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14-EPI-PONASTERONE A 22-GLUCOSIDE

Year of first isolation: 2008
Formula:C33H54O11
Molecular weight:626
Occurence in plants:
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: Leuzea carthamoides [Asteraceae]
Occurence in animals:
 
14-EPI-PONASTERONE A 22-GLUCOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)OC5C(C(C(C(O5)CO)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]1OC([C@H](C(C1O)O)O)CO)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14R,17S)-2,3,14-trihydroxy-17-[(2R,3R)-2-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101851583
InChiKey
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UPMZPXAMHPZSQX-WIKHOFDESA-N
InChIInChI=1S/C33H54O11/c1-16(2)6-7-25(44-29-28(40)27(39)26(38)23(15-34)43-29)32(5,41)24-9-11-33(42)18-12-20(35)19-13-21(36)22(37)14-30(19,3)17(18)8-10-31(24,33)4/h12,16-17,19,21-29,34,36-42H,6-11,13-15H2,1-5H3/t17-,19-,21+,22-,23+,24-,25+,26+,27-,28+,29-,30+,31+,32+,33-/m0/s1

MASS SPECTRUM

ESI-MS/MS m/z627 [M+H]+, 609 [M+H-H2O]+, 591 [M+H-2H2O]+, 573 [M+H-3H2O]+, 465 [M+H-C6H10O5]+, 447 [M+H-H2O-C6H10O5]+, 429 [M+H-2H2O-C6H10O5]+, 411 [M+H-3H2O-C6H10O5]+, 347, 329, 303, 145
HR-ESI-MS m/z627.3758 [M+H]+ (calculated for C33H55O11: 627.3758)

CARBON NMR

PROTON NMR

CD3OD
0137.22
0268.67
0368.39
0432.90
0550.98
06206.22
07123.14
08167.38
0937.25
1039.21
1122.20
1241.90
1352.77
1485.47
1541.14
1624.43
1757.30
1819.37
1924.67
2077.07
2121.83
2290.44
2331.00
2436.44
2529.36
2622.84
2723.25
[Glu] 1´105.95
[Glu] 2´75.27
[Glu] 3´77.94
[Glu] 4´77.90
[Glu] 5´71.41
[Glu] 6´62.31
CD3OD
01-Ha1.43 (dd, 13.2, 12.0)
01-He1.80 (dd, 13.3, 4.2)
02-Ha3.86 (ddd, 12.0, 4.2, 3.0)
03-He3.94 (q, 3, 3, 3)
04-Ha1.73
04-He1.60
05-H2.36 (dd, 13.2, 4.0)
07-H6.32 (dd, 2.4, 0.8)
09-Ha2.85 (m)
11-Ha1.66
11-He1.79
12-Ha1.75
12-He1.69
15-Ha2.28
15-Hb1.43
16-Ha1.86
16-Hb2.08
17-H1.91
18-Me1.26 (s)
19-Me0.94 (s)
21-Me1.32 (s)
22-H3.58 (dd, 10.0, 1.5)
23-Ha1.57
23-Hb1.48
24-Ha1.74
24-Hb1.24
25-H1.56
26-Me0.93 (d, 6.8)
27-Me0.93 (d, 6.8)
[Glu] 1'4.34 (d, 7.8)
[Glu] 2'3.26 (dd, 7.8, 8.8)
[Glu] 3'~3.36 (m)
[Glu] 4'~3.36 (m)
[Glu] 5'~3.36 (m)
[Glu] 6'a3.69 (dd, 11.8, 5.5)
[Glu] 6'b3.87 (dd, 11.8, 1.8)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20+ 59.2 ° (c 0.03; EtOH)
IR (KBr) ν max (cm-1)3413 (OH), 1652 (C=O), 1099, 1071, 1056, 1030 (C-O)
UV (MeOH) λ max (log ε)

CHROMATOGRAPHY

HPLC 
NP-HPLCcolumn Silasorb 600 (5 micro m, 250 x 4 mm) solvent dichloromethane-isopropanol-water (84:15:1), flow-rate 0.8 ml/min . Retention time 88.8 min (20E 90.9 min); and two other solvent systems.
RP-HPLCcolumn Separon SGX C-18 (5 micro m, 250 x 4 mm), solvent methanol-water (linear grad of 10-70%), flow-rate 0,6 ml/min. Retention time 47.3 min (20E 34.2 min);
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationBUDĚŠÍNSKÝ, M. et al. (2008) Steroids 73, 502-514 Search more

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© Université 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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