Formation of water-soluble vitamin derivatives from lipophilic vitamins by cultured plant cells

Tetrahedron Letters

Volumn 47, Issue 16, 2006, Pages 2695-2698

  Shimoda, Kei ^a   Kondo, Yoko ^b   Abe, Koichi ^c   Hamada, Hatsuyuki ^d   Hamada, Hiroki ^b  

^a OITA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^c EISAI CO LTD   (Japan)

^d NATIONAL INSTITUTE OF FITNESS AND SPORTS IN KANOYA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,5,7,8 TETRAMETHYL 2 (4 METHYLPENTYL) 6 CHROMANOL; 2,5,7,8 TETRAMETHYL 2 (4 METHYLPENTYL)CHROMAN 6 YL 6 O BETA D GLUCOPYRANOSYL BETA D GLUCOPYRANOSIDE; 2,5,7,8 TETRAMETHYL 2 (4 METHYLPENTYL)CHROMAN 6 YL BETA D GLUCOPYRANOSIDE; 2,5,7,8 TETRAMETHYL 2 (4,8 DIMETHYLNONYL)CHROMAN 6 YL BETA D GLUCOPYRANOSIDE; 2,5,7,8 TETRAMETHYL 2 (4,8 METHYLPENTYL) 6 CHROMANOL; 2,5,7,8 TETRAMETHYL 2 (4,8 METHYLPENTYL)CHROMAN 6 YL 6 O BETA D GLUCOPYRANOSYL BETA D GLUCOPYRANOSIDE; 2,5,7,8 TETRAMETHYL 2 (4,8,12 METHYLPENTYL) 6 CHROMANOL; 2,5,7,8 TETRAMETHYL 2 (4,8,12 TRIMETHYLTRIDECYL)CHROMAN 6 YL BETA D GLUCOPYRANOSIDE; ALPHA TOCOPHEROL; CHROMAN DERIVATIVE; PYRANOSIDE; RETINOL; UNCLASSIFIED DRUG; VITAMIN;

ARTICLE; CATHARANTHUS ROSEUS; DRUG ISOLATION; DRUG STRUCTURE; GLYCOSYLATION; LIPOPHILICITY; PLANT CELL CULTURE; POKEWEED;

CATHARANTHUS ROSEUS; PHYTOLACCA AMERICANA; PHYTOLACCACEAE;

EID: 33644975753     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.082     Document Type: Article

References (19)

1. M.L. Chiswick, J. Wynn, and N. Toner Ann. N. Y. Acad. Sci. 393 1982 109
2. G.S. Omenn, G.E. Goodman, M.D. Thornquist, J. Balmes, M.R. Cullen, A. Glass, J.P. Koegh, F.L. Meyskens, B. Valanis, J.H. Williams, S. Barnhart, and S. Hammar N. Engl. J. Med. 334 1996 1150
3. T. Miyakoshi, and A. Numata Yukagaku 43 1994 31
4. M. Lahmann, and J. Thiem Carbohydr. Res. 299 1997 23
5. R.K. Uhrig, M.A. Picard, K. Beyreuther, and M. Wiessler Carbohydr. Res. 325 2000 72
6. S. Witkowski, and P. Walejko Z. Naturforsch. 57b 2002 571
7. A.B. Barua, and J.A. Olson Int. J. Vitam. Nutr. Res. 62 1992 298
8. H. Hamada, R. Tomi, Y. Asada, and T. Furuya Tetrahedron Lett. 43 2002 4087
9. Y. Kondo, K. Shimoda, J. Takimura, H. Hamada, and H. Hamada Chem. Lett. 35 2006 324
10. H. Hamada, K. Nishida, T. Furuya, K. Ishihara, and N. Nakajima J. Mol. Catal. B: Enzymatic 16 2001 115
11. H. Hamada, Y. Fuchikami, Y. Ikematsu, T. Hirata, H. Williams, and A.I. Scott Phytochemistry 37 1994 1037
12. 13 Substrate 3 (RRR form) was purchased from Sigma-Aldrich Co.
13. Matsui, M.; Yamamoto, T. Jpn. Patent 292495, 1994.
14. Chem. Abstr. 125 13 1996 168389g
15. 3OD): δ 12.1 (C-10), 13.2 (C-12), 14.1 (C-11), 20.1 (C-23), 21.6 (C-3), 22.0 (C-16), 23.0, 23.1 (C-22, C-24), 24.1 (C-13), 25.8 (C-21), 29.1 (C-17), 30.7 (C-2), 33.8, 38.2, 38.6, 40.5, 40.8 (C-14, C-15, C-18, C-19, C-20), 62.7 (C-6″), 70.2 (C-6′), 71.5 (C-4″), 71.6 (C-4′), 74.9 (C-2″), 75.7 (C-1, C-2′), 76.8, 77.7, 77.8 (C-3′, C-3″, C-5′, C-5″), 104.4 (C-1″), 105.7 (C-1′), 118.4 (C-4), 123.3 (C-5), 127.7 (C-7), 129.7 (C-8), 147.0 (C-6), 149.1 (C-9).
16. J. Mastelic, I. Jerkovic, M. Vinkovic, Z. Dzolic, and D. Vikic-Topic Croat. Chem. Acta 77 2004 491
17. 17 method on the 15th day. The results were expressed as average of plasma IgE level of five rats administered a total of 10 mg/kg of each glycoside.
18. A. Koda, T. Miura, N. Inagaki, O. Sakamoto, A. Arimura, H. Nagai, and H. Mori Int. Arch. Allergy. Appl. Immunol. 92 1990 209
19. The suppressive action of β-glucosides of vitamin E and its homologues on IgE antibody formation, that is, 5 (184 of average of plasma IgE level), 6 (170), and 7 (195), was stronger than that of hydrocortisone (341). The results for β-gentiobiosides of vitamin E homologues 8 and 9, and retinyl β-glucoside 10 were 366, 353, and 372, respectively.