By Andrew G. Mercader, Alicia B. Pomilio
Biflavonoids include a bunch of the flavonoid kinfolk that own quite a few constructions and organic actions of excessive relevance, resembling anticancer, antibacterial, antifungal, antiviral, anti inflammatory, antinociceptive, antioxidant, vasodilator and anticlotting. The chemistry of biflavonoids is essential in lots of fields of analysis, specially simply because those compounds are structurally diverse bioactive molecules with strength for biomedical functions. This publication highlights the structural biflavonoid variability, rearrangements and diverse stereochemistry via approximately 470 buildings disbursed in a few species of Angiosperms, Gymnosperms, ferns and mosses.
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Extra resources for Biflavonoids: Occurrence, Structural Features and Bioactivity
Pomilio Taiwaniaflavone series has (I-3,II-3′)-biflavones (189-191). The following series possesses a (I-2′,II-2′)-biflavone (192) and a (I-2′,II-2′)-biflavonol (193). Biflavonoids linked by a (I-2′,II-6) bond were included in the Dicranolomin series, which has the following subsections: (I-2′,II-6)-biflavones (194,195); (I-2′,II-6)-flavanone-flavone dimers (196,197); (I-2′,II-6)-flavone-flavanone dimers (198,199); (I-2′,II-6)-biflavanone (200); and (I-2′,II-6)benzopyranobenzofuranbiflavone (201).
Pomilio (I-3,II-8)-Flavanone-flavone dimers R R1 O O R5 R2 O O R2 (+)-Volkensiflavone (+)-Volkensiflavone-II-7sulfate Spicataside (volkensiflavone-II-7-OD-glucoside) Spicataside nona-Oacetate I-5,7,4′,II-5,7,4′-Hexa-Omethylvolkensiflavone Fukugetin (+)-Morelloflavone-II-7sulfate I-5,7,4′,II-5,7,3′,4′-HeptaO-methyl-morelloflavone Fukugiside Morelloflavone I5,7,4′,II-5,7,3′,4′-heptaO-acetate I-5,7,3′,4′,II-5,7,4′Heptahydroxy-(I-3,II-8)flavanonylflavone R4 I O 3 8 O O R3 O II O O R2 (154) R H R1 H R2 H R3 H R4 H R5 H (155) H H H SO3H H H (156) H H H Glu H H (157) H Ac Ac 2,3,4,6-TetraO-acetylGlu H Ac (158) H Me Me Me H Me (159) H H H H OH H (160) H H H SO3H OH H (161) H Me Me Me OMe Me (162) H H H Glu OH H (163) H Ac Ac Ac OAc Ac (164) OH H H H H H (I-3,II-8)-Flavanone-flavonol dimers OH OH HO O I OH O HO OH 3 8 O II O OH Pancibiflavonol (165) OH Biflavonoid Structures 27 OH OH HO O I 3 O 8 OH O HO II OH O OH Garcinianin (atropisomers) (166) (I-3,II-8)-Biflavanones R1 O R O O R3 O R4 I R1 O 3 O 8 O II O R2 GB1a* I-5,7,4′,II-5,7,4′-Hexa-O-methylGB1a GB1a-II-7-O-β-D-glucopyranoside (+)-GB1b* ent-Naringeninyl-(I-3α,II-8)-II-4‘O-methylnaringenin GB2a GB2a-I-7-O-β-D-glucopyranoside GB2a-II-7-O-β-D-glucopyranoside (xanthochymuside) II-4′-O-Methyl-GB2a* I-5,7,4',II-3,5,7,3′,4′-Octahydroxy(I-3,II-8)-biflavanone R5 O O R (167) R H R1 H R2 H R3 H R4 H R5 H (168) Me Me Me Me H H (169) (170) H H H H Glu H H H H H H H (171) H H H Me H H (172) (173) H Glu H H H H H H OH OH H H (174) H H Glu H OH H (175) H H H Me OH H (175a) H H H H OH OH *Different stereochemistry.
Pomilio (Continued). Neochamaejasmin A (I-2S,3S;II-2S,3S) Neochamaejasmin B (I-2S,3S;II-2R,3S) I-7-O-Methylneochamaejasmin A (I-2S,3S;II2S,3S) Sikokianin A (I-2S,3S;II-2R,3R) Sikokianin B (I-2S,3R;II-2R,3R) Sikokianin C (I-2S,3R;II-2R,3S) Chamaejasmenin A (I-2S,3R;II-2R,3S) Chamaejasmenin B (I-2S,3S;II-2R,3R) Isochamaejasmenin B (I-2S,3S;II-2S,3S) Chamaejasmenin C (I-2S,3S;II-2R,3S) Chamaejasmenin D (I-2S,3S;II-2S,3S) Ruixianglangdusu A (I-2R,3R;II-2R,3R) Ruixianglangdusu B (I-2S,3R;II-2R,3S) (132) (133) H H OH OH H H H H H H OH OH (134) Me OH H H H OH (135) (136) (137) (138) (139) (140) (141) (142) (143) (144) H H H H H H Me Me H Me OH OH OH OH OH OH OH OH OH OH Me Me Me Me Me Me Me Me Me Me H Me Me H H H H H Me H H H H Me Me Me Me H Me Me OH OH OH OH OH OH OH OH OH OH Figure 6.