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AMARASTERONE A

Year of first isolation: 1968
Formula:C29H48O7
Molecular weight:508
Occurence in plants:
Cyathula capitata [Amaranthaceae] » Images of Cyathula capitata Wikipedia: Cyathula capitata [Amaranthaceae]
Occurence in animals:
 
AMARASTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCCC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)C(C)CO
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](C[C@H](C(CO)C)CC)O)O)O)C)C  » JSMol: View in 3D
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](C[C@H](C(CO)C)CC)O)O)O)C)C  » JSMol: View in 3D
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](C[C@H](C(CO)C)CC)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R,5R)-5-ethyl-2,3,7-trihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN20853-88-7
PubChem CID101297611
InChiKey
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GTRXMTZSWNWUAX-YAUYKCKZSA-N
InChIInChI=1S/C29H48O7/c1-6-17(16(2)15-30)11-25(34)28(5,35)24-8-10-29(36)19-12-21(31)20-13-22(32)23(33)14-26(20,3)18(19)7-9-27(24,29)4/h12,16-18,20,22-25,30,32-36H,6-11,13-15H2,1-5H3/t16?,17-,18+,20+,22-,23+,24+,25-,26-,27-,28-,29-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/z363 (M - C22-C29)+, 345, 327, 145 (C22-C29)+, 127, 109.
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

D2O
0138.3; 38.6
0270.2; 70.2
0370.1; 70.1
0434.1; 34.0
0553.3; 53.1
06211.4; n.d.
07124.1; 123.7
08n.d.; n.d.
0936.7; 36.4
1041.0; 40.8
1123.0; 22.8
1233.9; 33.8
1350.3; 50.0
1488.1; 87.4
1533.4; 33.0
1622.4; 22.4
1752.1; 52.0
1819.9; 19.8
1925.9; 25.8
2081.0; 80.6
2122.4; 22.3
2278.8; 76.8
2335.4; 33.2
2441.4; 39.0
2540.0; 38.3
2668.0; 68.4
2718.8; 13.7
2825.1; 25.5
2914.2; 14.0
CD3OD
0137.36
0268.70
0368.52
0432.86
0551.79
06206.44
07122.14
08167.94
0935.10
1039.26
1121.53
1232.52
1349.0*
1485.21
1531.79
1621.47
1750.34
1818.06
1924.41
2077.96
2120.90
2275.71
2332.02
2437.85
2537.60
2666.75
2711.51
2825.40
2912.29
CD3OD
01-Ha1.43 (dd, 13.4, 12.0)
01-He1.79 (dd, 13.4, 4.2)
02-Ha3.83 (ddd, 12.0, 4.2, 3.0)
03-He3.95 (q, 3, 3, 3)
04-Ha1.70-1.75
04-He1.70-1.75
05-H3.38 (dd, 12.6, 4.5)
07-H5.81 (d, 2.6)
09-Ha3.15 (ddd, 11.5, 7, 2.6)
11-Ha1.70
11-He1.81
12-Ha2.11 (td, 13, 13, 5)
12-He1.88
15-Ha1.96
15-Hb1.61
16-Ha1.75
16-Hb2.00
17-H2.34 (dd, 9.8, 8.4)
18-Me0.894 (s)
19-Me0.968 (s)
21-Me1.179 (s)
22-H3.45 (dd, 10.4, 2.3)
23-Ha1.21
23-Hb1.21
24-Hb1.68
25-H1.85
26-H3.50 (dd, 11.0, 7.3)
27-Me0.786 (d, 7.0)
28-Ha,b1.51, 1.28
29-Me0.935 (t, 6.4, 6.4)
D2O
01-Ha1.38; 1.38
01-He1.88; 1.88
02-Ha3.99 (w1/2=22); 3.99 (w1/2=22)
03-He4.07 (w1/2=8); 4.07 (w1/2=8)
04-Ha1.75; 1.75
04-He1.75; 1.75
05-H2.34 (t); 2.34 (t)
07-H5.97 (d, 2); 5.97 (d, 2)
09-Ha3.11 (w1/2=22); 3.11 (w1/2=22)
11-Ha1.73; 1.73
11-He1.86; 1.86
12-Ha1.99*; 1.99*
12-He1.96*, 1.96*
15-Ha1.65; 1.64
15-Hb2.05; 2.05
16-Ha1.89**; 1.89**
16-Hb1.80**; 1.80
17-H2.32 (m); 2.30 (m)
18-Me0.867 (s); 0.867 (s)
19-Me1.000 (s); 1.000 (s)
21-Me1.230 (s); 1.222 (s)
22-H3.54 (d, 10); 3.56 (d, 10)
23-Ha1.36; 1.29
23-Hb1.42; 1.24
24-Ha1.50; 1.56
25-H1.82; 1.88
26-Ha3.39 (dd, 10.8, 8.3); 3.46 (dd, 10.8, 7.2)
26-Hb3.65 (dd, 10.8, 5); 3.55 (m)
27-Me0.932 (d, 6.8); 0.809 (d, 6.8)
28-Ha1.40; 1.30
28-Hb1.40; 1.52
29-Me0.913 (t, 7.1); 0.896 (t, 7.4)

PHYSICAL PROPERTIES

M.P.210-211 °C
[α]D20 
IR (KBr) ν max (cm-1)-- (OH), 1650 (cyclohexenone)
UV (EtOH) λ max (log ε)244 ;

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 
NP-HPLCKromasil column (250 x 4.6 mm i.d.), solvent dichloromethane-isopropanol-water (125:30:1.5), flow rate 1 ml/min, ret. 15.6 and 12.0 min (20E: 27.8 min)
RP-HPLCSpherisorb 5ODS2 column (250 x 4.6 mm i.d.), solvent methanol-water (45:55), flow rate 0.7 ml/min, ret. 24.9 and 31,0 min (20E: 10,9 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 5.6 x 10-7M
Sarcophaga assay: highly active

REFERENCES

First isolationTAKEMOTO, T. et al. (1968) Tetrahedron Lett. 4953-4956 Search more
BioactivitiesBERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 Search more
BioactivitiesDINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 Search more
GeneralSNOGAN, E. et al. (2007) Phytochemical Analysis 18, 441-450 Search more
IdentificationBUDĚŠÍNSKÝ, M. et al. (2008) Steroids 73, 502-514 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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