Natural Compounds

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

1α-Angeloyloxy-5β,6β-epoxy-9α,10β(H)-cadin-3-ene

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_814

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Cadinanes – Cadalenes – Monoesters

Biological sources: Senecio pleistocephalus S. Moore [1]; S. microglossus DC. [2]

C20H30O3: 318.2195

Mp: colorless gum [1]

[α]24 (λ, nm): −12° (589), −12° (578), −16° (546), −31° (436) (c 0.5, CHCl3) [1]

IR (CCl4): 1720, 1650 [1]

MS: 219 [M + 1 − AngOH]+ (100), 201 (2), 158 (2) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.96 (3H, d, J = 7, H-13), 1.04 (3H, d, J = 7, H-14), 1.05 (3H, d, J = 7, H-12), 1.31 (1H, m, J = 15; 15, H-8b), 1.39 (1H, ddd, J = 3; 13; 3, H-8a), 1.44 (1H, m, H-9), 1.64 (1H, m, H-7b), 1.76 (3H, s, H-15), 1.89 (1H, ddd, J = 13; 3; 13, H-7a), 2.0 (1H, m, H-11), 2.0 (1H, m, H-10), 2.22 (1H, br dd, J = 17; ∼1.5, H-2b), 2.31 (1H, br dd, J = 17; ∼1, H-2a), 5.52 (H, br s, H-4), 5.74 (1H, ddd, J = 3.3; 6; 11.5, H-1); OAng: 1.88 (3H, dq, J = 1.5; 1.5, H-5′), 2.00 (3H, dq, J = 7; 1.5, H-4′), 6.03 (1H, qq, J...

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References

  1. 1.
    F. Bohlmann, C. Zdero, Phytochemistry 21(10), 2537 (1982)CrossRefGoogle Scholar
  2. 2.
    F. Bohlmann, N. Ates (Goren), R.M. King, H. Robinson, Phytochemistry 22 (7), 1675 (1983)CrossRefGoogle Scholar

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