Flavonoid complexes occurring in the medicinal plants Bryonia alba, Bryonia dioica and Lagenaria siceraria were found to be flavone C-glycosides. Flavonoids of these species were compared by HPLC and separation conditions were elaborated for C-glycosides using isocratic and gradient elution. The content of the major C-glycoside, saponarin, was determined. The highest saponarin level (2.481%) was found in Bryonia dioica.

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=c1cc(-c2ccc(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)cc2)oc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)c12

756.663 g/mol (C₃₃H₄₀O₂₀)

The structures and preferred conformations of cascarosides E [5] and F [6], two new O,C-diglucosylanthrones from Rhamnus purshiana bark, have been determined by spectroscopic methods.

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

Cc1cc(O)c2c(c1)C([C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1cccc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c1C2=O

564.54 g/mol (C₂₇H₃₂O₁₃)

The structures and preferred conformations of cascarosides E [5] and F [6], two new O,C-diglucosylanthrones from Rhamnus purshiana bark, have been determined by spectroscopic methods.

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
8	bDGlcp	105.09	74.97	77.29-78.65	71.28	77.29-78.65	62.56
10	bD1dGlcp
	Subst

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

Cc1cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2c(c1)C([C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1cc(O)cc(O)c1C2=O

580.539 g/mol (C₂₇H₃₂O₁₄)