Natural Compounds

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

2β-Acetoxy-6β-angeloyloxy-1β,10β-epoxy-furanoeremophilane

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1323

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

Biological sources: Senecio pyrenaicus subsp. caespitosus (Brot.) Franco [1]

C22H28O6: 388.1886

Mp: colorless oil [1]

IR (CCl4): 1750, 1730, 1645 [1]

MS: 388.189 [M]+ (0.5) (calc. for C22H28O6: 388.189), 306 (0.6), 288 (9), 228 (9), 199 (15), 83 (100), 55 (39) [1]

1H NMR (400 MHz, CDCl3): 1.12 (3H, d, J = 7, H-15), 1.22 (3H, s, H-14), 1.82 (3H, d, J = 1, H-13), 2.05 and 1.57 (2H, m, H-3), 2.08 (3H, s, OAc), 3.26 and 2.37 (1H, br d, J = 16, H-9), 3.36 (1H, d, J = 3.5, H-l), 5.19 (1H, ddd, J = 3.5; 3.5; 6, H-2), 6.23 (1H, br s, H-6), 7.06 (1H, br s, H-12), l.64 (1H, m, H-4); OAng: 1.92 (3H, dq, J = 1; 1, H-5′), 2.01 (3H, dq, J = 7; 1, H-4′), 6.16 (1H, qq, J = 7; 1, H-3′) [1]

13 C NMR (CDCl 3) [ 1]:

Table 1

C-1

61.4 d

C-9

30.3 t

OAc

21.0 q

2

68.1 d

10

65.9 s

OAng (assigned by 2D-correlated spectra)

167.4...

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References

  1. 1.
    J.M. Cardoso, J. Jakupovic, F. Bohlmann, Phytochemistry 26(8), 2321 (1987)CrossRefGoogle Scholar

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