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INTEGRISTERONE A 20,22-ACETONIDE

Year of first report:2008
Formula:C30H48O8
Molecular weight:536
Occurence in plants:
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: <br />
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Occurence in animals:
 
INTEGRISTERONE A 20,22-ACETONIDE

MASS SPECTRUM

EI-MS m/z (relative intensity %)
HRESI-MS m/z559.3243 [M+Na]+ (calculated for C30H48O8 Na : 559.3247)
CI-MS (NH3) m/z
ESI-MS/MS m/z537 [M+H]+, 519 [M+H-H20]+, 501 [M+H-2H20]+, 479 [M+H-C3H6O]+, 461 [M+H-C3H6O-H2O]+, 443 [M+H-C3H6O-2H2O]+, 425 [M+H-C3H6O-3H2O]+,

CARBON NMR

PROTON NMR

CD3OD
0176.41
0268.49
0370.98
0433.49
0546.79
06205.58
07122.18
08166.85
0935.68
1043.75
1121.89
1232.31
1349.0*
1485.15
1531.74
1622.33
1751.53
1817.67
1920.07
2085.83
2122.58
2283.30
2324.70
2442.21
2571.11
2629.34
2729.49
2xCH328.95, 27.18
OCO108.03
CD3OD
01-He3.82 (b)
02-Ha3.87 (t, 3.1, 3.1)
03-He4.04 (b)
04-Ha1.81
04-He1.78
05-H2.61 (dd, 12.4, 4.4)
07-H5.84 (d, 2.4)
09-Ha3.07 (bt)
11-Ha1.70
11-He1.73
12-Ha2.09 (td, 13, 13, 5)
12-He1.83
15-Ha1.97
15-Hb1.62
16-Ha1.87
16-Hb2.04
17-H2.31 (dd, 9.2, 8.4)
18-Me0.840 (s)
19-Me1.074 (s)
21-Me1.175 (s)
22-H3.68 (dd, 8.2, 3.5)
23-Ha1.52
23-Hb1.52
24-Ha1.73
24-Hb1.49
26-Me1.195 (s)
27-Me1.204 (s)
Me2C=1.39 (s), 1.32 (s)

PHYSICAL PROPERTIES

M.P.░C ;
[α]D20+ 31.6 ░ (c 0.23; EtOH)
IR (KBr) ν max (cm-1)3401 (OH), 1655 (C=O), 1177, 1062 (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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