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3-EPI-POSTSTERONE

Year of first isolation: 1992
Formula:C21H30O5
Molecular weight:362
Occurence in plants:
Serratula tinctoria [Asteraceae] » Images of Serratula tinctoria Wikipedia: Serratula tinctoria [Asteraceae]
Occurence in animals:
 
3-EPI-POSTSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2C(=O)C)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3S,5R,9R,10R,13R,14S,17S)-17-acetyl-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101642414
InChiKey
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VNLQNGYIXVTQRR-YJXCLCGISA-N
InChIInChI=1S/C21H30O5/c1-11(22)12-5-7-21(26)14-8-16(23)15-9-17(24)18(25)10-19(15,2)13(14)4-6-20(12,21)3/h8,12-13,15,17-18,24-26H,4-7,9-10H2,1-3H3/t12-,13+,15+,17+,18+,19-,20-,21-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/z380 (M+H+NH3)+, 363 (M+H)+, 345, 327
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
CD3OD
01-Ha1.10 (dd, 12,14)
01-Hb2.1
02-Ha3.65 (ddd, 4.5,11,12)
03-Ha3.40 (ddd, 6,9,11)
04-Ha1.53
04-He1.78
05-H2.18
07-H5.83 (d, 2.8)
09-Ha3.23 (ddd, 2.8,7,11)
11-Ha1.73
11-He1.92
12-Ha2.08
12-He1.65
15-Ha1.97
15-Hb1.67
16-Ha2.23
16-Hb1.9
17-H3.38 (dd, 8.5,9)
18-Me0.63 (s )
19-Me0.96 (s )
21-Me2.16 (s )

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
NP-HPLCRet 12.1 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, poststerone 13.7 min)
RP-HPLCRet 9.9 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, poststerone 9.2 min).

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationRUDEL, D. et al. (1992) Planta Med. 58, 358-364 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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