STRUCTURE OF CINERARIN, A TETRA-ACYLATED ANTHOCYANIN ISOLATED FROM THE BLUE GARDEN CINERARIA, SENECIO CRUENTUS

Article abstract of DOI:10.1016/S0040-4039(01)81749-4

Structure of cinerarin is determined to be 3-O-(6-O-malonyl-β-D-glucopyranosyl)-7-O-(6-O-(4-O-(6-O-caffeyl-β-D-glucopyranosyl)caffeyl)-β-D-glucopyranosyl)-3'-O-(6-O-caffeyl-β-D-glucopyranosyl)delphinidin.

Full text of DOI:10.1016/S0040-4039(01)81749-4

6024
(1982).
T. Kondo, H.
K. Kawahori, and H.
Tetrahedron lett., 24, 2181
7.
T.
(1983).
Cinerarin (1): UV (0.01%
nm
549
in Hz) (delphinidin) 8.41
H-6'), 6.76 s, H-6 8); (3 caffeic acids)
= 16, 3 x B-H), 6.17, 6.04 5.78 (each d, J 16, 3
4.85 (each d, J = 7-8, H-l x
12, H-6a 4.57, 4.17, 4.15
4); the proton signals of glucose moieties shown were
328
290
(500 MHz,
8.05
3%
at
H-2'), 7.32
H-4),
7.30, 7.24
(4
6.98 (each IH, d,
5.43, 5.05, 4.89
5.11, 5.01,
4.68
4.66 (each
H-6b
dd, J = 2
4.02 (each
J
x
by
q
8.5-10
12,
9.
Trisdeacylcinerarin
(0.01%
538
334 (14,000). 286
(20,300);
s, H-4). 7.88
H-6):
(500 MHz, 3%
H-6'), 7.77
(caffeic acid) 7.02
J = 5.93
3.70
at
(J in Hz) (delphinidin) 8.59
H-2'), 6.92
16). 6.49 d, J =
16); (glucose) 5.26 d, J
3.35
4.14
11,
H-81, 6.74
6.35
d, J
q
d, J
t, J
3.64
6.28
dd, J = 7
J = 9,
q
t, J
q
3.97
9
J
q
br.dd, J
3.76
4.92
7.5, A-l), 4.08
5.10
signals
=
d,
J
=
J
q
proton
were correlated by spin-spin decoupling experiments;
dd, J
8 (-12%
5.10
4.04
J
q
6
2'
4
H-6' (-23%
(-22%).
H-6
293 (26.500). 240
7.42 (each
C-G-C methyl ester (6 methyl ester): UV
321
in Hz) 7.56
7.03 d, J
d, J = 6.28
4.39
at
J
(19,900);
7.11
(500 MHz,
7.05
d, J
q
q
6.94
J
q
2
J
d,
J
6.86
4.85
dd, J = 2
6. 80
6.13 (each
d, J =
4.54
dd, J = 2.5
J
q
8
3.76
(3H.
Demalonylcinerarin (7):
11.
(0.01%
(E) 549
(J in Hz) 5.41
2 8
all proton signals of&glucose moiety were
decoupling experiments: (-7.8%). a-
(-2.5% -27.211, respectively).
328 (31,000). 290
3%
at
3.72
(36,600);
(500
3.47
8
3.99
td, J
4.98
J
q
2
4.17
dd, J = 9
by
NOE (at
l H-4
H-6
8
8
8
(Received in Japan 25 September 19841