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28-EPI-SENGOSTERONE

Year of first report:1996
Formula:C29H44O9
Molecular weight:536
Occurence in plants:
Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans var. atropurpurea Wikipedia: <br />
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Occurence in animals:
 
28-EPI-SENGOSTERONE

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
MS (thermospray) m/z (relat. intensity %)554 (M+NH4)+ (25), 537 (M+H) (100), 536 (M)+ (82), 519 (M+H-H20) (34), 501 (M+H-2H2O) (21)

CARBON NMR

PROTON NMR

C5D5N
0134.8
0267.9
0369.8
0435.9
0579.8
06200.9
07120.0
08166.6
0938.2
1044.8
1122.0
1232.1
1348.2
1483.9
1531.6
1621.3
1750.0
1817.9
1917.1
2076.7
2121.1
2276.4
2330.8
2446.0
2538.7
26179.1
2716.3
2878.7
2914.3
C5D5N
01-Ha 
01-He 
02-Ha4.27 (m, w1/2=24)
03-He4.18 (m, w1/2=15)
04-Ha 
04-He 
05-H?
07-H6.27 (d, 2.1)
09-H3.66 (m, w1/2=24)
11-Ha 
11-He 
12-Ha2.62
12-He2.08
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.88 (t, 8.4)
18-Me1.24 (s)
19-Me1.18 (s)
21-Me1.61 (s)
22-H3.90 (m, w1/2=20)
23-Ha1.81
23-Hb1.69
24-H2.48
25-H2.33 (dq, 11.4, 6.9)
27-Me1.17 (d, 7)
28-H5.01
29-Me1.31 (d, 6)
H-2 OH5.56 (w1/2=15)
H-22 OH5.56 W1/2=8)
H-3 OH5.88 (d, 8.1)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3416 (OH), 1749 (?-lactone), 1670 (cyclohexenone)
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC, column Tracer 30x0.78 cm packed with Spherisorb-ODS2 10?m, solvent iPrOH-H2O (13:87), flow-rate 3 mL.min-1, 23░C, Ret 22.5 min.

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationCALGANO, M.P. et al. (1996) Tetrahedron 52, 10137-10146 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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