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PONASTERONE C

Year of first isolation: 1968
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Podocarpus nakaii [Podocarpaceae] » Images of Podocarpus nakaii Wikipedia: Podocarpus nakaii [Podocarpaceae]
Dacrydium intermedium [Podocarpaceae] » Images of Dacrydium intermedium Wikipedia: Dacrydium intermedium [Podocarpaceae]
Occurence in animals:
 
PONASTERONE C

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C)O)O)O)O
Isomeric SMILES
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C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@@H](C(C)C)O)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,5-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN26191-89-9
PubChem CID15249992
InChiKey
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PXCOYCUFJMMDCP-CEPQAZHYSA-N
InChIInChI=1S/C27H44O8/c1-14(2)17(28)11-21(31)25(5,33)20-7-9-26(34)16-10-22(32)27(35)13-19(30)18(29)12-24(27,4)15(16)6-8-23(20,26)3/h10,14-15,17-21,28-31,33-35H,6-9,11-13H2,1-5H3/t15-,17-,18-,19+,20-,21+,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)(of the 20,22-benzylidene acetal) 584 (3), 379 (23), 362 (17), 206 (15), 143 (64), 135 (14), 134 (100), 125 (23), 107 (34), 105 (42), 91 (53)
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0134.6
0267.8
0369.7
0435.9
0579.7
06200.8
07119.8
08166.8
0938.2
1044.6
1121.3
1231.5
1348.0
1483.9
1532.0
1622.0
1740.8
1817.8
1917.0
2075.8
2121.5
2276.7 *
2335.6
2477.5 *
2534.0
2619.5
2717.0
C5D5N
01-Ha 
01-Hb 
02-Ha 4.12
03-He 4.03
04-Ha 
04-He 
07-H6.17 (d, 2.5) 6.26
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.17 1.19
19-Me1.12 1.13
21-Me1.54 1.57
22-H 
23-Ha 
23-Hb 
24-H 
25-H 
26-Me1.00 (d, 6) 1.02 (d, 6)
27-Me1.00 (d, 6) 1.02 (d, 6)

PHYSICAL PROPERTIES

M.P.270-272 °C
[α]D20 
IR (KBr) ν max (cm-1)3375 (OH), 1668 (cyclohexenone), 1626
UV (EtOH) λ max (log ε)244 (4.04), 326 (2.0)

CHROMATOGRAPHY

HPTLC 
TLCRf 0.23 (CHCl3-EtOH 4:1); Rf 0.38 (CHCl3-EtOH 5:1); Rf 0.65 (CHCl3-EtOH-Me2CO 6:2:1); Rf 0.59 (CHCl3-MeOH-Me2CO 6:2:1); Rf 0.05 (CH2Cl2-EtOH-Me2CO 16:1:4); Rf 0.45 (CH2Cl2-MeOH-C6H6 25:5:3). RP-TLC on paraffin coated silica gel Rf 0.34 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.33 (MeOH-H22O 65:35).
GLCRet 9.0 min (E 6.9 min) on 1.5% OV101 (0.9 m x 4.5 mm i.d.) at 285°C, following silyla-tion at 120°C for 5 h.
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster Kc-H cell assay: EC50 = 2.8 x 10-9M
Calliphora assay: ~100% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationNAKANISHI, K. et al. (1968) Tetrahedron Lett. (9), 1105-1110 Search more
GeneralKOREEDA, M. et al. (1970) Chem. Commun., 351-352 Search more
GeneralHORN, D.H.S. et al. (1971) In: Naturally Occuring Insecticides (eds. Jacobson M. and Crosby D.G) Marcel Dekker, New York, pp. 333-459 Search more
GeneralRUSSEL, G.B. et al. (1972) Aust. J. Chem. 25, 1935-1941 Search more
GeneralBLUNT, J.W. et al. (1979) Aust. J. Chem. 32, 779-782 Search more
BioactivitiesBERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 Search more
BioactivitiesCHERBAS, L. et al. (1980) W. Roux Arch. Devel. Biol. 189, 1-15 Search more
GeneralWILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 Search more
GeneralBIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 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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