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SHIDASTERONE [= STACHYSTERONE D]

Year of first isolation: 1968
Formula:C27H42O6
Molecular weight:462
Occurence in plants:
Blechnum niponicum [Blechnaceae] » Images of Blechnum niponicum Wikipedia: Blechnum niponicum [Blechnaceae]
Stachyurus praecox [Stachyuraceae] » Images of Stachyurus praecox Wikipedia: Stachyurus praecox [Stachyuraceae]
Vitex canescens [Lamiaceae (alt. Labiatae)] » Images of Vitex canescens Wikipedia: Vitex canescens [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
SHIDASTERONE [=  STACHYSTERONE D]

STRUCTURE DESCRIPTORS

Canonical SMILESCC1(CCC(O1)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C
Isomeric SMILES
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C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@](C)(C5CCC(O5)(C)C)O)O » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(1R)-1-(5,5-dimethyloxolan-2-yl)-1-hydroxyethyl]-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-RN26361-67-1
PubChem CID15227299
InChiKey
[ ChemIDPlus: search ]
JWXMXJQGIRXWDG-SASGHFKCSA-N
InChIInChI=1S/C27H42O6/c1-23(2)9-8-22(33-23)26(5,31)21-7-11-27(32)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-32H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22?,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)462 [M]+, 405 (1) 363 (19), 345 (50), 327 (15), 99 (C22-C27; 60), 81 (54), 43 (100).
FAB-MS m/z485 [M+Na]+ (13.7), 463 [M+H]+ (55), 445 (24.2), 123 (100).
HR-MS463.3028 (M+H)+, calculated 463.3059)

CARBON NMR

PROTON NMR

C5D5N
0137.7
0267.9
0367.9
0432.2
0551.2
06205.5
07121.5
08166.0
0934.2
1038.5
1121.0
1231.5
1347.5
1484.0
1531.5
1621.5
1751.2
1817.8
1924.3
2080.3
2121.0
2284.8
2327.6
2438.8
2575.4
2628.2
2728.7
CD3OD
0137.3
0268.6
0368.4
0432.7
0551.7
06206.4
07122.0
08167.9
0935.0
1039.2
1121.6
1232.2
1348.6
1485.2
1531.6
1621.4
1751.7
1818.0
1924.3
2076.9
2120.6
2285.4
2328.4
2439.5
2581.7
2628.3
2728.9
C5D5N
01-Ha 
01-Hb 
02-Ha~ 4.10 (m )
03-He4.19 (ddd )
04-Ha 
04-He 
05-H2.95 (dd )
07-H6.29 (d )
09-Ha3.53 (ddd )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.06 (s )
19-Me1.06 (s )
21-Me1.39 (s )
22-H4.06 (dd )
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.22 (s )
27-Me1.22 (s )
CD3OD
01-Ha1.42 (dd, 13, 12)
01-Hb 
02-Ha 
02-Ha ~3.84 (ddd, 12, 3, 3)
03-He3.94 (m, w1/2 = 20)
04-Ha 
04-He 
05-H2.36 (m, w1/2 = 25)
07-H5.81 (d, 2.5)
09-Ha3.15 (ddd, 12, 7.5, 2.5)
11-Ha 
11-He 
12-Ha2.15 (ddd, 13, 13, 4)
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.36 (m, w1/2 = 25)
18-Me0.84 (s )
19-Me0.96 (s )
21-Me1.21 (s )
22-H3.94 (m, w1/2 = 20)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.25 (s )
27-Me1.24 (s )

PHYSICAL PROPERTIES

M.P.245-250 °C (decomp.)
[α]D25+ 65.0° (c 0.18; CHCl3)
IR (CHCl3) ν max (cm-1)3600 (sharp, free OH), 3400 (broad, bonded OH), 1664
UV (EtOH) λ max (log ε)243 (4.04)

CHROMATOGRAPHY

HPTLC 
TLCRf 0.40 (CHCl3-EtOH 7:1, olive-green spot
GLC 
HPLCRP-HPLC, Column Spherisorb 5ODS2, MeOH-H2O 60:40 (v/v), Ret. 34.0 min

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 4.0 x 10-6M
Drosophila melanogaster BII cell assay: EC50 = 1.5 x 10-6M
Chilo dipping test: inactive

REFERENCES

First isolationTAKEMOTO, T. et al. (1968) Tetrahedron Lett. 6095-6098 Search more
GeneralTAKEMOTO, T. et al. (1969) Chem. Pharm. Bull. 17, 1973-1974 Search more
First isolationIMAI, S. et al. (1970) Chem. Commun., 352-353 Search more
GeneralHIKINO, H. et al. (1975) Tetrahedron 23, 1458-1479 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
GeneralROUSSEL, P.G. et al. (1995) J. Chem. Soc., Chem. Commun. 933-934 Search more
GeneralSUKSAMRARN, A. et al. (1997) Phytochemistry 45, 1149-1152 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 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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