Welcome to online ecdysteroids database !   .
Access data · History · Contact

BLECHNOSIDE A [= SILENOSIDE E]

Year of first isolation: 1986
Formula:C33H54O10
Molecular weight:610
Occurence in plants:
Blechnum minus [fern] » Images of Blechnum minus Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>60</b><br />
Silene brahuica [Caryophyllaceae] » Images of Silene brahuica Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>60</b><br />
Occurence in animals:
 
BLECHNOSIDE A [= SILENOSIDE E]

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)C)O)C(CCC(C)(C)O)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H](C1)O[C@H]1C([C@@H](C(C(O1)CO)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(3S,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID21626688
InChiKey
[ ChemIDPlus: search ]
KIYBOATYEXVQQC-LJFUCLFESA-N
InChIInChI=1S/C33H54O10/c1-17(23(35)9-10-30(2,3)40)19-8-13-33(41)21-15-24(36)22-14-18(6-11-31(22,4)20(21)7-12-32(19,33)5)42-29-28(39)27(38)26(37)25(16-34)43-29/h15,17-20,22-23,25-29,34-35,37-41H,6-14,16H2,1-5H3/t17-,18-,19+,20-,22-,23+,25+,26+,27-,28+,29+,31+,32+,33+/m0/s1

MASS SPECTRUM

DEI m/z (relative intenzity %)DCI-MS gives a parent ion at m/z 611 [M+1] (0.4%); 431 [M+1-glucose] (10%)
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0129.9 *
0229.5 *
0372.5
0427.6 *
0551.5
06203.0
07121.3
08165.9
0934.7
1036.8
1121.6
1231.8
1348.2
1484.1
1531.8
1626.8
1748.4
1815.9
1924.0
2043.0
2113.7
2274.1
2325.8
2442.5
2569.8
2630.0
2730.3
glu-1103.3
glu-275.3
glu-378.3
glu-471.9
glu-578.7
glu-663.0
C5D5N
01-Ha 
02-Ha 
02-He 
03-He3.84
04-Ha 
04-He 
05-H2.89
07-H6.17 (d )
09-Ha3.44
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.68 (s )
19-Me0.83 (s )
21-Me1.27 (d , 6.5)
22-Hb4.10
23-Ha 
24-Ha 
24-Hb 
26-Me1.37 (s )
27-Me1.37 (s )
glu sign.: 
glu- 1H4.86 (d, 7.5)
glu-(2-6)H4.0 - 4.5

PHYSICAL PROPERTIES

M.P.195-196 °C
[α]D20+ 44.4 ? 2° (c 0.80; MeOH)
IR (KBr) ν max (cm-1)3380-3430 (OH), 1655 (cyclohexenone)
UV (EtOH) λ max (log ε)245 (4.0) - 243 (4.02)

CHROMATOGRAPHY

HPTLC 
TLCSilica Rf 0.2 (vanillin spray gives a blue/green spot) [CHCl3-EtOH 80:20]
GLC 
HPLCNP-HPLC on Spherisorb S GP (50 cm x 8 mm) solvent CHCl3-EtOH (88:12)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: inactive

REFERENCES

First isolationSUKSAMRARN, A. et al. (1986) Phytochemistry 25, 1301-1304 Search more
First isolationSAATOV, E. et al. (1986) Khim. Prir. Soedin., 323-326 Search more
BioactivitiesDINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 Search more

see Important notice
© 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
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE