Table 1.
Metabolites identified from the total MeOH extract of R. graveolens.
| Identification | Molecular formula | Rt (min) | m/z | MS/MS fragments |
|---|---|---|---|---|
| Methyl cnidioside A | C18H22O9 | 0.95 | 383.01 | 369,284, 207, 122 |
| Daphnoretin methyl ether | C20H14O7 | 1.67 | 367.1 | 353, 339, 194, 116 |
| 1,4-Dihydro-4-methoxy-1,4-dimethyl-3-(3-methylbut-2-enyl) quinoline-2,7-diol | C17H23NO3 | 2.75 | 290.01 | 221, 207, 177, 163 |
| Epicatechin | C15H14O6 | 2.78 | 291.01 | 247, 207, 181 |
| Umbelliferone | C9H6O3 | 2.85 | 163.01 | 147, 135, 119 |
| Rutacultin | C16H18O4 | 3.82 | 275.01 | 260, 232, 220 |
| Vecenin-2 | C27H30O15 | 5.19 | 595.1 | 505, 475, 415 |
| Pinnarin | C16H18O4 | 5.83 | 275.01 | 260, 232, 220 |
| Rutaretin | C14H14O5 | 6.57 | 263.01 | 205, 189, 161 |
| Gossypetin 7-methyl ether 3-rutinoside | C28H32O17 | 6.63 | 641.1 | 495, 333, 303 |
| Gossypetin methyl ether | C16H12O8 | 6.67 | 333.1 | 303 |
| Rutin | C27H30O16 | 6.77 | 611.01 | 465, 303 |
| Quercetin 3-rhamnoside (Quercitrin) | C21H20O11 | 6.8 | 449.01 | 303 |
| Isoquercitrin, quercetin-3-O-b-D-glucopyranoside | C21H20O12 | 6.81 | 465.01 | 303 |
| Quercetin | C15H10O7 | 6.97 | 303.01 | 153, 108 |
| Isorhamnetin 3-O-Rutinoside | C28H32O16 | 7.24 | 625.1 | 317, 301 |
| Cnidioside A | C17H20O9 | 7.37 | 369.1 | 284, 207, 122 |
| 4-Hydroxy-2- undecylquinoline | C20H29NO | 7.77 | 300.01 | 198, 184, 172 |
| Bergapten | C12H8O4 | 7.81 | 217.01 | 161, 131 |
| Graveoline | C17H13NO3 | 8.01 | 280.01 | 266, 237, 207 |
| Graveolinine | C17H13NO3 | 9.01 | 280.01 | 266, 251, 223 |
| Skimmianine, Kokusaginin (4,6,7-Trimethoxyfuro[2,3-b] quinoline) | C14H13NO4 | 9.25 | 260.01 | 245, 230, 216, 199, 184 |
| Rutacridone | C19H17NO3 | 9.38 | 308.01 | 294, 253 |
| Psoralen | C11H6O3 | 9.41 | 187.01 | 159, 143, 131, 115 |
| γ -Fagarine | C13H11NO3 | 9.61 | 230.01 | 215, 201, 157, 129 |
| Rutacridone epoxide | C19H17NO4 | 10.02 | 324.01 | 295, 251 |
| Scopoletin | C10H8O4 | 10.12 | 193.01 | 178, 150, 132 |
| Dictamnine | C12H9NO2 | 10.38 | 200.01 | 185, 157, 129 |
| Caffeic acid | C9H8O4 | 10.45 | 181.01 | 163, 135 |
| Xanthotoxin, (Methoxsalen; 8-Methoxypsoralen) | C12H8O4 | 10.49 | 217.01 | 202, 174, 161, 145, 131 |
| Pteleine (6-Methoxydictamnine) | C13H11NO3 | 10.55 | 230.01 | 216, 202, 185, 157 |
| 3-(1,1-Dimethylallyl) herniarin | C15H16O3 | 10.83 | 245.01 | 230, 217, 175 |
| 2-Heptyl-4(1H)-quinolone | C16H21NO | 10.85 | 244.01 | 215, 186, 145 |
| Syringic acid | C9H10O5 | 10.92 | 199.01 | 184, 155 |
| 4-Hydroxy-2-decylquinoline | C19H27NO | 11.32 | 286.01 | 198, 172, 132 |
| Kaempferol | C15H10O6 | 11.33 | 287.01 | 231, 153, 107 |
| Gravacridonol | C19H17NO4 | 11.36 | 324.01 | 324, 308, 286 |
| (epi) Gallocatechin | C15H14O7 | 12.29 | 307.01 | 263, 221, 181, 167 |
| Chalepin | C19H22O4 | 13.4 | 315.01 | 300, 273, 259, 255, 213, 201 |
| Isorhamnetin | C16H12O7 | 13.37 | 317.01 | 303, 151, 107 |
| Arborinine | C16H15NO4 | 13.97 | 286.01 | 271, 253, 244, 225, 199 |
| 1-Methyl-2-nonyl-4(1H)- quinolone |
C19H27NO | 14.44 | 286.01 | 186, 159, 173 |
| Luteolin | C15H10O6 | 14.47 | 287.01 | 269, 245201, 153 |
| Apigenin | C15H10O5 | 14.71 | 271.01 | 253, 227, 199, 151 |
| 3-Caffeoylquinic acid | C16H18O9 | 15.04 | 355.01 | 193, 181 |
| Rosmarinic acid | C18H16O8 | 15.07 | 361.1 | 199, 181 |
| Gravacridontriol-O-18- β-D-glucoside | C25H29NO11 | 15.31 | 520.1 | 358, 267, 253 |
| Chalepensin | C16H14O3 | 15.44 | 255.01 | 199, 171 |
| 1-Methyl-2-decyl-4(1H)-quinolone | C20H29NO | 15.48 | 300.01 | 186, 173 |
| Gravacridonetriol | C19H19NO6 | 16.42 | 358.1 | 267, 253 |
| Rutamarin | C21H24O5 | 16.42 | 357.01 | 288, 256, 187 |
| 5-Caffeoylquinic acid | C16H18O9 | 16.75 | 355.1 | 193 |
| 1-Methyl-2-undecyl-4(1H)- quinolone | C21H31NO | 17.02 | 314.01 | 295, 272, 228, 186, 173 |
| Gravelliferone | C19H22O3 | 17.55 | 299.01 | 231, 215, 171 |
| 1-Methyl-2-dodecyl-4(1H)- quinolone | C22H33NO | 17.82 | 328.01 | 315, 283, 255, 221, 186, 173, 152 |
| Daphnoretin | C19H12O7 | 18.43 | 353.01 | 339, 194, 116 |
| Gravacridonediol | C19H19NO5 | 19.77 | 342.01 | 267, 253 |
| 4-Caffeoylquinic acid | C16H18O9 | 20.27 | 355.01 | 193, 175 |