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PONASTERONE A

Year of first isolation: 1966
Formula:C27H44O6
Molecular weight:464
Occurence in plants:
Taxus cuspidata [Taxaceae] » Images of Taxus cuspidata Wikipedia: Taxus cuspidata [Taxaceae]
various Ferns [Gymnosperms] » Images of various Ferns Wikipedia: various Ferns [Gymnosperms]
Tapinella panuoides [Fungi] » Images of Tapinella panuoides Wikipedia: Tapinella panuoides [Fungi]
Occurence in animals:
Gecarcinus lateralis [Gecarcinidae] » Images of Gecarcinus lateralis Wikipedia: Gecarcinus lateralis [Gecarcinidae]
Callinectes sapidus [Portunidae] » Images of Callinectes sapidus Wikipedia: Callinectes sapidus [Portunidae]
Carcinus maenas [Crustaceae] » Images of Carcinus maenas Wikipedia: Carcinus maenas [Crustaceae]
PONASTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN13408-56-5
PubChem CID115127
InChiKey
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PJYYBCXMCWDUAZ-JJJZTNILSA-N
InChIInChI=1S/C27H44O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h12,15-16,18,20-23,29-33H,6-11,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z482 (MH+NH3)+, 465 (M+H)+, 447, 429, 411, 363, 345, 327
EI-MS m/z (relative intensity %)344 (40), 300 (42), 83 (25), 18 (100)
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0137.9
0268.0
0368.0
0432.4
0551.3
06203.5
07121.7
08166.0
0934.4
1038.7
1121.4
1231.8
1348.1 *
1484.1
1531.9
1621.4
1750.0
1817.9
1924.4
2076.7
2121.1
2276.7
2330.2
2437.1
2528.1
2622.3
2723.3
CD3OD
0137.37
0268.73
0368.51
0432.88
0551.80
06206.50
07122.14
08168.00
0935.11
1039.26
1121.51
1232.53
13*
1485.25
1531.77
1621.51
1750.48
1818.02
1924.39
2077.86
2120.98
2277.99
2337.66
2430.48
2529.23
2622.74
2723.41
CD3OD
01-Ha1.43 (dd, 13.2, 12.4)
01-He1.79 (dd, 13.2, 4.5)
02-Ha3.82 (ddd, 12.0, 4.0, 3.4)
03-He3.94 (q )
04-Ha1.70
04-He1.74
05-H2.38 (dd, 12.8, 4.6)
07-H5.81 (d, 2.6)
09-Ha3.15 (ddd, 10.5, 7.0, 2.6)
11-Ha1.81
11-He1.70
12-Ha2.12 (dt, 13.0, 13.0, 5.0)
12-He1.88 (ddd, 12.8, 4.2, 2.0)
15-Ha1.96
15-Hb1.59
16-Ha1.99
16-Hb1.70
17-H2.37 (t, 8.8, 8.8)
18-Me0.890 (s )
19-Me0.967 (s )
21-Me1.175 (s )
22-Hb3.33 (dd, 10.0, 1.7)
23-Ha1.47
24-Ha1.46
24-Hb1.21
25-H1.56
26-Me0.924 (d, 6.5)
27-Me0.915 (d, 6.5)
C5D5N
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me 
18-Me 0.891.16
19-Me 
19-Me 0.961.03
21-Me 
21-Me 1.171.51
22-Hb 
23-Ha 
24-Ha 
24-Hb 
25-H 
26-Me 
26-Me 0.920.82 (d, 6)
27-Me 
27-Me 0.910.82 (d, 6)

PHYSICAL PROPERTIES

M.P.259-260°C (decomp.)
[α]D20 
IR (KBr) ν max (cm-1)3420 (OH), 1643 (CO)
UV (MeOH) λ max (log ε)244 (4.093), 326 (2.11)

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silicagel Rf 0.42 (CHCl3-EtOH 4:1); RP-TLC on paraffin coated silica gel Rf 0.19 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.21 (MeOH-H2O 65:35)
GLCGLC Ret 4.4 min on 1.5% OV101 (0.9 m x 4.5 mm i.d.) at 285°C after silylation at 140°C
HPLCRP-HPLC-RP, Ultrasphere-ODS (15 cm x 4.6 mm) MeOH-H2O, gradient 40 to 80% MeOH over 20 min, retention volume 17.2 ml (20E 9.4 ml).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 3.1 x 10-10M
Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-10M
Calliphora vicina imaginal disc assay: EC50 = 1.4 x 10-9M
Drosophila melanogaster imaginal disc assay: EC50 = 1.0 x 10-9M
Drosophila melanogaster Kc-H cell assay: EC50 = 1.8 x 10-9M
Galleria mellonella in vivo assay: ED50 = 12.5 ug/g
Sarcophaga bullata in vivo assay: ED50 = 7.3 ug/g
Dermestes vulpinus in vivo assay: ED50 = 17.0 ug/g
Calliphora assay: 100% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationNAKANISHI, K. et al. (1966) J. Chem. Soc., Chem. Commun. 915-917 Search more
GeneralTAKEMOTO, T. et al. (1967) Chem. Pharm. Bull. 15, 1816 Search more
GeneralIMAI, S. et al. (1967) Steroids 10, 557-565 Search more
GeneralTAKEMOTO, T. et al. (1968) Yakugaku Zasshi 88, 359 Search more
First isolationMcCARTHY, J.F. et al. (1979) Steroids 34, 799-806 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
BioactivitiesBERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 Search more
GeneralLACHAISE, F. et al. (1981) Hoppe-Seyler´s Z. Physiol. Chem. 521-529 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
BioactivitiesSLÁMA, K. et al. (1993) Insect Biochem. Molec. Biol. 23, 181-185 Search more
GeneralMINGSHEN, L. et al. (1998) Chin. J. Magn. Resonance 15, 539-542 Search more
IdentificationVOKÁČ, K. et al. (1998) Phytochemistry 49, 2109-2114 Search more
BioactivitiesDINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 Search more

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