Natural Compounds

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

8α-Angeloyloxy-bicyclogermacrene

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_798

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

Biological sources: Senecio cylindricus (A. Berger) Jacobsen [1] S. crassissimus Humbert [2]

C20H30O2: 302.2246

Mp: colorless oil [1]

[α]24 (λ, nm): +59.7° (589), +61.9° (578), +70.7° (546), +124.1° (436) (c 0.7, CHCl3) [1]

IR (CCl4): 1710, 1650, 850 [1]

MS: 302.225 [M]+ (4) (calc. for C20H30O2: 302.225), 202 (17), 187 (31), 159 (35), 83 (100) [1]

1H NMR (270 MHz, CDCl3, TMS): 0.96 (1H, dd, J = 9; 11, H-7), 1.08 (3H, s, H-13), 1.12 (3H, s, H-12), 1.55 (3H, br s, H-14), 1.57 (1H, dd, J = 12, 9, H-6), 1.69 (3H, s, H-15), 1.85 (1H, dd, J = 10; 12, H-9α), 2.0 (1H, m, H-11), 2.2 (4H, m, H-2, H-3), 2.81 (1H, dd, J = 5.5; 12, H-9β), 4.52 (1H, d, J = 12, H-5), 4.88 (1H, ddd, J = 11; 10; 5.5, H-8), 5.12 (1H, m, H-1); OAng: 1.89 (3H, dq, J = 1.5; 1.5, H-5′), 1.98 (3H, dq, J = 7; 1.5, H-4′), 6.12 (1H, qq, J = 7; 1.5, H-3′)...

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References

  1. 1.
    F. Bohlmann, J. Ziesche, Phytochemistry 18(9), 1489 (1979)CrossRefGoogle Scholar
  2. 2.
    F. Bohlmann, J. Ziesche, Phytochemistry 20(3), 469 (1981)CrossRefGoogle Scholar

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