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FIBRAURECDYSIDE [= MAKISTERONE A 3-β-D-GLUCOSIDE]

Year of first isolation: 2007
Formula:C34H56O12
Molecular weight:656
Occurence in plants:
Fibraurea tinctoria [Menispermaceae] » Images of Fibraurea tinctoria Wikipedia: Fibraurea tinctoria [Menispermaceae]
Occurence in animals:
 
FIBRAURECDYSIDE [= MAKISTERONE A 3-β-D-GLUCOSIDE]

STRUCTURE DESCRIPTORS

Canonical SMILESCC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)C)O)O)O)C(C)(C)O
Isomeric SMILES
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C[C@H](C[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)C)C)O)O)O)C(C)(C)O » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-17-[(2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]-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-6-one
CAS-RN960506-35-8
PubChem CID44445723
InChiKey
[ ChemIDPlus: search ]
MQWJGLSZBHVGLN-VBSSPFTJSA-N
InChIInChI=1S/C34H56O12/c1-16(30(2,3)42)11-25(38)33(6,43)24-8-10-34(44)18-12-20(36)19-13-22(45-29-28(41)27(40)26(39)23(15-35)46-29)21(37)14-31(19,4)17(18)7-9-32(24,34)5/h12,16-17,19,21-29,35,37-44H,7-11,13-15H2,1-6H3/t16-,17+,19+,21+,22-,23-,24+,25-,26-,27+,28-,29-,31-,32-,33-,34-/m1/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
HR-FAB-MS657.3853 [M+H]+ (calculated for C34H56O12, 657.3850)
FAB-MS m/z657 [M+H]+

CARBON NMR

PROTON NMR

C5D5N
0139.0
0267.5
0377.7
0430.6
0551.4
06203.0
07121.6
08166.3
0934.2
1038.7
1121.1
1232.0
1348.1
1484.2
1531.9
1621.4
1750.0
1818.0
1924.1
2077.0
2121.6
2274.7
2334.6
2441.9
2572.1
2626/5
2728.2
2815.5
[Glu] 1'104.2
[Glu] 2'74.7
[Glu] 3'76.6
[Glu] 4'71.6
[Glu] 5'78.5
[Glu] 6'62.6
C5D5N
01-Ha1.71 (dd, 12.9, 12.8)
01-He2.04 (dd, 12.9, 3.7)
02-Ha4.07 (dd, 12.8, 3.7)
03-He4.26
04-Ha1.68 (m)
04-He2.16 (m)
05-H2.90 (m)
07-H6.18 (d, 3.9)
09-H3.53 (m)
11-Ha1.64 (m)
11-He1.78 (m)
12-Ha2.50 (ddd, 12.7, 12.6, 4.6)
12-He2.13 (m)
15-Ha1.93
15-Hb1.93
16-Ha2.41 (dd, 9.4, 9.2)
16-Hb2.09 (m)
17-H2.89 (m)
18-Me1.16 (s)
19-Me0.85 (s)
21-Me1.54 (s)
22-H3.94 (d, 10.8)
23-Ha1.55 (m)
23-Hb1.55 (m)
24-H2.25 (m)
26-Me1.28 (s)
27-Me1.31 (s)
28-Me1.05 (d, 6.8)
[Glu] 1'4.85 (d, 7.8)
[Glu] 2'3.99 (dd, 8.3, 7.8)
[Glu] 3'4.16 (dd, 9.1, 8.3)
[Glu] 4'3.12 (dd, 9.1, 8.1)
[Glu] 5'3.86 (dd, 9.1, 5.4)
[Glu] 6'4.48 (dd, 11.6, 1.8)
[Glu] 6''4.24 (dd, 11.6, 5.4)

PHYSICAL PROPERTIES

M.P.> 300 °C ;
[α]D25+ 128.8 ° (c 0.07; MeOH)
IR (KBr) ν max (cm-1)3380, 2962, 2882, 1648, 1442
UV (EtOH) λ max (log ε)243 (3.32)

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSU, C.-R. et al. (2007) J. Nat. Prod. 70, 1930-1933 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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