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MURISTERONE A

Year of first isolation: 1972
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Ipomoea calonyction [Convolvulaceae] » Images of Ipomoea calonyction Wikipedia: <br />
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Occurence in animals:
 
MURISTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4(C3(CC(C(C4)O)O)C)O)O)C)O)O)O
Isomeric SMILES
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C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)CCC(C)C)O)O)C)O)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,11R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,5,11,14-pentahydroxy-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN38778-30-2
PubChem CID122217
InChiKey
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LRJUYAVTHIEHAI-LHBNDURVSA-N
InChIInChI=1S/C27H44O8/c1-14(2)6-7-20(31)25(5,33)19-8-9-26(34)15-10-21(32)27(35)13-17(29)16(28)11-24(27,4)22(15)18(30)12-23(19,26)3/h10,14,16-20,22,28-31,33-35H,6-9,11-13H2,1-5H3/t16-,17+,18+,19-,20+,22+,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
HR-MS496.3033 (calc. for C27H44O8 496.3034)

CARBON NMR

PROTON NMR

C5D5N
0136.2
0268.2 *
0369.9 *
0435.9
0580.0
06201.1
07120.3
08165.0
0946.2
1045.5
1169.6
1244.0
1348.2
1484.2
1531.7
1621.4
1749.4
1817.4
1918.8
2076.8
2121.4
2276.8
2330.1
2437.0
2528.2
2622.4 **
2723.4 **
C5D5N
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H6.28 (d, 2.5)
09-Ha 
11-Ha 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.24 (s )
19-Me1.38 (s )
21-Me1.53 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me0.82 (d, 6)
27-Me0.82 (d, 6)

PHYSICAL PROPERTIES

M.P.238-244 °C
[α]D20+49.6 ° (c 1; pyridine)
IR (KBr) ν max (cm-1)3600-3100 (OH), 1660, 1630
UV (EtOH) λ max (log ε)236 (3.95)

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silicagel Rf 0.27 (CHCl3-EtOH 4:1); RP-TLC on paraffin coated silica gel Rf 0.37 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.37 (MeOH-H2O 65:35)
GLCGLC Ret 5.1 min on 1.5% OV101 (0.9 m x 4.5 mm i.d.) at 285°C after silylation at 140°C
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 2.2 x 10-8M
Calliphora vicina imaginal disc assay: EC50 = 1.5 x 10-9M
Drosophila melanogaster Kc-H cell assay: EC50 = 2.0 x 10-9M
Drosophila melanogaster Kc-H cell assay: EC50 = 1.4 x 10-9M

REFERENCES

First isolationCANONICA, L. et al. (1972) Chem. Commun., 1060-1061 Search more
GeneralCANONICA, L. et al. (1975) Phytochemistry 14, 525-527 Search more
GeneralCANONICA, L. et al. (1977) Gazz. Chim. Ital. 107, 123-130 Search more
BioactivitiesCHERBAS, L. et al. (1980) W. Roux Arch. Devel. Biol. 189, 1-15 Search more
BioactivitiesCHERBAS, P. et al. (1982) J. Chem. Soc., Chem. Commun., 1307-1308 Search more
GeneralWILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 Search more
GeneralBIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 Search more
BioactivitiesCLEMENT, C.Y. et al. (1993) Insect Biochem. Molec. Biol. 23, 187-193 Search more
BioactivitiesTERENTIOU, P. et al. (1993) Insect Biochem. Molec. Biol. 23, 131-136 Search more

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