Essential structure of co-pigment for blue sepal-color development of hydrangea

Tetrahedron Letters

Volumn 46, Issue 39, 2005, Pages 6645-6649

  Kondo, Tadao ^a   Toyama Kato, Yuki ^a   Yoshida, Kumi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Al complex; Blue sepal color development; Co pigment; Hydrangea macrophylla; Synthesis of quinic acid derivatives

Indexed keywords

ALUMINUM; AROMATIC COMPOUND; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; HYDROXYL GROUP; PIGMENT;

ARTICLE; CHEMICAL STRUCTURE; COLOR; HYDRANGEA; HYDROPHOBICITY; IN VITRO STUDY; MOLECULAR INTERACTION; NONHUMAN; PH; REPRODUCIBILITY; SYNTHESIS;

HYDRANGEA; HYDRANGEA MACROPHYLLA;

EID: 23944526297     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.146     Document Type: Article

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18. 3OD, 600 MHz) δ 1.98 (dd, J = 11.0, 14.0 Hz, 1H), 2.14 (m, 1H), 2.16 (m, 1H), 2.28 (dd, J = 3.0, 15.0 Hz, 1H), 3.81 (dd, J = 3.0, 9.0 Hz, 1H), 4.22 (ddd, J = 4.0, 9.0, 11.0 Hz, 1H), 5.44 (q, J = 3.0 Hz, 1H), 6.47 (d, J = 16.0 Hz, 1H), 6.99 (d, J = 8.0 Hz, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.24 (s, 1H), 7.69 (d, J = 16.0, 1H).
19. Compound 2 was synthesized by Sefkow et al. using the similar synthetic route M. Sefkow, A. Kelling, and U. Schilde Eur. J. Org. Chem. 14 2001 2735 2742
20. During the deprotection reaction in aqueous acidic solution 5-O-acyl moiety was hydrolyzed simultaneously, therefore the reaction was low yield.
21. 2/Pd-C gave 10 in quantitative yield.
22. 3I/DMF. After desilylation with TBAF (16, 32%) the compound was acylated by treatment of cinnamoyl chloride, then deprotected to give 11 (11%).
23. 1,6ax = 12.5 Hz).
24. 2 (71%).
25. Y. Toyama-Kato, K. Yoshida, E. Fujimori, H. Haraguchi, Y. Shimizu, and T. Kondo Biochem. Eng. J. 14 2003 237 241
26. 3+ were mixed in 0.1 M acetate buffer at pH 4.0 at their final concentration to be 1 mM, 3 mM, 1 mM, respectively, then UV-vis spectrum and CD were recorded (cell length: 1 mm).
27. The precipitate was gathered by centrifugation, and the mass was washed with a small portion of ultra-pure water and dried under reduced pressure. The quantitative analysis of 1 and 4 by HPLC and Al by graphite furnace atomic absorption spectroscopy, respectively, showed that the mass was composed with 1 and Al. Compound 4 was not detected.
28. 1H: 600 MHz, at 25°C). The signal broadening may be caused by generation of phenoxy radical at the B-ring of 1.
29. 3+. These mixture gave precipitates gradually. Because of the low co-pigment effect of 8 and 10, small amount of blue hydrangea pigment may co-exist with self-associated 1.
30. 5,6ax = 10.0 Hz). The lack of co-pigmentation effect of 12 may be due to the difference of the conformation.