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ECDYSONE

Year of first report:1954
Formula:C27H44O6
Molecular weight:464
Occurence in plants:
Pharbitis purpurea [Convolvulaceae] » Images of Pharbitis purpurea Wikipedia: <br />
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Pteridium aquilinum [fern] » Images of Pteridium aquilinum Wikipedia: <br />
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Polypodium vulgare [fern] » Images of Polypodium vulgare Wikipedia: <br />
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Osmunda asiatica [fern] » Images of Osmunda asiatica Wikipedia: <br />
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Osmunda japonica [fern] » Images of Osmunda japonica Wikipedia: <br />
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Blechnum minus [fern] » Images of Blechnum minus Wikipedia: <br />
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Angiosperms [Plantae] » Images of Angiosperms Wikipedia: <br />
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Ipomoea calonyction [Convolvulaceae] » Images of Ipomoea calonyction Wikipedia: <br />
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Occurence in animals:
Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: <br />
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Manduca sexta [Lepidoptera] » Images of Manduca sexta Wikipedia: <br />
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various Insects [Insecta] » Images of various Insects Wikipedia: <br />
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ECDYSONE

MASS SPECTRUM

CI-MS (NH3) m/z482 (M+H+NH3)+, 465 (MH)+, 447, 429, 427, 413, 411, 409, 395, 349, 323, 321, 315, 313
EI-MS m/z (relative intensity %)446 (3), 428 (29), 413 (2), 410 (3), 359 (4), 348 (8), 330 (15), 300 (23), 99 (100), 81 (61).
FAB-MS m/z463 (M-H)-

CARBON NMR

PROTON NMR

C5D5N
0138.08 (t )
0268.10 (d )
0368.10 (d )
0432.45 (t )
0551.41 (d )
06203.36 (s )
07121.61 (d )
08165.53 (s )
0934.63 (d )
1038.76 (s )
1121.20 (t )
1231.49 (t )
1347.70 (s )
1483.97 (s )
1532.03 (t )
1626.74 (t )
1748.28 (d )
1815.89 (q )
1924.55 (q )
2043.04 (d )
2113.74 (q )
2274.07 (d )
2325.69 (t )
2442.55 (t )
2569.80 (s )
2630.09 (q )
2730.01 (q )
CD3OD
0137.33
0268.69
0368.50
0432.89
0551.79
06206.55
07122.01
08167.63
0935.23
1039.24
1121.57
1232.03
1348.11
1485.07
1532.07
1627.00
1748.79
1816.18
1924.46
2043.46
2113.22
2275.24
2325.30
2442.25
2571.41
2629.05
2729.61
C5D5N
01-Ha1.9
01-He2.1
02-Ha4.15 (m, w1/2=22)
03-He4.21 (m, w1/2=8)
04-Ha1.80
04-He2.03
05-H3.01 (dd, 13, 4)
07-H6.25 (d, 2.5)
09-Ha3.54 (m, w1/2=22)
11-Ha1.60
11-He1.8
12-Ha2.53
12-He1.83
15-Ha1.85*
15-Hb1.75*
16-Ha2.19$
16-Hb1.59$
17-H2.51
18-Me0.70 (s )
19-Me1.06 (s )
20-H2.12
21-Me1.28 (d, 7)
22-H4.05
23-Ha1.80
23-Hb1.94
24-Ha2.26
24-Hb1.79
26-Me1.37 (s )
27-Me1.37 (s )
CD3OD
01-Ha1.43
01-He1.78
02-Ha3.83 (ddd, 12, 3, 3)
03-He3.94 (ddd, 3, 3, 3)
04-Ha1.65
04-He1.75
05-H2.38 (dd, 12, 5)
07-H5.81 (d, 2.5)
09-Ha3.14 (m, w1/2=22)
11-Ha1.65
11-He1.78
12-Ha2.10 (ddd, 13,13,5)
12-He1.7-1.8
15-Ha2.00
15-Hb1.53
16-Ha1.98°
16-Hb1.48°
17-H2.01
18-Me0.73 (s )
19-Me0.97 (s )
20-H1.72
21-Me0.95 (d, 7.5)
22-H3.59 (m, w1/2=16)
23-Ha1.30
23-Hb1.60
24-Ha1.75
24-Hb1.45
26-Me1.19 (s )
27-Me1.20 (s )

PHYSICAL PROPERTIES

M.P.237-239 °C
[α]D20+ 64.7 ° (c ; EtOH)
IR (KBr) ν max (cm-1)3333 (OH), 1657 (cyclohexenone)
UV (EtOH) λ max (log ε)242 (4.093)

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silicagel Rf 0.21 (CHCl3-EtOH 4:1); RP-TLC on paraffin coated silica gel Rf 0.37 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.37 (MeOH-H2O 65:35)
GLCRet 5.85 min on 1.5% OV101 (0.9 m x 4.5 mm i.d.) at 285°C after silylation at 140°C for 60 h, presumed 2,3,14,22,25 pentakis-TMS ether. (many systems are available - only examples are given here)
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.1 x 10-6M
Drosophila melanogaster BII cell assay: EC50 = 1.0 x 10-6M
Drosophila melanogaster imaginal disc assay: EC50 = 1.5 x 10-5M
Drosophila melanogaster imaginal disc assay: EC50 = 2.2 x 10-5M
Drosophila melanogaster Kc-H cell assay: EC50 = 2.3 x 10-6M
Dermestes vulpinus in vivo assay: ED50 = 42.0 ug/g
Galleria mellonella in vivo assay: ED50 = 7.8 ug/g
Sarcophaga bullata in vivo assay: ED50 = 4.2 ug/g
Calliphora bioassay: 100% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationBUTEN, T et al. (1954) Z. Naturforsch. 9B, 389-391 Search more
GeneralKARLSON, P. et al. (1965) Chem. Ber. 98, 2394-2402 Search more
GeneralHUBER, R. et al. (1965) Chem. Ber. 98, 2403-2424 Search more
GeneralFURLENMEIER, A. et al. (1966) Helv. Chim. Acta 49, 1591-1606 Search more
GeneralSIDDALL, J.B. et al. (1966) J. Am. Chem. Soc. 88, 862-863 Search more
First isolationHEINRICH, G. et al. (1967) Experientia 23, 995 Search more
BioactivitiesCHIHARA, C.J. et al. (1972) J. Insect Physiol. 18, 1115-1123 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
BioactivitiesYUND, M.A. et al. (1980) In: Invert. Systems in Vitro pp. 229-237 Search more
BioactivitiesCHERBAS, L. et al. (1980) W. Roux Arch. Devel. Biol. 189, 1-15 Search more
GeneralWILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 Search more
GeneralBIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 Search more
GeneralGIRAULT, J.-P. et al. (1988) J. Insect Physiol. 34, 701-706 Search more
BioactivitiesSLAMA, K. et al. (1993) Insect Biochem. Molec. Biol. 23, 181-185 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more
BioactivitiesDINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 Search more
IdentificationBUDESINSKY, M. et al. (2008) Steroids 73, 502-514 Search more

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© Université 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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