Chelidonine

Reference work entry

CAS Registry Number: 476-32-4 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids

Biological sources: Chelidonium majus, Glaucium elegans, G. squamigerum

C20H19NO5: 353.1263

Mp: 135–136°C (EtOH) [1]

[α]D +115° (EtOH) [1]

UV: 206, 238, 289 [1]

IR(CHCl3): 3210, 3206 [1]

MSm/z: 353(M+), 352, 336, 335(100) [1]

1H NMR: 2.27(3H, s, NCH3), 2.98(1H, m), 3.08, 3.20(each 1H, d, J = 17.5), 3.43, 4.08(each 1H, d, J = 15.5), 3.57(1H, br s), 4.23(1H, br s, W1/2 = 7.9), 5.93, 5.94(each 1H, d, J = 1.5, CH2O2), 5.95, 5.99(each 1H, d, J = 1.5, CH2O2), 6.64, 6.66(each 1H, s, H-1, H-4), 6.73, 6.76(each 1H, d, J = 7.9, H-11, H-12) [2]

13 C NMR: [ 3]

Table 1

C-1

111.9

C-6

72.4

C-11

109.6

1a

128.9

6a

42.1

12

120.4

2

145.6

7a

62.9

12a

131.4

3

145.3

8

53.9

NCH3

42.4

4

107.4

9

143.1

2,3-CH2O2

101.1

4a

125.8

10

148.2

7,8-CH2O2

101.4

5

39.7

       

References

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  2. 2.
    M. Cushman, T.C. Choong, Heterocycles 14, 1935 (1980)Google Scholar
  3. 3.
    N. Takao, K. Iwasa, M. Kamigauchi, M. Sugiura, Chem. Pharm. Bull. 26, 1880 (1978)Google Scholar
  4. 4.
    N. Takao, N. Bessho, M. Kamigauchi, K. Iwasa, K. Tomita, T. Fujiwara, S. Fujii, Tetrahedron Lett. 20, 495 (1979)Google Scholar
  5. 5.
    H. Liang-Feng, W. Nowicky, V. Gutmann, J. Chromatogr. 543, 123 (1991)Google Scholar
  6. 6.
    F.S. Sadritdinov, A.G. Kurmukov, The Pharmacology of the Plant Alkaloids and Their Use in Medicine [in Russian] (UzSSR, Tashkent, 1980), p. 228Google Scholar

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