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TAXISTERONE

Year of first report:1982
Formula:C27H44O6
Molecular weight:464
Occurence in plants:
Taxus cuspidata [Taxaceae] » Images of Taxus cuspidata Wikipedia: <br />
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Silene nutans [Caryophyllaceae] » Images of Silene nutans Wikipedia: <br />
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Lychnis flos-culculi [Caryophyllaceae] » Images of Lychnis flos-culculi Wikipedia: <br />
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Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: <br />
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Occurence in animals:
Pycnogonum litorale [pantopod] » Images of Pycnogonum litorale Wikipedia: <br />
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Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: <br />
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TAXISTERONE

MASS SPECTRUM

CI-MS (NH3) m/z482 (M+H+NH3)+, 465 (M+H)+, 447, 429, 411
EI-MS m/z (relative intensity %)464 (M)+ (0.3), 446 (1.4), 431 (0.8), 428 (35), 418 (1), 413 (16), 410 (28), 400 (2.5), 395 (12), 385 (0.7), 343 (5), 327 (54), 325 (20), 320 (20), 309 (10), 302, 301 (19), 300 (35), 299 (27), 250 (30), 249 (15), 145 (20), 127 (97), 109 (100), 81 (20), 69 (54)
FAB-MS487 (2) [M+Na]+, 465 (6) [M+H]+, 447 (11), 429 (12), 411 (10), 397 (3), 371 (3), 355 (5), 303 (10), 301 (12), 249 (10), 213 (11), 181 (16), 165 (19), 145 (21), 128 (27), 109 (48), 91 (65), 69 (100)

CARBON NMR

PROTON NMR

CD3OD
0137.37
0268.72
0368.53
0432.86
0551.80
06206.51
07122.10
08168.14
0935.05
1039.26
1121.51
1232.38
1348.07
1485.54
1531.58
1621.96
1753.36
1818.12
1924.39
2075.99
2126.46
2245.89
2320.10
2445.50
2571.48
2629.33
2729.10
CDCl3
0138.4 (t )
0267.0 (d )
0368.7 (d )
0434.0 (t )
0551.0 (d )
06202.0 (s )
07121.5 (d )
08164.8 (s )
0933.6 (d )
1038.4 (s )
1120.4 (t )
1231.5 (t )
1346.9 (s )
1484.8 (s )
1530.9 (t )
1629.7 (t )
1752.2 (d )
1817.5 (q )
1923.8 (q )
2075.0 (s )
2126.5 (q )
2244.3 (t )
2318.7 (t )
2444.7 (t )
2571.0 (s )
2629.3 (q )
2729.5 (q )
D2O
01-Ha 
01-Hb 
02-Ha3.90 (m, w1/2 = 21)
03-He4.07 (m, w1/2 = 8)
04-Ha 
04-He 
05-H2.34 (t like )
07-H5.97 (d, 2.5)
09-Ha3.10 (m, w1/2 = 22)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.31 (m )
18-Me0.82 (s )
19-Me0.99 (s )
21-Me1.30 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.22 (s )
27-Me1.22 (s )
CD3OD
01-Ha1.42 (dd 13.3, 12.0)
01-Hb1.79 (dd 13.3, 4.4)
02-Ha3.84 (ddd 3.2, ~3.0, ~3.0)
03-He3.95 (q)
04-Ha1.75
04-He1.70
05-H2.38 (dd 12.0, 5.5)
07-H5.81
09-Ha3.15 (ddd 11.8, 7.0, 2.7)
11-Ha1.68
11-He1.78
12-Ha2.12 (dt)
12-He1.84
15-Ha1.95
15-Hb1.61
16-Ha1.71
16-Hb1.92
17-H2.34 (dd)
18-Me0.86 (s)
19-Me0.96 (s)
21-Me1.28 (s)
22-H1.38 - 1.52
23-Ha1.38 - 1.52
23-He1.38 - 1.52
24-Ha1.38 - 1.52
24-Hb1.38 - 1.52
26-Me1.19 (s)
27-Me1.19 (s)

PHYSICAL PROPERTIES

M.P.241-242 ░C
[α]D28+ 80.9 ? 2 ░ (c 0.42; MeOH)
IR (KBr) ν max (cm-1)3400-3430 (OH), 1710 (CO), 1647 (cyclohexenone)
UV (EtOH) λ max (log ε)244 (4.03)

CHROMATOGRAPHY

TLCRf 0.35 (CHCl3-MeOH-H2O 80:20:0.2) (20E 0.30); Rf 0.20 (EtOAc-MeOH-NH4OH 85:10:5) (20E : 0.18); Rf 0.17 (CH2Cl2-EtOH 85:15) (20E : 0.15)
GLC 
NP-HPLCNP-HPLC, column Zorbax-Sil 250 mm x 4.6 mm i.d., , flow-rate 1 ml.min-1, solvent CH2Cl2-iPrOH-H2O (125:40:3) Ret 13.4 min (20E : 16.8 min); solvent CH2Cl2-iPrOH-H2O (125:25:2) Ret 28.3 min (20E 37.4 min).
RP-HPLCRP-HPLC, column Spherisorb-5ODS2 250 mm x 4.6 mm i.d., flow-rate 1 ml.min-1, solvent ACN/ 0.1% TFA in H2O (23:77), Ret 13.9 min (20E : 5.5 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.4 x 10-8M
Drosophila melanogaster BII cell assay: EC50 = 9.5 x 10-8M
Calliphora assay: 1-2% (20-hydroxyecdysone = 100%)

REFERENCES

GeneralGALBRAITH, M.N. et al. (1969) Aust. J. Chem. 22, 1517-1524 Search more
GeneralKAPLANIS, J.N. et al. (1972) Steroids 20, 105-120 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
First isolationNAKANO, K. et al. (1982) Phytochemistry 21, 2749-2751 Search more
GeneralBALTAYEV, U.A. et al. (1985) Khim. Prir. Soedin., 62-66 Search more
GeneralB▄CKMANN, D. et al. (1986) J. Comp. Physiol., B 47, 257-267 Search more
GeneralGIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 Search more
GeneralKAMBA, M. et al. (1994) Insect Biochem. Molec. Biol. 24, 395-402 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more
IdentificationVOKAC, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 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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