Quercetin Glucosides in Flower Buds of Japanese Butterbur
1575
Measurement of the quercetin glucosides in the
329–332 (1999).
5) Zapesochnaya, G. G., Ivanova, S. Z., Medvedeva, S.
A., and Tyukavkina, N. A., -acylated ‰avonoid
‰
ower buds. Before puriˆcation, quercetin 4
?-
O
-b- -
D
O
glucoside (5), which had been isolated from fruits of
glycosides from Pinus silvestris needles. Khim. Prir.
Soedin., 2, 193–196 (1978).
onion and identiˆed by comparing the spectral data
1
7)
with those reported, was added as an internal stan-
dard. Each portion of the roughly puriˆed extract of
6
)
Tournaire, C., Croux, S., Maurette, M. T., Beck, I.,
Hocquaux, M., Braun, A. M., and Oliveros, E., An-
Frs. A and B (10 mg fr. wt. equivalent, Fig. 4) was
tioxidant activity of ‰avonoids: E‹ciency of singlet
analyzed by HPLC. The HPLC system (Hitachi) for
the measurement consisted of L-7100 pump (‰ow
1
oxygen (
g
D ) quenching, J. Photochem. Photobiol.
B
,, Biology 19, 205–215 (1993).
rate: 1.2 ml min), L-7300 column oven (tempera-
W
7) Masuda, T., Iritani, S., Yonemori, S., Oyama, Y.,
and Takeda, Y., Isolation and antioxidant activity of
galloyl ‰avonol glycosides from the seashore plant
Pemphis acidula. Biosci. Biotechnol. Biochem., 65,
ture: 40
detector. The column (Kanto Chem., Mightysil
RP-18 GP Aqua, 4.6 250 mm) was eluted with a
mixed solvent of 80 aq. MeOH (solvent A) and
9C ), L-7200 auto-sampler and L-7455 DAD
×
z
1
302–1309 (2001).
8
)
Ohnishi, M., Morishita, H., Toda, S., Yase, Y., and
Kido, R., Inhibition of in vitro linoleic acid peroxida-
tion and hemolysis by caŠeoyltryptophan. Phytoche-
mistry, 47, 1215–1218 (1998).
H O (solvent B), using a linear gradient with the ‰ow
2
rate of 1.2 ml min. The combination of A and B was
W
linearly converted from 0 min to 15 min, 7:3 to 8:2:
from 15 min to 23 min, 8:2 to 8:2: from 23 min to
9
)
Ohnishi, M., Morishita, H., Iwahashi, H., Toda, S.,
Shiratake, Y., Kimura, M., and Kido, R., Inhibitory
eŠects of the chlorogenic acids on linoleic acid peroxi-
dation and hemolysis. Phytochemistry, 36, 579–583
(1994).
2
5 min, 8:2 to 1:0. The typical retention times for
3
?
,4
?
O
,5,7-
-tetraacetylglucopyranoside (6),
tetraacetylquercetin 4 -2 ,3 ,4
O
-tetraacetylquercetin 3-
O
-
b
-
D
-2
!
, 3
!
, 4
!
,
6
!-
3
?
,3,5,7-
O
O
-
?-
O
-
b
-
D
!
!
!
,6
!
-
-tetraa-
cetylglucoside (7) and decaacetylrutin (8) were 15.63,
8.80 and 20.19 min, respectively. These acetylated
10) Faure, M., Lissi, E., Torres, R., and Videla, L. A.,
Antioxidant activities of lignans and ‰avonoids.
Phytochemistry, 29, 3773–3775 (1990).
1
compounds were synthesized from each corre-
sponding compound by treating it with a mixture of
pyridine and acetic anhydride, and the structures
1
1) Nagai, T., Miyaichi, Y., Tomimori, T., Suzuki, Y.,
and Yamada, H., Inhibition of in‰uenza virus siali-
dase and anti-in‰uenza virus activity by plant ‰avo-
noids. Chem. Pharm. Bull., 38, 1329–1332 (1990).
2) Iio, M., Ishimoto, S., Nishida, Y., Shiremizu, T.,
and Yumoki, H., EŠects of baicalein, a ‰avonoid,
and other anti-in‰ammatory agents on glyoxalase-I
activity. Agric. Biol. Chem., 50, 1073–1074 (1986).
1
were conˆrmed by H-NMR and FDMS spectra.
1
Acknowledgments
The authors thank Mr. Kenji Watanabe and Dr.
Eri Fukusi for FDMS and 2D-NMR measurements,
and Mr. Mitsuo Sakurai and Ms. Namie Suzuki,
Hokkaido Ashoro town o‹ce, for helping us to col-
lect the samples.
13) Kimura, Y., Kubo, M., Tani, T., Arichi, S.,
Ohminami, H., and Okuda, H., Studies on Scutellar-
iae radix. III. EŠects on lipid metabolism in serum,
liver and fat cells of rats. Chem. Pharm. Bull., 29,
2
308–2312 (1981).
1
1
1
4) Suolinna, E. M., Buchsbaum, R. N., and Racker, E.,
EŠect of ‰avonoids on aerobic glycolysis and growth
of tumor cells. Cancer Res., 35, 1865–1872 (1975).
5) Harborne, J. B. and Williams, C. A., Advances in
References
1
2
3
)
)
)
Frankel, E. N., Kanner, J., German, J. B., Parks, E.,
and Kinsella, J. E., Inhibition of oxidation of human
low-density lipoproteins by phenolic substances in red
wine. Lancet, 341, 454–457 (1993).
Kinsella, J. E., Frankel, E. N., German, J. B., and
Kanner, J., Possible mechanisms for the protective
role of antioxidants in wine and plant foods. Food
Technol., 47, 85–89 (1993).
‰
avonoids research since 1992. Phytochemistry, 55,
4
81–504 (2000).
6) Hirano, I., Mori, H., Yamada, K., Hirata, Y., Haga,
M., Tatematsu, H., and Kanie, S., Carcinogenic
activity of petasitenine, a new pyrrolizidine alkaloid
isolated from Petasites japonicus Maxim. J. Natl.
Cancer Inst., 58, 1155–1157 (1977).
Yamaguchi, T., Takamura, H., Matoba, T., and
Terao, J., HPLC method for evaluation of the
free-radical scavenging activity of foods by using
1
7) Price, R. K. and Rhodes, M. J., Analysis of the
major ‰avonol glycosides present in four varieties of
onion (Allium cepa) and changes in composition
resulting from autolysis. J. Sci. Food Agric., 74,
1
,1-diphenyl-2-picrylhydrazyl. Biosci. Biotechnol.
Biochem., 62, 1201–1204 (1998).
Beck, M. A. and Haberlein, H., Flavonol glycosides
from Escholtzia californica. Phytochemistry, 50,
3
31–339 (1997).
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)
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