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REPTANSTERONE

Year of first isolation: 1996
Formula:C29H44O8
Molecular weight:520
Occurence in plants:
Ajuga reptans [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans Wikipedia: Ajuga reptans [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
REPTANSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
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]2[C@](C)([C@H](O)C[C@@H]1CCOC(=O)C1C)O)O)C)C » JSMol: View in 3D
IUPAC Name 
CAS-RN 
PubChem CID 
InChiKey
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RIEJYAPWEYTGAC-NFVVRSECSA-N
InChIInChI=1S/C29H44O8/c1-15-16(7-10-37-25(15)34)11-24(33)28(4,35)23-6-9-29(36)18-12-20(30)19-13-21(31)22(32)14-26(19,2)17(18)5-8-27(23,29)3/h12,15-17,19,21-24,31-33,35-36H,5-11,13-14H2,1-4H3/t15?,16-,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/zMS (Thermospray) m/z (relative intensity %)
EI-MS m/z (relative intensity %) 
MS (thermospray) m/z (relat. intensity %)521 (M+H)+ (38), 503 (M+H-H2O)+ (100)
MS (thermospray) m/z (negative ions)565 M+HCOO)- (100), 547 M+HCOO-H2O) (55)

CARBON NMR

PROTON NMR

C5D5N
0137.9
0268.1
0368.0
0432.4
0551.4
06203.5
07121.6
08166.0
0934.4
1038.6
1121.0
1232.0
1348.1
1484.0
1531.6
1621.3
1749.8
1817.8
1924.4
2076.8
2121.1
2275.7
2336.9
2437.8
2541.2
26174.8
2716.5
2829.6
2967.2
C5D5N
01-Ha2.13
01-He1.93
02-Ha4.19
03-He4.25
04-Ha2.05
04-He1.81
05-H3.03 (m, w1/2=23)
07-H6.27 (d, 2.1)
09-H3.60 (m, w1/2=22)
11-Ha1.89
11-He1.74
12-Ha2.61
12-He2.04
15-Ha 
15-Hb 
16-Ha2.40 (m)
16-Hb1.98
17-H2.86 (t, 9.1)
18-Me1.22 (s)
19-Me1.06 (s)
21-Me1.56
22-H3.89 (m, w1/2=18)
23-Ha1.88
23-Hb1.57
24-H1.94
25-H2.56
27-Me1.39 (d, 6.9)
28-Ha2.04
28-Hb1.82
29-Ha4.26
29-Hb4.14

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3416 (OH), 1718 (delta-lactone), 1654 (cyclohexenone)
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLCsilicagel, successive elution with AcOEt:MeOH 100:8 and 8:1.2
GLC 
HPLCRP-HPLC, column Tracer 15x1 cm packed with Spherisorb-ODS2 5?m, solvent iPrOH-H2O (10:90), flow-rate 3 mL.min-1, 35°C, Ret 25.21 min.

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationCALGANO, M.P. et al. (1996) Tetrahedron 52, 10137-10146 Search more

see Important notice
© 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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