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POSTSTERONE

Year of first report:1970
Formula:C21H30O5
Molecular weight:362
Occurence in plants:
Cyathula capitata [Amaranthaceae] » Images of Cyathula capitata Wikipedia: <br />
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Silene otites [Caryophyllaceae] » Images of Silene otites Wikipedia: <br />
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Lychnis flos-cuculi [Caryophyllaceae] » Images of Lychnis flos-cuculi Wikipedia: <br />
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Serratula tinctoria [Asteraceae] » Images of Serratula tinctoria Wikipedia: <br />
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Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: <br />
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Occurence in animals:
Calliphora stygia [Diptera] » Images of Calliphora stygia Wikipedia: <br />
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POSTSTERONE

MASS SPECTRUM

CI-MS (NH3) m/z380 (M+H+NH3)+, 363 (M+H)+, 345, 327
EI-MS m/z (relative intensity %)362 (M)+, 344, 326, 301, 283
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0137.8
0267.9
0367.9
0432.2
0551.2
06203.1
07122.0
08164.3
0934.4
1038.6
1121.0 *
1231.8 **
1348.1
1483.9
1530.4 **
1621.9 *
1759.4
1817.1
1924.3
20209.0
2131.2
C5D5N
01-Ha 
01-Hb 
02-Ha4.09 (m )
03-He4.15 (m )
04-Ha 
04-He 
05-H2.90 (dd, 12, 4)
07-H6.09 (d , 2)
09-Ha3.46 (m )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H3.52 (dd , 8, 8)
18-Me0.68 (s )
19-Me1.00 (s )
21-Me2.12 (s )
CDCl3
01-Ha1.41 (dd, ~13,10)
01-Hb1.86
02-Ha3.89 (br m , w1/2=22)
03-He4.04 (br m, w1/2=8)
04-Ha1.63
04-He1.84
05-H2.44 (dd, 14, 4.5)
07-H5.84 (d, 2.5)
09-Ha3.02 (ddd, 11, 7, 2.5)
11-Ha1.64
11-He1.86
12-Ha2.08
12-He1.55
15-Ha2.0
15-Hb1.6
16-Ha2.27
16-Hb1.84
17-H3.27 (t, 8.5)
18-Me0.62 (s )
19-Me0.97 (s )
21-Me2.14 (s )

PHYSICAL PROPERTIES

M.P.240-242°C (softening at 237°C)
[α]D20 
IR (KBr) ν max (cm-1)3425 (OH), 1710 (acetyl), 1645 (cyclohexenone)
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

TLCNP-TLC on silica gel : Rf 0.32 (CHCl3-EtOH 4:1); Rf 0.27 (EtOAc-MeOH-NH4OH 85:10:5); Rf 0.42 (CH2Cl2-EtOH 85:15). RP-TLC on paraffin-coated silica gel Rf 0.45 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.42 (MeOH-H2O 65:35).
GLCRt on 1.5% OV101 (0.9 m x 4 mm i.d.) at 285°C of 1.3 min after silylation at 140°C for 60 h.
NP-HPLC(Zorbax-Sil) Ret 15.2 min (isooctane-iPrOH-H2O 100:30:2);
RP-HPLC(Spherisorb-ODS2) Ret 9.7 min (solvent ACN-0.1% TFA in H2O, 23:77) (20-hydroxyecdysone 5.5 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-5M
Calliphora assay: 0% (20-hydroxyecdysone = 100%)

REFERENCES

GeneralSIDDALL, J.B. et al. (1967) J. Chem. Soc., Chem. Commun., 899- Search more
GeneralGALBRAITH, M.N. et al. (1969) J. Chem. Soc., Chem. Commun., 1134-1135 Search more
First isolationHIKINO, H. et al. (1970) Steroids 16, 393-399 Search more
GeneralHIKINO, H. et al. (1975) Chem. Pharm. Bull. 23, 125- Search more
GeneralHIKINO, H. et al. (1975) Hoppe-Seyler´s Z. Physiol. Chem. 309-314 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
GeneralGIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 Search more
GeneralPETERSEN, Q.R. et al. (1993) Aust. J. Chem. 46, 1961-1964 Search more
IdentificationVOKAC, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 Search more
BioactivitiesDINAN, L. et al. (2003) J. Insect Sci. 3:6 (pp. 11) Search more

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