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VITICOSTERONE E

Year of first isolation: 1969
Formula:C29H46O8
Molecular weight:522
Occurence in plants:
Vitex megapotamica [Lamiaceae] » Images of Vitex megapotamica Wikipedia: <br />
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Serratula sogdiana [Asteraceae] » Images of Serratula sogdiana Wikipedia: <br />
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Lychnis flos-cuculi [Caryophyllaceae] » Images of Lychnis flos-cuculi Wikipedia: <br />
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Occurence in animals:
 
VITICOSTERONE E

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)OC(C)(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O
Isomeric SMILES
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[ ChemSpider: search ]
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](CCC(C)(C)OC(=O)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name[(5R,6R)-5,6-dihydroxy-2-methyl-6-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-2-yl] acetate
CAS-RN22033-96-1
PubChem CID11226211
InChiKey
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DWHBRFSKXQCVDN-FORVDKSSSA-N
InChIInChI=1S/C29H46O8/c1-16(30)37-25(2,3)10-9-24(34)28(6,35)23-8-12-29(36)18-13-20(31)19-14-21(32)22(33)15-26(19,4)17(18)7-11-27(23,29)5/h13,17,19,21-24,32-36H,7-12,14-15H2,1-6H3/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z523 (M+H)+, 505, 480, 463 (MH-60)+, 445, 427, 409, 363, 345
EI-MS m/z (relative intensity %)504 (M-18)+, 486, 468, 462 (M-60)+, 444, 426, 411, 408, 393, 363, 345, 300, 99, 81
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
28 
29 
C5D5N
01-Ha1.40
01-He1.85
02-Ha3.86 (m, w1/2=22)
03-He4.02 (m, w1/2=8)
04-Ha1.6
04-He1.8
05-H2.43 (dd )
07-H5.84 (d, 2.5)
09-Ha2.99 (m, w1/2=22)
11-Ha1.70
11-He1.78
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha2.0
16-Hb1.72
17-H2.33 (m )
18-Me1.20 (s )
19-Me1.07 (s )
21-Me1.60 (s )
22-Hb3.37 (d )
23-Ha1.2
23-Hb 
24-Ha2.17
24-Hb 
26-Me1.45 (s )
27-Me1.52 (s )
O-Ac1.95 (s )
CDCl3
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.85 (s )
19-Me0.97 (s )
21-Me1.20 (s )
22-Hb 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.40 (s )
27-Me1.44 (s )
O-Ac1.95 (s )

PHYSICAL PROPERTIES

M.P.198-199°C
[α]D20+ 60° (c 1.31; MeOH)
IR (KBr) ν max (cm-1)1720 (C=O), 1650 (cyclohexenone), 1615 (C=C)
UV (EtOH) λ max (log ε)243 (4.04)

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silica gel : Rf 0.81 (CHCl3-EtOH 4:1); Rf 0.40 (EtOAc-MeOH-NH4OH 85:10:5); Rf 0.43 (CH2Cl2-EtOH 85:15)
GLC 
NP-HPLC(Zorbax-SIL) Ret 10.6 min (CH2Cl2-iPrOH-H2O 125:30:2, 1 ml.min-1);
RP-HPLC(Spherisorb-5ODS2) Ret 18.4 min (ACN 0.1% TFA 23:77, 1 ml.min-1)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.0 x 10-7M
Drosophila melanogaster Kc-H cell assay: EC50 = 7.0 x 10-8M
Calliphora assay: 7% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationRIMPLER, H. et al. (1969) Tetrahedron Lett. (5), 329-333 Search more
GeneralZATSNY, I.L. et al. (1973) Khim. Prir. Soedin., 175-178 Search more
GeneralZATSNY, I.L. et al. (1975) Khim. Prir. Soedin., 155-158 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
GeneralSUKSAMRARN, A. et al. (1995) Tetrahedron 51, 10633-10650 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more

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