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LIMNANTHEOSIDE A

Year of first isolation: 1997
Formula:C32H52O11
Molecular weight:612
Occurence in plants:
Limnanthes douglasii [Limnanthaceae] » Images of Limnanthes douglasii Wikipedia: <br />
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Occurence in animals:
 
LIMNANTHEOSIDE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)OC5C(C(C(CO5)O)O)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
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)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,10R,13R,14S)-2,14-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID24984732
InChiKey
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TWFDWCNWDDFMIA-AYUKSNEASA-N
InChIInChI=1S/C32H52O11/c1-28(2,39)9-8-24(36)31(5,40)23-7-11-32(41)17-12-19(33)18-13-22(43-27-26(38)25(37)21(35)15-42-27)20(34)14-29(18,3)16(17)6-10-30(23,32)4/h12,16,18,20-27,34-41H,6-11,13-15H2,1-5H3/t16?,18-,20-,21+,22+,23?,24+,25-,26+,27-,29+,30+,31+,32+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z630 (M+H+NH3)+, 613 (M+H)+, 595, 559, 541, 496, 481, 463, 461, 445, 427, 363, 345, 301
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

D2O
0137.4
0268.8
0376.0
0429.8
0551.3
06 
07122.0
08 
0935.8
1038.9
1121.0
1231.8
1348.3
1486.3
1532.5
1621.1
1750.1
1818.0
1924.0
2078.1
2120.6
2279.0
2327.0
2441.8
2572.1
2628.5
2729.2
C-1'101.8
C-2'74.3
C-3'77.0
C-4'71.0
C-5'66.4
D2O
01-Ha1.46 (t, 13.0)
01-Hb1.98
02-Ha4.03 (dt, w1/2 = 22)
03-He4.15 (m, w1/2 = 8)
04-Ha1.75
04-He1.90
05-H2.43 (dd, 13.5, 3.5)
07-H5.98 (d, 2.5)
09-Ha3.12 (m, w1/2 = 22)
11-Ha1.75
11-He1.86
12-Ha1.95
12-He1.75
15-Ha2.05*
15-Hb1.65*
16-Ha1.85**
16-Hb1.80**
17-H2.33 (t, 9.6)
18-Me0.87 (s )
19-Me1.00 (s )
21-Me1.25 (s )
22-H3.43 (dd, 10.7, 1.4)
23-Ha1.33
23-Hb1.65
24-Ha1.52 (dt, 12.8, 3.4)
24-Hb1.80
26-Me1.23 (s )
27-Me1.24 (s )
s1-H'4.48 (d, 7.8)
s2-H'3.33 (dd, 7.8, 9.3)
s3-H'3.47 (t, 9.3)
s4-H'3.65 (ddd, 5.5, 9.2, 10.5)
s5-H"3.29 (dd, 10.5, 11.6)
s5-H'3.96 (dd, 5.5, 11.6)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε)241 (3.96)

CHROMATOGRAPHY

HPTLC 
TLC 
NP-HPLCcolumn Zorbax-Sil (250x4.6 mm), solvent cyclohexane-iPrOH-H2O (80:40:3), flow-rate 1 ml.min-1, Ret 23.2 min (20E 12.3 min); solvent CH2Cl2-iPrOH-H2O (125:50:5), flow-rate 1 ml.min-1, Ret 21.3 min (20E 10.1 min)
RP-HPLCcolumn Spherisob 5ODS2 (250x4.6 mm), solvent 18% ACN-iPrOH (5:2) in 0.1% TFA in H2O, flow-rate 1 ml.min-1, Ret 13.3 min (20E : 13.9 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.6 x 10-6M

REFERENCES

First isolationSARKER, S.D. et al. (1997) Phytochemistry 44, 513-521 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more

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