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MAKISTERONE C [= PODECDYSONE A, LEMMASTERONE]

Year of first isolation: 1968
Formula:C29H48O7
Molecular weight:508
Occurence in plants:
Lemmaphyllum microphyllum [Polypodiaceae] » Images of Lemmaphyllum microphyllum Wikipedia: Lemmaphyllum microphyllum [Polypodiaceae]
Podocarpus elatus [Podocarpaceae] » Images of Podocarpus elatus Wikipedia: Podocarpus elatus [Podocarpaceae]
Podocarpus macrophyllus [Podocarpaceae] » Images of Podocarpus macrophyllus Wikipedia: Podocarpus macrophyllus [Podocarpaceae]
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: Leuzea carthamoides [Asteraceae]
Serratula coronata [Asteraceae] » Images of Serratula coronata Wikipedia: Serratula coronata [Asteraceae]
Diploclisia glaucescens [Menispermaceae] » Images of Diploclisia glaucescens Wikipedia: Diploclisia glaucescens [Menispermaceae]
Microsorum scolopendria [Polypodiaceae] » Images of Microsorum scolopendria Wikipedia: Microsorum scolopendria [Polypodiaceae]
Occurence in animals:
Dysdercus fasciatus [Pyrrhocoridae] » Images of Dysdercus fasciatus Wikipedia: Dysdercus fasciatus [Pyrrhocoridae]
MAKISTERONE C [= PODECDYSONE A, LEMMASTERONE]

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)(C)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](O)CC(C(C)(C)O)CC)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](O)C[C@H](C(C)(C)O)CC)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](O)C[C@@H](C(C)(C)O)CC)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-5-ethyl-2,3,6-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-RN 
PubChem CID101249757
InChiKey
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CIQDSODCPIIBBH-BFSOYOPGSA-N
InChIInChI=1S/C29H48O7/c1-7-16(25(2,3)34)12-24(33)28(6,35)23-9-11-29(36)18-13-20(30)19-14-21(31)22(32)15-26(19,4)17(18)8-10-27(23,29)5/h13,16-17,19,21-24,31-36H,7-12,14-15H2,1-6H3/t16?,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)508 (M)+, 493, 490, 475, 472, 457, 454, 439, 363, 345, 189, 171, 145 (M-363)+, 127, 109
HR-MS 

CARBON NMR

PROTON NMR

D2O
0137.9
0269.9
0369.9
0433.8
0552.9
06211.5
07124.2
08-
0936.6
1040.8
1122.3
1233.4
1349.9
1487.6
1532.9
1622.4
1751.2
1819.7
1925.8
2080.6
2122.2
2277.7
2335.2
2450.1
2577.5
2628.7
2728.7
2826.0
2916.6
CD3OD
0137.36
0268.69
0368.50
0432.84
0551.78
06206.43
07122.10
08168.01
0935.09
1039.25
1121.53
1232.50
1349.50
1485.17
1531.79
1621.62
1750.41
1818.07
1924.43
2078.01
212096
2277.20
2325.97
2450.28
2574.11
2625.60
2729.10
2833.02
2914.37
D2O
01-Ha1.38
01-Hb1.88
02-Ha3.99 (m, w1/2=22)
03-He4.07 (m, w1/2=8)
04-Ha1.75
04-He1.75
05-H2.36 (t)
07-H5.97 (db, 1.6)
09-Ha3.11 (m, w1/2=22)
11-Ha1.74
11-He1.86
12-Ha1.99*
12-He1.96*
15-Ha1.66
15-Hb2.06 (m)
16-Ha1.90*
16-Hb1.80*
17-H2.34 (m)
18-Me0.872 (s)
19-Me1.000 (s)
21-Me1.240 (s)
22-H3.56 (d, 10)
23-Ha1.44
23-Hb1.44
24-Hb1.49
26-Me1.198 (s)
27-Me1.209 (s)
28-Ha1.61
28-Hb1.25
29-Me0.997 (t, 7.5)
CD3OD
01-Ha1.43
01-Hb1.79
02-Ha3.84 (m, w1/2=22)
03-He3.94 (m, w1/2=8)
04-Ha1.65
04-He1.75
05-H2.37 (dd, 12, 5)
07-H5.80 (d, 2.5)
09-Ha3.16 (m, w1/2=22)
11-Ha1.66
11-He1.79
12-Ha2.13
12-He1.87
15-Ha2.00
15-Hb1.55
16-Ha2.00
16-Hb1.77
17-H2.39 (m )
18-Me0.89 (s )
19-Me0.96 (s )
21-Me1.20 (s )
22-Hb3.42
23-Ha1.43
23-Hb1.55
24-Ha1.45
26-Me1.21 (s )
27-Me1.10 (s )
28-CH2-1.14, 1.53
29-Me1.01 (t, 6.5)

PHYSICAL PROPERTIES

M.P.258-259°C
[α]D20 
IR (KBr) ν max (cm-1)3400-3470 (OH), 1643-1650 (cyclohexenone)
UV (EtOH) λ max (log ε)243-244 (4.146)

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silica gel : Rf 0.28 (CHCl3-EtOH 4:1); Rf 0.49 (EtOAc-MeOH-NH4OH 85:10:5); Rf 0.46 (CH2Cl2-EtOH 85:15)
GLC 
HPLCNormal phase (Zorbax-Sil) Ret 17.2 min (solvent : CH2Cl2-iPrOH-H2O 125:25:2) (20E: 53.2 min); Reverse phase (Spherisorb-5ODS-2) Ret 17.5 min (solvent : ACN-0.1% TFA in H2O 23:77) (20E 5.5 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-7M
Drosophila melanogaster Kc-H cell assay: EC50 = 1.3 x 10-7M
Calliphora assay: 100% (20-hydroxyecdysone = 100%)
Musca assay: 0% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationIMAI, S. et al. (1968) Tetrahedron Lett. 3883-3886 Search more
GeneralGALBRAITH, M.N. et al. (1968) J. Chem. Soc., Chem. Commun. 971-972 Search more
GeneralTAKEMOTO, T. et al. (1968) Tetrahedron Lett. 4061-4064 Search more
BioactivitiesCHERBAS, L. et al. (1980) W. Roux Arch. Devel. Biol. 189, 1-15 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
GeneralGIRAULT, J.-P. et al. (1988) Phytochemistry 27, 737-741 Search more
GeneralFELDLAUFER, M.F. et al. (1991) Arch. Insect Biochem. Physiol. 18, 71-80 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more
IdentificationVOKÁČ, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 Search more
GeneralJAYASINGHE, L. et al. (2003) Steroids 68, 447-450 Search more
GeneralSNOGAN, E. et al. (2007) Phytochemical Analysis 18, 441-450 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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