Natural Compounds

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

13-Senecioyloxy-bicyclogermacrene

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_800

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

Biological sources: Othonna cf. graveolens O. Hoffm. [1]

C20H30O2: 302.2246

Mp: colorless oil [1]

IR (CHCl3): 1715, 1650 [1]

MS: 302.225 [M]+ (0.6) (calc. for C20H30O2: 302.225), 202 (7.5), 187 (9), 83 (100), 55 (35) [1]

PTLC: CH2Cl2 –C6H6 (1:1) × 2, Rf 0.61 or Rf 0.55 [1]

1H NMR (CDCl3): 0.82 (1H, ddd, J = 11; 8; 5, H-7), 1.19 (3H, s, H-12), 1.31 (1H, dddd, J = 11; 13; 4; 12, H-8β), 1.48 (3H, d, H-14), 1.49 (1H, dd, J = 11; 8, H-6), 1.67 (3H, d, H-15), 1.73 (1H, ddd, J = 13; 4; 12, H-9α), 1.85 (1H, m, J = 12, H-3α), 2.03 (1H, m, J = 5; 13; 4; 4, H-8α), 2.03 (1H, m, J = 6; 12, H-2α), 2.10 (1H, br d, J = 12; 12; 3, H-2β), 2.21 (1H, ddd, J = 12; 3; 3, H-3β), 2.43 (1H, ddd, J = 13; 4; 4, H-9β), 4.14 (1H, d, J = 12, H-13b), 4.22 (1H, d, J = 12, H-13a), 4.40 (1H, br d, J = 11, H-5), 4.84 (1H, br dd, J = 6; 12, H-1);...

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References

  1. 1.
    J. Jakupovic, V.P. Pathak, M. Grenz, S. Banerjee, C. Wolfrum, R.N. Baruah, F. Bohlmann, Phytochemistry 26(4), 1049 (1987)CrossRefGoogle Scholar

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