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MAKISTERONE C 2,3;20,22-DIACETONIDE

Year of first report:2009
Formula:C35H56O7
Molecular weight:588
Occurence in plants:
Silene viridiflora [Caryophyllaceae] » Images of Silene viridiflora Wikipedia: <br />
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Occurence in animals:
 
MAKISTERONE C 2,3;20,22-DIACETONIDE

MASS SPECTRUM

HR-ESI-MS611.3913, calculated 611.3924 for C35H56O7Na+
ESI-MS m/z (relative intensity %)627 (42) [M+K]+, 612 (41) [M+H+Na]+, 611 (100) [M+Na]+, 588 (6.4) [M]+, 576 (55) [M+H+Na-2H2O]+, 563 (41), 545 (55), 531 (40) [M+H-Me2CO]+, 513 (42) [M+H-H2O-Me2CO]+, 495 (20) [M+H-2H2O-Me2CO]+, 473 (17) [M+H-2Me2CO]+, 455 (24) [M+H-H2O-2Me2CO]+, 437 (25) [M+H-2H2O-2Me2CO]+, 419 (56) [M+H-3H2O-2Me2CO]+, 391 (86), 381 (28), 338 (25), 333 (29)

CARBON NMR

PROTON NMR

CD3OD
0138.9
0273.8
0373.3
0427.8
0552.6
06205.8
07122.0
08167.0
0935.9
1039.0
1121.8
1232.5
1349.0
1485.4
1531.8
1622.7
1750.4
1817.8
1924.2
2086.1
2122.6
2281.5
2330.9
2450.0
2574.4
2626.8
2727.9
2825.3
2914.9
Me2C [2,3]108.1, 27.2, 29.7
Me2C [20,22]109.6, 26.8, 29.0
CD3OD
01-Ha1.23 (t, ~14.5)
01-He1.99 (d, ~15.0)
02-Ha4.27 (dt, 9.4, 5.0)
03-He4.30 (q, 4.0)
04-Ha1.91-2.01 (m)
04-He1.91-2.01 (m)
05-H2.245 (dd, 9.3, 8.2)
07-H5.80 (d, 2.5)
09-H2.935 (ddd, 11.7, 7.0, 2.5)
11-Ha1.65-1.70 (m)
11-He1.74-1.81 (m)
12-Ha2.105 (td, 13.0, 4.9)
12-He1.81-1.89 (m)
15-Ha1.58-1.67 (m)
15-Hb1.96-2.02 (m)
16-Ha1.83-1.90 (m)
16-Hb2.03-2.10 (m)
17-H2.304 (t, 8.9)
18-Me0.825 (s)
19-Me0.96 (s)
21-Me1.173 (s)
22-H3.834 (d, 10.0)
23-Ha1.16-1.25 (m)
23-Hb1.71-1.79 (m)
24-Ha1.45 (ddd, 12.5, 6.6, 3.0)
26-Me1.16 (s)
27-Me1.18 (s)
28-Ha1.18-1.24 (m)
28-Hb1.63-1.72 (m)
29-Me1.006 (t, 7.5)
Me2C [2,3]1.325 (s); 1.39 (s)
Me2C [20,22]1.320 (s); 1.47 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25+65 ° (c 0.005; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)240 (3.4)

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSIMON, A. et al. (2009) Helv. Chim. Acta 92, 753-761 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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