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Volumn 8, Issue 16, 2006, Pages 3609-3612

Novel and efficient synthesis of cyanidin 3-O-β-D-glucoside from (+)-catechin via a flav-3-en-3-ol as a key intermediate

Author keywords

[No Author keywords available]

Indexed keywords

ANTHOCYANIN; CATECHIN; CYANIDIN 3 O GLUCOSIDE; CYANIDIN 3-O-GLUCOSIDE; GLUCOSIDE;

EID: 33747311409     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0614976     Document Type: Article
Times cited : (27)

References (40)
  • 4
    • 33747243156 scopus 로고    scopus 로고
    • 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
  • 6
    • 0000678144 scopus 로고
    • 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 scopus 로고
    • Robinson, R. Ber. 1934, 67A, 85-105.
    • (1934) Ber. , vol.67 , pp. 85-105
    • Robinson, R.1
  • 12
    • 0029024455 scopus 로고
    • (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
  • 14
    • 33646263017 scopus 로고    scopus 로고
    • 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
  • 18
    • 0342395016 scopus 로고
    • 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
  • 31
    • 33747265572 scopus 로고    scopus 로고
    • note
    • 3,4 = 3.5 Hz.
  • 32
    • 33747221577 scopus 로고    scopus 로고
    • note
    • 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.
  • 37
    • 33747207937 scopus 로고    scopus 로고
    • note
    • 1a
  • 38
    • 33747297300 scopus 로고    scopus 로고
    • note
    • 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.
  • 39
    • 33747246081 scopus 로고    scopus 로고
    • note
    • max 280 nm).
  • 40
    • 33747305572 scopus 로고    scopus 로고
    • note
    • 9c


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.