Natural Compounds

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

3β-Angeloyloxy-6β,15-dihydroxy-10βH-furanoeremophilane

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1120

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

Biological sources: Othonna leptodactyla Harv. [1]

C20H28O5: 348.1937

Mp: colorless oil [1]

[α]D24 +5° (c 0.9, CHCl3) [1]

IR (CCl4): 3450, 1720, 1650 [1]

MS: 330.183 [M − H2O]+ (40) (calc. for C20H26O4: 330.183), 230 (24), 83 (100), 55 (82) [1]

PTLC: Et2O – petrol (3:7), Rf 0.6 [1]

1H NMR (400 MHz, CDCl3, TMS): 1.35 (3H, s, H-14), 1.41 (1H, br d, J = 15, H-1b), 1.90 (2H, m, H-2), 1.99 (3H, d, J = 1, H-13), 2.16 (1H, m, H-1a), 2.26 (1H, ddd, J = 5; 7.5; 11, H-4), 2.56 (2H, m, H-9), 3.67 (1H, dd, J = 11; 12, H-15b), 3.92 (1H, dd, J = 7.5; 12, H-15a), 4.57 (1H, br s, H-6), 5.30 (1H, ddd, J = 5, H-3), 7.00 (1H, br s, H-12); OAng: 1.78 (3H, dq, J = 1.5; 1.5, H-5′), 1.98 (3H, dq, J = 7; 1.5, H-4′), 6.05 (1H, qq, J = 7; 1.5, H-3′) [1]

13 C NMR (CDCl 3) [ 1]:

Table 1

C-1

25.6 t

C-8

148.3 s

C-15

67.0 t

2

22.9...

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References

  1. 1.
    J. Jakupovic, V.P. Patnak, M. Grenz, S. Banerjee, C. Wolfrum, R.N. Baruah, F. Bohlmann, Phytochemistry 26(4), 1049 (1987)CrossRefGoogle Scholar

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