Natural Compounds

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

3α-Senecioyloxy-10αH-furanoeremophil-9-one (Eurypsonol Senecioate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1272

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

Biological sources: Senecio smithii DC. [1]

C20H26O4: 330.1831

Mp: 195°C (Et2O) [1]

[α]24 (λ, nm): −61.8° (589), −65.0° (578), −76.7° (546), −159.0° (436), −206.3° (365) (c 0.6, CHCl3) [1]

Mp: 195°C (Et2O) [1]

IR (CHCl3): 1715, 1680 [1]

MS: 330.183 [M]+ (10) (C20H26O4), 230 (41), 215 (28), 162 (44), 83 (100), 55 (74) [1]

1H NMR (400, MHz, CDCl3): 0.84 (3H, s, H-14), 0.94 (3H, d, J = 7, H-15), 1.33 (1H, dddd, J = 3; 12; 11, H-2α), 1.53 (1H, dddd, J = 12; 3.5; 12, H-1β), 1.74 (1H, dq, J = 7, H-4), 1.98 (3H, br s, H-13), 2.19 (1H, dddd, J = 3; 3.5; 12; 4.5, H-2β), 2.28 (1H, dddd, J = 3; 3.5; 12, H-1α), 2.41 (1H, dd, H-10), 2.47 (1H, d, J = 16.5, H-6a), 2.74 (1H, d, J = 16.5, H-6b), 4.75 (1H, ddd, J = 4.5, H-3β), 7.36 (1H, br s, H-12); OSen: 1.89 (3H, br s, H-4′), 2.17 (3H, br s, H-5′), 5.68 (1H, br...

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References

  1. 1.
    F. Bohlmann, C. Zdero, R.M. King, H. Robinson, Phytochemistry 20(10), 2389 (1981)CrossRefGoogle Scholar

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