Natural Compounds

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

3β-Angeloyloxy-bicyclogermacrene

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_797

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

Biological sources: Othonna dentata L. [1], O. arborescens L. [1, 2]

C20H30O2: 302.2246

Mp: 130°C/0.1 mm [1]

IR (CCl4): 1720, 1650 [1]

Found: C, 79.47; H, 9.97. Calc.: C, 79.44; H, 10.00% [1]

MS: 302.225 [M]+ (12) (calc. for C20H30O2: 302.225), 220 [M − O=C=C(CH3)CH=CH2]+ (8), 219 [M − CH3CH=CH(CH3)C=O + H]+ (8), 202 [M − AngOH]+ (30), 83 (100) [1]

1H NMR (100 MHz, C6D6, TMS): 1.07 (3H, s, H-12), 1.10 (3H, s, H-13), 1.15 (1H, m, H-7), 1.30 (1H, m, H-6), 1.48 (3H, d, J = 1.6, H-14), 1.70 (2H, m, H-8), 1.70 (3H, d, J = 1.3, H-15), 2.35 (2H, m, H-10), 2.35 (2H, m, H-2), 4.52 (1H, br d, J = 11, H-5), 4.78 (1H, br dd, J = 10; 5, H-1), 5.25 (1H, br dd, J = 10.5; 6, H-3); OAng: 1.91 (3H, dq, J = 1; 1, H-5′), 1.99 (3H, dq, J = 7; 1, H-4′), 5.97 (1H, qq, J = 7; 1, H-3′) [1]

References

  1. 1.
    F. Bohlmann, C. Zdero, M. Grenz, Chem. Ber. 107, 3928 (1974)CrossRefGoogle Scholar
  2. 2.
    F. Bohlmann, K.-H. Knoll, Phytochemistry 17(3), 461 (1978)CrossRefGoogle Scholar

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