Natural Compounds

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

3α-[(E)-3-Methoxyacryloyloxy]-7βH-eremophila-9(10),11(12)-dien-8-one (Petasinone A)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1065

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

Biological sources: Petasites formosanus Kitam. [1]

C19H26O4: 318.1831

Mp: colorless oil [1]

[α]D25 +11° (c 1.0, MeOH) [1]

UV (MeOH): 240 (4.46), 276 (3.58) [1]

IR (film): 3020, 1705, 1665. 1650. 1625, 1210, 1150, 1000, 890, 800 [1]

EI-MS: 318 [M]+ (8), 216(92), 161 (90), 148 (60), 85(100) [1]

HR-MS: 318.1826 [M]+ (calc. for C19H26O4: 318. 832) [1]

1H NMR (300 MHz, CDCl3): 0.94 (1H, d, J = 6.6, H-15), 1.11 (3H, s, H-14), 1.73 (3H, s, H-13), 3.09 (1H, dd, J = 14.4; 4.5, H-7β), 3.68 (3H, s, OCH3), 4.80 (1H, br s, H-12a), 4.93 (1H, td, J = 11.0; 4.8, H-3), 4.97 (1H, br s, H-12b), 5.17 (1H, d, J = 12.6, H-2′), 5.76 (1H, d, J = 1.5, H-9), 7.60 (1H, d, J = 12.6, H-3′) [1]

13 C NMR (300 MHz, CDCl 3): [ 1]

Table 1

C-1

30.6

C-8

98.6

C-14

17.2

2

31.6

9

124.5

15

10.4

3

72.5

10

167.8

1′

166.9

4

47.4

11

143.0

2′

95.9

5

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References

  1. 1.
    Y.-L. Lin, J.-C. Ou, C-Fu Chrn, Y.-H. Kuo, Chem. Pharm. Bull. 46, 1807 (1998)CrossRefGoogle Scholar

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