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TENUIFOLIOSIDE B

Year of first isolation: 1989
Formula:C33H56O10
Molecular weight:612
Occurence in plants:
Lilium tenuifolium [Liliaceae] » Images of Lilium tenuifolium Wikipedia: Lilium tenuifolium [Liliaceae]
Occurence in animals:
 
TENUIFOLIOSIDE B

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CCC3C2CC(=O)C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)C)O)O)O
Isomeric SMILES
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C1[C@]2([C@H](C[C@H](C1)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)C(=O)CC1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@H](C[C@H](C1)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)C(=O)C[C@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@H](C[C@H](C1)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(3S,5S,8R,9S,10R,13R,14R,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID14542295
InChiKey
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KTYXGLHTBUYJCL-OEFXEBJNSA-N
InChIInChI=1S/C33H56O10/c1-17(2)6-7-25(36)32(5,40)24-10-13-33(41)20-15-22(35)21-14-18(8-11-30(21,3)19(20)9-12-31(24,33)4)42-29-28(39)27(38)26(37)23(16-34)43-29/h17-21,23-29,34,36-41H,6-16H2,1-5H3/t18-,19-,20+,21+,23+,24-,25+,26+,27+,28+,29+,30+,31+,32+,33+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)SIMS m/z
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0137.0 a
0227.2
0376.9 b
0429.6
0556.4
06211.4
0742.8
0840.9
0946.7
1040.7
1121.2
1233.0
1348.8
1483.9
1532.4
1621.7
1750.2
1817.8
1912.8
2076.8
2121.3
2276.7 b
2330.3
2437.2 a
2528.2
2622.5
2723.2
s1'99.6
s2'73.0
s3'72.4
s4'69.3
s5'76.0
s6'63.2
C5D5N
01-Ha 
01-Hb 
02-Ha 
03-He3.89 (m, w1/2 = 24.5)
04-Ha 
04-He 
05-H 
07-Ha2.87 (dd, 12.6, 12.6)
07-He2.44 (dd, 12.6, 4.5)
08-H2.28 (ddd, 12.6, 12.6, 4.2)
09-Ha2.13 (ddd, 12.6, 12.6, 4.2)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.85 (t, 9.1)
18-Me1.34 (s )
19-Me0.72 (s )
21-Me1.57 (s )
22-H3.79 (br d, 10.2)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me0.84 (d, 6.5)a
27-Me0.83 (d, 6.5)a
H-1'5.49 (d, 7.8)
H-2'3.98 (dd, 7.8, 2.8)
H-3'4.76 (dd, 2.8, 2.8)
H-4'4.22 (dd, 9.6, 2.8)
H-5'4.51 (ddd, 9.6, 5.3, 2.1)
H-6'a4.57 (dd, 11.6, 2.1)
H-6'b4.39 (dd, 11.6, 5.3)

PHYSICAL PROPERTIES

M.P. 
[α]D26-19.0 ° (c 0.20; MeOH)
IR (KBr) ν max (cm-1)3430 (OH), 2945, 2870, 1695 (C=O), 1460, 1455, 1380, 1360,
UV (EtOH) λ max (log ε)230sh (589), 281 (249), 320sh (147)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationMIMAKI, Y. et al. (1989) Phytochemistry 28, 3454-3458 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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