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LIMNANTHEOSIDE C

Year of first isolation: 2001
Formula:C38H62O16
Molecular weight:774
Occurence in plants:
Limnanthes alba [Limnanthaceae] » Images of Limnanthes alba Wikipedia: Limnanthes alba [Limnanthaceae]
Occurence in animals:
 
LIMNANTHEOSIDE C

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O[C@H]1C(C([C@@H](CO1)O)O[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](O)CCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-3-(((2S,5R)-3,5-dihydroxy-4-(((2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,14-dihydroxy-10,13-dimethyl-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 ]
CLHMVLWTBMDTQO-LOWAPULFSA-N
InChIInChI=1S/C38H62O16/c1-34(2,48)9-8-26(43)37(5,49)25-7-11-38(50)18-12-20(40)19-13-23(21(41)14-35(19,3)17(18)6-10-36(25,38)4)52-32-30(47)31(22(42)16-51-32)54-33-29(46)28(45)27(44)24(15-39)53-33/h12,17,19,21-33,39,41-50H,6-11,13-16H2,1-5H3/t17-,19-,21-,22+,23+,24?,25-,26+,27+,28?,29?,30?,31?,32-,33+,35+,36+,37+,38+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
LSI-MS (positive ion mode) m/z775 [M+H]+
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

CD3OD
0137.2
01"103.6
01'101.8
0266.6
02"74.1
02'72.4
0375.1
03"76.5
03'85.5
0429.0
04"72.2
04'68.5
0550.3
05"77.0
05'65.2
06204.9
07120.7
08166.9
0933.7
1037.8
1120.2
1231.1
13**
1483.8
1530.4
1620.1
1749.1
1816.6
1922.8
2076.6
2119.6
2276.8
2325.9
2441.0
2569.9
2628.3
2727.6
6''61.3
CD3OD
01-Ha1.42
01-He1.84
02-Ha3.85 (m, w1/2 = 22)
03-He4.06 (m, w1/2 = 8)
04-Ha1.69
04-He1.88
05-H2.43 (dd, 13, 3.8)
07-H5.82 (d, 2.2)
09-H3.15 (m, w1/2 = 21)
11-Ha1.68
11-He1.82
12-Ha2.14 (ddd, 13, 13, 5)
12-He1.88
15-Ha1.96
15-Hb1.59
16-Ha2.00
16-Hb1.73
17-H2.39 (m)
18-Me0.89 (s)
19-Me0.97 (s)
1"ax4.61 (d, 7.6)
1'ax4.38 (d, 7.3)
21-Me1.20 (s)
22-H3.33
23-Ha1.29
23-Hb1.67
24-Ha1.81
24-Hb1.42
26-Me1.19 (s)
27-Me1.20 (s)
2"ax3.28 (dd, 7.6, 9.0)
2'ax3.49 (dd, 7.3, 8.9)
3"ax3.40 (t, 9.0)
3'ax3.54 (t, 8.9)
4"ax3.29 (t, 9.0)
4'ax3.63 (ddd, 5.1, 8.9, 11)
5"ax3.32 (ddd 2.0, 5.8, 9.0)
5'ax3.94 (dd, 5.1, 11.5)
5'eq3.26 (dd, 11, 11.5)
6"ax3.64 (dd, 11.8, 5.8)
6"eq(dd, 11.8, 2.0)

PHYSICAL PROPERTIES

M.P.°C ; white amorphous
[α]D20° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)243 (4.12) ;

CHROMATOGRAPHY

HPLCRP-HPLC C6 column, solvent MeOH-H2O (40:60); NP-HPLC Diol column, solvent CH2Cl2-MeOH (97:3)
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationMENG, Y. et al. (2001) J. Biosciences 56, 998-994 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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