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AJUGASTERONE C 3-ACETATE

Year of first isolation: 2009
Formula:C29H46O8
Molecular weight:522
Occurence in plants:
Cyanotis longifolia [Commelinaceae] » Images of Cyanotis longifolia Wikipedia: Cyanotis longifolia [Commelinaceae]
Occurence in animals:
 
AJUGASTERONE C 3-ACETATE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)OC(=O)C)C(=O)C=C3[C@@H]2[C@@H](C[C@]4([C@]3(CCC4[C@](C)([C@@H](CCC(C)C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S)-17-((2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl)-2,11,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
FUQCPFMYIHWDOX-JINJHCMASA-N
InChIInChI=1S/C29H46O8/c1-15(2)7-8-24(34)28(6,35)23-9-10-29(36)18-11-19(31)17-12-22(37-16(3)30)20(32)13-26(17,4)25(18)21(33)14-27(23,29)5/h11,15,17,20-25,32-36H,7-10,12-14H2,1-6H3/t17-,20-,21+,22+,23?,24+,25+,26-,27+,28+,29+/m0/s1

MASS SPECTRUM

HR-MS
EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z 523 [MH]+, 505 [MH-H2O]+, 487 [MH-2H2O]+, 469 [MH-3H2O]+, 463 [MH-CH3COOH]+, 451 [MH-4H2O]+, 445 [MH-H2O-CH3COOH]+, 427 [MH-2H2O-CH3COOH]+, 409 [MH-3H2O-CH3COOH]+

CARBON NMR

PROTON NMR

D2O
0140.4
0268.2
0373.3
0433.7
0553.7
06209.7
07123.9
08167.7
0943.7
1040.9
1170.6
1244.0
1349.4
1486.7
1532.6
1622.1
1750.9
1819.8
1925.4
2080.0
2121.6
2279.2
2330.9
2437.9
2529.6
2623.8
2724.5
Ac [CH3] 22.9
Ac [CO]176.4
D2O
01-Ha1.51 (t, 13.3)
01-He2.60 (dd, 12.8, 3.8)
02-Ha4.23 (m, w1/2 = 22)
03-He5.20 (m)
04-Ha1.78*
04-He1.84*
05-H2.32
07-H6.00 (d, 2.3)
09-H3.14 (dd, 8.5, 2.5)
11-Ha4.25 (m)
12-Ha2.06*
12-He2.29*
15-Ha2.05*
15-Hb1.66*
16-Ha1.88*
16-Hb1.81*
17-H2.36 (t, 9.5)
18-Me0.87 (s)
19-Me1.13 (s)
21-Me1.25 (s)
22-H3.44 (d, 9.3)
23-Ha1.28
23-Hb1.61
24-Ha1.28
24-Hb1.38
25-H1.58
26-Me0.90 (d, 6.4)
27-Me0.92 (d, 6.4)
CH3CO2.19 (s)

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

RP-HPLCcolumn YMC C18, 250 mm x 20.2 mm i.d, solvent MeOH/H2O 1:1, flow-rate 10 ml/min, Ret 33.3 min (20E : 12.4 min)
HPLC
NP-HPLCcolumn Zorbax-SIL 250 mm x 4.6 mm i.d., solvent cyclohexane-isopropanol-water, flow-rate 1 mL/min, Ret 7.9 min (20E : 15.8 min)
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationCROUZET, S. et al. (2009) Arch. Insect Biochem. Physiol. 72, 194-209 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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