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SILENEOSIDE D

Year of first report:1984
Formula:C33H54O12
Molecular weight:642
Occurence in plants:
Silene brahuica [Caryophyllaceae] » Images of Silene brahuica Wikipedia: <br />
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Occurence in animals:
 
SILENEOSIDE D

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)624 (M-18)+ (0.5), 606 (0.8), 588 (5), 570 (1), 514 (0.8), 507 (0.7), 490 (0.9), 473 (0.6), 462 (1), 444 (1), 426 (11), 411 (2), 408 (3), 393 (1), 375 (1), 363 (5), 345 (55), 327 (13), 309 (10), 300 (11), 284 (11), 145 (10), 143 (12), 135 (11), 99 (100), 81 (55), 69 (53).
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
0268.0
0379.0 *
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
1484.2
15 
16 
17 
18 
19 
2076.8
21 
2277.5
23 
24 
2569.6
26 
27 
s1'103.5
s2'70.9
s3'71.6
s4'70.9
s5'73.3
s6'62.5
C5D5N
01-Ha 
01-He 
02-Ha3.96 (m )
03-He3.96 (m )
04-Ha 
04-He 
05-H 
07-H6.10
09-Ha3.37
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.09
19-Me0.86
21-Me1.48
22-H3.75
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.25
27-Me1.25
H-1'5.48 (d, 3.9)
CDCl3 (hepta-OAc)
01-Ha 
01-He 
02-Ha5.13 (m, w1/2=21)
03-He4.09 (m, w1/2=8)
04-Ha 
04-He 
05-H 
07-H6.07
09-Ha3.49
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.01
19-Me0.89
21-Me1.49
22-H5.29 (d br )
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.32
27-Me1.33
H-1'5.63 (d, 3.6)

PHYSICAL PROPERTIES

M.P.240-242 ░C
[α]D20+ 91.2 ? 2 ░ (c 1.01; MeOH)
IR (KBr) ν max (cm-1)3380-3430 (OH), 1648 (cyclohexenone)
UV (EtOH) λ max (log ε)247 (4.15)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 
LCsilicagel with CHCl3-MeOH (4:1, v/v)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 3.0 x 10-5M

REFERENCES

First isolationSAATOV, Z. et al. (1984) Khim. Prir. Soedin., 741-744 Search more
BioactivitiesDINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 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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