Table 1.
Flavonoids experimentally characterized by LC-MS/MS in 12 angiosperm species and Marchantia polymorpha.
| Group | Representative structure | Name | |||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Marchantiales | Asparagales | Poales | Solanales | Gentianales | Brassicales | Fabales | |||||||||
| Marchantia polymorphia | Allium cepa | Oryza Sativa | Zea mays | Lycopersicon esculentum | Nicotiana tabacum | Solanum tuberosum | Optiorriza pumila | Arabidopsis thaliana | Glycine max | Glycyrrhiza glabra | Glycyrrhiza uralensis | Medicago truncatula | |||
| Flavanone |  |
Eriodictyol, hesperetin, isookanin, liquirtigenin, naringenin, sakuranetin, etc. | 0 (0) | 1 (0) | 0 (2) | 0 (0) | 2 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 2 (0) | 10 (5) | 7 (17) | 1 (0) |
| Flavone |  |
Apigenin, baicalein, chrysoeriol, luteolin, scutellarein, tricin, etc. | 5 (3) | 1 (5) | 30 (19) | 23 (17) | 2 (0) | 2 (13) | 3 (0) | 1 (0) | 0 (0) | 10 (4) | 15 (2) | 11 (5) | 12 (0) |
| Isoflavone |  |
Afrormosin, biochanin, daizein, formononetin, genistein, etc. | 0 (0) | 0 (0) | 0 (0) | 1 (0) | 0 (0) | 0 (6) | 0 (0) | 8 (0) | 0 (0) | 18 (18) | 14 (8) | 17 (3) | 5 (0) |
| Flavanol/flavandiol |  |
Catechin, procyanidin | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 2 (0) | 2 (0) | 0 (0) |
| Flavonol |  |
Gossypetin, isorhamnetin, kaempferide, kaempferol, laricitrin, myricetin, patuletin, quercetin, syringetin | 0 (0) | 10 (3) | 2 (0) | 6 (3) | 7 (0) | 3 (1) | 10 (3) | 0 (0) | 9 (1) | 6 (9) | 19 (2) | 19 (0) | 15 (0) |
| Anthocyanidin |  |
Cyanidin, delphnidin, petunidin, riccionidin, etc. | 1 (2) | 0 (10) | 0 (0) | 1 (0) | 1 (0) | 0 (0) | 0 (6) | 0 (0) | 0 (3) | 1 (0) | 2 (0) | 2 (0) | 0 (0) |
| Prenylated flavonoid |  |
Bolusanthol, gancaonin, glabrol, kievitone, licoisoflavone, sigmoidin, etc. | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (0) | 0 (4) | 13 (49) | 10 (40) | 0 (0) |
The numbers of flavonoids characterized by Tsugawa et al. (2019) are shown. The numbers of flavonoids stored in the Dictionary of Natural Products are shown in parentheses. A conventional type of reverse phase LC-MS/MS was used for these analyses. On the basis of the ontology in the FSEA, the flavonoids are summarized into seven groups. Flavonoids with the prenyl moiety are grouped together as the prenylated flavonoid group. Prenylations (29 patterns) occur in chalcones/dihydrochalcones, flavanones, flavones, flavonols/dihydroflavonols, and isoflavones (Barron and Ibrahim, 1996). Flavonoids consisting of unmodified aglycones and glycosylated, acylated, etherated, and/or prenylated flavonoids were characterized in this study.