Natural Compounds

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

6β-Isobutyroyloxy-3β-hydroxy-1β,10β-epoxy-furanoeremophilane (Nemosenin C)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1191

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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]

C19H26O5: 334.1780

Mp: non-crystalline [1]

[α]D25 −34.4° (c 0.46, CHCl3) [1]

UV (EtOH) 218 (3.75) [1]

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

MS: 334 [M]+, 246, 264 [1]

TLC: light petroleum – ether (6:4), Rf 0.52 [1]

1H NMR (100 MHz, CDCl3, TMS): 1.01 (3H, J = 7.2, H-15), 1.24 (3H, s, H-14), 1.56 (1H, J = 4.4; 7.2, H-4), 1.83 (3H, J = 1.2, H-13), 1.94 (1H, J = 0; 15; 10.7, H-2b), 2.22 (1H, J = 1.2; 17.3, << 0.5 (DR), H-9b), 2.22 (1H, J = 5.0; 15; 7.2, H-2a), 3.09 (1H, J = 5.0, H-1), 3.19 (1H, J = 2.5; 17.3; << 0.5 (DR), H-9a), 4.21 (1H, J = 7.2; 10.7; 4.4, H-3), 6.36 (1H, J = 2.5; 1.2, H-6), 7.06 (1H, J = 1.2, <<0.5(DR), H-12); OiBu: 1.23 (3H, d, J = ∼7, H-4′), 1.25 (3H, d, J = ∼7, H-3′), 2.67 (1H, s, H-2′) [1]

References

  1. 1.
    L. Novotny, M. Krojidlo, Z. Samek, J. Kohoutova, F. Sorm, Collect. Czech. Chem. Commun. 38(3), 739 (1973)CrossRefGoogle Scholar

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