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LEUZEASTERONE

Year of first isolation: 1999
Formula:C29H42O8
Molecular weight:518
Occurence in plants:
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: Leuzea carthamoides [Asteraceae]
Occurence in animals:
 
LEUZEASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C5CC(=CC(=O)O5)C(C)(C)O)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H]1OC(=O)C=C(C1)C(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2R)-4-(2-hydroxypropan-2-yl)-2-[(1R)-1-hydroxy-1-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-2,3-dihydropyran-6-one
CAS-RN 
PubChem CID 15908337
InChiKey
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MUCBZHHNTRNVMC-UYQGPDJCSA-N
InChIInChI=1S/C29H42O8/c1-25(2,34)15-10-23(37-24(33)11-15)28(5,35)22-7-9-29(36)17-12-19(30)18-13-20(31)21(32)14-26(18,3)16(17)6-8-27(22,29)4/h11-12,16,18,20-23,31-32,34-36H,6-10,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)500 (2), 482 (10), 464 (6), 345 (8), 327 (13), 301 (22), 281 (9), 267 (11), 250 (10), 225 (12), 213 (12), 197 (11), 182 (14), 173 (16), 155 (18), 145 (20), 137 (28), 121 (21), 105 (23), 95 (28), 91 (28), 81 (27), 69 (50), 43 (100).
FAB-MS m/z (relative intensity %)519.30463 (19) [M+H] for C29H43O8 required 519.29579, 501 (79), 485 (15), 465 (7), 347 (9), 331 (11) 329 (11), 303 (75), 276 (22), 185 (100)

CARBON NMR

PROTON NMR

CD3OD
0137.35
0268.70
0368.51
0432.82
0551.78
06206.40
07122.34
08168.22
0935.05
1039.30
1121.49 *
1232.42
13 ***49,0***
1485.30
1531.78
1621.54 *
1750.52
1818.20
1924.38
2076.46
2121.42
2284.90
2326.45
24169.78 **
2572.65
2628.38
2727.77
28113.16
29167.50 **
CD3OD
01-Ha 1.44 (dd, 13.3, 4.5)
01-He 1.79 (dd, 13.3, 12.2)
02-H 3.84 (ddd, 12.2, 4.5, 3.0)
03-H 3.95 (bq, ~3.0)
04-Ha 1.73
04-He 1.70
05-H 2.39 (dd, 13.0, 4.2)
07-H 5.82 (d, 2.6)
09-H 3.17 (ddd, 11.1, 6.9, 2.6)
11-Ha 1.71
11-He 1.82
12-Ha 2.21
12-He 1.83
15-Ha 2.00
15-Hb 1.64
16-Ha 1.77
16-Hb 2.01
17-H 2.49 (dd,)
18-Me 0.90 (s)
19-Me 0.97 (s)
21-Me 1.35 (s)
22-H 4.23 (dd, 13.1, 3.2)
23-Ha 2.62 (dd, 17.8, 3.2)
23-Hb 2.40 (ddd, 17.8, 13.1, 2.6)
26-Me 1.40 (s)
27-Me 1.38 (s)
28-H 6.02 (d, 2.6)

PHYSICAL PROPERTIES

M.P. 
[α]D20+ 51.6 ° (c; 0.41, MeOH)
IR (KBr) ν max (cm-1)3340, 1705, 1653

CHROMATOGRAPHY

NP-HPLCcolumn Silasorb 600 (4 x 250 mm), solvent n-hexane ? EtOH ? H2O (812:180:8), flow rate 0.8 ml.min-1. Ret 66.0 min (20E 50.7 min).
HPTLC 
GLC 
HPLCRP-HPLC: column Separon SIX C18 (4 x 250 mm), solvent MeOH - H2O, linear gradient 10 to 70% MeOH in 50 min, flow rate 0.6 ml.min-1. Ret 35.6 min (20E 34.2 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.7 x 10-8M

REFERENCES

First isolationVOKÁČ, K. et al. (1999) 18th Conference on Isoprenoids, Prachatice, Chemické Listy, Symposia 93, p. 60 Search more
Struct. analysisVOKÁČ, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 Search more
BioactivitiesDINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 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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