Effective conversion of three diacetyl-C-(β-D-glycopyranosyl) phloroglucinols to spiroketal derivatives by refluxing in water

Journal of Carbohydrate Chemistry

Volumn 27, Issue 2, 2008, Pages 86-102

  Sato, Shingo ^a   Miura, Masahiro ^a   Sekito, Takashi ^a   Kumazawa, Toshihiro ^a  

^a YAMAGATA UNIVERSITY   (Japan)

Author keywords

Diacetylphloroglucinol C D glycopyranoside; Kinetic controlled product; Spiro(benzofuran 2H furan); Spiro(benzofuran 2H pyran); Thermodynamic controlled product

Indexed keywords

EID: 45849122506     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300802030811     Document Type: Article

References (24)

1. (a) Nakatsuka, T.; Tomimori, Y.; Fukuda, Y.; Nukaya, H. First total synthesis of structurally unique flavonoids and their strong anti-inflammatory effect. Bioorg. Med. Chem. Lett. 2004, 14, 3201-3203;
2. (b) Furuta, T.; Kimura, T.; Kondo, S.; Mihara, H.; Wakimoto, T.; Nukaya, H.; Tsuji, K.; Tanaka, K. Concise total synthesis of flavones C-glycoside having potent anti-inflammatory activity. Tetrahedron 2004, 60, 9375-9379.
3. Zhang, P.-C.; Xu, S.-X. Flavonoid ketohexosefuranosides from the leaves of Crataegus pinnatifida Bge. Var. major N.E.Br. Phytochemistry 2001, 57, 1249-1253.
4. Takahashi, Y.; Miyasaka, N.; Tasaka, S.; Miura, I.; Urano, S.; Ikura, M.; Hikichi, K.; Matsumoto, T. Wada, Constitution of coloring matters in the flower petals of Carthamus tinctorius L. M. Tetrahedron Lett. 1982, 23, 5163-5166.
5. (a) Zavodnik, L.B. Antioxidant and radioprotective effect. Radiats Biol. Radioecol. 2003, 43 (4), 432-438;
6. (b) Kawaguchi, K.; Melloalves, S.; Watanabe, T.; Kikuchi, S.; Satake, M.; Kumazawa, Y. Colony stimulating factor-inducing activity of isoflavone C-glucosides from the bark of Dalbergia monetaria. Planta Med. 1998, 329, 855-859;
7. (c) Ricketts, M.-L.; Moore, D.D.; Banz, W.J.; Mezei, O.; Shay, N.F. Molecular mechanisms of action of the soy isoflavones includes activation of promiscuous nuclear receptors. J. Nutr. Biochem. 2005, 16, 321-330;
8. (d) Kulling, S.E.; Lehmann, L.; Metzler, M. Oxidative metabolism and genotoxic potential of major isoflavone phytoestrogens. J. Chromatgr. B 2002, 777, 211-218;
9. (e) Zavodnik, L.B.; Zavodnik, I.B.; Lapshina, E.A.; Shkodich, A.P.; Bryszewska, M.; Buko, V.V. Inhibition of the HOCl-dependent damage of erythrocyte. Biochemistry (Mosc.) 2000, 65 (8), 946-951;
10. (f) Lin, R.C.; Li, T.K. Suppression of alcohol drinking in alcohol preferring rats, high alcohol drinking rats, and monkeys. Am. J. Clin. Nutr. 1998, 68 (6 Suppl), 1512S;
11. (g) Matsubara, Y.; Suekuni, H.; Honda, S.; Kakehi, K.; Murakami, T.; Okamoto, K.; Miyake, H. Hypotensive substances in citrus fruit peels. Jpn. Heart J. 1980, 21, 583;
12. (h) Iizuka, Y.; Murakami, T.; Matsubara, Y.; Yokoi, K.; Okamoto, K.; Miyake, H.; Honda, S.; Kakehi, K. Isolation and identification of hypotensive substances in chlorella extract. Jpn. Heart J. 1980, 21, 584;
13. (i) Kumamoto, H.; Matsubara, Y.; Iizuka, Y.; Okamoto, K.; Yokoi, K. Structure and hypotensive effect of flavonoid glycosides in orange (Citrus sinensis OSBECK) peelings. Agric. Biol. Chem. 1986, 50, 781;
14. (j) Matsubara, Y.; Sawabe, A. Biologically active compounds in citrus fruit peels. J. Synth. Org. Chem. Jpn. 1994, 52, 318-327;
15. (k) Kawasaki, M.; Hayashi, T.; Arisawa, M.; Morita, N.; Berganza, L.H. 8-hydroxytricetin 7-glucuronide, a β-glucuronidase inhibitor from Scoparia dulcis. Phytochemistry 1988, 27, 3709-3711;
16. (l) Ohsugi, T.; Nishida, R.; Fukami, H. Oviposition stimulant of Papilio xuthus, a citrus-feeding swallowtail butterfly. Agric. Biol. Chem. 1985, 49, 1897-1900;
17. (m) Basile, A.; Sorbo, S.; Lopez-Saez, J.A.; Cobianchi, R.C. Effects of seven pure flavonoids from mosses on germination and growth of Tortula muralis HEDW. (bryophyte) and Raphanus satires L. (magnoliophyta). Phytochemistry 2003, 62, 1145-1152.
18. (a) Rubio, E.M.; Gracia-Moreno, M.I.; Balbuena, P.; Mellet, C.O.; Garcia Fernandez, J.M. Rigid spacer-mediated synthesis of bis-spiroketal ring systems: stereoselective synthesis of nonsymmetrical spiro disaccharides. Org. Lett. 2005, 7 (4), 729-731;
19. 2-symmetric difructose dianhydrides. J. Org. Chem. 2006, 71, 2257-2266.
20. (c) For review: Manley-Harris, M.; Richards, G.N. Dihexulose dianhydrides. Adv. Carbohydr. Chem. Biochem. 1997, 52, 207-266.
21. (a) Kumazawa, T.; Ashahi, N.; Matsuba, S.; Sato, S.; Onodera, J.-i. Conversion of β-D-C-glucopyranosylphloroacetophenone to a spiroketal compound. Carbohydr. Res. 1998, 308, 213-216;
22. (b) Kumazawa, T.; Chiba, M.; Matsuba, S.; Sato, S.; Onodera, J.-i. The conversion of 3-C-β-D-galactopyranosylphloroacetophenone to a spiroketal derivative. Carbohydr. Res. 2000, 328, 599-603.
23. Sato, S.; Kumazawa, T.; Watanabe, K.; Matsuba, S.; Onodera, J.-i. Conversion of diacetyl-C-(β-D-glucopyranosyl)phloroglucinol to spiroketal compounds. Carbohydr. Res. 2004, 339, 429-433.
24. - and di-C-glucosylflavonoids. Carbohydr. Res. 2004, 339, 2611-2614.