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15-HYDROXYPONASTERONE A

Year of first report:2008
Formula:C27H44O7
Molecular weight:480
Occurence in plants:
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: <br />
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Occurence in animals:
 
15-HYDROXYPONASTERONE A

MASS SPECTRUM

EI-MS m/z (relative intensity %)
ESI-MS m/z503.2990 [M+Na]+ (calculated for C27H44O7Na : 503.2985)
CI-MS (NH3) m/z
ESI-MS/MS m/z481 [M+H]+, 463 [M+H-H20]+, 455 [M+H-2H20]+, 427 [M+H-3H2O]+, 409 [M+H-4H2O]+, 401 [M+H-2H2O-C3H8]+, 329, 317, 311, 299, 279 HR

CARBON NMR

PROTON NMR

CD3OD
0137.40
0268.66
0368.59
0432.70
0551.47
06206.68
07124.56
08165.77
0935.17
1039.58
1121.28
1234.01
1347.48
1485.19
1576.84
1635.59
1749.96
1818.11
1924.22
2077.58
2121.00
2277.92
2337.62
2430.38
2529.22
2622.73
2723.42
CD3OD
01-Ha1.43
01-He1.79
02-Ha3.81 (ddd, 12.2, 4.2, 3.0)
03-He3.96 (q, 3, 3, 3)
04-Ha1.79
04-He1.72
05-H2.37 (dd, 13.2, 4.4)
07-H6.47 (d, 2.6)
09-Ha3.13 (ddd, 11.5, 7.0, 2.6)
11-Ha1.75-1.80
11-He1.75-1.80
12-Ha2.11 (td, 13, 13, 5)
12-He1.85
15-H4.13 (m)
16-Ha1.92
16-Hb2.24
17-H2.25
18-Me1.137 (s)
19-Me1.002 (s)
21-Me1.188 (s)
22-H3.30 (dd, 11, 1.5)
23-Ha1.48
23-Hb1.22
24-Ha1.51
24-Hb1.22
25-H1.57
26-Me0.908 (d, 6.5)
27-Me0.920 (d, 6.5)

PHYSICAL PROPERTIES

M.P.░C ;
[α]D20+ 41.2 ░ (c 0.17; EtOH)
IR (KBr) ν max (cm-1)3585, 3563, 3370 (OH), 1646 (C=O), 1055, 1008, 988 (C-O)
UV (MeOH) λ max (log ε)

CHROMATOGRAPHY

HPLCRP-HPLC Separon SGX C-18 (250 x 4 mm), solvent methanol-water (linear grad of 10-70%), flow-rate 0,6 ml/min (Ret 55.0 min); NP-HPLC Silasorb 600 (250 x 4 mm) solvent dichloromethane-isopropanol-water (84:15:1), flow-rate 0.8 ml/min (Ret 28.0 min); and two other systems.
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationBUDESINSKY, M. et al. (2008) Steroids 73, 502-514 Search more

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© UniversitÚ Pierre & Marie Curie, Paris 6, France
© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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