Natural Compounds

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

3α-(3′-Methylsulfinylacryloyloxy)-eremophila-9(10),11(12)-dien-8-one (Eremopetasinsulphoxide)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1056

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

Biological sources: Petasites japonicus (Siebold et Zucc.) Maxim. [1]

C19H26O4S: 350.1552

[α]D24 +17.0° (c 0.30, EtOH)

IR: 1715, 1670

CI-HR-MS: 351.1639 [M + 1]+ (C19H27O4S requires 351.1630)

CI-MS: 351 [M + 1]+, 333, 287, 245, 231, 217 (base), 201, 189, 148, 135, 105

CD: [θ] 323 nm + 1235 (MeOH)

1H NMR (600 MHz): 0.96 (3H, d, J = 6.8, H-15), 1.24 (3H, s, H-14), 1.55 (1H, m, H-2α), 1.64 (1H, m, H-4α), 1.75 (3H, br s, H-13), 1.91 (1H, t, J = 14, H-6α), 2.04 (1H, dd, J = 14; 4; 4.6, H-6β), 2.21 (1H, m, H-2β), 2.39 (1H, dq, J = 14; 2, H-1α), 2.51 (1H, td, J = 14; 6, H-1β), 3.12 (1H, dd, J = 14; 4.6, H-7β), 4.83 (1H, br s, H-12Z), 4.95 (1H, m, H-3β), 5.00 (1H, q, J = 1.6, H-12E), 5.80 (1H, t, J = 1.9, H-9α); acyl group: 2.851 (3H, s, S(O)CH3)a, 2.854 (3H, s, S(O)CH3)b, 6.820 (1H, d, J = 10.4, H-2′)a,...

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References

  1. 1.
    M. Tori, M. Kawahara, M. Sono, Phytochemistry 47(3), 401 (1998)CrossRefGoogle Scholar

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