215, 187, 147 | 167.14 ± 9.52 | 874.85 ± 31.24 |
| X8 | Tetrahydroxy-one-methoxyxanthone | 57.7 | 254, 286, 328 | 289 | 274, 175 | n.d. | 448.65 ± 9.44 |
| X9 | Xanthone derivative 3 | 59.2 | 244, 280, 316 | 353 | 273 | n.d. | 276.57 ± 9.29 |
| X10 | 1,3,5-Trihydroxy-6-methoxyxanthone | 63.3 | 250, 284, 326 | 273 | 258,225 | n.d. | 150.86 ± 12.62 |
| X11 | Mangiferin C-prenyl isomer | 73.5 | 238, 260, 312, 372 | 489 | 399, 369, 327 | 433.68 ± 82.56 | n.d. |
| X12 | 1,3,6,7-Tetrahydroxyxanthone 8-prenylxanthone | 73.9 | 248, 312, 366 | 327 | 325, 297, 258, 201 | 547.65 ± 15.21 | 737.48 ± 65.39 |
| X13 | 1,3,5,6-Tetrahydroxyxanthone 8-prenylxanthone | 74.9 | 242, 260, 320, 368 | 327 | 325, 297, 258, 201 | 368.17 ± 21.70 | n.d. |
| X14 | 1,3,7-Trihydroxy-2-(2-hydroxy-3-methyl-3-butenyl)xanthone | 75.3 | 238, 260, 314, 388 | 327 | 309, 257 | 588.66 ± 49.31 | 854.53 ± 31.88 |
| X15 | Toxyloxanthone | 76.2 | 242, 262, 330, 384 | 325 | 307, 283, 272 | 577.03 ± 5.09 | 1542.09 ± 129.21 |
| X16 | 1,3,7-Trihydroxy-6-methoxy-8-prenylxanthone | 76.5 | 240, 260, 318, 370 | 341 | 326, 311, 297, 285 | 650.13 ± 34.77 | n.d. |
| X17 | 1,3,6,7-Tetrahydroxyxanthone 2-prenylxanthone | 76.7 | 248, 312, 368 | 327 | 325, 283, 271 | 1402.03 ± 85.98 | 656.33 ± 37.25 |
| X18 | γ-Mangostin isomer | 77.1 | 254, 286, 324 | 395 | 326, 283, 271 | 1226.31 ± 185.52 | 1480.32 ± 130.06 |
| X19 | 1,3,6-Trihydroxy-7-methoxy-8-prenylxanthone | 77.2 | 240, 256, 312, 370 | 341 | 293, 256 | 3240.28 ± 140.14 | n.d. |
| X20 | 1,3,5,6-Tetrahydroxyxanthone 2-prenylxanthone | 77.4 | 238, 260, 318, 372 | 327 | 297, 258 | n.d. | 699.36 ± 49.61 |
| X21 | Paxanthone | 78.0 | 244, 264, 324, 386 | 339 | 324, 307 | n.d. | 4040.70 ± 209.82 |
| X22 | γ-Mangostin isomer | 78.9 | 260, 316, 370 | 395 | 351, 339, 326, 283 | 3629.15 ± 338.08 | n.d. |
| X23 | Trihydroxy-1-methoxy-C-prenylxanthone | 79.4 | 260, 286, 314 | 341 | 326 | 11314.34 ± 469.01 | 10067.14 ± 561.72 |
| X24 | Xanthone derivative 4 | 79.9 | 260, 308, 374 | 295 | 277, 251, 195, 171 | n.d. | 2778.02 ± 81.11 |
| X25 | γ-Mangostin | 80.0 | 246, 262, 320 | 395 | 351, 339, 326, 283 | 7861.71 ± 415.11 | n.d. |
| X26 | Banaxanthone D | 80.2 | 244, 268, 332 | 461 | 393, 341, 297 | 1784.69 ± 88.90 | n.d. |
| X27 | Xanthone derivative 5 | 80.5 | 254, 310 | 355 | 340, 325, 297, 285, 271 | 2266.19 ± 191.89 | 1765.42 ± 36.19 |
| X28 | Garcinone E | 81.2 | 256, 286, 332 | 463 | 394, 351, 339, 297, 285 | 8229.95 ± 537.14 | 10844.13 ± 288.29 |
| X29 | Xanthone derivative 6 | 82.2 | 262, 288, 322 | 393 | / | 421.44 ± 36.66 | 370.43 ± 45.16 |
| X30 | Banaxanthone E | 82.6 | 252, 302, 330 | 477 | 419, 393, 339, 297 | n.d. | 499.91 ± 38.44 |
| X31 | Xanthone derivative 7 | 83.6 | 270, 330, 400 | 467 | 398, 383, 327, 271, 234 | n.d. | 429.57 ± 7.82 |
| X32 | Garcinone C | 83.9 | 286, 340 | 413 | 369, 344, 301, 233 | 1185.94 ± 149.05 | 943.63 ± 55.98 |
| X33 | Xanthone derivative 8 | 84.4 | 254, 284, 326 | 481 | 412, 397, 327, 271, 234 | 562 ± 38.99 | 126.80 ± 1.69 |
an.d.: not detected; DW: dry weight; sh: shoulder; t R: retention time. MS2 ions in bold indicate the base peak. For information on peak numbers, see Figure 1.