Table 2.
Qualitative and semi-quantitative composition of small molecules in PBJ identified by HPLC coupled with a high-resolution MS.
| Peak | Compound | RT | [M-H]- | MS/MS | [M+H]+ | MS/MS | Ionic Relative % |
|---|---|---|---|---|---|---|---|
| 1 | Quinic acid | 1.3 | 191.0564 | 147 | - | - | 1.7 |
| 2 | Betonicine | 1.4 | - | - | 160.0967 | 88-98-102-114-160 | <1.0 |
| 3 | Stachydrine | 1.4 | - | - | 144,1019 | 84-144 | <1.0 |
| 4 | Citric acid | 1.5 | 191.0202 | 111-147 | 193.0349 | 129-147-157 | 7.5 |
| 5 | HMG-glucoside | 1.9 | 323.0974 | - | - | - | <1.0 |
| 6 | N-(1-Deoxy-1-fructosyl)leucine | 2 | - | - | 294.1549 | 144-230-248-258 | <1.0 |
| 7 | Luteolin-6,8-di-C-glucoside | 6.7 | 609.1443 | 369-399-429-471-489-519 | 611.1612 | 371-473 | <1.0 |
| 8 | Feruloyl glucoside isomer 1 | 7.1 | 355.1029 | 193 | 357.1182 | 287-195 | <1.0 |
| 9 | Sinapoyl glucoside | 7.8 | 385.1133 | 223 | 387.1288 | 225 | <1.0 |
| 10 | Citrusin F | 8.6 | 519.1714 | 195-357 | - | - | <1.0 |
| 11 | Apigenin-6,8-di-C-glucoside | 9.4 | 593.1495 | 353-383-473-503 | 595.1657 | 355-457 | 2.3 |
| 12 | Chrysoeriol-6,8-di-C-glucoside | 11.3 | 623.1612 | 312-383-413-503-533 | 625.1762 | 385-487-505 | <1.0 |
| 13 | 2-Hydroxy-4-methoxyhydrocinnamoyl-2-O-glucoside | 11.6 | 357.1179 | 151-177-195 | - | - | <1.0 |
| 14 | p-Coumaric acid | 11.8 | 163.0406 | 119 | - | - | <1.0 |
| 15 | Diosmetin-6,8-di-C-glucoside | 12.9 | 623.1604 | 312-383-413-503-533 | 625.1761 | 385-487-505 | 1.4 |
| 16 | Neoeriocitrin-O-glucoside/eriocitrin-O-glucoside | 13.2 | 757.2193 | 287-595 | 759.2349 | - | <1.0 |
| 17 | Luteolin-C-glucoside | 13.6 | 447.0924 | 285 | 449.1079 | 287-329 | <1.0 |
| 18 | Naringin-glucoside | 13.9 | 741.2249 | 271 | - | - | <1.0 |
| 19 | Unknown 1 | 14.5 | 611.1617 | 449-475 | 613.1762 | - | <1.0 |
| 20 | 6-(beta-D-glucopyranosyloxy)-5-benzofuranpropanoic acid | 16.9 | 367.1028 | 161-205 | - | - | <1.0 |
| 21 | Eriodictyol-7-O-glucoside | 18.2 | 449.108 | 287 | 451.1235 | 289 | <1.0 |
| 22 | Apigenin-8-C-glucoside | 18.3 | 431.0983 | 283-311-341 | 433.1131 | 283-397 | <1.0 |
| 23 | Eriodictyol 7-O-neohesperidoside (Neoeriocitrin) | 18.8 | 595.1651 | 287-449 | 597.1813 | 451 | <1.0 |
| 24 | Apigenin-6-C-glucoside | 19.1 | 431.0979 | 283-311-341 | 433.113 | 283-313-337-367-379-397 | <1.0 |
| 25 | Apigenin-di-O-glucoside-O-HMG | 19.3 | 737.1903 | 431-635-675 | - | - | <1.0 |
| 26 | Eriodictyol 7-O-rutinoside (Eriocitrin) | 20.6 | 595.1657 | 287 | 597.1812 | 289-451 | 11.7 |
| 27 | 6-(beta-D-glucopyranosyloxy)-4-methoxy-5-benzofuranpropanoic acid | 20.7 | 397.1135 | 176-191-217-235 | 399.1288 | 202-219-237-245-263-285-288-313-325-339 | <1.0 |
| 28 | Chrysoeriol-8-C-glucoside | 22.7 | 461.1084 | - | 463.1234 | 325-343-367-381-397-409-427-445 | <1.0 |
| 29 | Eriodictyol-O-diglucoside-O-HMG | 23 | 755.2003 | 287-449-491 | - | - | <1.0 |
| 30 | Diosmetin-di-C-glucoside-O-HMG | 23.7 | 767.1998 | 299-461 | - | - | <1.0 |
| 31 | Luteolin-7-O-neohesperidoside | 24.1 | 593.1496 | 285-447 | 595.1653 | 287-449 | 2.5 |
| 32 | Diosmetin-8-C-glucoside | 24.5 | 461.109 | 341-371 | 463.1228 | 343-367-397-409-427 | <1.0 |
| 33 | Naringenin 7-O-rutinoside (Narirutin) | 25.2 | 579.1713 | 271 | 581.1863 | 435 | <1.0 |
| 34 | Naringenin-7-O-glucoside (Prunasin) | 26.5 | 433.1133 | 271 | - | - | <1.0 |
| 35 | Neoeriocitrin-glucoside-O-HMG | 26.5 | 901.2591 | 287-595-637-677-799 | - | - | <1.0 |
| 36 | Hesperetin-di-C-glucoside | 26.8 | 625.1776 | 301-343-505 | 627.1924 | 303 | <1.0 |
| 37 | Chrysoeriol-di-O-glucoside-O-HMG | 26.9 | 767.1998 | 461 | - | - | <1.0 |
| 38 | Diosmetin-di-O-glucoside-O-HMG | 28 | 767.2006 | - | - | - | <1.0 |
| 39 | Bergamjuicin (Melitidin-glucoside) | 28 | 885.264 | 459-579-621-661-723-741-783 | 887.282 | 273 | <1.0 |
| 40 | Naringenin 7-O-neohesperidoside (Naringin) | 28.4 | 579.1705 | 271 | 581.1863 | 417-435 | 11.4 |
| 41 | Apigenin-O-glucoside | 29.1 | 431.0976 | - | 433.1132 | - | <1.0 |
| 42 | Neohesperidin-glucoside-O-HMG | 29.2 | 915.273 | - | - | - | <1.0 |
| 43 | Apigenin-7-O-neohesperidoside | 31 | 577.1557 | 269 | 579.1705 | 271-433 | 2.3 |
| 44 | Hesperetin 7-O-rutinoside (Hesperidin) | 31.4 | 609.1816 | 301-489 | 611.1971 | - | <1.0 |
| 45 | Chrysoeriol-7-O-glucoside | 32.4 | 461.1079 | - | 463.1232 | 301 | <1.0 |
| 46 | Diosmetin-7-O-glucoside | 33.2 | 461.1082 | 284-299 | 463.1233 | 301 | <1.0 |
| 47 | Eriodictyol 7-O-glucoside-O-HMG | 33.5 | 593.1495 | 287-449-491-531 | 595.1654 | - | <1.0 |
| 48 | Hesperetin-O-glucoside isomer 1 | 33.7 | 463.1239 | 301 | - | - | <1.0 |
| 49 | Eriocitrin-O-HMG | 34.1 | 739.2052 | 287-595-637-677 | 741.2234 | - | <1.0 |
| 50 | Chrysoeriol-7-O-neohesperidoside | 34.3 | 607.1655 | 284-299-461 | - | - | <1.0 |
| 51 | Demethoxycentaureidin-7-O-glucoside | 35 | 491.1199 | 314-329 | 493.1339 | 331 | <1.0 |
| 52 | Hesperetin 7-O-neohesperidoside (Neohesperidin) | 35 | 609.1809 | 301-489 | 611.1965 | 303 | 16.5 |
| 53 | Diosmetin-7-O-neohesperidoside | 36.2 | 607.1655 | 284-299 | - | - | 1.8 |
| 54 | Hesperetin-O-glucoside isomer 2 | 36.5 | 463.1241 | - | - | - | <1.0 |
| 55 | Neoeriocitrin-O-HMG | 36.5 | 739.2067 | 595-637-677 | 741.2233 | - | 3.8 |
| 56 | 6-(beta-D-glucopyranosyloxy)-4-methoxy-5-benzofuranpropanoic acid-O-HMG | 36.7 | 541.1556 | 191-217-235-397-439-479 | 543.1704 | 325-367-499 | 1.1 |
| 57 | 6-hydroxy-4-methoxy-5-benzofuranpropanoic acid | 38 | 235.0611 | 176-191 | - | - | <1.0 |
| 58 | Luteolin-7-O-neohesperidoside-O-HMG | 38.5 | 737.1934 | 593-635-675 | 739.2083 | 593-677 | <1.0 |
| 59 | Eriodictyol | 39.2 | 287.056 | - | - | - | <1.0 |
| 60 | Nomilin glucoside | 41.7 | 693.2748 | 427-471-565-607-633 | - | - | 3.2 |
| 61 | Naringenin-acetyl-C-neohesperidoside | 42.6 | 621.1812 | 271-459-501-579 | - | - | <1.0 |
| 62 | Naringenin-O-rutinoside-O-HMG | 42.7 | 723.2142 | 579-621-661 | 725.2291 | - | <1.0 |
| 63 | Naringenin 7-O-glucoside-O-HMG | 43 | 577.1554 | 271-433 | 579.1711 | - | <1.0 |
| 64 | Nomilinic acid glucoside | 44.6 | 711.285 | 607-651 | - | - | 4.1 |
| 65 | Melitidin (Naringin-O-HMG) | 44.6 | 723.2148 | 579-621-661 | 725.2289 | 689 | 6.7 |
| 66 | Apigenin-7-O-neohesperidoside-O-HMG | 46.3 | 721.1959 | 577-619-659 | 723.2133 | 271 | <1.0 |
| 67 | Chrysoeriol-O-glucoside-O-HMG | 47.4 | 605.1508 | 299-461-503 | 607.1652 | 301-463 | <1.0 |
| 68 | Diosmetin-acetyl-O-neohesperidoside | 47.8 | 649.1771 | 284-299-607 | - | - | <1.0 |
| 69 | Obacunone glucoside | 48.3 | 633.2535 | 331-359-427 | - | - | <1.0 |
| 70 | Diosmetin-7-O-neohesperidoside-O-HMG | 48.3 | 751.2095 | 607-649-689 | 753.2227 | 607-691 | <1.0 |
| 71 | Hesperetin-O-rutinoside-O-HMG | 48.4 | 753.2223 | 609-651-691 | 755.2392 | 301-609 | 1.4 |
| 72 | Hesperetin 7-O-glucoside-O-HMG | 48.8 | 607.1651 | 301-463-505 | - | <1.0 | |
| 73 | Brutieridin (Neohesperidin-O-HMG) | 49.2 | 753.2221 | 301-609-651-691 | 755.2389 | 301-609 | 6.9 |
| 74 | Diosmetin-O-glucoside-O-HMG | 49.3 | 605.1505 | 299-461-503-543 | 607.1655 | 301 | <1.0 |
| 75 | Demethoxycentaureidin-7-O-glucoside-HMG | 49.8 | 635.1604 | 329-491-533 | 637.1761 | 331 | <1.0 |
| 76 | Unknown 2 | 51.3 | 417.0819 | 129-173-251-295 | - | - | <1.0 |
| 77 | Naringenin | 51.5 | 271.0608 | 107-151-177 | - | - | <1.0 |
| 78 | Unknown 3 | 52.5 | 417.0816 | 129-173-251-295 | - | - | <1.0 |
| 79 | 255-C-glucoside-O-rhamnoside-O-HMG | 53.1 | 707.2159 | 255-357-563-605-645 | 709.2337 | - | <1.0 |
| 80 | Isosakuranetin-7-O-neohesperidoside-O-HMG | 53.4 | 737.2266 | 285-593-635-675 | 739.244 | - | <1.0 |
| 81 | Deacetylnomilinic acid | 56.1 | 489.2125 | 325-333-411 | 491.2275 | 341-369-385-411-455 | <1.0 |
| 82 | Limonoate A-ring lactone | 56.7 | 487.1953 | 383-427 | 489.2119 | 369-383-427-445 | <1.0 |
| 83 | Limonin | 58.7 | 469.1872 | 229-278-283-306-321-381 | 471.2012 | 367-409-425 | <1.0 |
| 84 | Obacunoic acid | 59.4 | 471.2017 | 307-325-409 | 473.2172 | - | <1.0 |
| 85 | Nomilinic acid | 59.4 | 531.222 | 427-471-489 | 533.2383 | 341-369-411 | <1.0 |
| 86 | Deacetylnomilin | 60.2 | 471.2015 | 307-325-409 | 473.2173 | - | <1.0 |