Table 2.
Identification of intestinal metabolites of Ougan PMF-rich fraction by HPLC–ESI–MS/MS.
| Peak No. | Retention Time (min) | [M + H]+ or [M − H]− (m/z) | Formula | Fragment Ions (m/z) | Tentative Compounds |
|---|---|---|---|---|---|
| 1 | 13.1284 | 609.1825 (-) | C28H34O15 | 489, 343, 325, 301, 286, 257, 242, 164 | Neohesperidin |
| 2 | 16.3972 | 563.1460 (-) | C26H28O14 | 387, 372, 357, 342, 314, 299, 175, 113 | Nobelitin-O-glucuronide (1) |
| 3 | 18.8731 | 535.1449 | C25H26O13 | 359, 344, 329, 314, 311, 301, 298, 286, 283, 257 | Tangeretin-O-glucuronide (1) |
| 4 | 19.5825 | 565.1555 | C26H28O14 | 389, 374, 359, 345, 344, 343, 341, 331, 328, 327, 316, 315, 313 | Nobelitin-O-glucuronide (2) |
| 5 | 19.8712 | 565.1551 | C26H28O14 | 389, 374, 359, 345, 344, 343, 341, 339, 331, 329, 328, 327, 316, 315, 313, 310, 301, 298 | Nobelitin-O-glucuronide (3) |
| 6 | 20.1621 | 375.1078 | C19H18O8 | 360, 345, 330, 327, 317, 302, 299, 197, 169, 149 | Dihydroxy-tetramethoxyflavone (1) |
| 7 | 21.0102 | 287.0917 | C16H14O5 | 161, 153, 135, 133, 125, 121, 118, 111, 103, 97, 69, 67 | Dihydroxy-monomethoxyflavone |
| 8 | 21.5526 | 345.0974 | C18H16O7 | 330, 315, 297, 287, 272, 197, 169 | Dihydroxy-trimethoxyflavone |
| 9 | 22.4321 | 375.1081 | C19H18O8 | 360, 345, 330, 327, 317, 302, 197, 169 | Dihydroxy-tetramethoxyflavone (2) |
| 10 | 22.6898 | 327.0874 (-) | C18H16O6 | 327, 312, 297, 282, 269, 254, 226, 182, 177, 117 | Monohydroxy-trimethoxyflavone |
| 11 | 23.5766 | 535.1449 | C25H26O13 | 359, 344, 329, 311 | Tangeretin-O-glucuronide(2) |
| 12 | 24.0618 | 375.1081 | C19H18O8 | 360, 345, 331, 330, 327, 317, 314, 302, 301, 299, 287, 285, 274, 273, 271, 211, 183, 168, 165, 147, 139, 137, 135, 134, 127 | Dihydroxy-tetramethoxyflavone (3) |
| 13 | 24.2942 | 375.1084 | C19H18O8 | 360, 345, 331, 330, 327, 325, 317, 314, 313, 302, 299, 287, 285, 274, 273, 271, 230, 211, 183, 168, 137, 135, 127 | Dihydroxy-tetramethoxyflavone (4) |
| 14 | 24.6514 | 565.1555 | C26H28O14 | 389, 374, 359, 356, 341 | Nobelitin-O-glucuronide (4) |
| 15 | 25.8876 | 389.1237 | C20H20O8 | 374, 359, 356, 341, 331, 316, 285, 244, 197, 169, 163, 148, 113 | Monohydroxy-pentamethoxyflavone (1) |
| 16 | 26.0809 | 271.0607 | C15H10O5 | 253, 243, 215, 197, 169, 153, 149, 115, 91 | Trihydroxy-flavone |
| 17 | 26.6764 | 359.1135 | C19H18O7 | 344, 343, 341, 329, 327, 325, 315, 301, 300, 298, 297, 283, 272, 255, 227, 181, 153 | Monohydroxy-tetramethoxyflavone (1) |
| 18 | 27.7937 | 389.1238 | C20H20O8 | 374, 359, 344, 343, 341, 331, 316, 197, 169, 165, 163 | Monohydroxy-pentamethoxyflavone (2) |
| 19 | 28.4142 | 359.1128 | C19H18O7 | 344, 329, 315, 314, 311, 309, 301, 298, 297, 286, 285, 283, 271, 268, 258, 257, 255, 240, 230, 228, 215, 214, 212, 211, 200, 193, 187, 183, 168, 165, 139, 131, 127, 121 | Monohydroxy-tetramethoxyflavone (2) |
| 20 | 29.1096 | 389.1234 | C20H20O8 | 374, 359, 345, 344, 343, 341, 339, 331, 328, 326, 316, 315, 313, 310, 301, 299, 288, 287, 285, 270, 260, 245, 230, 217, 211, 193, 183, 168, 151, 127 | Monohydroxy-pentamethoxyflavone (3) |
| 21 | 29.5447 | 359.0772 | C17H14O6 | 344, 329, 314, 311, 301, 286, 283, 258, 242, 230, 214, 202, 193, 177, 174, 133 | Dihydroxy-dimethoxyflavone |
| 22 | 30.7912 | 359.1135 | C19H18O7 | 344, 329, 314, 311, 301, 286, 283, 197, 169, 133 | Monohydroxy-tetramethoxyflavone (3) |
| 23 | 31.4917 | 343.1182 | C19H18O6 | 328, 313, 285, 181, 153, 133 | Tetramethoxyflavone |
| 24 | 33.2004 | 403.1395 | C21H22O8 | 388, 387, 373, 359, 358, 357, 355, 353, 345, 343, 341, 339, 330, 327, 325, 315, 313, 311, 301, 299, 259, 257, 244, 231, 211, 193, 183, 175, 168, 163, 162 | Nobiletin |
| 25 | 35.6699 | 373.1291 | C20H20O7 | 358, 343, 325, 315, 300, 297, 283, 271, 269, 229, 211, 193, 183, 168, 135 | Tangeretin |
| 26 | 37.6439 | 389.1241 | C20H20O8 | 374, 359, 356, 341, 343, 328, 316, 313, 197, 169, 163 | 5-demethylnobiletin |