Natural Compounds

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

6β-Senecioyloxy-1β,10β-epoxy-furanoeremophil-9-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1284

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Eremophilanes – Furanoeremophilanes – Monoesters

Biological sources: Senecio glastifolius L.f. [1]; S. vellereus Franch. [2]; S. andreuxii DC. [3]; Euryops evansii Schltr., E. multifidus DC. [4]

C20H24O5: 344.1624

Mp: 138–140°C [1]

IR: 1725, 1653, 1705 [1]

MS: 344.162 [M]+ (2.5) (calc. for C20H24O5 344.162), 262 [M – O = C = CHC(CH3) = CH2]+ (14), 244 [M – C4H7COOH]+ (12), 83 (100) [1]

1H NMR (CDCl3): 1.23 (3H, d, J = 6.7, H-15), 1.23 (3H, s, H-14), 1.90 (3H, d, H-13), 3.37 (1H, br d, J = 4, H-1α), 6.67 (1H, s, H-6α), 7.44 (1H, q, J = 1, H-12); OSen: 1.98 (3H, d, H-4′), 2.26 (3H, d, H-5′), 5.82 (1H, qq, H-2′) [1]

13 C NMR (20 MHz, CDCl 3) [ 2]:

Table 1

C-1

68.29

C-8

146.64

C-15

15.85

2

25.01

9

181.07

1′

166.01

3

19.54

10

65.55

2′

114.91

4

32.26

11

121.87

3′

160.68

5

45.30

12

146.65

4′

20.62

6

62.21

13

8.24

5′

27.64

7

137.51

14

15.62

   
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References

  1. 1.
    F. Bohlmann, C. Zdero, Chem. Ber. 107, 2912 (1974)CrossRefGoogle Scholar
  2. 2.
    F. Bohlmann, K.-H. Knoll, C. Zdero, P.K. Mahanta, M. Grenz, A. Suwita, D. Ehlers, N.L. Van, W.-R. Abraham, A.A. Natu, Phytochemistry 16(7), 965 (1977)CrossRefGoogle Scholar
  3. 3.
    B. Reyes, G. Delgado, Heterocycles 31, 1405 (1990)CrossRefGoogle Scholar
  4. 4.
    F. Bohlmann, C. Zdero, Phytochemistry 17(7), 1135 (1978)CrossRefGoogle Scholar

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