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20-HYDROXYECDYSONE 2-β-D-GLUCO-PYRANOSIDE

Year of first isolation: 1997
Formula:C33H54O12
Molecular weight:642
Occurence in plants:
Xerophyllum tenax [Melanthiaceae] » Images of Xerophyllum tenax Wikipedia: Xerophyllum tenax [Melanthiaceae]
Occurence in animals:
 
20-HYDROXYECDYSONE 2-β-D-GLUCO-PYRANOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)OC5C(C(C(C(O5)CO)O)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)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)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID102210228
InChiKey
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KUHPYTJXVKKPHR-RVRQMSSNSA-N
InChIInChI=1S/C33H54O12/c1-29(2,41)9-8-24(37)32(5,42)23-7-11-33(43)17-12-19(35)18-13-20(36)21(14-30(18,3)16(17)6-10-31(23,33)4)44-28-27(40)26(39)25(38)22(15-34)45-28/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/z 
EI-MS m/z (relative intensity %)463 [M-C6H11O6], 462, 446, 444, 443, 428, 427, 426, 408, 376, 368, 346, 345, 344, 330, 329, 328, 327, 326, 302, 301, 300, 285, 284, 267, 266, 189, 188, 179 [C6H11O6], 178, 177, 163, 159, 113, 99, 69, 55.
FAB-MS (negative mode, in glycerol)641 [M-H] ?

CARBON NMR

PROTON NMR

C5D5N
0135.9
0275.8
0364.6
0431.3
0551.3
06202.9
07121.7
08133.0
0934.4
1038.6
1120.9
1231.9
1348.0
1484.1
1531.6
1621.4
1750.0
1817.8
1924.2
2076.8
2121.6
2277.5
2327.6
2442.6
2569.5
2630.0
2730.1
glu-1'101.7
glu-2'75.4
glu-3'78.7
glu-4'71.6
glu-5'78.6
glu-6'62.7
C5D5N
01-Ha1.94
01-He2.16
02-Ha4.29 (M)
03-He4.36 (m)
04-Ha2.04
04-He1.80
05-H2.96
07-H6.23 (d, 2.3)
11-Ha1.72
11-He1.89
12-Ha2.46 (ddd 13, 13, 5)
12-He1.92
15-Ha2.14
15-Hb1.90
16-Ha2.43
16-Hb2.04
17-H2.94
18-Me1.19 (s)
19-Me1.03 (s)
21-Me1.58 (s)
22-H3.87 (br d, 10)
23-Ha2.12
23-Hb1.85
24-Ha2.28
24-Hb1.83
26-Me1.39 (s)
27-Me1.39 (s)
glu-H1'5.02 (d, 7.9)
glu-H2'4.05 (t, 8.0)
glu-H3'4.32
glu-H4'4.25 (t, 9.0)
glu-H5'4.0 (m)
glu-H6',6"4.36, 4.54 (d, 11.8)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε)244 (4.09), 320 (3.15)

CHROMATOGRAPHY

HPTLC 
TLC 
RP-HPLCcolumn Spherisorb 5ODS2 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with 18% ACN-iPrOH (5:2) in 0.1% TFA in H2O, Ret 10.2 min (20E 13.9 min); column Separon SGX-C18 25 cm long, 8 mm i.d., flow-rate 4 ml.min-1, eluted with 40% MeOH in water, Ret 13.5 min.
NP-HPLCNP-HPLC, column Zorbax-SIL 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with cyclohexane-iPrOH-H2O (125:50:5), Ret 50.4 min (20E 10.1 min), NP-HPLC, column Zorbax-SIL 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with cyclohexane-iPrOH-H2O (80:40:3), Ret 31.1 min (20E 12.3 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-5M

REFERENCES

GeneralPIS, J. et al. (1994) Tetrahedron 50, 9679-9690 Search more
GeneralPIS, J. et al. (1995) Eur. J. Entomol. 92, 41-50 Search more
BioactivitiesHARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 Search more
First isolationALISON, B. et al. (1997) Biochem. Syst. Ecol. 25, 255-261 Search more
GeneralSARKER, S.D. et al. (1997) Phytochemistry 44, 513-521 Search more

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