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PONASTERONE A 22-APIOSIDE

Year of first isolation: 2012
Formula:C32H52O10
Molecular weight:596
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: Serratula wolffii [Asteraceae]
Occurence in animals:
 
PONASTERONE A 22-APIOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@H](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(C)C)OC1C(C(CO1)(O)CO)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-((2R,3R)-3-((3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-2-hydroxy-6-methylheptan-2-yl)-2,3,14-trihydroxy-10,13-dimethyl-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 ]
IZZSIVXWZMRKEQ-MYTIXXAXSA-N
InChIInChI=1S/C32H52O10/c1-17(2)6-7-25(42-27-26(37)31(39,15-33)16-41-27)30(5,38)24-9-11-32(40)19-12-21(34)20-13-22(35)23(36)14-28(20,3)18(19)8-10-29(24,32)4/h12,17-18,20,22-27,33,35-40H,6-11,13-16H2,1-5H3/t18-,20-,22+,23-,24-,25+,26?,27?,28+,29+,30+,31?,32+/m0/s1

MASS SPECTRUM

HR-ESI-MS 597.36234, calculated 597.36332 for C32H53O10
CI-MS (NH3) m/z
ESI-MS m/z (relative intensity %) 597 (0.5) (M+H)+, 465 (100) (M+H-C5H8O4), 447 (28) (M+H-C5H8O4-H2O), 429 (15) (M+H-C5H8O4-2H2O), 299 (5) (C19H23O3)

CARBON NMR

PROTON NMR

CD3OD
0137.5
0268.9
0368.7
0433.0
0552.0
06206.6
07122.3
08168.1
0935.2
1039.4
1121.7
1232.8
1348.8
1485.4
1531.9
1621.5
1751.2
1818.3
1924.5
2077.3
2122.6
2290.2
2330.8
2436.9
2529.4
2622.8
2723.5
Api-1'113.0
Api-2'77.9
Api-3'80.3
Api-4'74.7
Api-5'64.8
CD3OD
01-Ha1.43 (dd, 13.1, 12.0)
01-He1.79 (m)
02-Ha3.84 (ddd, 12.0, 4.1, 3.4)
03-He3.95 (m)
04-Ha1.75 (m)
04-He1.70 (m)
05-H2.38 (dd, 13.0, 4.1)
07-H5.81 (d, 2.6)
09-H3.15 (ddd, 10.8, 7.4, 2.5)
11-Ha1.69 (m)
11-He1.81 (m)
12-Ha2.11 (td, 12.9, 4.7)
12-He1.88 (ddd, 12.9, 4.7, 1.8)
15-Ha1.58 (m)
15-Hb1.98 (m)
16-Ha1.67 (m)
16-Hb2.01 (m)
17-H2.30 (t, 9.0)
18-Me0.88 (s)
19-Me0.97 (s)
21-Me1.195 (s)
22-H3.35 (dd, 10.6, 1.6)
23-Ha1.37 (m)
23-Hb1.61 (m)
24-Ha1.25 (m)
24-Hb1.51 (m)
25-H1.55 (qui, 6.7)
26-Me0.92 (d, 6.7)
27-Me0.93 (d, 6.7)
[Api] H-1'4.98 (d, 3.6)
[Api] H-2'3.96 (d, 3.6)
[Api] H-4'3.79 (d, 9.6)
[Api] H-4''4.10 (d, 9.6)
[Api] H-5'3.55 (d, 11.5)
[Api] H-5''3.58 (d, 11.5)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D27+9 ° (c 0.1 ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)242 (2.81) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationVÁNYOLÓS, A. et al. (2012) The Scientific World Journal article ID 651275, 5p 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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