-
1
-
-
33751137605
-
-
(a) Goto, T.; Kondo, T. Angew. Chem., Int. Ed. Engl. 1991, 30, 17-33.
-
(1991)
Angew. Chem., Int. Ed. Engl.
, vol.30
, pp. 17-33
-
-
Goto, T.1
Kondo, T.2
-
3
-
-
33744953132
-
-
Anderson, O. M., Markham, K. R., Eds.; CRC Press: Boca Raton
-
(c) Anderson, O. M.; Jordheim, M. In Flavonoids Chemistry, Biochemistry and Applications; Anderson, O. M., Markham, K. R., Eds.; CRC Press: Boca Raton, 2006; pp 471-551.
-
(2006)
Flavonoids Chemistry, Biochemistry and Applications
, pp. 471-551
-
-
Anderson, O.M.1
Jordheim, M.2
-
4
-
-
33747243156
-
-
Davis, K., Ed.; Annual Plant Reviews; CRC Press: Boca Raton
-
Lila, M. A. In Plant Pigments and their Manipulation; Davis, K., Ed.; Annual Plant Reviews; CRC Press: Boca Raton, 2004; Vol 14., pp 248-274.
-
(2004)
Plant Pigments and Their Manipulation
, vol.14
, pp. 248-274
-
-
Lila, M.A.1
-
5
-
-
0031556680
-
-
Cherepy, N. J.; Smestad, G. P.; Grätzel, M.; Zhang, J. Z. J. Phys. Chem. B 1997, 101, 9342-9351.
-
(1997)
J. Phys. Chem. B
, vol.101
, pp. 9342-9351
-
-
Cherepy, N.J.1
Smestad, G.P.2
Grätzel, M.3
Zhang, J.Z.4
-
6
-
-
0000678144
-
-
For a review of the chemical synthesis of anthocyanins: Iacobucci, G. A.; Sweeny, J. G. Tetrahedron 1983, 39, 3005-3038.
-
(1983)
Tetrahedron
, vol.39
, pp. 3005-3038
-
-
Iacobucci, G.A.1
Sweeny, J.G.2
-
9
-
-
33747308863
-
-
Robinson, R. Ber. 1934, 67A, 85-105.
-
(1934)
Ber.
, vol.67
, pp. 85-105
-
-
Robinson, R.1
-
10
-
-
0000653427
-
-
(a) Shibata, K.; Shibata, Y.; Kasiwagi, I. J. Am. Chem. Soc. 1919, 41, 208-220.
-
(1919)
J. Am. Chem. Soc.
, vol.41
, pp. 208-220
-
-
Shibata, K.1
Shibata, Y.2
Kasiwagi, I.3
-
11
-
-
33747232264
-
-
(b) Krishnamurty, H. G.; Krishnamoorthy, V.; Seshadri, T. R. Phytochemistry 1963, 2, 47-60.
-
(1963)
Phytochemistry
, vol.2
, pp. 47-60
-
-
Krishnamurty, H.G.1
Krishnamoorthy, V.2
Seshadri, T.R.3
-
12
-
-
0029024455
-
-
(c) Elhabiri, M.; Figueiredo, P.; Fougerousse, A.; Brouillard, R. Tetrahedron Lett. 1995, 36, 4611-4614. Elhabiri et al. reported the yield was 60%. However, we reexamined the reduction of rutin under HCl-MeOH with zinc amalgam, zinc powder, or magnesium powder to obtain cyanidin 3-O-rutinoside in less than 30% yield at the optimized condition. This might be due to the fact that the value of the molar absorption coefficients for cyanidin 3-O-rutinoside reported by Elhabiri et al. (7000 at 510 nm) is too low compared to the theoretical value (around 20 000 in our results); therefore, they miscalculated the yield.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 4611-4614
-
-
Elhabiri, M.1
Figueiredo, P.2
Fougerousse, A.3
Brouillard, R.4
-
13
-
-
0000206283
-
-
Harborne, J. B., Ed.; Chapman & Hall: London
-
(a) Heller, W.; Forkmann, G. In The Flavonoids Advances in Research since 1986; Harborne, J. B., Ed.; Chapman & Hall: London, 1994; pp 499-535.
-
(1994)
The Flavonoids Advances in Research since 1986
, pp. 499-535
-
-
Heller, W.1
Forkmann, G.2
-
14
-
-
33646263017
-
-
Davis, K., Ed.; Annual Plant Reviews, CRC Press: Boca Raton
-
(b) Schwinn, K. E.; Davies, K. M. In Plant Pigments and their Manipulation; Davis, K., Ed.; Annual Plant Reviews, CRC Press: Boca Raton, 2004; Vol 14. pp 92-149.
-
(2004)
Plant Pigments and Their Manipulation
, vol.14
, pp. 92-149
-
-
Schwinn, K.E.1
Davies, K.M.2
-
15
-
-
85056430639
-
-
Anderson, O. M., Markham, K. R., Eds.; CRC Press: Boca Raton
-
(c) Davies, K. M.; Schwinn, K. E. In Flavonoids Chemistry, Biochemistry and Applications; Anderson, O. M., Markham, K. R., Eds.; CRC Press: Boca Raton, 2006; pp 143-218.
-
(2006)
Flavonoids Chemistry, Biochemistry and Applications
, pp. 143-218
-
-
Davies, K.M.1
Schwinn, K.E.2
-
16
-
-
0035854832
-
-
(d) Nakajima, J.; Tanaka, Y.; Yamazaki, M.; Saito, K. J. Biol. Chem. 2001, 276, 25797-25803.
-
(2001)
J. Biol. Chem.
, vol.276
, pp. 25797-25803
-
-
Nakajima, J.1
Tanaka, Y.2
Yamazaki, M.3
Saito, K.4
-
17
-
-
0346463040
-
-
(e) Turnbull, J. J.; Nakajima, J.; Welford, R. W. D.; Yamazaki, M.; Saito, K.; Schofield, C. J. J. Biol. Chem. 2004, 279, 1206-1216.
-
(2004)
J. Biol. Chem.
, vol.279
, pp. 1206-1216
-
-
Turnbull, J.J.1
Nakajima, J.2
Welford, R.W.D.3
Yamazaki, M.4
Saito, K.5
Schofield, C.J.6
-
18
-
-
0342395016
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-
In previous studies, the authors did not isolate anthocyanidins but reported the observation of red coloration or identification of visible absorption spectra using a reaction mixture. All the experiments were conducted with leucoanthocyanidin or flaven-3-ol without any glycosyl residues: (a) Sweeny, J. G.; Iacobucci, G. A. Tetrahedron 1977, 33, 2923-2926.
-
(1977)
Tetrahedron
, vol.33
, pp. 2923-2926
-
-
Sweeny, J.G.1
Iacobucci, G.A.2
-
22
-
-
33747281570
-
-
(b) Hayashi, K.; Abe, Y. Bot. Mag., Tokyo 1955, 68, 299-308.
-
(1955)
Bot. Mag., Tokyo
, vol.68
, pp. 299-308
-
-
Hayashi, K.1
Abe, Y.2
-
23
-
-
0001419018
-
-
(c) Yoshida, K.; Sato, Y.; Okuno, R.; Kameda, K.; Isobe, M.; Kodo, T. Biosci. Biotechnol. Biochem., 1996, 60, 589-593.
-
(1996)
Biosci. Biotechnol. Biochem.
, vol.60
, pp. 589-593
-
-
Yoshida, K.1
Sato, Y.2
Okuno, R.3
Kameda, K.4
Isobe, M.5
Kodo, T.6
-
24
-
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0000550472
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-
Kawamoto, H.; Nakatsubo, F.; Murakami, K. Mokuzai Gakkaishi 1991, 37, 488-493.
-
(1991)
Mokuzai Gakkaishi
, vol.37
, pp. 488-493
-
-
Kawamoto, H.1
Nakatsubo, F.2
Murakami, K.3
-
25
-
-
84985624827
-
-
(a) Schmidt, R. R.; Michel, J. Angew. Chem., Int. Ed. Engl. 1980, 19, 731-732.
-
(1980)
Angew. Chem., Int. Ed. Engl.
, vol.19
, pp. 731-732
-
-
Schmidt, R.R.1
Michel, J.2
-
27
-
-
0000889081
-
-
(a) Steenkamp, J. A.; Ferreira, D.; Roux, D. G. Tetrahedron Lett. 1985, 26, 3045-3048.
-
(1985)
Tetrahedron Lett.
, vol.26
, pp. 3045-3048
-
-
Steenkamp, J.A.1
Ferreira, D.2
Roux, D.G.3
-
28
-
-
0025730858
-
-
(b) Steenkamp, J. A.; Mouton, C. H. L.; Ferreira, D. Tetrahedron 1991, 47, 6705-6716.
-
(1991)
Tetrahedron
, vol.47
, pp. 6705-6716
-
-
Steenkamp, J.A.1
Mouton, C.H.L.2
Ferreira, D.3
-
29
-
-
0037538675
-
-
Tückmantel, W.; Kozikowski, A. P.; Romanczyk, L. J., Jr. J. Am. Chem. Soc. 1999, 121, 12073-12081.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 12073-12081
-
-
Tückmantel, W.1
Kozikowski, A.P.2
Romanczyk Jr., L.J.3
-
30
-
-
0034661916
-
-
(d) Ohmori, K.; Ohrui, H.; Suzuki, K. Tetrahedron Lett. 2000, 41, 5537-5541.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 5537-5541
-
-
Ohmori, K.1
Ohrui, H.2
Suzuki, K.3
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31
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33747265572
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note
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3,4 = 3.5 Hz.
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32
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33747221577
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note
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Develosil ODS-HG-5 column (2.0 mm φ × 250 mm) with linear gradient elution from 10% aqueous to 90% MeCN containing 0.5% TFA; flow rate of 0.2 mL/min, detection with a photodiode array, and a temperature of 40 °C.
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33
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0028030658
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In this reaction, the oxidation to anthocyanin might proceed by a radical process via a phenoxyl radical intermediate: (a) Jovanovic, S. V.; Steenken, S.; Tosic, M.; Marjanovic, B.; Simic, M. G. J. Am. Chem. Soc. 1994, 116, 4846-4851.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 4846-4851
-
-
Jovanovic, S.V.1
Steenken, S.2
Tosic, M.3
Marjanovic, B.4
Simic, M.G.5
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34
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0029888128
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(b) Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Free Radical Biol. Med. 1996, 20, 933-956.
-
(1996)
Free Radical Biol. Med.
, vol.20
, pp. 933-956
-
-
Rice-Evans, C.A.1
Miller, N.J.2
Paganga, G.3
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35
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2242461345
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(c) Cren-Olivé, C.; Hapiot, P.; Pinson, J.; Rolando, C. J. Am. Chem. Soc. 2002, 124, 14027-14038.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 14027-14038
-
-
Cren-Olivé, C.1
Hapiot, P.2
Pinson, J.3
Rolando, C.4
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36
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37049068853
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In general, the phenolic TBS group is relatively stable in acidic conditions, but we found that the TBS group of polyphenols such as flavonoides was deprotected easily from our preliminary experiments: Davies, J. S.; Higginbotham, C. L.; Tremeer, E. J.; Brown, C.; Treadgold, R. C. J. Chem. Soc., Perkin Trans. 1 1992, 3043-3048.
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(1992)
J. Chem. Soc., Perkin Trans. 1
, pp. 3043-3048
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Davies, J.S.1
Higginbotham, C.L.2
Tremeer, E.J.3
Brown, C.4
Treadgold, R.C.5
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37
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33747207937
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note
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1a
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38
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33747297300
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note
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In the case of the deprotection and oxidation of 6, 5% HCl was required. However, the reactions of 9 smoothly proceeded using 1% HCl, and the starting material was completely consumed.
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39
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33747246081
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note
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max 280 nm).
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40
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33747305572
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note
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9c
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