Six anthocyanins were isolated from the brownish-red flowers of Ipomoea purpurea. Cyanidin 3-sophoroside was identified as the parent anthocyanin. The other five anthocyanins are acylated derivatives with glucosylcaffeic acid and/or caffeic acid. The structures of three were unambiguously determined to be cyanidin 3-O-[2-O-(6-O-(trans-4-O-(6-O-(trans-3-O-(β-D- glucopyranosyl)-caffeoyl)-β-D-glucopyranosyl)-caffeoyl)-β-D- glucospyranosyl)-β-D-glucopyranoside], cyanidin 3-O-[2-O-(6-O-(trans- caffeoyl)-β-D-glu-copyranosyl)-β-D-glucopyranoside] and cyanidin 3-O-[2-O- (β-D-glucopyranosyl)-6-O-(trans-caffeoyl)-β-D-glucopyranoside]. The remaining two pigments could not be determined because of their small yields. In these flowers, the major pigments are cyanidin 3- glucosylcaffeoylglucosylcaffeoyl-sophoroside, cyanidin 3-sophoroside and cyanidin 3-caffeoylsophoroside. They are considered to play an important role in producing the dusky colour of these petals.

Convolvulaceae, brownish-red flower colour, Ipomoea purpurea, mono- and di-caffeoylcyanidin 3-sophorosides

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
3,2	bDGlcp	4.65	2.98	3.05	2.72	3.10	3.19-3.33
3	bDGlcp	5.66	3.97	3.64	3.33	3.59	3.52-3.73
	xXCyanidin	-	-	-	8.86	-	6.72	-	6.93	-	-	-	8.03	-	-	7.07	8.21

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

OC[C@H]1O[C@@H](O[C@H]2[C@H](Oc3cc4c(O)cc(O)cc4[o+]c3-c3ccc(O)c(O)c3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

611.529 g/mol (C₂₇H₃₁O₁₆⁺)

Six anthocyanins were isolated from the brownish-red flowers of Ipomoea purpurea. Cyanidin 3-sophoroside was identified as the parent anthocyanin. The other five anthocyanins are acylated derivatives with glucosylcaffeic acid and/or caffeic acid. The structures of three were unambiguously determined to be cyanidin 3-O-[2-O-(6-O-(trans-4-O-(6-O-(trans-3-O-(β-D- glucopyranosyl)-caffeoyl)-β-D-glucopyranosyl)-caffeoyl)-β-D- glucospyranosyl)-β-D-glucopyranoside], cyanidin 3-O-[2-O-(6-O-(trans- caffeoyl)-β-D-glu-copyranosyl)-β-D-glucopyranoside] and cyanidin 3-O-[2-O- (β-D-glucopyranosyl)-6-O-(trans-caffeoyl)-β-D-glucopyranoside]. The remaining two pigments could not be determined because of their small yields. In these flowers, the major pigments are cyanidin 3- glucosylcaffeoylglucosylcaffeoyl-sophoroside, cyanidin 3-sophoroside and cyanidin 3-caffeoylsophoroside. They are considered to play an important role in producing the dusky colour of these petals.

Convolvulaceae, brownish-red flower colour, Ipomoea purpurea, mono- and di-caffeoylcyanidin 3-sophorosides

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
3,2,6	xXCaf?	-	6.83	-	-	6.74	6.80	5.94	7.16	-
3,2	bDGlcp	4.77	3.08	3.21	3.34	3.64	3.91-3.95
3	bDGlcp	5.56	3.90	3.68	3.33	3.52	3.49-3.70
	xXCyanidin	-	-	-	8.91	-	6.67	-	6.91	-	-	-	8.00	-	-	7.07	8.21

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=C(/C=C/c1ccc(O)c(O)c1)OC[C@H]1O[C@@H](O[C@H]2[C@H](Oc3cc4c(O)cc(O)cc4[o+]c3-c3ccc(O)c(O)c3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

773.673 g/mol (C₃₆H₃₇O₁₉⁺)

Six anthocyanins were isolated from the brownish-red flowers of Ipomoea purpurea. Cyanidin 3-sophoroside was identified as the parent anthocyanin. The other five anthocyanins are acylated derivatives with glucosylcaffeic acid and/or caffeic acid. The structures of three were unambiguously determined to be cyanidin 3-O-[2-O-(6-O-(trans-4-O-(6-O-(trans-3-O-(β-D- glucopyranosyl)-caffeoyl)-β-D-glucopyranosyl)-caffeoyl)-β-D- glucospyranosyl)-β-D-glucopyranoside], cyanidin 3-O-[2-O-(6-O-(trans- caffeoyl)-β-D-glu-copyranosyl)-β-D-glucopyranoside] and cyanidin 3-O-[2-O- (β-D-glucopyranosyl)-6-O-(trans-caffeoyl)-β-D-glucopyranoside]. The remaining two pigments could not be determined because of their small yields. In these flowers, the major pigments are cyanidin 3- glucosylcaffeoylglucosylcaffeoyl-sophoroside, cyanidin 3-sophoroside and cyanidin 3-caffeoylsophoroside. They are considered to play an important role in producing the dusky colour of these petals.

Convolvulaceae, brownish-red flower colour, Ipomoea purpurea, mono- and di-caffeoylcyanidin 3-sophorosides

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16
3,2,6,4,6,4	bDGlcp	?	?	?	?	?	60.6
3,2,6,4,6	xXCaf?	125.8	116.2	145.6	149.5	116.3	124.3	114.8	145.2	166.6
3,2,6,4	bDGlcp	101.4	?	?	?	74.0-75.6	63.2-70.1
3,2,6	xXCaf?	128.6	115.2	146.1	147.3	116.8	120.7	115.6	144.3	166.0
3,2	bDGlcp	104.5	?	?	?	76.0	62.8
3	bDGlcp	100.1	82.1	?	?	77.3-77.5	60.9
	xXCyanidin	-	161.7	143.6	135.5	155.8	102.3	168.5	94.1	157.7	111.7	119.5	117.4	146.7	154.4	115.9	126.9


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16
3,2,6,4,6,4	bDGlcp	4.82	3.32	3.18	3.32-3.48	3.32-3.48	3.32-3.56
3,2,6,4,6	xXCaf?	-	7.48	-	-	6.84	7.02	6.44	7.52	-
3,2,6,4	bDGlcp	4.90	3.37	3.28-3.35	3.28-3.35	3.73	4.28-4.44
3,2,6	xXCaf?	-	7.01	-	-	7.06	6.86	6.03	7.17	-
3,2	bDGlcp	4.77	3.08	3.21	3.32	3.65	3.90-3.98
3	bDGlcp	5.56	3.90	3.64	3.32	3.50	3.49-3.69
	xXCyanidin	-	-	-	8.90	-	6.66	-	6.82	-	-	-	8.01	-	-	7.06	8.18


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
3,2,6,4,6,4	bDGlcp	?/4.82	?/3.32	?/3.18	?/3.32-3.48	?/3.32-3.48	60.6/3.32-3.56
3,2,6,4,6	xXCaf?		116.2/7.48			116.3/6.84	124.3/7.02	114.8/6.44	145.2/7.52	
3,2,6,4	bDGlcp	101.4/4.90	?/3.37	?/3.28-3.35	?/3.28-3.35	74.0-75.6/3.73	63.2-70.1/4.28-4.44
3,2,6	xXCaf?		115.2/7.01			116.8/7.06	120.7/6.86	115.6/6.03	144.3/7.17	
3,2	bDGlcp	104.5/4.77	?/3.08	?/3.21	?/3.32	76.0/3.65	62.8/3.90-3.98
3	bDGlcp	100.1/5.56	82.1/3.90	?/3.64	?/3.32	77.3-77.5/3.50	60.9/3.49-3.69
	xXCyanidin				135.5/8.90		102.3/6.66		94.1/6.82				117.4/8.01			115.9/7.06	126.9/8.18

The spectrum also has 14 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=C(/C=C/c1ccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(O)c1)OC[C@H]1O[C@@H](Oc2ccc(/C=C/C(=O)OC[C@H]3O[C@@H](O[C@H]4[C@H](Oc5cc6c(O)cc(O)cc6[o+]c5-c5ccc(O)c(O)c5)O[C@H](CO)[C@@H](O)[C@@H]4O)[C@H](O)[C@@H](O)[C@@H]3O)cc2O)[C@H](O)[C@@H](O)[C@@H]1O

1260.099 g/mol (C₅₇H₆₃O₃₂⁺)

Six anthocyanins were isolated from the brownish-red flowers of Ipomoea purpurea. Cyanidin 3-sophoroside was identified as the parent anthocyanin. The other five anthocyanins are acylated derivatives with glucosylcaffeic acid and/or caffeic acid. The structures of three were unambiguously determined to be cyanidin 3-O-[2-O-(6-O-(trans-4-O-(6-O-(trans-3-O-(β-D- glucopyranosyl)-caffeoyl)-β-D-glucopyranosyl)-caffeoyl)-β-D- glucospyranosyl)-β-D-glucopyranoside], cyanidin 3-O-[2-O-(6-O-(trans- caffeoyl)-β-D-glu-copyranosyl)-β-D-glucopyranoside] and cyanidin 3-O-[2-O- (β-D-glucopyranosyl)-6-O-(trans-caffeoyl)-β-D-glucopyranoside]. The remaining two pigments could not be determined because of their small yields. In these flowers, the major pigments are cyanidin 3- glucosylcaffeoylglucosylcaffeoyl-sophoroside, cyanidin 3-sophoroside and cyanidin 3-caffeoylsophoroside. They are considered to play an important role in producing the dusky colour of these petals.

Convolvulaceae, brownish-red flower colour, Ipomoea purpurea, mono- and di-caffeoylcyanidin 3-sophorosides

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
3,2	bDGlcp	4.66	2.99	3.06	2.75	3.11	3.18-3.38
3,6	xXCaf?	-	6.88	-	-	6.76	6.87	6.21	7.38	-
3	bDGlcp	5.69	4.01	3.69	3.38	3.96	4.19-4.46
	xXCyanidin	-	-	-	8.82	-	6.69	-	6.97	-	-	-	7.98	-	-	7.05	8.20

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=C(/C=C/c1ccc(O)c(O)c1)OC[C@H]1O[C@@H](Oc2cc3c(O)cc(O)cc3[o+]c2-c2ccc(O)c(O)c2)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O

773.673 g/mol (C₃₆H₃₇O₁₉⁺)