Two new flavone glycosides with an unusual interglycosidic linkage have been isolated from the petals of Salvia uliginosa and identified by NMR spectroscopy as apigenin 7-O-β-D-glucopyranosyl-(1''' → 4'')-β-D- glucopyranoside and apigenin 7-O-β-D-glucopyranosyl-(1''' → 4'')-β-D- glucopyranoside-4'-O-β-D-glucopyranoside. The NMR and UV spectra of these compounds were compared with those of the known compound, apigenin 7,4'-O,O- di-β-D-glucopyranoside, which was isolated from the same source.

Lamiaceae, apigenin 7, 4'-O, O- diglucoside, apigenin 7-O- cellobioside, apigenin 7-O-cellobioside-4'-O-glucoside, copigment, petals, Salvia uliginosa

13C NMR data:
missing...
1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16
7,4	bDGlcp	4.31	3.04	3.19	3.08	3.21	3.44-3.73
7	bDGlcp	5.16	3.34	3.49	3.45	3.66	3.67-3.78
	xXApigenin	-	-	6.85	-	-	6.47	-	6.83	-	-	-	7.95	6.95	-	6.95	7.95

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=c1cc(-c2ccc(O)cc2)oc2cc(O[C@@H]3O[C@H](CO)[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)cc(O)c12

594.522 g/mol (C₂₇H₃₀O₁₅)

Two new flavone glycosides with an unusual interglycosidic linkage have been isolated from the petals of Salvia uliginosa and identified by NMR spectroscopy as apigenin 7-O-β-D-glucopyranosyl-(1''' → 4'')-β-D- glucopyranoside and apigenin 7-O-β-D-glucopyranosyl-(1''' → 4'')-β-D- glucopyranoside-4'-O-β-D-glucopyranoside. The NMR and UV spectra of these compounds were compared with those of the known compound, apigenin 7,4'-O,O- di-β-D-glucopyranoside, which was isolated from the same source.

Lamiaceae, apigenin 7, 4'-O, O- diglucoside, apigenin 7-O- cellobioside, apigenin 7-O-cellobioside-4'-O-glucoside, copigment, petals, Salvia uliginosa

13C NMR data:
missing...
1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16
7	bDGlcp	5.07	3.30	3.31	3.19	3.47	3.49-3.72
4'	bDGlcp	5.03	3.30	3.31	3.19	3.47	3.49-3.72
	xXApigenin	-	-	6.97	-	-	6.47	-	6.86	-	-	-	8.07	7.21	-	7.21	8.07

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=c1cc(-c2ccc(O[C@@H]3O[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)cc(O)c12

594.522 g/mol (C₂₇H₃₀O₁₅)

Two new flavone glycosides with an unusual interglycosidic linkage have been isolated from the petals of Salvia uliginosa and identified by NMR spectroscopy as apigenin 7-O-β-D-glucopyranosyl-(1''' → 4'')-β-D- glucopyranoside and apigenin 7-O-β-D-glucopyranosyl-(1''' → 4'')-β-D- glucopyranoside-4'-O-β-D-glucopyranoside. The NMR and UV spectra of these compounds were compared with those of the known compound, apigenin 7,4'-O,O- di-β-D-glucopyranoside, which was isolated from the same source.

Lamiaceae, apigenin 7, 4'-O, O- diglucoside, apigenin 7-O- cellobioside, apigenin 7-O-cellobioside-4'-O-glucoside, copigment, petals, Salvia uliginosa

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16
7,4	bDGlcp	103.1	73.1	76.3	69.9	76.5	60.8
7	bDGlcp	99.4	72.7	74.6	79.6	74.9	59.8
4'	bDGlcp	100.0	72.9	76.4	69.4	77.1	60.6
	xXApigenin	-	?	104.2	?	?	99.6	?	94.9	?	?	?	128.2	116.6	?	116.6	128.2


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16
7,4	bDGlcp	4.32	3.04	3.19	3.08	3.21	3.44-3.72
7	bDGlcp	5.16	3.33	3.49	3.46	3.67	3.68-3.78
4'	bDGlcp	5.03	3.29	3.31	3.18	3.41	3.48-3.72
	xXApigenin	-	-	6.96	-	-	6.48	-	6.88	-	-	-	8.06	7.21	-	7.21	8.06


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10	C11/H11	C12/H12	C13/H13	C14/H14	C15/H15	C16/H16
7,4	bDGlcp	103.1/4.32	73.1/3.04	76.3/3.19	69.9/3.08	76.5/3.21	60.8/3.44-3.72
7	bDGlcp	99.4/5.16	72.7/3.33	74.6/3.49	79.6/3.46	74.9/3.67	59.8/3.68-3.78
4'	bDGlcp	100.0/5.03	72.9/3.29	76.4/3.31	69.4/3.18	77.1/3.41	60.6/3.48-3.72
	xXApigenin			104.2/6.96			99.6/6.48		94.9/6.88				128.2/8.06	116.6/7.21		116.6/7.21	128.2/8.06

The spectrum also has 9 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=c1cc(-c2ccc(O[C@@H]3O[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]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)cc(O)c12

756.663 g/mol (C₃₃H₄₀O₂₀)