Natural Compounds

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

3α-Senecioyloxy-7αH-eremophila-9(10),11(12)-dien-8-one (Senecioyloxy-neopetasol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1071

CAS Registry Number: 67604-58-4 Open image in new window

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

Biological sources: Petasites hybridus (L.) (= P. officinalis Moench) [1]; Senecio greyi Hook f. [2]; S. cathcartensis O. Hoffm. [3]; S. erubescens Aiton var. crepidifolius DC. [4]; S. ovirensis (Koch) DC. [5]

C20H28O3: 316.2039

Mp: mix. with the methylacryloyloxy-neopetasol [1]

Mp: oil [2]

UV (cyclohexane) 226 [1]

IR (CCl4): 1720, 1680, 1650, 1620 [2]

MS: 316.204 [M]+ (9) (calc. for C20H28O6: 316.204), 216 (35), 148 (100), 83 (33) [2]

CD: Δε363 −0.25, Δε347 −0.7, Δε333 −0.8, Δε320 −0.65, Δε216 +8.4 [3]

HPLC [1]

1H NMR (360 MHz, CDCl3, TMS): 0.98 (3H, d, J = 7, H-15), 1.16 (3H, s, H-14), 1.45 (1H, q, J = 5; 11, H-2ax), 1.78 (3H, s, H-13), 1.97 (1H, t, J = 14; 12.5, H-6ax), 2.0 (1H, t, J = 11; 7, H-4ax), 2.03 (1H, t, J = 14; 5, H-6eq), 2.26 (1H, dd, J = 14; 5; 2.5, H-1eq)...

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References

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    F. Bohlmann, C. Zdero, Phytochemistry 17(8), 1337 (1978)CrossRefGoogle Scholar
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    F. Bohlmann, C. Zdero, D. Berger, A. Suwita, P. Mahanta, C. Jeffrey, Phytochemistry 18(1), 79 (1979)CrossRefGoogle Scholar
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    F. Bohlmann, P.K. Mahanta, Phytochemistry 18(4), 678 (1979)CrossRefGoogle Scholar

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