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11α,20,26-TRIHYDROXYECDYSONE

Year of first report:2000
Formula:C27H44O9
Molecular weight:512
Occurence in plants:
Vitex canescens [Lamiaceae] » Images of Vitex canescens Wikipedia: <br />
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Occurence in animals:
 
11α,20,26-TRIHYDROXYECDYSONE

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
HR-FAB-MS(negative mode): 511.2906 and 511.2908 for the two epimers, respectivelly, [M-H]- (calc. 511.2907 for C27H44O9 -H)

CARBON NMR

PROTON NMR

C5D5N
0139.65 39.64
0268.20 68.20
0367.94 67.94
0432.64 32.66
0552.26 52.26
06203.74 203.76
07122.02 122.01
08164.07 164.09
0942.53 42.53
1039.30 39.30
1168.62 68.62
1243.93 43.93
1347.96 47.96
1484.01 84.01
1531.65 31.65
1621.40 21.41
1749.78 49.78
1818.68 18.68
1924.65 24.65
2076.62 76.61
2121.29 21.32
2277.29 77.43
2326.57 26.51
2437.35 37.31
2572.41 72.37
2670.63 70.44
2724.32 24.52
C5D5N
01-Ha ?3.43 (dd, 12.4, 3.5) 3.44 (dd, 12.5, 3.5)
01-He 
02-Ha4.58 (m) 4.58 (m)
03-He4.20 (br, s) 4.21 (br, s)
04-Ha 
04-He 
05-H3.00 3.00
07-H6.28 (d, ca. 2) 6.28 (br, s)
09-H3.85-3.89 3.85-3.89
11-Ha4.58 (m) 4.58 (m)
12-Ha3.02 3.02
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H3.09 (t, 9.1) 3.09 (t, 8.9)
18-Me1.24 (s) 1.24 (s)
19-Me1.30 (s) 1.30 (s)
21-Me1.56 (s) 1.56 (s)
22-H3.85-3.89 3.85-3.89
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-H (2)3.85-3.89 3.85-3.89
26-Me? ?
27-Me1.45 (s) 1.45 (s)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3448, 2952, 1660, 1385, 10535; 3448, 2927, 1660, 1385, 1053
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

TLC 
GLC 
RP-HPLCcolumn ?Bondapak C18, 10 ?m, 300x3.9 mm, solvent MeOH-H2O (18:82), flow-rate 1.0 ml.min-1, Ret 34.4 and 40.8 min.
NP-HPLCcolumn Hypersil Si, 5 ?m, 250x4.6 mm; solvent CHCl3-MeOH (90:10), flow-rate 1.2 ml.min-1, Ret 16.4 min (for both epimers).

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSUKSAMRARN, A. et al. (2000) Phytochemistry 53, 921-924 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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