Natural Compounds

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

6β-Angeloyloxy-3β-hydroxy-1β,10β-epoxy-furanoeremophilane (Nemosenin A)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1155

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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]

C20H26O5: 346.1780

Mp: non-crystalline [1]

[α]D25 −35.3° (c 0.44, CHCl3) [1]

UV (EtOH) 220 (4.09) [1]

IR (CHCl3): 3600, 3490, 1709, 1646, 1565, 1156 [1]

MS: 346 [M]+, 246, 100, 83, 55 [1]

TLC: light petroleum – ether (6:4), Rf 0.57 [1]

1H NMR (100 MHz, CDCl3, TMS): 1.01 (3H, J = 7.2, H-15), 1.25 (3H, s, H-14), 1.80 (1H, J = 4.4; 7.2, H-4), 1.80 (3H, J = 1.2, H-13), 1.95 (1H, J = 0; 10.5, H-2b), 2.15 (1H, J = 4.2; 7.3, H-2a), 2.23 (1H, J = 1.5; 17.4, << 0.5(DR), H-9b), 3.12 (1H, J = 4.2, H-1), 3.21 (1H, J = 2.5; 17.4; <<0.5(DR), H-9a), 4.27 (1H, J = 7.3; 10.5; 4.4, H-3), 6.45 (1H, J = 2.5; 1.5, H-6), 7.06 (1H, J = 1.2, << 0.5(DR), H-12); OAng: 1.94 (3H, dq, H-5′), 2.03 (3H, dq, H-4′), 6.18 (1H, qq, H-3′) [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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