Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1345

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

Biological sources: Senecio erosus Wedd. [1]; S. dryophyllus Meyen et Walp. [2]

C22H28O7: 404.1835

Mp: 168−169°C (ether), colorless crystals [1]

[α]24 (λ, nm): −44.5° (589), −46.4° (578), −52.2° (546), −77.1° (436) (c 1.6, CHCl3) [1]

IR (CCl4): 3470, 1750, 1725, 1685, 1645, 1230 [1]

MS: 404.184 [M]+ (8) (calc. for C22H28O7: 404.184), 344 (6), 304 (1), 262 (21), 178 (51), 83 (100) [1]

1H NMR (270 MHz, CDCl3, TMS): 1.01 (3H, s, H-14), 1.19 (3H, d, J = 7, H-15), 1.42 (1H, m, H-3β), 1.66 (1H, m, H-2α), 1.74 (1H, m, H-4α), 1.92 (3H, d, J = 1.5, H-13), 2.20 (3H, s, OAc), 2.33 (2H, m, H-2β, H-3α), 3.98 (H, s, OH), 4.85 (1H, dd, J = 2.5; 2.5, H-1β), 7.05 (1H, s, H-6α), 7.41 (1H, q, J = 1.5, H-12); OAng: 1.56 (3H, dq, J = 1.5; 1.5, H-5′), 1.89 (3H, dq, J = 7; 1.5, H-4′), 5.92 (1H, qq, J = 7; 1.5, H-3′) [1]

References

  1. 1.
    F. Bohlmann, J. Ziesche, Phytochemistry 18(9), 1489 (1979)CrossRefGoogle Scholar
  2. 2.
    S. Dupre, M. Grenz, J. Jakupovic, F. Bohlmann, H.M. Niemeyer, Phytochemistry 30(4), 1211 (1991)CrossRefGoogle Scholar

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