Table 4.
Retention times, UV-Vis characteristics and accurate mass measurements of the compounds observed and identified from the RYR dietary supplements analyzed with UHPLC.
| Compound Name | Retention Time (min) |
UV-Vis λmax (nm) |
Formula (Monoisotopic Mass) | Calculated Mass (m/z) |
Measured Mass (m/z) | Mass Error (mDa) | Relative Mass Error (ppm) | Major ions of [M + H]+ MS/MS Fragmentation Unless Otherwise Indicated (m/z) |
|
|---|---|---|---|---|---|---|---|---|---|
| Monacolin J hydroxyl acid (MJA) | 0.90 | 230, 239, 244 | C19H30O5 (338.2172) |
[M − H]− | 337.2015 | 337.2010 | −0.5 | −1.5 | Not recorded |
| Citrinin | 1.45 | 243, 326 1 | C13H14O5 (250.0841) |
[M + H]+ | 251.0919 | 251.0922 | +0.3 | +1.2 | Not recorded |
| Monacolin J (MJ) | 1.98 | 230, 239, 246 | C19H28O4 (320.1988) |
[M + H]+ [M + Na]+ [M − H]− |
321.2066 343.1885 319.1909 |
321.2067 343.1881 319.1910 |
+0.1 −0.4 +0.1 |
+0.3 −1.2 +0.3 |
303.1945, 285.1847, 267.1711, 205.1604, 199.1451, 159.1162 |
| Rubropunctamine | 2.70 | 252, 303, 415, 525 | C21H23NO4 (353.1627) |
[M + H]+ [M + Na]+ [M − H]− |
354.1705 376.1525 352.1549 |
354.1710 376.1521 352.1551 |
+0.5 −0.4 +0.2 |
+1.4 −1.1 +0.6 |
337.1308, 294.0762, 267.0523, 256.0866, 239.0580 |
| Monacolin N (MN) | 3.89 | 230, 239, 247 | C21H30O5 (362.2093) |
[M + H]+ [M + Na]+ |
363.2171 385.1991 |
363.2159 385.1988 |
−1.2 −0.3 |
−3.3 −0.8 |
345.2052, 285.1865, 267.1750, 243.1711, 199.1490, 173.1335, 159.1173, 143.0856 |
| Monacolin L hydroxyl acid (MLA) | 4.05 | 230, 239, 247 | C19H30O4 (322.2144) |
[M + H]+ [M + Na]+ [M − H]− |
323.2222 345.2042 321.2066 |
323.2220 345.2037 321.2072 |
−0.2 −0.5 +0.6 |
−0.6 −1.5 +1.9 |
305.2126, 287.1986, 269.1901, 225.1640, 203.1800, 159.1172 |
| Monacolin X (MX) | 4.38 | 230, 239, 246 | C24H34O6 (418.2355) |
[M + H]+ [M + Na]+ |
419.2434 441.2253 |
419.2434 441.2250 |
0 −0.3 |
0 −0.7 |
303.1961, 285.1855, 267.1749, 243.1751, 225.1643, 199.1489, 173.1331, 159.1173, 143.0712 |
| 7-(2-hydroxyethyl)-monascorubramine (PP-R) | 4.66 | 251, 302, 423, 530 | C25H31NO5 (425.2202) |
[M + H]+ [M + Na]+ |
426.2280 448.2100 |
426.2265 448.2092 |
−1.5 −0.8 |
−3.5 −1.8 |
Not recorded |
| Monascorubramine | 5.55 | 251, 307, 412, 530 | C23H27NO4 (381.1940) |
[M + H]+ [M + Na]+ [M − H]− |
382.2018 404.1838 380.1862 |
382.2018 404.1842 380.1867 |
0 +0.4 +0.5 |
0 +1.0 +1.3 |
365.1624, 294.0765, 267.0528, 250.0870, 239.0582 |
| Monacolin K hydroxyl acid (MKA) | 5.64 | 229, 238, 246 | C24H38O6 (422.2669) |
[M + H]+ [M + Na]+ [M − H]− [M – H + CO]− |
423.2747 445.2566 421.2590 449.2539 |
ND2 445.2561 421.2589 449.2540 |
−0.5 −0.1 +0.1 |
−1.1 −0.2 +0.2 |
MS/MS [M − H]− 319.1902, 101.0602, 85.0286 |
| Monascuspiloin (dihydromonascin) |
5.92 | 233, 291, 390 | C21H28O5 (360.1937) |
[M + H]+ [M + Na]+ |
361.2015 383.1834 |
361.2009 383.1836 |
−0.6 +0.2 |
−1.7 +0.5 |
345.2045, 300.2883, 261.1133, 215.1081, 187.1134 |
| Monacolin L (ML) | 6.09 | 230, 238, 246 | C19H28O3 (304.2039) |
[M + H]+ [M + Na]+ |
305.2117 327.1936 |
305.2116 327.1935 |
−0.1 −0.1 |
−0.3 −0.3 |
287.2004, 269.1902, 251.1179, 225.1649, 203.1797, 201.1643, 199.1488, 173.1333, 159.1174, 145.1015 |
| Compactin (CP) (mevastatin) |
6.18 | 230, 238, 246 | C23H34O5 (390.2406) |
[M + H]+ [M + Na]+ |
391.2484 413.2304 |
391.2488 413.2305 |
+0.4 +0.1 |
+1.0 +0.2 |
289.1793, 271.1693, 253.1588, 229.1587, 211.1481, 185.1324, 159.1168 |
| Monasfluore A | 6.28 | 379 3 | C21H24O5 (356.1624) |
[M + H]+ [M + Na]+ |
357.1702 379.1521 |
357.1701 379.1522 |
−0.1 +0.1 |
−0.3 +0.3 |
Not recorded |
| Monaphilone B | 7.23 | 227, 285, 386 | C20H28O4 (332.1988) |
[M + H]+ [M + Na]+ |
333.2066 355.1885 |
333.2062 355.1880 |
−0.4 −0.5 |
−1.2 −1.4 |
287.2012, 217.1234, 201.0911, 189.1385, 173.0970 |
| Monacolin K (MK) (lovastatin) |
7.79 | 229, 238, 246 | C24H36O5 (404.2563) |
[M + H]+ [M + Na]+ [2M + Na]+ |
405.2641 427.2460 831.5023 |
405.2642 427.2461 831.5026 |
+0.1 +0.1 +0.3 |
+0.3 +0.3 +0.4 |
303.1995, 285.1855, 267.1753, 243.1751, 225.1652, 199.1490, 173.1328, 159.1176, 143.0854 |
| Monascin | 8.19 | 232, 291, 392 | C21H26O5 (358.1781) |
[M + H]+ [M + Na]+ |
359.1859 381.1678 |
359.1854 381.1684 |
−0.5 +0.6 |
−1.4 +1.6 |
343.2274, 315.2317, 261.1112, 215.1073, 187.1121 |
| Dihydromonacolin K (DiMK) | 9.78 | ND 4 | C24H38O5 (406.2719) |
[M + H]+ [M + Na]+ |
407.2798 429.2617 |
407.2796 429.2618 |
−0.2 +0.1 |
−0.5 +0.2 |
305.2115, 287.2015, 269.1899, 227.1797, 203.1802 |
| Monasfluore B | 9.97 | 378 3 | C23H28O5 (384.1937) |
[M + H]+ [M + Na]+ |
385.2015 407.1835 |
ND 2 407.1839 |
+0.4 |
+1.0 |
Not recorded |
| Dehydromonacolin L (DeML) | 10.15 | 230, 238, 246 | C19H26O2 (286.1933) |
[M + H]+ [M + Na]+ |
287.2011 309.1830 |
287.2007 ND 2 |
−0.4 |
−1.4 |
269.1896, 225.1636, 201.1645, 199.1483, 173.1329, 159.1171, 145.1013 |
| Monaphilone A | 11.15 | 230, 289, 389 | C22H32O4 (360.2301) |
[M + H]+ [M + Na]+ |
361.2379 383.2198 |
361.2380 ND 2 |
+0.1 |
+0.3 |
287.2020, 217.1322, 189.1390, 173.0952 |
| Dehydromonacolin K (DeMK) | 11.42 | 230, 238, 246 | C24H34O4 (386.2457) |
[M + H]+ [M + Na]+ [2M + Na]+ |
387.2535 409.2355 795.4812 |
387.2532 409.2356 795.4821 |
−0.3 +0.1 +0.9 |
−0.8 +0.3 +1.1 |
345.2037, 285.1851, 267.1747, 249.1625, 199.1484, 173.1325, 159.1167, 143.0858 |
| Ankaflavin | 11.75 | 232, 290, 391 | C23H30O5 (386.2093) |
[M + H]+ [M + Na]+ |
387.2172 409.1991 |
387.2173 409.1994 |
+0.1 +0.3 |
+0.3 +0.7 |
359.2238, 315.2325, 261.1117, 215.1076, 187.1125 |
1 The UV absorption bands at 243 and 326 nm (low broad) match well with the UV profile reported in the literature for UHPLC-DAD analytical conditions similar to those used in our study (λmax at 240, 282 (shoulder) and 333 (low broad) nm) [35]. 2 ND: not detected. 3 This low and broad UV absorption band is in agreement with the mean of the λmax of the two enlarged and poorly separated peaks at 371 and 386 nm reported in the literature [36]. 4 ND: not detected at the wavelength used in this study (238 nm).