Natural Compounds

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

6β-(2′-Methylbutyroyloxy)-3β-hydroxy-1β,10β-epoxy-furanoeremophilane (Nemosenin B)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1242

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

Biological sources: Senecio nemorensis L. subsp. fuchsii (C. Gmelin) Celak [1]

C20H28O5: 348.1937

Mp: non-crystalline [1]

[α] D 25 −19.0° (c 0.35, CHCl3) [1]

UV (EtOH) 218 (3.76) [1]

IR (CHCl3): 3600, 3490, 1724, 1566, 1157 [1]

MS: 348 [M]+, 102, 85, 57 [1]

TLC: light petroleum – ether (6:4), Rf 0.55 [1]

1 H NMR (100 MHz, CDCl3, TMS): 1.00 (3H, J = 7.3, H-15), 1.24 (3H, s, H-14), 1.60 (1H, J = 4.3; 7.3, H-4), 1.85 (3H, J = 1.3, H-13), 1.94 (1H, J = 0; 15; 10.8, H-2b), 2.21 (1H, J = 1.2; 17.5, << 0.5(DR), H-9b), 2.22 (1H, J = 5.0; 7.2, H-2a), 3.09 (1H, J = 5.0, H-1), 3.20 (1H, J = 2.5; 17.5; <<0.5(DR), H-9a), 4.21 (1H, J = 7.2; 10.8; 4.3, H-3), 6.37 (1H, J = 2.5; 1.2, H-6), 7.06 (1H, J = 1.3, << 0.5(DR), H-12); OMeBu: 0.96 (3H, t, J = 7.5, H-4′), 1.23 (3H, d, J = 7, H-5′), 2.47 (1H, s, H-2′) [1]

References

  1. 1.
    L. Novotny, M. Krojidlo, Z. Samek, J. Kohoutova, F. Sorm, Collect. Czech. Chem. Commun. 38, 739 (1973)CrossRefGoogle Scholar

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