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TURKESTERONE

Year of first isolation: 1975
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Ajuga turkestanica [Lamiaceae (alt. Labiatae)] » Images of Ajuga turkestanica Wikipedia: <br />
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Vitex glabrata [Lamiaceae] » Images of Vitex glabrata Wikipedia: <br />
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Vitex canescens [Lamiaceae] » Images of Vitex canescens Wikipedia: <br />
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Tapinella panuoides [Fungi] » Images of Tapinella panuoides Wikipedia: <br />
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Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: <br />
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Occurence in animals:
 
TURKESTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CC(C3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@H](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](CCC(C)(C)O)O)O)O)C)O)C » 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)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN41451-87-0
PubChem CID14376672
InChiKey
[ ChemIDPlus: search ]
WSBAGDDNVWTLOM-XHZKDPLLSA-N
InChIInChI=1S/C27H44O8/c1-23(2,33)8-7-21(32)26(5,34)20-6-9-27(35)15-11-16(28)14-10-17(29)18(30)12-24(14,3)22(15)19(31)13-25(20,27)4/h11,14,17-22,29-35H,6-10,12-13H2,1-5H3/t14-,17+,18-,19+,20-,21+,22+,24-,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)460 [M-2H2O], 442, 424, 409, 379, 361, 343, 325, 300, 143, 125, 99, 81, 69.
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0139.6
0268.0 *
0368.2 *
0432.6
0552.5
06204.0
07122.1
08164.2
0942.4
1039.3
1168.7 *
1243.9
1348.0
1484.1
1531.7
1621.4
1749.8
1818.7
1924.6
2076.7
2121.4
2277.4
2327.2
2442.5
2569.5
2629.8
2729.8
CD3OD
0139.09
0268.94
0368.57
0433.28
0552.78
06206.66
07122.74
08165.74
0942.94
1039.91
1169.51
1243.79
13a
1484.87
1531.86
1621.52
1750.35
1818.89
1924.62
2077.83
2121.02
2278.42
2327.35
2442.40
2571.29
2629.73
2728.95
C5D5N
01-Ha 
01-He 
02-Ha4.45
03-He4.06
04-Ha 
04-He 
05-H 
07-H6.12
09-Ha3.75
11-Ha4.45
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.12 (s )
19-Me1.18 (s )
21-Me1.45 (s )
22-Hb3.75
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.24 (s )
27-Me1.24 (s )
CD3OD
01-Ha1.38 (dd, 13.0, 12.0)
01-He2.59 dd, 13.0, 4.3)
02-Ha4.01 (ddd, 12.0, 4.3, 3.4)
03-He3.95 (q )
04-Ha1.78
04-He1.68 (dt, 14.2, 3.9, 3.5)
05-H2.33 (dd, 13.2, 3.9)
07-H5.80 (dd, 2.6, 1.0)
09-Ha3.15 (dd, 9.0, 2.6)
11-Ha4.10 (ddd, 10.6, 9.0, 6.2)
12-Ha2.22 (dd, 12.4, 10.6)
12-He2.16 (dd, 12.4, 6.2)
15-Ha1.95
15-Hb1.58
16-Ha2.00
16-Hb1.75
17-H2.43
18-Me0.877 (s )
19-Me1.057 (s )
21-Me1.193 (s )
22-Hb3.32 (dd, 11.0, 1.8)
23-Ha1.66
23-Hb1.29
24-Ha1.80
24-Hb1.43 (ddd, 13.6, 11.6, 4.3)
26-Me1.206 (s )
27-Me1.220 (s )

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3300-3500 (OH), 1660 (CO)
UV (EtOH) λ max (log ε)244 (3.95)

CHROMATOGRAPHY

NP-HPLCcolumn Silasorb 600 (4 x 250 mm), flow-rate 0.8 ml.min-1, solvent Et2O-hexane-MeOH-H2O (440:430:120:10), Ret 97.9 min (20E 47.5 min)
HPTLC 
TLC 
GLC 
RP-HPLCcolumn Separon SIX C18 (4 x 250 mm), solvent MeOH-H2O, linear gradient 10 to 70 % MeOH in 50 min, flow-rate 0.6 ml.min-1, Ret 33.9 min (20E 42.7 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.3 x 10-6M
Drosophila melanogaster BII cell assay: EC50 = 3.0 x 10-7M
Drosophila melanogaster BII cell assay: EC50 = 8.0 x 10-7M
Galleria mellonella in vivo assay: ED50 = 62.5 ug/g
Sarcophaga bullata in vivo assay: ED50 = 0.3 ug/g
Dermestes vulpinus in vivo assay: ED50 = 4.2 ug/g

REFERENCES

First isolationUSMANOV, B.Z. et al. (1975) Khim. Prir. Soedin. 466-470 Search more
GeneralWERAWATTANAMETIN, K. et al. (1986) J. Nat. Prod. 49, 365-366 Search more
BioactivitiesCLEMENT, C.Y. et al. (1993) Insect Biochem. Molec. Biol. 23, 187-193 Search more
BioactivitiesSLÁMA, K. et al. (1993) Insect Biochem. Molec. Biol. 23, 181-185 Search more
GeneralSUKSAMRARN, A. et al. (1997) Phytochemistry 45, 1149-1152 Search more
IdentificationVOKÁČ, K. et al. (1998) Phytochemistry 49, 2109-2114 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
GeneralBUDĚŠÍNSKÝ, M. et al. (2008) Steroids 73, 502-514 Search more

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