Natural Compounds

2013 Edition
| Editors: Shakhnoza S. Azimova, Ashraf I. Saidkhodzhaev

2β,6α-Diangeloyloxy-5α(H)-dauc-8-ene-4β,10α-diol (Desoxodehydrolaserpitine)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_963

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Daucanes (Carotanes) – Diesters

Biological sources: Laserpitium latifolium L. [1, 2]; Ferula tingitana L. [3]

C25H38O6: 434.2668

Mp: 59–60°C [1]

IR (KBr): 3470, 2960, 1690, 1640, 1450, 1380, 1350, 1250, 1230, 1170, 1080, 1040, 980, 950, 850, 750 [1, 3]

1H NMR (200 MHz, CDCl3): 0.92 (3H, d, J = 7, H-12), 0.98 (3H, d, J = 7, H-13), 1.20 (3H, s, H-14), 1.3–2.9 (5H, m, H-3, H-7, H-5), 1.82 (3H, br s, H-15), 3.7 (1H, d, J = 7, H-10), 5.04 (1H, dd, J = 8; 10, H-2), 5.38 (1H, dt, J = 3; 10, H-6), 5.7 (1H, br d, J = 8, H-9); 2 × OAng: 1.88 (6H, t, J = 1, H-5′, H-5″), 2.00 (6H, tt, J = 1; 7, H-4′, H-4″), 6.13 (2H, br q, J = 7; 10, H-3′, H-3″) [3]

13 C NMR (22.6 MHz, CDCl 3) [ 3]:

Table 1

C-1

46.3 s

C-9

135.5 d

C-2′

126.9 s

2

73.7 d

10

67.8 d

2″

126.9 s

3

39.1 t

11

35.9 d

3′

137.7 d

4

80.9 s

12

14.7 q

3″

137.7 d

5

48.5 d

13

14.7 q

4′

17.4 q

6

69.3 d

14

11.3...

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References

  1. 1.
    M. Holub, Z. Samek, V. Herout, F. Sorm, Collect. Czech. Chem. Commun. 24, 3934 (1959)Google Scholar
  2. 2.
    M. Holub, Z. Samek, V. Herout, F. Sorm, Monatsh. Chem. 98, 1138 (1967)CrossRefGoogle Scholar
  3. 3.
    M. Miski, A. Ulubelen, T.J. Mabry, W.H. Watson, I. Vickovic, M. Holub, Tetrahedron 40, 5197 (1984)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013