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5,20,26-TRIHYDROXYECDYSONE 20,22-ACETONIDE

Year of first report:2008
Formula:C30H48O9
Molecular weight:552
Occurence in plants:
Silene viridiflora [Caryophyllaceae] » Images of Silene viridiflora Wikipedia: <br />
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Occurence in animals:
 
5,20,26-TRIHYDROXYECDYSONE 20,22-ACETONIDE

MASS SPECTRUM

ESI-MS m/z (relative intensity %)575 [M+Na]+ (46), 553 [M+H]+ (100), 537 [M-CH3]+ (5), 535 [M+H-H2O]+ (3), 520 [M+H-H2O-CH3]+ (2), 495 [M+H-acetone]+ (59), 481 (1), 477 (3), 437 (3), 359 (3), 328 (14)
HR-ESI-MS m/z553.3366 [M+H]+ (calc. for C30H49O9, 553.3363)

CARBON NMR

PROTON NMR

CD3OD
0134.3
0268.6
0370.4
0436.3
0580.4
06202.5
07120.7
08167.4
0939.2
1045.5
1122.65
1232.6
1348.7
1485.3
1531.8
1622.5
1750.5
1817.8
1917.1
2086.0
2122.7
2283.6
2324.0
2437.2
2573.6
2670.7
2723.9
2xMe 
Me227.3, 29.5
O-C-O108.2
CD3OD
01-Ha1.73 (m)
01-He1.73 (m)
02-Ha3.95 (ddd, 10.0, 7.4, 3.6)
03-He3.99 (q, 3)
04-Ha1.77 (dd, 14.9, 3.0)
04-He2.075 (dd, 14.7, 3.0)
07-H5.86 (d, 2.8)
09-H3.19 (ddd, 11.3, 7.0, 2.7)
11-Ha1.74 (m)
11-He1.81 (m)
12-Ha2.12 (td, 13.1, 5.0)
12-He1.86 (m)
15-Ha1.61 (m)
15-Hb1.97 (m)
16-Ha1.87 (m)
16-Hb2.03 (m)
17-H2.31 (dd, 9.4, 8.1)
18-Me0.83 (s)
19-Me0.915 (s)
21-Me1.18 (s)
22-H3.695 (t, 6)
23-Ha1.53 (m)
23-Hb1.55 (m)
24-Ha1.52 (m)
24-Hb1.71 (m)
26-CH2OH3.375 (d, 11), 3.355 (d, 11)
27-Me1.15 (s)
Me2CO1.39 (s), 1.32 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25+ 89 ° (c 0.05; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)242 (3.76) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTÓTH, N. et al. (2008) J. Nat. Prod. 71, 1461-1463 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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