Natural Compounds

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

1α-Acetoxy-6β-angeloyloxy-10β-hydroxy-furanoeremophil-9-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1314

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

Biological sources: Senecio dryophyllus Meyen et Walp. [1]

C22H28O7: 404.184

Mp: 152°C [1]

[α]D24 −27° (c 0.3, CHCl3) [1]

IR (CCl4): 3460, 1760, 1730, 1680 [1]

MS: 404.184 [M]+ (0.5) (calc. for C22H28O7: 404.184), 362 [M – ketene]+ (0.2), 344 [M – CH3COOH]+ (2.5), 321 [M – C4H7CO]+ (2), 262 [362 – C4H7COOH]+ (11), 178 (50), 83 [C4H7CO]+ (100) [1]

1H NMR (400 MHz, CDCl3): 1.00 (3H, s, H-14), 1.18 (3H, d, J = 7, H-15), 1.70 (1H, m, H-2b), 1.70 (1H, m, J = 7, H-4), 1.92 (3H, br s, H-13), 2.21 (3H, s, OAc), 2.32 (m, H-2a), 2.32 (2H, m, H-3), 3.99 (1H, s, OH), 4.84 (1H, br s, H-1), 7.05 (1H, s, H-6), 7.43 (1H, br s, H-12); OAng: 1.54 (3H, dq, J = 1.5; 1.5, H-5′), 1.90 (3H, dq, J = 7; 1.5, H-4′), 5.95 (1H, qq, J = 7; 1.5, H-3′) [1]

References

  1. 1.
    S. Dupre, M. Grenz, J. Jakupovic, F. Bohlmann, H.M. Niemeyer, Phytochemistry 30(4), 1211 (1991)CrossRefGoogle Scholar

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