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POLYPODOSIDE A

Year of first isolation: 1988
Formula:C45H72O17
Molecular weight:884
Occurence in plants:
Polypodium glycyrrhiza [Polypodiaceae] » Images of Polypodium glycyrrhiza Wikipedia: Polypodium glycyrrhiza [Polypodiaceae]
Occurence in animals:
 
POLYPODOSIDE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC1CCC(OC1OC2C(C(C(C(O2)C)O)O)O)C(C)C3CCC4C3(CCC5C4=CC(=O)C6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)C)O)O)O)C)C
Isomeric SMILES
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C1[C@]2([C@H](C[C@H](C1)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O[C@H]1C(C([C@H](C(O1)C)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H]([C@H]1CC[C@@H]([C@H](O1)O[C@H]1C(C([C@H](C(O1)C)O)O)O)C)C)C)C » JSMol: View in 3D
IUPAC Name(3R,5R,9S,10R,13R,14S,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-17-[(1S)-1-[(2R,5S,6R)-5-methyl-6-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]ethyl]-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one
CAS-RN119784-25-7
PubChem CID147894
InChiKey
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OFFJUHSISSNBNT-NZWHLKEESA-N
InChIInChI=1S/C45H72O17/c1-18-7-10-29(59-40(18)62-42-38(55)35(52)32(49)21(4)57-42)19(2)24-8-9-25-23-16-28(47)27-15-22(11-13-45(27,6)26(23)12-14-44(24,25)5)58-43-39(36(53)33(50)30(17-46)60-43)61-41-37(54)34(51)31(48)20(3)56-41/h16,18-22,24-27,29-43,46,48-55H,7-15,17H2,1-6H3/t18-,19-,20-,21-,22+,24+,25+,26+,27-,29+,30+,31-,32-,33+,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44+,45+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)[M]+ 884 (missing), 430 [aglycone]+ (1), 412 [aglycone-H2O]+ (23), 395 (32), 379 (5), 342 (5), 285 (6), 261 (8), 147 (12), 128 (17), 97 (37), 43 (100).
FAB-MS (DTE/DTT) m/z907 [M+Na]+, 885 [M+H]+, 739, 721, 577, 559, 431, 413, 395, 309
HR-MSHR-FABMS found 885.4843, calc. 885.4848

CARBON NMR

PROTON NMR

C5D5N
0136.86 (t )
0229.22 (t )
0376.31 (d )
0426.98 (t )
0553.13 (d )
06198.69 (s )
07123.21 (d )
08163.02 (s )
0949.91 (d )
1038.39 (s )
1121.89 (t )
1238.85 (t )
1344.69 (s )
1455.05 (d )
1522.90 (t )
1626.83 (t )
1752.88 (d )
1812.09 (q )
1913.10 (q )
2040.38 (d )
2113.85 (q )
2278.11 (d )
2323.98 (t )
2431.49 (t )
2536.45 (d )
26107.32 (d )
2716.68 (q )
s-1'99.53
s-2'79.47
s-3'78.30
s-4'71.87
s-5'78.11
s-6'62.74
s1"102.17
s2"72.78
s3"72.50
s4"73.95
s5"69.49
s6"18.75
su1"'102.03
su2"'72.78
su3"'72.14
su4"'74.12
su5"'70.48
su6"'18.44
C5D5N
01-Ha 1' 5.02 (d, 6.6)
01-Hb 2'
02-Ha 3'
03-He3.84 (m ) 4'
04-Ha 5'
04-He 6'
05-H 
07-H5.84 (br,s )
09-Ha 1" 6.26 (br,s )
11-Ha 2"
11-He 3"
12-Ha 4"
12-He 5"
14-H 6"-Me 1.74 (d, 6)
15-Ha 
15-Hb 
16-Ha 1"' 5.61 (br,s )
16-Hb 2"'
17-H 3"'
18-Me0.48 (s ) 4"'
19-Me0.86 (s ) 5"'
21-Me1.01 (d, 6) 6"'-Me 1.66 (d, 6)
22-H3.46 (m )
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-H4.45 (d, 8)
27-Me0.91 (d, 6)

PHYSICAL PROPERTIES

M.P.198-200 °C
[α]D20-37 ° (c 0.3; MeOH)
IR (KBr) ν max (cm-1)3435 (OH), 1667 (unsaturated ketone), 1460, 1453, 1225, 1036
UV (EtOH) λ max (log ε)244 (4.03)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationKIM, J. et al. (1988) J. Nat. Prod. 51, 1166-1172 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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