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20-HYDROXYECDYSONE 25-β-D-GLUCOSIDE

Year of first isolation: 1988
Formula:C33H54O12
Molecular weight:642
Occurence in plants:
Pfaffia iresinoides [Amaranthaceae] » Images of Pfaffia iresinoides Wikipedia: Pfaffia iresinoides [Amaranthaceae]
Silene otites [Caryophyllaceae] » Images of Silene otites Wikipedia: Silene otites [Caryophyllaceae]
Occurence in animals:
Parascaris equorum [Nematoda] » Images of Parascaris equorum Wikipedia: Parascaris equorum [Nematoda]
20-HYDROXYECDYSONE 25-β-D-GLUCOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)OC5C(C(C(C(O5)CO)O)O)O)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[C@H]1C(C([C@@H](C(O1)CO)O)O)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R)-2,3-dihydroxy-6-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-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-RN 
PubChem CID18394235
InChiKey
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VJAXSGXKVCCJNY-HMWOVMMSSA-N
InChIInChI=1S/C33H54O12/c1-29(2,45-28-27(41)26(40)25(39)22(15-34)44-28)9-8-24(38)32(5,42)23-7-11-33(43)17-12-19(35)18-13-20(36)21(37)14-30(18,3)16(17)6-10-31(23,33)4/h12,16,18,20-28,34,36-43H,6-11,13-15H2,1-5H3/t16-,18-,20+,21-,22+,23-,24?,25+,26-,27+,28-,30+,31+,32+,33+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z660 (M + NH4)+, 643 (M+H)+, 625, 607, 480, 463, 445, 427, 363, 345
EI-MS m/z (relative intensity %) 
FAB-MS m/z665 [M+Na], 647 [M+Na-H2O], 643 [M+H], 625 [M+H-H2O]
HR-MS[M+H] found 643.3656, calc. 643.3694

CARBON NMR

PROTON NMR

C5D5N
0137.9
0268.1
0368.0
0432.4
0551.4
06203.7
07121.7
08166.1
0934.4
1038.6
1121.1
1232.0
1348.1
1484.3
1531.7
1621.4
1750.0
1817.9
1924.4
2076.9
2121.7
2277.7
2326.6
2439.8
2577.4
2627.5
2727.6
glu-01'98.8
glu-02'75.5
glu-03'78.7*
glu-04'72.1
glu-05'78.5*
glu-06'63.4
C5D5N
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
05-H2.99 (dd, 13.2, 4)
07-H6.21 (d, 2.2)
09-Ha3.55 (br t, 9.0)
11-Ha 
11-He 
12-Ha2.52 (dt, 13.2, 4.2)
12-He 
15-Ha 
15-Hb 
16-Ha2.42 (q, 10.4)
16-Hb 
17-H2.94 (t, 8.8)
18-Me1.18 (s )
19-Me1.04 (s )
21-Me1.56 (s )
22-H3.83 (br d, 9.4)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.31 (s )
27-Me1.37 (s )
glu-H1´5.00 (d, 7.6)
D2O
01-Ha1.4
01-Hb1.9
02-Ha3.99 (m, w1/2=22)
03-He4.07 (m, w1/2=8)
04-Ha1.75
04-He1.75
05-H2.34 (t-like )
07-H5.97 (d, 2.5)
09-Ha3.11 (m, w1/2=22)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.32 (m )
18-Me0.88 (s )
19-Me1.01 (s )
21-Me1.25 (s )
22-H3.45
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.30 (s )
27-Me1.30 (s )
glu-H1'4.79 (d, 7.6)
glu-H1´ 
glu-H2´3.20
glu-H3´3.51
glu-H4´3.33
glu-H5´3.45
glu-H6´3.90 (dd, 12.3, 2.2)
glu-H6´´3.67 (dd, 12.3, 6.4)

PHYSICAL PROPERTIES

M.P.158-163 °C
[α]D20+ 26.0° (c 1.5, MeOH)
IR (KBr) ν max (cm-1)3420 (-OH), 1652 (C=O), 1052 (C-O)
UV (EtOH) λ max (log ε)243 (4.02)

CHROMATOGRAPHY

HPTLC 
TLCRf 0.20 (CHCl3/MeOH/H2O) 13:7:2, lower phase); Rf 0.33 (EtOAc/EtOH/H2O, 8:2:1) (20E 0.61); Rf 0.13 (CHCl3/MeOH/Me2CO, 6:2:1) (20E 0.47)
GLC 
HPLCRetention time 8.7 min (Reverse-phase, Spherisorb 5ODS2 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with 17% ACN in 0.1% TFA in water).Retention time 11.5 min (RP-HPLC, Separon SGX-C18 25 cm long, 8 mm i.d., flow-rate 4 ml.min-1, eluted with 40% MeOH in water).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 8.5 x 10-6M

REFERENCES

First isolationNISHIMOTO, N. et al. (1988) Phytochemistry 27, 1665-1668 Search more
GeneralGIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 Search more
GeneralO'HANLON, J.M. et al. (1991) Parasitol. Res. 77, 271-272 Search more
SynthesisPIS, J. et al. (1994) Tetrahedron 50, 9679-9690 Search more
BioactivitiesHARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 Search more
IdentificationSARKER, S.D. et al. (1998) Biochem. Syst. Ecol. 26, 135-137 Search more
GeneralLI, X. et al. (2000) Shenyang Yaoke Daxue Xuebao 17, 260-262 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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