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29-NORCYASTERONE

Year of first isolation: 1982
Formula:C28H42O8
Molecular weight:506
Occurence in plants:
Ajuga reptans [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans Wikipedia: <br />
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Occurence in animals:
 
29-NORCYASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1C(COC1=O)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)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]2[C@](C)([C@H](O)C[C@@H]1COC(=O)[C@H]1C)O)O)C)C » JSMol: View in 3D
IUPAC Name(3S,4S)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl]-3-methyloxolan-2-one
CAS-RN 
PubChem CID14693886
InChiKey
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KIUYPOUMVLICAJ-KNKPZWPBSA-N
InChIInChI=1S/C28H42O8/c1-14-15(13-36-24(14)33)9-23(32)27(4,34)22-6-8-28(35)17-10-19(29)18-11-20(30)21(31)12-25(18,2)16(17)5-7-26(22,28)3/h10,14-16,18,20-23,30-32,34-35H,5-9,11-13H2,1-4H3/t14-,15+,16-,18-,20+,21-,22-,23+,25+,26+,27+,28+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z524 (M+NH4)+, 507 (M+H)+, 489, 471, 453, ?, 363, 345, 329, ?
EI-MS m/z (relative intensity %)488 (M-18)+, 363, 345, 327, 309, 187, 169, 143,
HR-MS 

CARBON NMR

PROTON NMR

CDCl3
0138.0 (t )
0268.2 (d )
0368.2 (d )
0432.6 *
0551.5 (d )
06203.9 (s )
07121.9 (d )
08166.2 (s )
0934.6 (d )
1038.8 (s )
1121.6 $
1231.9 *
1348.3 (s )
1484.3 (s )
1531.2 *
1621.7 $
1750.3 (d )
1818.0 (q )
1924.6 (q )
2076.9 (s )
2121.4 $
2276.2 (d )
2334.8 (t )
2440.5 (d )
2543.5 (d )
26181.1 (s )
2714.6 (q )
2873.1 (t )
C5D5N
0137.96
0268.09
0368.02
0432.44
0551.38
06203.43
07121.76
08165.90
0934.39
1038.67
1121.09
1232.02
1348.17
1484.09
1531.83
1621.36
1750.12
1817.89
1924.45
2076.66
2121.24
2275.97
2334.74
2440.67*
2543.31*
26179.78
2714.44
2872.90
CDCl3
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H6.25 (d, 2)
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.20 (s )
19-Me1.04 (s )
21-Me1.55 (s )
22-H 
23-Ha 
23-Hb 
24-H 
25-H 
26-Me?
27-Me1.18 (d, 7)
28-Ha 
28-Hb 
C5D5N
01-Ha 
01-He 
02-Ha4.17 (m, w1/2= 21.0)
03-He4.22 (m, w1/2= 8.5)
04-Ha 
04-He 
05-H3.01 (dd, 12.9, 3.6)
07-H6.27 (d, 2.2)
09-Ha3.60
11-Ha 
11-He 
12-Ha2.63
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.87 (brt, 8.5)
18-Me1.23 (s )
19-Me1.07 (s )
21-Me1.57 (s )
22-H3.89
23-Ha 
23-Hb 
24-H 
25-H2.22 (dq, 10.5, 7.2)
26-Me?
27-Me1.16 (d, 6.9)
28-Ha4.65 (dd, 9.0, 7.8)
28-Hb3.96 (dd, ca. 10.4, 8.8)

PHYSICAL PROPERTIES

M.P.152-155 °C
[α]D20+ 32.4 ° (c 6.25; MeOH)
IR (KBr) ν max (cm-1)1750 (lactone), 1650 (cyclohexenone)
UV (EtOH) λ max (log ε)241 (3.991)

CHROMATOGRAPHY

NP-HPLCcolumn Zorbax-SIL (25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1), solvent cyclohexane-iPrOH-H2O (100:40:3), Ret 21.6 min (20E 19.2 min); solvent CH2Cl2-iPrOH-H2O (125:40:3) Ret 9.2 min (20E 19.5 min).
TLC 
GLC 
RP-HPLCcolumn Spherisorb-5ODS2 (25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1) solvent iPrOH-H2O (7:93), 35°C, Ret 15.8 min (20E 19.8 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.2 x 10-8M

REFERENCES

First isolationCAMPS, F. et al. (1982) Chem. Lett., 1313-1316 Search more
GeneralMORGAN, E.D. et al. (1989) Invertebr. Reprod. Devel. 18, 55-66 Search more
GeneralCALGANO, M.P. et al. (1995) Eur. J. Entomol. 92, 287-294 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more

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