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INOKOSTERONE 20,22-ACETONIDE

Year of first report:2008
Formula:C30H48O7
Molecular weight:520
Occurence in plants:
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: <br />
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Occurence in animals:
 
INOKOSTERONE 20,22-ACETONIDE

MASS SPECTRUM

FAB-MS543 (45) [M+Na]+, 521 (80) [M+H]+, 503 (100) [M+H-H20]+, 445 (20), 427 (15), 329 (20), 301 (22), 279 (12), 249 (19).
EI-MS m/z (relative intensity %)
HRESI-MS543.3282 [M+Na]+ (calculated for C30H48O7 Na : 543.3290)
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

CD3OD
0137.35
0268.72
0368.49
0432.87
0551.77
06206.43
07122.15
08167.56
0935.14
1039.21
1121.51
1232.32
1348.44
1485.34
1531.72
1622.43
1750.46
1817.69
1924.45
2085.75
2122.54
2283.13
2327.43
2432.05
2537.01
2668.23
2717.04
Me29.36, 27.19
OCO107.98
CD3OD
01-Ha1.43 (dd, 13.2, 12.0)
01-He1.78 (dd, 13.2, 4.3)
02-Ha3.83 (ddd, 12.0, 4.3, 3.2)
03-He3.95 (q, 3, 3, 3)
04-Ha1.68-1.78
04-He1.68-1.78
05-H2.38 (dd, 12.8, 4.7)
07-H5.82 (d, 2.6)
09-Ha3.15 (ddd, 11.5, 7.0, 2.6)
11-Ha1.69
11-He1.80
12-Ha2.11 (td, 13, 13, 4.8)
12-He1.85
15-Ha1.63
15-Hb1.96
16-Ha1.86
16-Hb2.04
17-H2.29 (dd, 9.6, 8.2)
18-Me0.826 (s)
19-Me0.963 (s)
21-Me1.162 (s)
22-H3.69 (dd, 9.4, 2.9)
23-Ha1.47
23-Hb1.47
24-Ha1.15
24-Hb1.68
25-H1.63
26-Me3.36 (dd, 10.7, 5.8), 3.43 (dd, 10.7, 6.4)
27-Me0.937 (d, 6.6)
Me2C=1.39 (s), 1.32 (s)

PHYSICAL PROPERTIES

M.P.░C ;
[α]D20+ 42.9 ░ (c 0.29; EtOH)
IR (KBr) ν max (cm-1)3429 (OH), 1655 (C=O), 1109, 1055 (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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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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