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JAPONICONE [= 24-METHYLENESHIDASTERONE]

Year of first report:2010
Formula:C28H42O6
Molecular weight:474
Occurence in plants:
Sagina japonica Ohwi (Caryophyllaceae) [Fungus] » Images of Sagina japonica Ohwi (Caryophyllaceae)
Occurence in animals:
 
JAPONICONE [= 24-METHYLENESHIDASTERONE]

MASS SPECTRUM

FAB-MS m/z (relative intensity %) 473 [M-H] (100), 455 [M-H2O] (10), 361 (20), 318 (18), 125 (15)
EI-MS m/z (relative intensity %) negative
HR-ESI-MS 497.2959 [M+Na]+, calculated 497.2936 for C28H42O6Na

CARBON NMR

PROTON NMR

C5D5N
0138.68 (t)
0268.16 (d)
0368.11 (d)
0432.49 (t)
0551.47 (s)
06203.36 (s)
07121.74 (d)
08165.96 (s)
0934.50 (d)
1038.04 (s)
1121.78 (t)
1231.73 (t)
1347.63 (s)
1484.21 (s)
1532.49 (t)
1621.05 (t)
1751.41 (d)
1817.94 (q)
1924.45 (q)
2075.23 (s)
2121.05 (q)
2281.84 (d)
2334.85 (d)
24157.67 (s)
2581.84 (s)
2628.92 (q)
2727.68 (q)
28103.42 (t)
C5D5N
01-Ha1.92 (m)
01-He2.10 (m)
02-Ha4.17 (br, s)
03-He4.11 (br, d)
04-Ha2.14 (m)
04-He2.67 (m)
05-H3.02 (dd, 2.24, 11.03)
07-H6.25 (br, s)
09-H3.61 (t, 10.24)
11-Ha1.75 (m)
11-He1.91 (m)
12-Ha1.92 (m)
12-He2.08 (m)
14-OH6.36 (s)
15-Ha1.94 (m)
15-Hb2.13 (m)
16-Ha2.10 (m)
16-Hb2.25 (m)
17-H2.92 (t, 7.21)
18-Me1.04 (s)
19-Me1.41 (s)
21-Me1.07 (s)
22-H4.09 (m)
23-Ha2.48 (m)
23-Hb2.64 (m)
26-Me1.38 (s)
27-Me1.32 (s)
28-CH24.81 (s), 4.87 (s)

PHYSICAL PROPERTIES

M.P.231-232 ░C ;
[α]D18+ 75.8 ░ (c 0.13; MeOH)á; different from 24-methyleneshidasterone (isomeric?)
IR (KBr) ν max (cm-1)3427, 2930, 1645 (CO), 1059 (OH), 879 (RCH=CH2)
UV (MeOH) λ max (log ε)224 (1.32) ;

CHROMATOGRAPHY

LCSephadex LH20, RP-18, MCI-gel CHP 20P eluted with MeOH-H2O (45-80%)
HPLC
GLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationJIA, A. et al. (2010) Chem. Nat. Compd. 46, 738-740 Search more

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© UniversitÚ 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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