Natural Compounds

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

9α-(2′-Methylbutyroyloxy)-3α-senecioyloxy-7β,10αH-eremophil-11(13)-en-8-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1098

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

Biological sources: Senecio speciosus Willd. [1]

C25H38O5: 418.2720

Mp: colorless oil [1]

[α]D −168° (c 0.8, CHCl3) [1]

IR (CCl4): 1730, 1720, 1650, 900 [1]

MS: 418.272 [M]+ (10) (calc. for C25H38O5: 418.272), 316 (100), 216 (46), 201 (14), 85 (40), 83 (82), 5 (100), 55 (83) [1]

TLC: Et2O – petrol (1:2), Rf 0.4 [1]

1H NMR (400 MHz, CDCl3, TMS): 0.93 (3H, d, J = 7, H-15), 1.17 (3H, s, H-14), 1.51 (1H, m, H-4), 1.57 (1H, m, H-6b), 1.75 (3H, br s, H-13), 2.08 (1H, dd, J = 14; 14, H-6a), 3.24 (1H, dd, J = 14; 5.5, H-7), 4.73 (1H, br s, H-12b), 4.82 (1H, ddd, J = 11; 11; 5, H-3), 4.95 (1H, br s, H-12a), 5.06 (1H, d, J = 11; 3.5, H-9), H-10 – overlapped multiplets; OMeBu: 0.88 (3H, t, H-4′), 1.16 (3H, d, H-5′), 1.42 (1H, m, H-3′b), 1.6 (1H, m, H-3′a), 2.47 (1H, tq, H-2′); OSen: 1.89 (3H, d, H-4″), 2.17 (3H,...

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References

  1. 1.
    F. Bohlmann, C. Zdero, J. Jakupovic, L.N. Misra, S. Banerjee, P. Singh, R.N. Baruah, M.A. Metwally, G. Schmeda-Hirschmann, L.P.D. Vincent, R.M. King, H. Robinson, Phytochemistry 24(6), 1249 (1985)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013