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SILENOSTERONE [= 3-DEHYDRO-2-DEOXYECDYSONE]

Year of first report:1979
Formula:C27H42O5
Molecular weight:446
Occurence in plants:
Silene praemixta [Caryophyllaceae] » Images of Silene praemixta Wikipedia: <br />
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Occurence in animals:
Locusta migratoria [Orthoptera] » Images of Locusta migratoria Wikipedia: <br />
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SILENOSTERONE [= 3-DEHYDRO-2-DEOXYECDYSONE]

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)446 (M)+ (0.3), 428 (5), 413 (4), 410 (8), 400 (3), 395 (10), 377 (3), 359 (3), 341 (8), 330 (7), 312 (10), 297 (10), 283 (14), 282 (16), 261 (10), 233 (33), 232 (25), 231 (17), 99 (100), 81 (92).
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
C5D5N
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H6.00
09-Ha3.45
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.60 (s )
19-Me0.94 (s )
21-Me1.15 (d )
22-H3.90
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.25 (s )
27-Me1.25 (s )

PHYSICAL PROPERTIES

M.P.115-117 °C
[α]D28+ 86.9 ? 2° (c 0.92; MeOH)
IR (KBr) ν max (cm-1)3420 (OH), 1710 (CO), 1660 (cyclohexenone)
UV (EtOH) λ max (log ε)246 (4.05)

CHROMATOGRAPHY

HPTLC 
TLCon silica gel : Rf 0.46 (CHCl3-EtOH 9:1)
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 4.6 x 10-5M

REFERENCES

First isolationSAATOV, Z. et al. (1979) Khim. Prir. Soedin., 793-797 Search more
GeneralTSOUPRAS, G. et al. (1982) Thesis, Strasbourg, France Search more
GeneralTSOUPRAS, G. et al. (1983) Tetrahedron 39, 1789-1796 Search more
BioactivitiesDINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 Search more

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© Université 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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