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7,8-DIHYDROPONASTERONE A

Year of first isolation: 2007
Formula:C27H46O6
Molecular weight:466
Occurence in plants:
Taxus cuspidata [Taxaceae] » Images of Taxus cuspidata Wikipedia: Taxus cuspidata [Taxaceae]
Occurence in animals:
 
7,8-DIHYDROPONASTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CCC3C2CC(=O)C4C3(CC(C(C4)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)CC1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,8R,9S,10R,13R,14R,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101187643
InChiKey
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XKRVOXLOQKYJKV-ORCMZSNMSA-N
InChIInChI=1S/C27H46O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h15-18,20-23,29-33H,6-14H2,1-5H3/t16-,17+,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z
HR-FABMS m/z489.3193 [M+Na]+, calc. for C27H46O6Na 489.3192, 505.2921 [M+K]+, calc for C27H46O6K 505.2931

CARBON NMR

PROTON NMR

CDCl3
0137.2
0267.1
0367.8
0431.9
0553.3
06215.1
0737.0
0839.1
0932.8
1040.0
1120.2
1232.2
1347.8
1484.7
1532.3
1620.4
1749.3
1817.4
1922.9
2076.9
2120.3
2276.6
2329.3
2436.3
2527.9
2622.9
2722.5
CDCl3
01-Ha1.38 (m)
01-He1.81 (m)
02-Ha3.82 (dt, 12.3, 3.8)
03-He4.04 (ddd, 2.9)
04-Ha1.99 (m)
04-He1.84 (m)
05-H2.42 (dd, 13.5, 3.9)
07-Ha2.55 (dd, 14.3, 12.0)
07-He2.06 (dd, 14.3, 3.6)
08-H2.14 (m)
09-H2.18 (m)
11-Ha1.46 (m)
11-He1.79 (m)
12-Ha1.84 (m)
12-He1.60 (m)
15-Ha1.35 (m)
15-Hb1.84 (m)
16-Ha1.65 (m)
16-Hb1.99 (m)
17-H2.21 (t, 9.3)
18-Me1.00 (s)
19-Me0.91 (s)
21-Me1.18 (s)
22-H3.38 (br, d, 8.6)
23-Ha1.46 (m)
23-Hb1.22 (m)
24-Ha1.44 (m)
24-Hb1.21 (m)
25-H1.54 (m)
26-Me0.91 (d, 6.4)
27-Me0.90 (d, 6.4)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D22+ 76 ° (c 0.20; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)() ;

CHROMATOGRAPHY

HPLC
HPTLC
TLCRf 0.40 (EtOAc-EtOH 100:6)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSHI, Q.-W. et al. (2007) J. Nat. Prod. 71, 1294-1296 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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