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RHAPONTISTERONE [= PUNISTERONE]

Year of first isolation: 1991
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Rhaponticum uniflorum [Asteraceae] » Images of Rhaponticum uniflorum Wikipedia: Rhaponticum uniflorum [Asteraceae]
Occurence in animals:
 
RHAPONTISTERONE [=  PUNISTERONE]

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(CC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)O)O)O
Isomeric SMILES
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CC(C)[C@H](C[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(C[C@H]([C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)O)C)O)O)O)O » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,5-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN137476-71-2
PubChem CID11799446
InChiKey
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PJHYXCVCRWJEMV-XYFSXPBDSA-N
InChI1S/C27H44O8/c1-13(2)16(28)10-22(33)26(5,34)21-6-7-27(35)15-9-17(29)14-8-18(30)19(31)11-24(14,3)23(15)20(32)12-25(21,27)4/h9,13-14,16,18-23,28,30-35H,6-8,10-12H2,1-5H3/t14-,16-,18+,19-,20+,21-,22+,23+,24-,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z496 (M+H+NH3-H2O)+, 479, 461, 443, 425, 407, 391, 362
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

D2O*
0136.9
0266.9
0366.9
0431.4
0551.1
06206.4
07121.5
08164.9
0941.1
1038.2
1168.1
1241.5
1347.1
1484.3
1530.2
1619.9
1748.5
1817.4
1922.9
2077.6
2118.9
2275.2
2334.7
2475.5
2531.2
2615.1
2718.5
C5D5N
0139.5
0268.1
0367.9
0432.5
0552.2
06203.6
07121.3
08163.9
0942.5
1039.3
1168.6
1243.8
1347.9
1483.9
1531.7
1621.3
1749.6
1818.7
1924.7
2076.4
2121.3
2277.4
2335.4
2476.6
2533.8
2616.9
2719.4
D2O
01-Ha1.39 (t, 13)
01-He2.48 (dd, 13, 3.5)
02-Ha4.09 (m, w1/2 = 12)
03-He4.09 (m, w1/2 = 12)
04-Ha1.75*
04-He1.75*
05-H2.32
07-H5.98 (d, 2)
09-Ha3.12 (dd, 9, 2)
11-Ha4.22 (m, w1/2 = 24)
12-Ha2.05*
12-He2.72 (dd, 12, 5.6)
15-Ha2.06*
15-Hb1.66*
16-Ha1.9*
16-Hb1.8*
17-H2.3
18-Me0.86 (s)
19-Me1.09 (s)
21-Me1.27 (s)
22-H3.61 (d, 10)
23-Ha1.47 (ddd, 13, 10, 7)
23-Hb1.8*
24-Ha3.71 (m, w1/2 = 12)
25-H1.78
26-Me0.89 (d, 6.8)
27-Me0.96 (d, 6.8)
C5D5N
01-Ha2.25 *
01-He2.5 *
02-Ha4.15 (m )
03-He4.21 (m )
04-Ha2.05 *
04-He1.8 *
05-H3.05*
07-H6.32 (d, 2.5)
09-Ha3.87 (dd, 8.7,2.5)
11-Ha4.59 (m, w1/2=26)
12-Ha3.05 *
12-He2.27 (dd, 12, 5.6)
15-Ha2.5 *
15-Hb1.95 *
16-Ha1.9 *
16-Hb2.2*
17-H3.05*
18-Me1.33 (s )
19-Me1.27 (s )
21-Me1.59 (s )
22-H4.13 (db, 10)
23-Ha1.80*
23-Hb2.00 *
24-Ha3.94 (m, w1/2=22)
25-H1.70 *
26-Me1.003 (d, 6.8)
27-Me1.006 (d, 6.8)

PHYSICAL PROPERTIES

M.P.234-236 °C (decomp)
[α]D20 
IR (KBr) ν max (cm-1)1650, 997, 952, 909
UV (EtOH) λ max (log ε)241.4 (4.08)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC, column Spherisorb-5ODS2 (250x4.6 mm), flow-rate 1 ml.min-1, eluted with a gradient 30 to 100% MeOH over 30 min, ret 15.6 min (20E 16.4 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 8.3 x 10-7M

REFERENCES

First isolationGAO, C. et al. (1991) Bopuxue Zazhi (Chinese J. Magn. Reson.) 8, 379-386 Search more
GeneralSARKER, S.D. et al. (1996) J. Nat. Prod. 59, 789-793 Search more
GeneralMINGSHEN, L. et al. (1998) Chin. J. Magn. Resonance 15, 539-542 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
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