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LYGODIUMSTEROSIDE A

Year of first isolation: 2009
Formula:C35H54O12
Molecular weight:666
Occurence in plants:
Lygodium japonicum [Lygodiaceae] » Images of Lygodium japonicum Wikipedia: Lygodium japonicum [Lygodiaceae]
Occurence in animals:
 
LYGODIUMSTEROSIDE A

STRUCTURE DESCRIPTORS

Canonical SMILESCCC1CC(OC(=O)C1C)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)OC6C(C(C(C(O6)CO)O)O)O)O)C)C)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](C(O1)CO)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H]1OC(=O)[C@H]([C@@H](C1)CC)C)O)O)C)C » JSMol: View in 3D
IUPAC Name(4R,6R)-6-[(1R)-1-[(2R,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-6-oxo-3-[(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-17-yl]-1-hydroxyethyl]-4-ethyl-3-methyloxan-2-one
CAS-RN 
PubChem CID102422558
InChiKey
[ ChemIDPlus: search ]
SVCLWTYQLVQMLJ-JMUVMLHESA-N
InChIInChI=1S/C35H54O12/c1-6-17-11-26(47-30(42)16(17)2)34(5,43)25-8-10-35(44)19-12-21(37)20-13-23(45-31-29(41)28(40)27(39)24(15-36)46-31)22(38)14-32(20,3)18(19)7-9-33(25,35)4/h12,16-18,20,22-29,31,36,38-41,43-44H,6-11,13-15H2,1-5H3/t16?,17-,18+,20+,22-,23-,24-,25+,26-,27-,28+,29-,31-,32-,33-,34-,35-/m1/s1

MASS SPECTRUM

ESI-MS m/z (negative mode)665.6 [M-H]-
HR-ESI-MS m/z701.3309 [M+Cl]+, calculated for C35H54O12Cl 701.3309

CARBON NMR

PROTON NMR

C5D5N
0138.0
0266.8
0377.1
0429.9
0550.7
06202.3
07121.1
08165.4
0933.5
1038.4
1120.3
1231.2
1347.2
1483.4
1531.1
1620.7
1749.2
1817.3
1923.4
2075.1
2120.7
2285.3
2329.0
2439.5
2540.7
26183.9
2715.2
2825.9
299.6
glu-1'103.5
glu-2'74.0
glu-3'78.0
glu-4'70.9
glu-5'77.8
glu-6'61.9
C5D5N
01-H1.72 (t, 12.6), 2.05 (m)
02-Ha4.06 (brd, 11.4)
03-He4.29 (brs)
04-H1.66 (m), 2.16 (m)
05-H2.90 (m)
07-H6.18 (brs)
09-H3.50 (brt)
11-H1.64 (m), 1.77 (m)
12-H1.86 (m), 2.57 (m)
15-H1.86 (m), 2.12 (m)
16-H2.05 (m), 2.57 (m)
17-H2.93 (m)
18-Me1.09 (s)
19-Me0.86 (s)
21-Me1.44 (s)
22-H4.44 (dd, 11.5, 2.5)
23-H1.41 (m), 2.05 (m)
24-H1.41 (m)
25-H2.17 (m)
27-Me1.28 (d, 7.2)
28-H1.01 (m), 1.37 (m)
29-Me0.67 (t, 7.2)
H-1'4.89 (d, 7.8)
H-2'4.01 (t-like)
H-3'4.18 (overlap)
H-4'4.06 (overlap)
H-5'3.90 (t-like)
H-6"4.49 (brd, 11.5)
H-6'4.31 (m)

PHYSICAL PROPERTIES

M.P.245-246 °C ;
[α]D20° (c ; MeOH)
IR (KBr) ν max (cm-1)3416 (OH), 1730 (?-lactone), 1646 (cyclohexenone)
UV (MeOH) λ max (log ε)243 (nm) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationZHU, L. et al. (2009) J. Nat. Med. 63, 215-219 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
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