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CYASTERONE

Year of first report:1968
Formula:C29H44O8
Molecular weight:520
Occurence in plants:
Cyathula capitata [Amaranthaceae] » Images of Cyathula capitata Wikipedia: <br />
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Ajuga chia [Lamiaceae (alt. Labiatae)] » Images of Ajuga chia Wikipedia: <br />
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Ajuga decumbens [Lamiaceae (alt. Labiatae)] » Images of Ajuga decumbens Wikipedia: <br />
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Ajuga incisa [Lamiaceae (alt. Labiatae)] » Images of Ajuga incisa Wikipedia: <br />
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Ajuga nipponensis [Lamiaceae (alt. Labiatae)] » Images of Ajuga nipponensis Wikipedia: <br />
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Ajuga remota [Lamiaceae (alt. Labiatae)] » Images of Ajuga remota Wikipedia: <br />
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Ajuga reptans [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans Wikipedia: <br />
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Occurence in animals:
 
CYASTERONE

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z520 [M]+, 505 [M-15]+, 502 [M-18]+, 484, 466, 451, 448, 433, 415, 363, 345, 327, 300, 201, 183, 157, 43
HR-MS 
EI-MS m/z (relative intensity %)520 (0.4), 505 (0.2), 502 (6), 487 (1), 484 (16), 469 (7), 466 (13), 451 (7), 448 (4), 433 (8), 430 (1), 363 (7), 345 (29), 327 (30), 300 (17), 183 (28).

CARBON NMR

PROTON NMR

CDCl3
0137.9
0268.0
0368.0
0432.0 *
0551.3
06201.0
07122.2
08166.1
0934.8
1038.6
1121.3
1231.8 *
1348.7
1484.1
1532.4 *
1621.0 **
1750.0
1817.8
1924.4
2076.7
2121.1 **
2273.9
2334.4
2448.1
2542.2
26179.3
2715.8
2879.8
2919.3
C5D5N
0137.97
0268.10
0368.03
0432.46
0551.39
06203.44
07121.84
08165.84
0934.48
1038.70
1121.09
1232.04
1348.18
1484.13
1531.92
1621.34
1750.01
1817.92
1924.47
2076.77
2120.96
2273.94
2334.38
2448.64
2542.43
26179.20
2715.94
2879.82
2919.32
CDCl3
01-Ha 
02-Ha~ 5.01
03-He5.31 (ddd )
04-Ha 
04-He 
05-H 
07-H5.85 (d )
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.02 (s )
19-Me0.85 (s )
21-Me1.25 (s )
22-H~ 4.98
23-Ha 
24-H 
25-H 
27-Me1.28 (d )
28-H4.10 (dq )
29-Me1.41 (d )
C5D5N
01-Ha 
02-Ha4.16 (m, w1/2=21.0)
03-He4.22 (m, w1/2=8.0)
04-Ha 
04-He 
05-H3.01 (dd, 13.2, 3.7)
07-H6.31 (d , 3.3)
09-Ha3.59 (dq )
11-Ha 
11-He 
12-Ha2.65 (ddd, 12.9, 12.9, 5.1)
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.86 (brt, 8.8)
18-Me1.24 (s )
19-Me1.07 (s )
21-Me1.57 (s )
22-H3.94 (m, w1/2=13.0)
23-Ha 
24-H 
25-H2.37 (dq, 11.1, 6.9)
27-Me1.36 (d, 6.9 )
28-H 
29-H1.31 (d, 6.0)
29-Me1.31 (d, 6.0)

PHYSICAL PROPERTIES

M.P.164-166 ░C (semihydrate)
[α]D20+64.5░ (c 1.0, H2O)
IR (KBr) ν max (cm-1)3425, 1750 (gama-lactone), 1650
UV (EtOH) λ max (log ε)243 (4.11)

CHROMATOGRAPHY

TLCNP-TLC silica, Rf 0.54 (CHCl3-EtOH-Me2CO 60:20:10 v/v/v), Rf 0.33 (CHCl3-MeOH 80: 20); RP-TLC on paraffin coated silica gel Rf 0.59 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.44 (MeOH-H2O 65:35)
GLCRet 19.5 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.(E : 5.85 min)
HPLCRP-HPLC Spherisorb-ODS ret 13.0 min, ACN-H2O 15:85, flow-rate 1 ml.min-1) (20E : 6.8 min); Nucleosil-ODS ret 9.5 min, ACN-H2O 15:85, flow-rate 1 ml.min-1) (20E : 4.4 min)
LCsilica (preparative) CHCl3-MeOH (9:1)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 5.3 x 10-8M
Drosophila melanogaster BII cell assay: EC50 = 1.2 x 10-8M
Drosophila melanogaster imaginal disc assay: EC50 = 5.5 x 10-8M
Drosophila melanogaster Kc-H cell assay: EC50 = 2.8 x 10-8M
Galleria mellonella in vivo assay: ED50 = 3.8 ug/g
Sarcophaga bullata in vivo assay: ED50 = 10.4 ug/g
Dermestes vulpinus in vivo assay: ED50 = 21.0 ug/g
Musca assay: 100% (20-hydroxyecdysone = 100%)
Sarcophaga assay: 100% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationHIKINO, H. et al. (1968) Tetrahedron 24, 4895-4906 Search more
GeneralIMAI, S. et al. (1969) Chem. Pharm. Bull. 17, 340-342 Search more
GeneralTAKEMOTO, T. et al. (1971) Tetrahedron Lett., 3191-3194 Search more
GeneralIKAN, R. et al. (1971) Phytochemistry 10, 1659-1661 Search more
BioactivitiesCHIHARA, C.J. et al. (1972) J. Insect Physiol. 18, 1115-1123 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. (1982) J. Chromatogr. 236, 224-229 Search more
BioactivitiesSLAMA, K. et al. (1993) Insect Biochem. Molec. Biol. 23, 181-185 Search more
GeneralCALGANO, M.P. et al. (1995) Eur. J. Entomol. 92, 287-294 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more
BioactivitiesDINAN, L. et al. (2003) J. Insect Sci. 3:6 (pp. 11) Search more

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© 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
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