Natural Compounds

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

1β-Acetoxy-6α-hydroxy-eremophila-7(11),9(10)-dien-8-on-12-oic Acid

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_984

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

Biological sources: Ligularia sagitta Mattf. ex Rehder et Kobuski [1]

C17H22O6: 322.1416

C18H24O6: 336.1573 (methyl ester: 1β-acetoxy-6α-hydroxy-eremophila-7(11),9(10)-dien-8-on-12-oic acid methyl ester)

Mp: colorless gum (isolated as its methyl ester) [1]

[α]D20 (methyl ester) −104° (c 0.1, CHCl3) [1]

IR (KBr) (methyl ester): 3442, 1720, 1662, 1630, 1448, 1329, 1307, 1240, 1028, 943 [1]

EI-MS (methyl ester): 336 [M]+ (5), 276 [M – HOAc]+ (18), 246 (20), 187 (45), 151 (60), 122 (100), 91 (35), 41 (30) [1]

1H NMR (400 MHz, CDCl3) (methyl ester): 1.00 (3H, d, J = 6.5, H-14), 1.20 (1H, m, H-4), 1.34 (1H, m, H-3α), 1.43 (1H, m, H-3β), 1.50 (3H, s, H-15), 1.65 (1H, m, H-2α), 2.08 (3H, s, H-13), 2.10 (1H, m, H-2β), 2.15 (3H, s, OAc), 3.80 (3Hs, OMe), 4.70 (1H, s, H-6), 5.40 (1H, t, J = 3.0, H-1), 6.00 (1H,...

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References

  1. 1.
    H.-R. Peng, Y.-P. Shi, Z.-J. Jia, Planta Med. 63, 335 (1997)CrossRefGoogle Scholar

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