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LIMNANTHEOSIDE B

Year of first isolation: 1997
Formula:C32H52O10
Molecular weight:596
Occurence in plants:
Limnanthes douglasii [Limnanthaceae] » Images of Limnanthes douglasii Wikipedia: Limnanthes douglasii [Limnanthaceae]
Occurence in animals:
 
LIMNANTHEOSIDE B

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)OC5C(C(C(CO5)O)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)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)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,14-dihydroxy-10,13-dimethyl-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 CID24984733
InChiKey
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YVYGCJBVFDRKJN-BDDLOYOMSA-N
InChIInChI=1S/C32H52O10/c1-16(2)6-7-25(36)31(5,39)24-9-11-32(40)18-12-20(33)19-13-23(42-28-27(38)26(37)22(35)15-41-28)21(34)14-29(19,3)17(18)8-10-30(24,32)4/h12,16-17,19,21-28,34-40H,6-11,13-15H2,1-5H3/t17?,19-,21-,22+,23+,24?,25+,26-,27+,28-,29+,30+,31+,32+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z614 (M+H+NH3)+, 597 (M+H)+, 579, 561, 543, 481, 465, 447, 429, 363, 345, 191, 166, 150, 116, 102
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

D2O
0137.2
0267.6
0375.3
0429.1
0551.3
06 
07122.1
08 
0934.8
1038.9
1121.0
1231.8
1348.3
1486.3
1531.3
1620.9
1750.1
1818.0
1924.0
2078.9
2120.5
2277.9
2329.8
2436.9
2528.4
2622.6
2723.5
C-1'101.8
C-2'73.9
C-3'77.0
C-4'70.5
C-5'66.3
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-Me1.23 (s )
22-H3.45 (dd, 10.7, 1.4)
23-Ha1.25
23-Hb1.60
24-Ha1.37
24-Hb1.26
25-H1.55
26-Me0.89 (d, 6.8)
27-Me0.91 (d, 6.8)
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)242 (4.00)

CHROMATOGRAPHY

HPTLC 
TLC 
NP-HPLCcolumn Zorbax-Sil (250x4.6 mm), solvent cyclohexane-iPrOH-H2O (80:40:3), flow-rate 1 ml.min-1, Ret 8.6 min (20E 12.3 min, PoA 5.4 min); solvent CH2Cl2-iPrOH-H2O (125:50:5), flow-rate 1 ml.min-1, Ret 7.2 min (20E 10.1 min, PoA 4.4 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 146.3 min (PoA : 155.1 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.5 x 10-5M

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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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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