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Anonaine

Reference work entry

CAS Registry Number: 1862-41-5 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids – Aporphine Alkaloids

Biological sources: Liriodendron tulipiferum, Magnolia grandiflora, M. kobus, M. soulangeana, Roemeria refracta

C17H15NO2: 265.1103

Mp: 122–123°C (Et2O), 277°C (dec., hydrochloride) [1]; 270°C (dec., hydrochloride, H2O) [2], 231–233°C (N-Ac) [3]

[α]D −52° (CHCl3) [1], −56° (c 0.15, CHCl3) [2]

UV: 234, 272, 315 (4.12, 4.20, 3.53) [2]

IR: 1040, 945 [2]

MSm/z: 265(M+), 264, 250, 236, 235, 132.5 (++) [2]

1H NMR: 1.84(NH), 5.82, 5.96(each 1H, d, J = 1.5, CH2O2), 6.54(1H, s, H-3), 7.05–8.00(3H, m), 8.00(1H, m, H-11) [2]

13 C NMR: [ 4]

Table 1

C-1

142.5

C-7

37.4

 1a

116.3

 7a

135.4

2

146.8

8

127.0*

3

108.0

9

127.1*

4

29.6

10

127.5*

4a

128.7

11

128.1*

5

43.6

11a

131.4

6a

53.6

OCH2O

100.6

References

  1. 1.
    R. Shakirov, M.V. Telezhenetskaya, I.A. Bessonova, S.F. Aripova, I.A. Israilov, M.N. Sultankhodzhaev, V.I. Vinogradova, V.I. Akhmedzhanova, T.S. Tulyaganov, B.T. Salimov, V.A. Tel’nov, Chem. Nat. Comp. 32, 216 (1996)Google Scholar
  2. 2.
    S.R. Johns, J.A. Lamberton, A.A. Sioumis, Aust. J. Chem. 21, 1383 (1968)Google Scholar
  3. 3.
    A. Urzua, B.K. Cassels, Phytochemistry 21, 773 (1982)Google Scholar
  4. 4.
    H. Guinaudeau, M. Leboeuf, A. Cave, J. Nat. Prod. 42, 325 (1979)Google Scholar
  5. 5.
    F.S. Sadritdinov, A.G. Kurmukov, The Pharmacology of the Plant Alkaloids and Their Use in Medicine [in Russian] (UzSSR, Tashkent, 1980), p. 200Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

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