Natural Compounds

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

6α-(4′-Hydroxy-benzoyloxy)-4β,8β-dihydroxy-5α(H)-dauc-9-one (Kuhistanicaol J)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_898

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

Biological sources: Ferula kuhistanica Korov. [1]

C22H30O5: 402.2093

[α]D +41.6° (c 0.30, MeOH) [1]

UV 258 (4.0) [1]

IR: 3734, 1703, 1609, 1508, 1278 [1]

1H NMR: 0.73 (3H, d, J = 6.8, H-12), 0.83 (3H, d, J = 6.8, H-13), 1.43 (3H, s, H-15), 1.16 (3H, s, H-14), 1.82 (1H, m, H-11), 2.54 (2H, q, J = 12.2, H-10α, H-10β), 2.15 (1H, dd, J = 2.1; 16.5, H-7α), 2.36 (1H, dd, J = 5.0; 16.5, H-7β), 5.47 (1H, ddd, J = 2.1; 5.0; 11.1, H-6), 2.40 (1H, d, J = 11.1, H-5), 1.46 (1H, m, H-3α), 1.93 (1H, m, H-3β), 1.37 (1H, m, H-2α), 1.51 (1H, m, H-2β); Op-HOBz: 6.71 (2H, d, J = 8.7, H-3′, H-5′), 7.79 (2H, d, J = 8.7, H-2′, H-6′) [1]

13 C NMR [ 1]:

Table 1

C-1

43.0

C-9

215.0

C-1′

123.0

2

42.2

10

51.9

2′

133.0

3

33.2

11

37.6

3′

116.1

4

85.9

12

17.8

4′

163.4

5

53.1

13

18.8

5′

116.1

6

71.9

14

27.7

6′

133.0

7

43.2

15

22.6

C=O

168.1

8

78.3...

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References

  1. 1.
    K. Tamemoto, Y. Takaishi, B. Chen, K. Kawazoe, H. Shibata, T. Higuti, G. Honda, M. Itoh, Y. Takeda, O.K. Khodjimatov, O. Ashurmetov, Phytochemistry 58(5), 763 (2001)CrossRefGoogle Scholar

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