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26-HYDROXYPOLYPODINE B

Year of first isolation: 1990
Formula:C27H44O9
Molecular weight:512
Occurence in plants:
Lychnis flos-culculi [Caryophyllaceae] » Images of Lychnis flos-culculi Wikipedia: Lychnis flos-culculi [Caryophyllaceae]
Silene nutans [Caryophyllaceae] » Images of Silene nutans Wikipedia: Silene nutans [Caryophyllaceae]
Silene viridiflora [Caryophyllaceae] » Images of Silene viridiflora Wikipedia: Silene viridiflora [Caryophyllaceae]
Occurence in animals:
 
26-HYDROXYPOLYPODINE B

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C1(CCC2C(C)(C(CCC(C)(CO)O)O)O)O
Isomeric SMILES
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C1[C@]2([C@@](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(CO)(C)O)O)O)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@](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](CC[C@@](CO)(C)O)O)O)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@](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](CC[C@](CO)(C)O)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID12148979
InChiKey
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FVXSLSHKONBKBF-HEEVUBGMSA-N
InChIInChI=1S/C27H44O9/c1-22(33,14-28)8-7-20(31)25(4,34)19-6-10-26(35)16-11-21(32)27(36)13-18(30)17(29)12-24(27,3)15(16)5-9-23(19,26)2/h11,15,17-20,28-31,33-36H,5-10,12-14H2,1-4H3/t15-,17-,18+,19-,20+,22?,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z513 (M+H)+, 495, 477, 459, 441, 396, 379 (M+H - C22--C27)+, 363, 361, 345
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0134.4
0268.6
0370.4
0436.3
0580.4
06202.5
07120.7
08167.7
0939.1
1045.6
1122.6
1232.7
1348.9
1485.2
1531.9
1621.6
1750.6
1818.2
1917.1
2078.0
2121.2
2278.6
2326.7
2437.3
2573.8
2670.9
2723.7
CD3OD
01-Ha 
01-He 
02-Ha3.94 (m )
03-He3.97 (m )
04-Ha 
04-He 
07-H5.84 (d, 2.5)
09-Ha3.14 (m, w1/2=22)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.35 (m )
18-Me0.88 (s )
19-Me0.90 (s )
21-Me1.20 (s )
22-H3.33 (d br, 10)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-CH2-OH3.35 (s )
27-Me1.14, 1.15 (s ) (2 isomers 25R and 25S)

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

TLC on silicaRf 0.50 (EtOAc-EtOH-H2O, 8:2:1) (20E 0.61); Rf 0.29 (CHCl3-MeOH-Me2CO, 6:2:1) (20E 0.47)
RP-HPLCRetention time 4.7 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN- 0.1% TFA in H2O 23:77 v/v, flow-rate 1 ml.min-1] (20E 5.5 min)
NP-HPLCRetention time 30.9 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min); Retention time 77.2 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 4.8 x 10-7M

REFERENCES

First isolationGIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 Search more
BioactivitiesCLEMENT, C.Y. et al. (1993) Insect Biochem. Molec. Biol. 23, 187-193 Search more
IdentificationSIMON, A. et al. (2009) Helv. Chim. Acta 92, 753-761 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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