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INOKOSTERONE [= CALLINECDYSONE A]

Year of first report:1967
Formula:C27H44O7
Molecular weight:480
Occurence in plants:
Morus sp [Moraceae] » Images of Morus sp Wikipedia: <br />
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Achyranthes fauriei [Amaranthaceae] » Images of Achyranthes fauriei Wikipedia: <br />
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Occurence in animals:
Callinectes sapidus [crab] » Images of Callinectes sapidus Wikipedia: <br />
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INOKOSTERONE [= CALLINECDYSONE A]

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)462 (M -18)+, 444, 426 (M- 3x18)+ , 411, 363, 345, 311, 126, 99, 81, 43
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
(I), (II)25R+25S pure 25S
0137.9 38.4
0268.0 68.6
0368.0 68.5
0432.2 32.6
0551.3 51.9
06203.3 204.1
07121.6 122.2
08165.9 166.7
0934.4 34.5
1038.6 39.2
1121.4 * 21.6
1231.7 $ 32.2
1348.1 48.6
1484.1 84.6
1532.0 $ 32.6
1621.6 * 22.0
1750.0 50.6
1817.8 18.4
1924.4 25.0
2076.7 77.3
2121.1 22.1
2277.2 77.4 77.7
2330.1 30.7
2431.7 32.0 32.6
2536.4 36.7 37.2
2667.3 68.0 67.8
2717.0 17.8 18.4
C5D5N
(I), (II)25R+25S pure 25S
01-Ha 1.91
01-Hb 2.18 (dd, 3.7, 14)
02-Ha 4.20 (m, w1/2 = 22)
03-He 4.26 (m, w1/2 = 8)
04-Ha 1.80
04-He 2.05
05-H 3.05 (dd, 3.2, 12.9)
07-H 6.28 (d, 2.5)
09-Ha 3.62 (m, w1/2= 22)
11-Ha 1.75
11-He 1.90
12-Ha 2.62 (ddd, 5, 13, 13)
12-He 2.05
15-Ha 2.10
15-Hb 1.85
16-Ha 2.48
16-Hb 2.05
17-H 2.98 (t, 9.4)
18-Me1.19 (s ) 1.25 (s )
19-Me1.07 (s ) 1.10 (s )
21-Me1.52 (s ) 1.60 (s )
22-H 3.87 (brd, 1.4, 10.7)
23-Ha 1.85
23-Hb 2.14
24-Ha 2.25
24-Hb 1.48
25-H 1.83
26-Ha 3.81 (dd, 5.5, 10.4)
26-Hb 3.69 (dd, 6.4, 10.3)
27-Me1.03 (d, 6) 1.08 (s )

PHYSICAL PROPERTIES

M.P.255 ░C (decomp.)
[α]D27+ 59.4 ░ (c 0.78; MeOH)
IR (KBr) ν max (cm-1)3400 (OH), 1645 (cyclohexenone)
UV (EtOH) λ max (log ε)243 (4.084)

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silica gel : Rf 0.17 (CHCl3/EtOH 4:1); RP-TLC : Rf 0.47 (C18 bonded silica gel MeOH/H2O 65:35; Rf 0.49 (paraffin coated silica gel MeOH/H2O 50:50)
GLCRt of 8 min on 1.5% OV101 (0.9 m x 4 mm i.d. at 285░C) following silylation for 60 h at 140░C (ecdysone : 5.85 min).
HPLCRet 22.8 and 25.0 min (2 isomers) (20E : 18.1 min) (column Zorbax C8, 250 mm x 4.6 mm i.d., solvent ACN/H2O 12:88, flow-rate 2 ml.min-1)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.1 x 10-7M (25R/25S)
Drosophila melanogaster BII cell assay: EC50 = 1.5 x 10-7M (25R); EC50 = 2.7 x 10-7M (25S)
Calliphora vicina imaginal disc assay: EC50 = 1.5 x 10-7M
Drosophila melanogaster imaginal disc assay: EC50 = 4.5 x 10-7M
Drosophila melanogaster Kc-H cell assay: EC50 = 1.3 x 10-7M
Calliphora assay: 100% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationTAKEMOTO, T. et al. (1967) Yakugaku Zasshi 87, 325-327 Search more
GeneralTAKEMOTO, T. et al. (1967) Yakugaku Zasshi 87, 748 Search more
GeneralTAKEMOTO, T. et al. (1967) Yakugaku Zasshi 87, 1469-1473 Search more
GeneralTAKEMOTO, T. et al. (1967) Yakugaku Zasshi 87, 1474-1477 Search more
GeneralFAUX, A. et al. (1969) Chem. Commun., 175-176 Search more
BioactivitiesCHIHARA, C.J. et al. (1972) J. Insect Physiol. 18, 1115-1123 Search more
GeneralHIKINO, H. et al. (1976) Tetrahedron 32, 3015-3021 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
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
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
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more

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