1268
S.F. Farag et al. / Phytochemistry 57 (2001) 1263–1268
ꢀ
1
tral data: see Table 1. HRFAB–MS m/z 595.1681
177, 1073, 1002, 924, 827 cm 1. 1H and 13C NM R spec-
and then dried in vacuo. The residue was separated by Si
gel column chromatography using CHCl –MeOH (98:2)
3
+
[
M+1] , m/z 595.1663 calculated for C H O .
2
to give an aglycone (3.0 mg, 58% yield). The aglycone
1
7
31 15
was identified as biochanin A by comparison of its H
NMR spectral data with those of an authentic sample
(commercially available from Sigma-Aldrich Co).
4
. Acetylation of 1
Compound 1 (9.4 mg) was treated with 0.25 ml of
acetic anhydride and 2 mg of DMAP in 0.5 ml of pyri-
dine at room temperature for 24 h. After dilution with 5
ml of water, the reaction mixture was extracted twice
with 5 ml of ethyl acetate. The organic layer was washed
with water and brine and dried over magnesium sulfate.
The crude product obtained by evaporation was pur-
ified by Si gel column chromatography using CHCl3–
MeOH (98:2) to give the corresponding nonacetate 8
6. Acid-catalyzed hydrolysis of 3
Compound 3 (17 mg) was treated in the same manner as
compound 1 to give an aglycone (3.4 mg, 40% yield). The
aglycone was identified as tectorigenin by comparison of
1
its H NMR spectral data with those of an authentic
sample derived from tectoridin (Farag et al., 1999).
(
11.0 mg, yield 76%). Compound 8: colorless amor-
Acknowledgements
phous powder. IR (KBr)ꢁmax: 3400, 1652, 1612, 1165,
ꢀ
075, 825 cm ; H NMR (600 MHz, CDCl ) ꢀ 7.927
3
1 1
The authors thank Dr. Susumu Teramoto, Faculty of
Science, Kumamoto University, Japan for an authentic
sample of prunetin 4 -O-[b-d-glucopyranoside].
1
0
0
(
1H, s: H-2), 7.418 (2H, d, J=8.8 Hz: H-2 and H-6 ),
.978 (1H, d, J=2.6 Hz: H-8), 6.930 (2H, d, J=8.8 Hz:
0
6
H-3 and H-5 ), 6.634(1H, d, J=2.6 Hz: H-6), 5.332
0
0
0000 00
000
.303 (1H, d, J=0.7 Hz: H-2 ), 5.266 (1H, dd, J=9.5,
(
1H, s: H-2 ), 5.312 (1H, dd, J=9.5, 9.2 Hz: H-3 ),
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7
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.956 (1H, br.s: H-1 ), 4.705 (1H, d, J=12.5 Hz: H-
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0000
000
(
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J=11.0, 2.2 Hz: H-6 a), 3.552 (1H, dd, J=11.0, 7.3 Hz:
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00
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4
(
1
), 151.1 (C: C-5), 102.2 (CH: C-8), 159.9 (C: C-7), 110.2
CH: C-6), 158.7 (C: C-9), 113.6 (C: C-10), 123.9 (C: C-
0
0 0 0 0
), 130.5 (CH: C-2 (6 )), 114.7 (CH: C-3 (5 )), 159.8 (C:
0
00
00
C-4 ), 98.3 (CH: C-1 ), 71.1 (CH: C-2 ), 72.78 (CH: C-
00
00 00 00
), 68.6 (CH: C-4 ), 73.8 (CH: C-5 ), 66.3 (CH : C-6 ),
2
06.5 (CH: C-1 ), 76.6 (CH: C-2 ), 84.5 (C: C-3 ), 73.2
3
1
000
000
000
0
000
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CH : C-4 ), 67.5 (CH : C-5 ), 106.0 (CH: C-1 ), 76.3
2 2
(
(
(
0
000
0000
0000
CH: C-2 ), 83.3 (C: C-3 ), 72.82 (CH : C-4 ), 63.3
2
0
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CH : C-5 ), 55.4 (CH :-OCH ), 21.2, 20.8, 20.5 (each
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1
3
3
3
70.6, 170.3, 169.9, 169.77, 169.76, 169.5, 169.3, 169.29,
+
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3
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5
0
57 27
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5
. Acid-catalyzed hydrolysis of 1
Compound 1 (13 mg) was heated in 1 ml of 2 MHCl
ꢁ
at 100 C for 2 h. The reaction mixture was evaporated