Foliar flavonoids of 31 species of the Annonaceae native to Brazil, amounting to 76 compounds, were isolated and identified. All phenols found were glycosides of either flavones (apigenin, scutellarein, hispidulin and luteolin) or flavonols (kaempferol, rhamnocitrin, 6-hydroxyrhamnocitrin, quercetin, isorhamnetin and rhamnetin), with the latter predominating. Some members of the tribe Bocageeae are distinctive for accumulating 6-oxygenated flavones and flavonols, in addition to 7-O-methylated flavonols, a feature possibly linked to the assumed advanced condition of the tribe within the family. Members of Duguetia stand out for the apparent absence of quercetin glycosides. Anaxagorea dolichocharpa seemingly lacks flavones and flavonols entirely. A UPGMA analysis based on the distribution of flavonoids does not group the analyzed species according to the available tribal division of the Annonaceae. However, several taxonomically meaningful groupings emerged through the multivariate analysis.
- Compound ID: 23824
Structure type: oligomer
Trivial name: glucoluteolin
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavone glycoside
Reference(s) to other database(s): CCSD:
27029, CBank-STR:939
- Compound ID: 24353
Structure type: oligomer
Trivial name: astragalin
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Reference(s) to other database(s): CCSD:
34076, CBank-STR:4070
- Compound ID: 24354
Structure type: oligomer
Trivial name: isoquercitrin
Compound class: glycoside, flavonoid glycoside
- Compound ID: 24444
Structure type: oligomer
Trivial name: vitexin, isovitexin
Compound class: saponin glycoside, glycoside, flavonoid glycoside
- Compound ID: 24544
Structure type: oligomer
Trivial name: vitexin, isovitexin
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
- Compound ID: 26230
Structure type: oligomer
C15H10O6
Trivial name: afzelin, kaempferol
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside
Reference(s) to other database(s): CCSD:
38788, CBank-STR:605
- Compound ID: 26276
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Reference(s) to other database(s): CCSD:
38906, CBank-STR:931
- Compound ID: 26721
Structure type: oligomer
Trivial name: f6
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Reference(s) to other database(s): CCSD:
49909, CBank-STR:2586
- Compound ID: 26722
Structure type: oligomer
Trivial name: f2
Compound class: glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside
Reference(s) to other database(s): CCSD:
49908, CBank-STR:2587
- Compound ID: 26723
Structure type: oligomer
Trivial name: f5
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Reference(s) to other database(s): CCSD:
49907, CBank-STR:2107
- Compound ID: 28292
Structure type: oligomer
Trivial name: f7
Compound class: glycoside, flavonoid glycoside
- Compound ID: 31914
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32145
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32786
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32787
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b-D-Glcp-(1-6)-Subst
Subst = scutellarein = SMILES O=C(C1=C(C={7}C(O){6}C(O)={5}C1O)O2)C=C2C3=CC={54}C(O)C=C3 |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32788
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b-D-Glcp-(1-?)-b-D-Glcp-(1-6)-Subst
Subst = scutellarein = SMILES O=C(C1=C(C={7}C(O){6}C(O)={5}C1O)O2)C=C2C3=CC={54}C(O)C=C3 |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32789
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b-D-Glcp-(1-?)-b-D-Glcp-(1-7)-Subst
Subst = hispidulin = SMILES COc1{7}c(O)cc2oc(-c3cc{54}c(O)cc3)cc(=O)c2{5}c1O |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32790
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a-L-Rhap-(1-?)-b-D-Glcp-(1-7)-Subst
Subst = 6-hydroxyluteolin = SMILES O=C(C1={5}C(O){6}C(O)={7}C(O){8}C=C1O2)C=C2C3=C{53}C(O)={54}C(O)C=C3 |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32791
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32792
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32793
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32794
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32795
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32796
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32797
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32798
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32799
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32800
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32801
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32802
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32803
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32804
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32805
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32806
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32807
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32808
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32809
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32810
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b-D-Glcp-(1-3)-Subst7Me
Subst = 6-hydroxykaempferol = SMILES O=C(C1=C(C={7}C(O){6}C(O)={5}C1O)O2){3}C(O)=C2C3=CC={54}C(O)C=C3 |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32811
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32812
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32813
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32814
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32815
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32816
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32817
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32818
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32819
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32820
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32821
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32822
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32823
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32824
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32825
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32826
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32827
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32828
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32829
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a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-3')-Quercetin
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a-L-Rhap-(1-7)-+ |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32830
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b-D-Galp-(1-3)-Subst
Subst = isorhamnetin = SMILES O{3}C1=C(C2=CC={54}C(O)C(OC)=C2)OC3=C({5}C(O)=C{7}C(O)=C3)C1=O |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32831
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b-D-Glcp-(1-3)-Subst
Subst = isorhamnetin = SMILES O{3}C1=C(C2=CC={54}C(O)C(OC)=C2)OC3=C({5}C(O)=C{7}C(O)=C3)C1=O |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32832
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b-D-Galp-(1-?)-b-D-Galp-(1-3)-Subst
Subst = isorhamnetin = SMILES O{3}C1=C(C2=CC={54}C(O)C(OC)=C2)OC3=C({5}C(O)=C{7}C(O)=C3)C1=O |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32833
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b-D-Galp-(1-?)-a-L-Rhap-(1-3)-Subst
Subst = isorhamnetin = SMILES O{3}C1=C(C2=CC={54}C(O)C(OC)=C2)OC3=C({5}C(O)=C{7}C(O)=C3)C1=O |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32834
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b-D-Glcp-(1-?)-b-D-Glcp-(1-3)-Subst
Subst = isorhamnetin = SMILES O{3}C1=C(C2=CC={54}C(O)C(OC)=C2)OC3=C({5}C(O)=C{7}C(O)=C3)C1=O |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32835
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a-L-Rhap-(1-?)-b-D-Glcp-(1-3)-Subst
Subst = isorhamnetin = SMILES O{3}C1=C(C2=CC={54}C(O)C(OC)=C2)OC3=C({5}C(O)=C{7}C(O)=C3)C1=O |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32836
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32837
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32838
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside