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ATROTOSTERONE B

Year of first report:1995
Formula:C28H44O7
Molecular weight:492
Occurence in plants:
Paxillus atrotomentosus [Fungi] » Images of Paxillus atrotomentosus Wikipedia: <br />
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Occurence in animals:
 
ATROTOSTERONE B

MASS SPECTRUM

EI-MS m/z (relative intensity %)492 (M)+ (0), 456 (M-2H2O)+ (1), 438 (2), 423 (1), 409 (1), 395 (1), 367 (2), 343 (7), 325 (8), 309 (5), 300 (25), 285 (25), 267 (21), 185 (13), 171 (17), 157 (15), 139 (13), 129 (17), 118 (33), 83 (45), 71 (43), 55 (53), 43 (100)
FAB-MS m/z515 (M+Na)+ (8), 493 (M+H)+ (10), 475 (35), 457 (7), 439 (3), 316 (10), 299 (8), 283 (8), 281 (8), 250 (58), 231 (11), 213 (13), 133 (55), 115 (35), 105 (33), 91 (60), 83 (87), 71 (55), 55 (100)

CARBON NMR

PROTON NMR

CD3OD
0139.09
0268.95
0368.58
0433.30
0552.78
06206.71
07122.71
08165.70
0942.96
1039.89
1169.47
1243.52
13a
1484.69
1531.84
1621.88
1754.26
1818.75
1924.60
2072.80
2124.01
2266.75
2359.93
2443.11
2534.42
2620.85
2719.90
2813.94
CD3OD
01-Ha1.38 (dd, 12.8, 12.0)
01-He2.59 (dd, 12.8, 4.2)
02-Ha4.01 (dt, 12.0, 4.2, 3.3)
03-He3.96 (q )
04-Ha1.78 (dt, 14.0, 13.0, 2.4)
04-He1.69 (ddd (14.0, 4.0, 3.0)
05-H2.34 (dd, 13.0, 4.0)
07-H5.81 (dd, 2.7, 1.0)
09-H3.16 (dd, 9.0, 2.7)
11-Ha4.10 (ddd, 10.7, 9.0, 5.8)
12-Ha2.25 (dd, 12.2, 10.7)
12-He2.14 (dd, 12.2, 5.8)
15-Ha ~1.96 (m )
15-Hb1.62 (m )
16-Ha ~1.96 (m )
16-Hb ~1.96 (m )
17-H2.49 (dd, 9.5, 8.5)
18-Me0.843 (s )
19-Me1.055 (s )
21-Me1.306 (s )
22-H2.85 (d, 2.4)
23-H2.72 (dd, 7.8, 2.4)
24-H1.12 (m )
25-H1.68 (m )
26-Me0.987 (d, 6.8)
27-Me0.962 (d, 6.8)
28-Me0.987 (d, 6.8)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3406 (OH), 1657 (cyclohexenone), 1061 (C-O)
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

NP-HPLCcolumn Silasorb 600 (4 x 250 mm), flow-rate 0.8 ml.min-1, solvent Et2O-CH3CN-H2O (780:190: 30), Ret 17.7 min (20E 31.7 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 56.3 min (20E 42.7 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 6.5 x 10-6M

REFERENCES

First isolationVOKAC, K. et al. (1995) 16th Conference on Isoprenoids, Prague, Abstracts, pp. 77-78 Search more
BioactivitiesHARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 Search more
IdentificationVOKAC, K. et al. (1998) Tetrahedron 54, 1657-1666 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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