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5β-HYDROXYRUBROSTERONE

Year of first report:1992
Formula:C19H26O6
Molecular weight:350
Occurence in plants:
Serratula tinctoria [Asteraceae] » Images of Serratula tinctoria Wikipedia: <br />
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Polypodium vulgare [fern] » Images of Polypodium vulgare Wikipedia: <br />
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Occurence in animals:
 
5β-HYDROXYRUBROSTERONE

MASS SPECTRUM

CI-MS (NH3) m/z368 (M+H+NH3)+, 351, 333, 315, 245
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0134.3
0268.5
0370.3
0436.3
0580.6
06202.2
07121.2
08164.4
0939.8
1045.7
1121.8
1225.2
1354.2
1480.4
1529.2
1634.1
17220.0
1817.7
1917.3
20 
21 
22 
23 
24 
25 
26 
27 
CD3OD
01-Ha1.74
01-Hb1.74
02-Ha3.94 (ddd, 8.7, 8.3, 3.3)
03-He4.00 (q, 3.1)
04-Ha2.07 (dd, 14.8, 3.0)
04-He1.80
05-H 
07-H5.97 (d, 2.8)
09-Ha3.22 (ddd, 11.5, 6.9, 2.8)
11-Ha1.71 (ddd, 11.6, 13.6, 4.9)
11-He1.92 (dddd, 13.6, 6.7, 4.6, 2.1)
12-Ha2.13 (td, 13.2, 4.8)
12-He1.59 (ddd, 13.0, 4.9, 2.0)
15-Ha2.30
15-Hb2.02
16-Ha2.36
16-Hb2.51
17-H 
18-Me0.88 (s)
19-Me0.94 (s)
20-H 
21-Me 
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me 
27-Me 
CD3OD-d4
01-Ha1.6 (dd 3, 13)
01-Hb2.1
02-Ha3.93 (ddd 3, 3, 12)
03-He4.0 (q 3.05)
04-Ha2.08
04-He1.8
05-H 
07-H5.97 (d 2.5)
09-Ha3.2 (m, w 1/2 = 22)
11-Ha1.7
11-He1.9
12-Ha2.1
12-He1.6
15-Ha2.4
15-Hb2.05
16-Ha2.25
16-Hb2.5
17-H 
18-Me0.88 (s)
19-Me0.95 (s)
20-H 
21-Me 
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me 
27-Me 

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

RP-HPLCRet 5.1 min (Column Spherisorb-5ODS2, 25 cm x 4.6 mm i.d., solvent ACN : 1? TFA in H2O 23:77 v/v, flow-rate 1ml.min-1) (20E 5.2 min)
TLC 
GLC 
NP-HPLCRet 16.1 min (Column Zorbax-Sil, 25 cm x 4.6 mm i.d., solvent isoC8-iPrOH-H2O, 100:30:2 v/v/v, flow-rate 1ml.min-1) (20E 22.6 min)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationRUDEL, D. et al. (1992) Planta Med. 58, 358-364 Search more
IdentificationSIMON, A. et al. (2011) Steroids 76, 1419-1424 Search more

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© Université Pierre & Marie Curie, Paris 6, France
© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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