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RUBROSTERONE

Year of first report:1968
Formula:C19H26O5
Molecular weight:334
Occurence in plants:
Achyranthes rubrofusca [Amaranthaceae] » Images of Achyranthes rubrofusca Wikipedia: <br />
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Lychnis flos-culculi [Caryophyllaceae] » Images of Lychnis flos-culculi Wikipedia: <br />
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Silene otites [Caryophyllaceae] » Images of Silene otites Wikipedia: <br />
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Palisota schweinfurthii [Commelinaceae] » Images of Palisota schweinfurthii Wikipedia: <br />
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Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: <br />
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Occurence in animals:
 
RUBROSTERONE

MASS SPECTRUM

CI-MS (NH3) m/z352 (M+H+NH3)+, 335 (M+H)+, 317
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0137.3
0268.4 *
0368.6 *
0432.8
0552.0
06205.8
07122.4
08164.6
0935.8
1039.3
1120.6
1224.9
1354.1
1480.4
1529.1
1634.0
17214.8
1817.6
1924.6
C5D5N
01-Ha1.43 (dd, 13, 12)
01-Hb1.78
02-Ha3.83 (ddd, 12, 4, 3)
03-He3.94 (q, 3)
04-Ha1.73
04-He1.78
05-H2.4 (dd, 12, 5)
07-H5.91 (d, 2.5)
09-Ha3.18 (m, w1/2=22)
11-Ha1.7
11-He1.9
12-Ha2.1
12-He1.5
15-Ha2.3
15-Hb2.0
16-Ha2.4
16-Hb2.05
18-Me0.88 (s )
19-Me0.99 (s )
CDCl3
01-Ha 
01-Hb 
02-Ha4.94 (ddd )
03-He5.32 (ddd )
04-Ha 
04-He 
05-H 
07-H5.94 (d )
09-Ha3.11 (ddd )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
18-Me0.85 (s )
19-Me1.04 (s )

PHYSICAL PROPERTIES

M.P.230 ░C (decomp.)
[α]D20+ 119 ░ (c ; MeOH)
IR (KBr) ν max (cm-1)3410 (OH), 1741 (cyclopentanone), 1646 (cyclohexenone)
UV (EtOH) λ max (log ε)240 (?)

CHROMATOGRAPHY

TLCNP-TLC on silica gel : Rf 0.26 (EtOAc-MeOH-NH4OH, 85:10:5) (20E : 0.18); Rf 0.41 (CH2Cl2-EtOH 85:15) (20E : 0.15); Rf 0.41 (CHCl3-EtOH 4:1)
GLC 
NP-HPLCNP-HPLC, Ret 6.2 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min); Ret 10.1 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min);
RP-HPLCRP-HPLC, Ret 6.0 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN-0.1% TFA in H2O 23:77 v/v, flow-rate 1 ml.min-1] (20E 5.4 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = >10-4M
Drosophila melanogaster imaginal disc assay: EC50 = 7.9 x 10-3M
Sarcophaga assay: inactive

REFERENCES

First isolationTAKEMOTO, T. et al. (1968) Tetrahedron Lett. (26), 3053-3056 Search more
GeneralHORN, D.H.S. et al. (1971) In: Naturally Occuring Insecticides (eds. Jacobson M. and Crosby D.G) Marcel Dekker, New York, pp. 333-459 Search more
BioactivitiesCHIHARA, C.J. et al. (1972) J. Insect Physiol. 18, 1115-1123 Search more
GeneralTOM, W.-M. et al. (1975) J. Chem. Soc., Chem. Commun., 24-25 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
GeneralGIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 Search more
GeneralKUSAMBA, C. et al. (1995) Fitoterapia LXVI, 175-178 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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