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24-METHYLENESHIDASTERONE

Year of first report:2007
Formula:C28H42O6
Molecular weight:474
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: <br />
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Occurence in animals:
 
24-METHYLENESHIDASTERONE

MASS SPECTRUM

HRESI-MS474.2975 (calculated for C28H42O6 474.2970)
CI-MS (NH3) m/z
ESI-MS m/z (relative intensity %)497 (10) [M+Na]+, 475 (100) [M+H]+, 457 (72) [M+H-H2O]+, 439 (5.7) [M+H-2H2O]+, 421 (3) [M+H-3H2O]+, 364 (2)

CARBON NMR

PROTON NMR

CD3OD
0137.5
0268.9
0368.7
0433.2
0551.9
06206.6
07122.3
08168.1
0935.3
1039.4
1121.6
1232.45
1348.4
1485.4
1531.8
1622.0
1752.0
1818.35
1924.5
2076.8
2120.7
2282.4
2335.6
24158.3
2583.2
2627.9
2729.7
28 CH2=104.1
CD3OD
01-Ha1.43 (dt, 13.1, 12.5)
01-He1.795
02-Ha3.84 (ddd, 12.1, 4.3, 3.3)
03-He3.95 (q, 2.9)
04-Ha1.72*
04-He1.76*
05-H2.38 (dt, 8.1, 4.7)
07-H5.81 (d, 2.7)
09-H3.15 (ddd, 11.3, 7.1, 2.7)
11-Ha1.67
11-He1.80
12-Ha2.165 (td, 13.3, 4.8)
12-He1.84
15-Ha1.62
15-Hb1.97
16-Ha1.83
16-Hb2.00
17-H2.42 (dd, 9.5, 8.2)
18-Me0.84 (s)
19-Me0.96 (s)
21-Me1.21 (s)
22-H3.91 (t, 8.1)
23-Ha2.545 (dt, 8.2, 2.2)
23-Hb2.545 (dt, 8.2, 2.2)
26-Me1.28 (s)
27-Me1.33 (s)
28 CH2=4.805 (t, 2.3), 4.895 (t, 2.2)

PHYSICAL PROPERTIES

M.P.- °C ;
[α]D28+3 ° (c 0.05 ; MeOH) ; different for Japonicone (isomeric ?)
UV (MeOH) max (log )241.8 (3.7) ;
IR (KBr) ν max (cm-1)

CHROMATOGRAPHY

HPLCNP-HPLC, solvent cyclohexane-isopropanol-water 100:40:3; RP-HPLC, solvent methanol-water 60:40.
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSIMON, A. et al. (2007) Steroids 72, 751-755 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
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