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JAPONICONE [= 24-METHYLENESHIDASTERONE]

Year of first isolation: 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]

STRUCTURE DESCRIPTORS

Canonical SMILESCC1(C(=C)CC(O1)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C
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)(C1OC(C(=C)C1)(C)C)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(1R)-1-[(2R)-5,5-dimethyl-4-methylideneoxolan-2-yl]-1-hydroxyethyl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101431681
InChiKey
[ ChemIDPlus: search ]
IPJLOFDOKBDRGY-IJYGRGDZSA-N
InChIInChI=1S/C28H42O6/c1-15-11-23(34-24(15,2)3)27(6,32)22-8-10-28(33)17-12-19(29)18-13-20(30)21(31)14-25(18,4)16(17)7-9-26(22,28)5/h12,16,18,20-23,30-33H,1,7-11,13-14H2,2-6H3/t16-,18-,20+,21-,22-,23+,25+,26+,27+,28+/m0/s1

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) ; 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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