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INTEGRISTERONE A

Year of first report:1977
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Rhaponticum integrifolium [Compositae] » Images of Rhaponticum integrifolium Wikipedia: <br />
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Serratula xeranthemoides [Asteraceae] » Images of Serratula xeranthemoides Wikipedia: <br />
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Silene nutans [Caryophyllaceae] » Images of Silene nutans Wikipedia: <br />
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Silene otites [Caryophyllaceae] » Images of Silene otites Wikipedia: <br />
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Lychnis flos-culculi [Caryophyllaceae] » Images of Lychnis flos-culculi Wikipedia: <br />
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Silene viridiflora [Caryophyllaceae] » Images of Silene viridiflora Wikipedia: <br />
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Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: <br />
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Occurence in animals:
 
INTEGRISTERONE A

MASS SPECTRUM

CI-MS (NH3) m/z497 (MH)+, 479, 461, 443, 425, 379, 361, 345, 343
EI-MS m/z (relative intensity %)478 (14), 460(20), 442 (94), 424 (33), 409 (10), 391 (6), 379 (15), 374 (12), 368 (42), 361 (100), 343 (90), 325 (30), 316 (25), 301 (15), 283 (24), 143 (12), 125 (12), 99 (49), 81 (27), 69 (27)
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0176.43
0270.98
0368.50
0443.80
0546.79
06205.57
07122.17
08167.19
0935.65
10 
1121.91
1232.54
13~49.0
1485.10
1531.80
1621.40
1750.58
1818.02
1920.01
2077.89
2121.05
2278.43
2327.36
2442.38
2571.29
2629.70
2728.97
C5D5N
01-Ha--
01-Hb4.15
02-Ha4.15
03-He4.15
04-Ha1.78
04-He1.78
05-H2.62 (t-like )
07-H6.14
09-Ha3.42
11-Ha1.75
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha1.9
16-Hb1.75
17-H2.33 (t, 8.5)
18-Me1.07
19-Me1.26
21-Me1.43
22-H3.71
23-Ha1.31
23-Hb1.66
24-Ha 
24-Hb 
26-Me1.24
27-Me1.24
D2O
01-Ha 
01-Hb3.92
02-Ha4.03 (t, 3.2)
03-He4.15 (m, w1/2 = 8)
04-Ha 
04-He 
05-H 
07-H6.00 (d, 2.5)
09-Ha3.04 (m, w1/2= 22)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.87 (s )
19-Me1.09 (s )
21-Me1.22 (s )
22-H3.43 (d br, 10)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.22 (s )
27-Me1.22 (s )

PHYSICAL PROPERTIES

M.P.244-246 °C
[α]D20+ 33.7 ? 2 ° (c 0.92; MeOH)
IR (KBr) ν max (cm-1)3300-3500 (OH), 1605 (cyclohexenone)
UV (EtOH) λ max (log ε)245 (4.09)

CHROMATOGRAPHY

TLCNP-TLC (silica gel plates) Rf : 0.13 (EtOAc/MeOH/NH4OH 85:10:5), 0.12 (CH2Cl2/EtOH 85:15), 0.55 (EtOAc/EtOH/H2O 8:2:1), 0.39 (CHCl3/MeOH/Me2CO 6:2:1) (Rf 20E : respect-ively 0.18, 0.15, 0.61, 0.47); RP-TLC (on Merck C18 bonded plates) Rf : 0.45 (MeOH/H2O 50:50) (20E : 0.44)
GLC 
HPLC1- Retention time 20.0 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2/iPrOH/H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min); 2-Retention time 48.4 min [ Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2/iPrOH/H2O 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min); 3-Retention time 4.6 min [ Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN- 0.1% TFA in H2O 23:77 /v/v, flow-rate 1 ml.min-1] (20E 5.5 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-7M
Galleria mellonella in vivo assay: ED50 = 15.6 ug/g
Sarcophaga bullata in vivo assay: ED50 = 15.6 ug/g

REFERENCES

First isolationBALTAYEV, U.A. et al. (1977) Khim. Prir. Soedin. 813-819 Search more
GeneralKHOLODOVA, YU. D. et al. (1979) Khim. Prir. Soedin. 171-174 Search more
GeneralWILSON, I.D. et al. (1988) J. Planar Chromatogr. 1, 116-122 Search more
GeneralGIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 Search more
BioactivitiesSLAMA, K. et al. (1993) Insect Biochem. Molec. Biol. 23, 181-185 Search more
IdentificationVOKAC, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 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
GeneralSIMON, A. et al. (2007) Steroids 72, 751-755 Search more

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