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MALACOSTERONE

Year of first report:1986
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Tapinella panuoides [Fungi] » Images of Tapinella panuoides Wikipedia: <br />
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Occurence in animals:
Cepaea nemoralis [snail] » Images of Cepaea nemoralis Wikipedia: <br />
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MALACOSTERONE

MASS SPECTRUM

CI-MS (NH3) m/z497 (M+H)+, 479, 461, 443, 425, 407, 379, 363, 361, 345, 343
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0137.32
0268.70
0368.50
0432.86
0551.81
06206.36
07122.09
08167.00
0934.90
1039.29
1121.39
1232.42
13*
1483.27
1544.95
1673.34
1751.66
1816.41
1924.42
2080.82
2120.64
2277.79
2327.77
2442.57
2571.29
2629.79
2728.89
D2O
01-Ha 
01-He 
02-Ha3.97 (m, w1/2=22)
03-He4.07 (m, w1/2=8)
04-Ha 
04-He 
05-H2.36
07-H5.96 (d, 2.5)
09-Ha3.11 (m, w1/2=22)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha2.36 (m )
15-Hb2.14 (m )
16-Ha4.73 (m, w1/2=22)
17-H2.34 (d, 7.8)
18-Me1.11 (s )
19-Me1.02 (s )
21-Me1.24 (s )
22-H3.86 (d )
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.23 (s )
27-Me1.23 (s )
CD3OD
01-Ha1.79 (dd, 13,0, 4.5)
01-He1.43 (dd, 8.0, 12.3)
02-Ha3.82 (ddd, 12.0, 4.0, 3.5)
03-He3.94 (q 3.0)
04-Ha1.72
04-He1.68
05-H2.40 (dd, 12.6, 4.8)
07-H5.81 (d, 2.5)
09-Ha3.16 (ddd 10.5, 7.0, 2.5)
11-Ha1.70
11-He1.82
12-Ha2.14 (dt, 12.5, 12.5, 5.2)
12-He1.93 (ddd)
15-Ha2.25 (dd, 13.6, 7.6)
15-Hb2.08 (dd, 13.6, 4.7)
16-Ha4.68 (dt, 7.6, 7.6, 4.7)
17-H2.44 (d, 7.6)
18-Me1.136 (s )
19-Me0.990 (s )
21-Me1.197 (s )
22-H3.88 (dd, 10.6, 1.5)
23-Ha1.67
23-Hb1.36
24-Ha1.86 (ddd 13.3 12.0, 5.0)
24-Hb1.50 (ddd 13.3 11.5, 4.0)
26-Me1.197 (s )
27-Me1.213 (s )

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
NP-HPLCcolumn Zorbax-Sil 250x4.6 mm, solvent CH2Cl2-iPrOH-H20 (125:25:2), flow-rate gradient 0.5 to 1 ml.min-1 in 80 min, Ret 64.6 min (20E 49.4 min).
RP-HPLCcolumn Ultrasphere ODS 250x4.6 mm, solvent linear gradient (60 min) from 8 to 40% CH3CN in 20 mM Tris-HClO4, pH 7.5, flow-rate 1 ml.min-1, Ret 26.6 min (20E 29.2 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 9.0 x 10-6M

REFERENCES

First isolationGARCIA, M. et al. (1986) Int. J. Invertebr. Reprod. Develop. 9, 43-58 Search more
GeneralGARCIA, M. et al. (1995) Comp. Endocrinol. 97, 76-85 Search more
BioactivitiesHARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 Search more
Struct. analysisVOKAC, K. et al. (1998) Phytochemistry 49, 2109-2114 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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