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

POLYPODINE B 2-β-D-GLUCOSIDE

Year of first isolation: 2011
Formula:C33H54O13
Molecular weight:658
Occurence in plants:
Polypodium vulgare [Polypodiaceae] » Images of Polypodium vulgare Wikipedia: Polypodium vulgare [Polypodiaceae]
Occurence in animals:
 
POLYPODINE B 2-β-D-GLUCOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@](C[C@H]([C@H]1O[C@H]1C(C([C@@H](C(C1)CO)O)O)O)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@@]([C@@H](CCC(C)(C)O)O)(C)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14S,17S)-3,5,14-trihydroxy-10,13-dimethyl-2-(((1R,4R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl)oxy)-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
XUCDRNZCANVMMA-YWNWQKCDSA-N
InChIInChI=1S/C34H56O12/c1-29(2,42)9-8-24(37)32(5,43)23-7-11-33(44)19-13-25(38)34(45)14-20(36)22(15-31(34,4)18(19)6-10-30(23,33)3)46-21-12-17(16-35)26(39)28(41)27(21)40/h13,17-18,20-24,26-28,35-37,39-45H,6-12,14-16H2,1-5H3/t17?,18-,20+,21+,22-,23-,24+,26+,27?,28?,30+,31+,32+,33+,34+/m0/s1

MASS SPECTRUM

HRESI-MS/MS [M+H]+ = 659.3639, calculated for C33H55O13, 659.3637, delta 0.3 ppm
ESI-MS/MS m/z (relative intensity %) 497 (100) [M+H-C6H10O5]+, 479 (9) [M+H-C6H10O5-H2O]+, 461 (33) [M+H-C6H10O5-2H2O]+, 443 (17) [[M+H-C6H10O5-3H2O]+, 425 (1) [M+H-C6H10O5-4H2O]+, 387 (1), 363 (1) 331 (11)

CARBON NMR

PROTON NMR

CD3OD
0133.0
0276.4
0368.1
0435.8
0580.4
06 
07120.9
08 
0939.1
1045.9
1122.4
1232.7
1348.6
1485.2
1531.8
1621.6
1750.6
1818.2
1916.9
2078.0
2121.2
2278.6
2327.5
2442.5
2571.4
2629.1
2729.9
[sugar] 1'103.4
[sugar] 2'75.4
[sugar] 3'78.0
[sugar] 4'71.8
[sugar] 5'78.2
[sugar] 6'62.9
CD3OD
01-Ha1.90*
01-He1.82*
02-Ha4.15 (ddd, 12.1, 4.8, 3.5)
03-He4.21 (q, 3.0)
04-Ha2.08 (dd, 14.9, 3.0)
04-He1.81
05-H-
07-H5.85 (d 2.7)
09-H3.20
11-Ha1.72
11-He1.92
12-Ha2.13 (td, 13.1, 5.0)
12-He1.89
15-Ha1.60
15-Hb1.96
16-Ha1.73
16-Hb1.99
17-H2.39
18-Me0.90 (s)
19-Me0.93 (s)
20-H-
21-Me1.197 (s)
22-H3.32
23-Ha1.29
23-Hb1.66
24-Ha1.44
24-Hb1.80
26-Me1.19 (s)
27-Me1.202 (s)
[sugar] H1'4.45 (d, 7.8)
[sugar] H2'3.23 (dd, 8.8, 7.9)
[sugar] H3'3.38, (t, 9.0)
[sugar] H4'3.32
[sugar] H5'3.31
[sugar] H6'3.70 (dd, 11.8, 5.3)
[sugar] H6''3.89 (dd, 12.0, 1.8)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D2813 ° (c = 0.1 ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)238 (3.83) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSIMON, A. et al. (2011) Steroids 76, 1419-1424 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