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GERARDIASTERONE

Year of first report:1986
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Serratula tinctoria [Asteraceae] » Images of Serratula tinctoria Wikipedia: <br />
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Occurence in animals:
Gerardia savaglia [Zoanthidae] » Images of Gerardia savaglia Wikipedia: <br />
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GERARDIASTERONE

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)496 (M)+, 393 (0.4), 363 (17), 133 (5), 103 (4)
HR-MS 
FAB-MS m/z497 (M+H)+, 479, 461, 443, 425

CARBON NMR

PROTON NMR

D2O
0136.3
02 
03 
04 
0551.4
06 
07 
08 
0935.1
1039.1
11 
1231.8
1347.8
1486.1
15 
16 
1750.5
1818.3
1924.2
2079.8
2122.1
2278.5
23 
2448.3
2572.5
2629.5
2729.6
C5D5N*
2123.22 (q )
2278.83 (d )
2368.88 (d )
2448.23 (t )
C5D5N
01-Ha1.93
01-He2.12
02-Ha4.18 (m, w1/2= 22)
03-He4.24 (br s, w1/2= 8)
04-Ha1.80
04-He2.04
05-H3.02 (dd, 13, 4)
07-H6.27 (d, 2.1)
09-Ha3.60 (m )
11-Ha1.69
11-He1.82
12-Ha2.68 (ddd, 12, 12, 4.5)
12-He2.04
15-Ha2.18
15-Hb2.18
16-Ha2.22*
16-Hb2.45*
17-H3.33 (dd, 8.5, 8.5)
18-Me1.14 (s )
19-Me1.09 (s )
21-Me1.77 (s )
22-H3.75 (br s, w1/2= 4)
23-H4.80 (br d, 9.7)
24-Ha2.45**
24-Hb1.82**
26-Me1.44 (s )
27-Me1.47 (s )
D2O
01-Ha1.4 (t, 13)
01-He1.85
02-Ha3.99 (m, w1/2= 22)
03-He4.07 (m, w1/2= 8)
04-Ha1.75
04-He1.75
05-H2.34 (t )
07-H5.98 (d, 2.5)
09-Ha3.08 (m, w1/2= 22)
11-Ha1.75
11-He1.85
12-Ha1.75
12-He1.95
15-Ha2.05 (m )
15-Hb1.65
16-Ha1.85
16-Hb1.9
17-H2.56 (t )
18-Me0.83 (s )
19-Me1.00 (s )
21-Me1.36 (s )
22-H3.37 (s, w1/2= 3)
23-H4.25 (dd, 9.2, 2.5)
24-Ha1.9
24-Hb1.7
26-Me1.30 (s )
27-Me1.32 (s )

PHYSICAL PROPERTIES

M.P.143-146░C
[α]D22+ 52.3░ (c 0.35 ; MeOH)
IR (KBr) ν max (cm-1) 
UV (MeOH) λ max (log ε)243 (4.097)

CHROMATOGRAPHY

NP-HPLCColumn Zorbax-SIL9.4x250 mm, flow-rate 4 ml.min-1Solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v, Ret 45.2 min (20E 35.2 min). Solvent Cyclohexane-iPrOH-H2O 80:40:3 v/v/v, Ret 17.0 min (20E 13.4 min)
HPTLC 
TLC 
GLC 
RP-HPLCColumn Merck Lichrosorb RP-18, 7 ?m, 10x250 mm, flow-rate 5 ml.min-1 eluted with a gradient from MeOH-H2O 1:4 to pure MeOH in 11 min. Rt 10.5 min (20E 11 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 4.0 x 10-7M

REFERENCES

First isolationGUERRIERO, A. et al. (1986) J. Chem. Soc., Chem. Commun., 40-41 Search more
GeneralHONDA, T. et al. (1993) Tetrahedron Lett. (34), 8275-8278 Search more
GeneralTSUBUKI, M. et al. (1996) Tetrahedron 52, 14515-14532 Search more
GeneralBATHORI, M. et al. (1998) J. Nat. Prod. 61, 415-417 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 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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