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PONASTEROSIDE B

Year of first isolation: 2014
Formula:C33H54O11
Molecular weight:626
Occurence in plants:
Lepidogrammitis drymoglossoides [Polypodiaceae] » Images of Lepidogrammitis drymoglossoides Wikipedia: Lepidogrammitis drymoglossoides [Polypodiaceae]
Occurence in animals:
 
PONASTEROSIDE B

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)OC5C(C(C(C(O5)CO)O)O)O)C)C)O)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-3,14-dihydroxy-10,13-dimethyl-2-[(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 CID122386164
InChiKey
[ ChemIDPlus: search ]
MUCWXHWKVGNJLW-UFZISXJTSA-N
InChIInChI=1S/C33H54O11/c1-16(2)6-7-25(37)32(5,41)24-9-11-33(42)18-12-20(35)19-13-21(36)22(14-30(19,3)17(18)8-10-31(24,33)4)43-29-28(40)27(39)26(38)23(15-34)44-29/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

EI-MS m/z (relative intensity %)
HR-ESI-MS m/z 627.3746 [M+H]+, calculated 627.3744
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

CD3OD
0136.1
0276.4
0366.0
0432.1
0551.8
06206.3
07122.1
08169.0
0935.0
1039.5
1121.3
1232.4
1348.6
1485.3
1531.7
1621.5
1750.4
1818.1
1924.2
2077.9
2121.0
2277.9
2330.4
2437.6
2529.2
2623.4
2724.8
[glc] C-1'102.7
[glc] C-2'75.1
[glc] C-3'77.8
[glc] C-4'71.6
[glc] C-5'77.9
[glc] C-6'62.7
CD3OD
01-Ha1.51 (m)
01-Hb 
02-Ha4.02 (br, d, 8.4)
03-He4.14 (m)
04-Ha1.74 (m)
04-He1.88 (m)
05-H2.36 (m)
07-H5.81 (s)
09-Ha3.15 (m)
11-Ha1.94 (m)
11-He 
12-Ha2.09 (m)
12-He1.86 (m)
15-Ha1.60 (m)
15-Hb1.96 (m)
16-Ha1.48 (m)
16-Hb 
17-H2.36 (m)
18-Me0.87 (s)
19-Me0.95 (s)
21-Me1.17 (s)
22-H3.35 (m)
23-Ha1.23 (m)
23-Hb 
24-Ha1.21 (m)
24-Hb 
25-H1.52 (m)
26-Me0.91 (d, 4.0)
27-Me0.90 (d, 4.0)
[glc] H-1'4.44 (d, 7.6)
[glc] H-2'3.20 (m)
[glc] H-3'3.35 (m)
[glc] H-4'3.35 (m)
[glc] H-5' 3.37 (m)
[glc] H-63.87 (dd, 2.0, 11.6)
[glc] H-6'3.36 (ff, 5.2, 11.6)

PHYSICAL PROPERTIES

M.P.
[α]D24+ 3.5 ° (c 1.18, CH3OH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationYAO, J.-N. et al. (2014) J. Carb. Chem. 33, 206-211 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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