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20,26-DIHYDROXYECDYSONE [= PODECDYSONE C]

Year of first report:1967
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Podocarpus elatus [Podocarpaceae] » Images of Podocarpus elatus Wikipedia: <br />
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Lychnis flos-culculi [Caryophyllaceae] » Images of Lychnis flos-culculi Wikipedia: <br />
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Silene nutans [Caryophyllaceae] » Images of Silene nutans Wikipedia: <br />
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Silene otites [Caryophyllaceae] » Images of Silene otites Wikipedia: <br />
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Palisota schweinfurthii [Commelinaceae] » Images of Palisota schweinfurthii Wikipedia: <br />
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Occurence in animals:
Manduca sexta [Lepidoptera] » Images of Manduca sexta Wikipedia: <br />
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Hymenolepis diminuta [Platyhelminthes] » Images of Hymenolepis diminuta Wikipedia: <br />
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20,26-DIHYDROXYECDYSONE  [=  PODECDYSONE C]

MASS SPECTRUM

CI-MS (NH3) m/z514, 497 (MH)+, 479, 461, 443, 380, 363 (MH - C22-C27)+, 347, 345, 329.
EI-MS m/z460 (M - 2x18)+, 442 (M - 3x18)+, 427, 409, 391, 363 (MH - C22-C27)+, 345, 133 (C22-C27)+, 115.
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0137.34
0268.70
0368.51
0432.87
0551.79
06206.50
07122.15
08167.94
0935.09
1039.27
1121.50
1232.52
1349.0*
1485.26
1531.77
1621.50
1750.48
1818.04
1924.41
2077.82
2121.01
2278.22
2330.17
2432.10
2537.06
2668.13
2717.52
D2O
01-Ha1.4
01-He1.9
02-Ha3.99 (m, w1/2=22)
03-He4.07 (m, w1/2=8)
04-Ha1.75
04-He1.75
05-H2.34 (t-like )
07-H5.97 (d, 2.5)
09-Ha3.11 (m, w1/2=21)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.32 (m )
18-Me0.87 (s )
19-Me1.00 (s )
21-Me1.24 (s )
22-H3.43 (d br, 10)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-CH2-OH3.45, 3.46 (s )*
27-Me1.16, 1.18 (s )*
CD3OD
01-Ha1.43 (dd, 13.5; 12.2)
01-He1.79 (dd, 13.5; 4.2)
02-Ha3.84 (ddd, 12.2; 4.2; 3.0)
03-He3.95 (q, 3; 3; 3)
04-Ha1.71-1.77
04-He1.71-1.77
05-H2.38 (dd, 13.0; 4.4)
07-H5.81 (d, 2.6)
09-Ha3.15 (ddd, 11.5; 7.0; 2.6)
11-Ha1.71
11-He1.81
12-Ha2.12 (td, 13; 13; 5)
12-He1.88
15-Ha1.96
15-Hb1.60
16-Ha1.72
16-Hb2.0
17-H2.37 (t, 9.0; 9.0)
18-Me0.890 (s)
19-Me0.967 (s)
21-Me1.178 (s)
22-H3.33 (dd, 10.3; 1.6)
23-Ha1.63
23-Hb1.19
24-Ha1.71
24-Hb1.11
25-H1.60
26-CH2-OH3.46 (dd, 10.8; 5.6); 3.34 (dd, 10.8; 6.8)
27-Me0.945 (d, 6.8)

PHYSICAL PROPERTIES

M.P.149-153 ░C ;
[α]D20 
IR (KBr) ν max (cm-1)3486 (OH), 1652 (cyclohexenone).
UV (EtOH) λ max (log ε)242 (4.041) ;

CHROMATOGRAPHY

TLCRf 0.44 (EtOAc-EtOH-H2O, 8:2:1) (20E 0.61); Rf 0.25 (CHCl3-MeOH-Me2CO, 6:2:1) (20E 0.47); Rf 0.17 (CHCl3-96% EtOH, 7:3) (20E 0.35).
GLCRetention time 18.25 min, 25 m x 0.22 mm fused silica column, 0.1 ?m film of BP-1 oven temperature 50░C at injection raised immediatelly to 200░C than programmed at 8░C.min-1 to 320░C than isothermal; carrier gas He at 100 ml.min-1 (20E: retention time 12 min).
HPLC1- Retention time 43.9 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min) 2- Retention time 4.1 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN-1? TFA in H2O, 23:77 v/v, flow-rate 1 ml.min-1] (20E 5.5 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 7.3 x 10-6M
Calliphora assay: 10% (20-hydroxyecdysone = 100%)
Musca assay: 7-10% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationTHOMPSON, M.J. et al. (1967) Chem. Commun., 650-653 Search more
First isolationTHOMPSON, M.J. et al. (1973) Experientia 29, 782 Search more
BioactivitiesBERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 Search more
GeneralMENDIS, A.H.W. et al. (1983) Mol. Biochem. Parasitol. 9, 209-226 Search more
GeneralEVERSHED, R.P. et al. (1987) J. Chromatogr. 390, 357-369 Search more
GeneralGIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 293-302 Search more
GeneralKUSAMBA, C. et al. (1995) Fitoterapia LXVI, 175-178 Search more
GeneralSUKSAMRARN, A. et al. (1998) Tetrahedron 54, 14565-14572 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
Struct. analysisBUDESINSKY, M. et al. (2008) Steroids 73, 502-514 Search more

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