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DACRYHAINANSTERONE [= 5-DEOXYKALADASTERONE]

Year of first report:1982
Formula:C27H42O6
Molecular weight:462
Occurence in plants:
Dacrydium pierrei [Podocarpaceae] » Images of Dacrydium pierrei Wikipedia: <br />
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Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: <br />
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Serratula coronata [Asteraceae] » Images of Serratula coronata Wikipedia: <br />
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Occurence in animals:
 
DACRYHAINANSTERONE [= 5-DEOXYKALADASTERONE]

MASS SPECTRUM

CI-MS (NH3) m/z463 (MH)+, 445, 427, 361, 343, 325
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0136.2
0267.4
0366.9
0435.0
0550.2
06204.0
07117.8
08162.2
09145.0
1039.4
11132.4
1237.7
1347.0
1483.1
1530.0
1620.3
1749.1
1816.7
1930.0
2076.2
2119.3
2276.6
2329.1
2436.0
2527.8
2621.3
2721.9
CD3OD
01-Ha1.7
01-Hb2.1
02-Ha3.72 (m )
03-He3.84 (m )
04-Ha1.6
04-He1.78
05-H2.40
07-H5.75 (br s, w1/2=4)
09-Ha--
11-Ha6.3 (ddd, 6.5, 2, 2)
11-He--
12-Ha2.72 (br d, 18)
12-He2.42
15-Ha 
15-Hb 
16-Ha2.05
16-Hb1.75
17-H2.45
18-Me0.89 (s )
19-Me1.10 (s )
21-Me1.18 (s )
22-H3.33 (dd, 11, 2)
23-Ha1.35
23-Hb1.55
24-Ha 
24-Hb 
25-H1.55
26-Me0.91 (d, 6.5)
27-Me0.94 (d, 6.5)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε)298 (4.152), 235 (3.806)

CHROMATOGRAPHY

HPTLC 
TLCRf 0.56 (EtOAc-MeOH-NH4OH 85:10:5); Rf 0.67 (CH2Cl2-EtOH 85:15).
GLC 
HPLCNormal phase (Zorbax-Sil) Ret. 10.4 min (CH2Cl2-iPrOH-H2O, 125:25:2)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 5.2 x 10-9M

REFERENCES

First isolationHOU, S. et al. (1982) Zhiwu Xuebao 24, 347-354 Search more
GeneralGIRAULT, J.-P. et al. (1988) Phytochemistry 27, 737-741 Search more
GeneralSZENDREI, K. et al. (1988) J. Nat. Prod. 51, 993-995 Search more
GeneralVOLODIN, V.V. et al. (1997) Planta Med. 26, 459-461 Search more
BioactivitiesBOURNE, P. et al. (2002) J. Insect Sci. 2:11 (pp. 11) Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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