Welcome to online ecdysteroids database !   .
Access data · History · Contact

MAKISTERONE A

Year of first report:1968
Formula:C28H46O7
Molecular weight:494
Occurence in plants:
Podocarpus macrophyllus [Podocarpaceae] » Images of Podocarpus macrophyllus Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>53</b><br />
Podocarpus elatus [Podocarpaceae] » Images of Podocarpus elatus Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>53</b><br />
Lychnis flos-cuculi [Caryophyllaceae] » Images of Lychnis flos-cuculi Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>53</b><br />
Palisota schweinfurthii [Commelinaceae] » Images of Palisota schweinfurthii Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>53</b><br />
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>53</b><br />
Occurence in animals:
Oncopeltus fasciatus [Hemiptera] » Images of Oncopeltus fasciatus Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>68</b><br />
Drosophila melanogaster [Diptera] » Images of Drosophila melanogaster Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>68</b><br />
Apis mellifera [Hymenoptera] » Images of Apis mellifera Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>68</b><br />
Callinectes sapidus [crab] » Images of Callinectes sapidus Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>68</b><br />
MAKISTERONE A

MASS SPECTRUM

EI-MS m/z (relative intensity %)494 (M)+, 363 (100), 345 (78), 131 (24), 113 (59), 95 (30), 70 (100)
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0137.8
0268.0
0368.0
0432.3
0551.3
06203.6
07121.6
08166.1
0934.4
1038.6
1121.1
1231.7
1348.1
1484.2
1532.0
1621.3
1749.9
1817.9
1924.4
2077.0
2121.5
2274.7
2334.4
2441.7
2572.2
2626.3 *
2728.2 *
2815.4
CD3OD
0137.3
0268.5
0368.7
0432.6
0551.7
06206.4
07122.1
08167.9
0935.1
1039.3
1121.5
1231.8
1485.2
1532.8
1621.4
1750.4
1818.1
1924.4
2077.9
2121.0
2275.3
2334.4
2441.5
2573.7
2627.4
2726.1
2814.9
D2O
01-Ha 
01-Hb 
02-Ha3.99 (m, w1/2=22)
03-He4.07 (m, w1/2=8)
04-Ha 
04-He 
05-H2.34 (t
07-H5.97 (d, 2)
09-Ha3.11 (m, w1/2=22)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.29 (m, t )
18-Me0.87 (s )
19-Me1.00 (s )
21-Me1.23 (s )
22-Hb3.56 (d, 10.6)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.17 (s )
27-Me1.20 (s )
28-Me0.95 (d, 6.9)
Me2CO-d6
01-Ha 
01-Hb 
02-Ha3.82 dt (11.3, 3.8, 3.8)
03-He3.90 um
04-Ha 
04-He 
05-H2.33 dd (10.2, 7.1)
07-H5.71 d (2.6)
09-Ha3.16 ddd (10.0, 7.0, 2.6)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.43 t (9.1)
18-Me0.92 s
19-Me0.94 s
21-Me1.19 s
22-Hb3.46 br d (11.0, <2)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.15 s
27-Me1.11 s
28-Me0.92 d (6.8)

PHYSICAL PROPERTIES

M.P.263-265░C
[α]D20+ 60.3░ (dioxane)
IR (KBr) ν max (cm-1)3420, 1655, 1630
UV (MeOH) λ max (log ε)243 (4.09)

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC silica : Rf 0.21 (EtOAc-MeOH-NH4OH 85:10:5); Rf 0.19 (CH2Cl2-EtOH 85:15)Rf 0.16 (CHCl3-EtOH 4:1); Rf 0.20 (CHCl3-EtOH 4:1); RP-TLC on paraffin-coated silica gel : Rf 0.33 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel : Rf 0.40 (MeOH-H2O 65:35)
GLCRet 9.15 min on 1.5% OV101 (0.9m x 4mm i.d.) at 285░C following silylation at 140░C for 60 h.
NP-HPLC(Zorbax-Sil) Ret. 12.7 min (solvent CH2Cl2-iPrOH-H2O, 125:40:3) (20E : 16.8 min);
RP-HPLC(Spherisorb-ODS2) Ret. 7.3 min (solvent ACN-0.1% TFA in H2O, 23:77) (20E : 5.5 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.3 x 10-8M
Calliphora vicina imaginal disc assay: EC50 = 1.2 x 10-7M
Drosophila melanogaster Kc-H cell assay: EC50 = 2.3 x 10-8M
Calliphora assay: 100% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationIMAI, S. et al. (1968) Tetrahedron Lett. 3883-3886 Search more
GeneralGALBRAITH, M.N. et al. (1969) J. Chem. Soc., Chem. Commun. 402-403 Search more
GeneralFAUX, A. et al. (1969) J. Chem. Soc., Chem. Commun. 175-176 Search more
Struct. analysisDANIELI, B. et al. (1974) Chem. Commun., 745-746 Search more
GeneralKAPLANIS, J.N. et al. (1975) Science 190, 681-682 Search more
BioactivitiesCHERBAS, L. et al. (1980) W. Roux Arch. Devel. Biol. 189, 1-15 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
GeneralREDFERN, C.P.F. et al. (1984) Proc. Natl. Acad. Sci. U.S.A. 81, 5643-5647 Search more
GeneralFELDLAUFER, M.F. et al. (1986) Insect Biochem. 16, 45-48 Search more
BioactivitiesCLEMENT, C.Y. et al. (1993) Insect Biochem. Molec. Biol. 23, 187-193 Search more
BioactivitiesTERENTIOU, P. et al. (1993) Insect Biochem. Molec. Biol. 23, 131-136 Search more
IdentificationPIS, J. et al. (1994) Phytochemistry 37, 707-711 Search more
GeneralKUSAMBA, C. et al. (1995) Fitoterapia LXVI, 175-178 Search more

see Important notice
© 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
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE