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2,14,22,25-TETRADEOXYECDYSONE

Year of first report:1969
Formula:C27H44O2
Molecular weight:400
Occurence in plants:
Peniocereus greggi [Cactaceae] » Images of Peniocereus greggi Wikipedia: <br />
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Occurence in animals:
Locusta migratoria [Orthoptera] » Images of Locusta migratoria Wikipedia: <br />
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2,14,22,25-TETRADEOXYECDYSONE

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)(for its 3-acetate): 442(M)+
HR-MS 

CARBON NMR

PROTON NMR

CD2Cl2
0129.5 *
0228.9 *
0365.3
0436.2
0550.7
06202.0
07121.3
08165.0
0939.8
1038.2
1122.5
1239.7
1346.2
1456.7
1525.1
1628.1
1756.7
1812.3
1924.1
2034.1
2118.8
2236.6
2325.1
2439.7
2528.2
2622.5 $
2722.7 $
CDCl3
01-Ha 
01-He 
02-Ha 
03-He4.02 (m )
04-Ha 
04-He 
05-H2.43
07-H5.70
09-Ha2.35
11-Ha 
11-He 
12-Ha 
12-He 
14-H2.15*
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.10*
18-Me0.59
19-Me1.01
21-Me0.93
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me0.86 (d, 5)
27-Me0.86 (d, 5)
C6D6 (3-OAc)
01-Ha 
01-He 
02-Ha 
03-He5.10
04-Ha 
04-He 
05-H 
07-H5.72
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.63
19-Me0.98
21-Me 
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me 
27-Me 

PHYSICAL PROPERTIES

M.P.176-177 ░C
[α]D20+ 60.2 ░ (c 1.08; MeOH)
IR (KBr) ν max (cm-1)1743, 1667, 1627, 1278 ; 1660, 1390, 1053 (free form)
UV (CH3CN) λ max (log ε)243 (4.114)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC : column Spherisorb 5-ODS-2, solvent linear gradient (in 30 min) of 20% to 100% ACN-iPrOH (5:2) in 0.1% TFA in H2O, flow-rate 1 ml.min-1, Rt 39.9 min (2dE : 17.0 min, 2,22,25dE : 35.9 min)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationKNIGHT, J.C. et al. (1969) Phytochemistry 8, 477-482 Search more
GeneralGALBRAITH, M.N. et al. (1974) Aust. J. Chem. 27, 1087-1095 Search more
GeneralHORN, D.H.S. et al. (1976) Insect Biochem. 6, 601-604 Search more
First isolationHETRU, C. et al. (1978) Life Sci. 22, 2141-2154 Search more
GeneralFAUX, A.F. et al. (1979) Insect Biochem. 9, 101-105 Search more
GeneralHAAG, T. et al. (1987) Insect Biochem. 17, 291-301 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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