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Baptifoline (13-Hydroxyanagyrine)

Reference work entry

CAS Registry Number: 732-50-3 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinolizidine Alkaloids

Biological sources: Sophora alopecuroides, S. flavescens

C15H20N2O2: 260.1525

Mp: 210°C (Me2CO), 256°C (hydrochloride), 145°C (picrate) [1]

[α]D −149° (c 0.243, EtOH) [1]

UV: 233, 309(3.84, 3.91) [2]

IR: 3610, 3360, 3010, 2990, 2890, 2810, 1650, 1565, 1550, 1472, 1460, 1442, 1428, 1379, 1358, 1331, 1315, 1288, 1270, 1175, 1160, 1148, 1118, 1103, 1080, 1070, 1040, 1020, 1003, 990, 962, 941, 930, 910, 899, 890, 862, 852, 830 [2]

MSm/z: 260(M+, 27), 241(4), 160(13), 146(27), 145(11), 114(100), 96(31), 70(37), 43(33) [1, 3]

1H NMR(CDCl3): 1.25(1H, br d, J = 14, Hβ-12), 1.31(1H, br d, J = 13.5, Hβ-14), 1.67(1H, br d, J = 13, H-8R), 1.85(1H, dt, J = 13.5, 13.5, 2, Hα-14), 1.97(1H, br d, J = 13, H-8S), 2.08(1H, m, H-9), 2.10(1H, br dt, J = 14, 2.5, Hα-12), 2.37(1H, br d, J = 14, Hα-15), 2.45(1H, br d, J = 10.7, Hβ-17), 2.95(1H, m, H-7),...

References

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    T.E. Monakhova, N.F. Proskurnina, O.N. Tolkachev, V.S. Kabanov, M.E. Perel’son, Chem. Nat. Comp. 9, 52 (1973)CrossRefGoogle Scholar
  2. 2.
    J. Holubek, O. Strouf, Spectral Data and Physical Constants of Alkaloids (Prague Publishing House, Czechoslovak Academy of Sciences/Heyden & Son Ltd, London, 1970), 5, No. 614Google Scholar
  3. 3.
    S.W. Pelletier (ed.), Alkaloids, Chemical and Biological Perspectives, vol. 2 (Wiley, New York, 1984), p. 105Google Scholar
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    E.J. Kennelly, T.J. Flynn, E.P. Mazzola, J.A. Roach, T.G. McCloud, D.E. Danfold, J.M. Bets, J. Nat. Prod. 62, 1385 (1999)CrossRefGoogle Scholar
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    A.L. Sagen, J. Gertsch, R. Becker, J. Heilmann, O. Sticher, Phytochemistry 61, 975 (2002)CrossRefGoogle Scholar
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    A. Ueno, K. Morinaga, S. Fukushima, S. Okuda, Chem. Pharm. Bull. 26, 1832 (1978)CrossRefGoogle Scholar

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