Natural Compounds

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

1α-Acetoxy-8α-angeloyloxy-10αH-eremophil-11(13)-en-9-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1082

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

Biological sources: Senecio portalesianus Remy [1]

C22H32O5: 376.2250

[α]D +12° (c 0.5, CHCl3) [1]

IR (CCl4): 1740 [1]

MS: 376.225 [M]+ (0.3) (calc. for C22H32O5: 376.225), 316 [M – HOAc]+ (1), 277 [M – OAng]+ (5), 216 [316 – AngOH]+ (92), 201 (22), 83 [C4H7CO]+ (100) [1]

TLC: Et2O – petrol (1:1), Rf 0.5 [1]

1H NMR (400 MHz, CDCl3): 0.81 (3H, s, H-14), 0.86 (3H, d, J = 7, H-15), 1.51 (1H, m, H-4), 1.74 (2H, br s, H-13), 1.78 (1H, dd, J = 14; ∼8, H-6b), 1.93 (1H, m, H-6a), 2.96 (1H, d, J = 10, H-10), 3.11 (1H, ddd, J = ∼8; ∼8; ∼8, H-7), 4.85 (3H, br s, H-12b), 4.90 (3H, br s, H-12a), 5.00 (1H, d, J = ∼8, H-8), 5.13 (1H, dt, J = 10; 10; 5, H-1); OAng: 1.89 (3H, dq, J = ∼1.5; ∼1.5, H-5′), 1.96 (3H, dq, J = 7; ∼1.5, H-4′), 6.09 (1H, qq, J = 7; ∼1.5, H-3′) [1]

References

  1. 1.
    J. Jakupovic, M. Grenz, F. Bohlmann, H.M. Niemeyer, Phytochemistry 30(8), 2691 (1991)CrossRefGoogle Scholar

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