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PTEROSTERONE

Year of first isolation: 1967
Formula:C27H44O7
Molecular weight:480
Occurence in plants:
Lastrea thelypteris [fern] » Images of Lastrea thelypteris Wikipedia: <br />
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Onoclea sensibilis [fern] » Images of Onoclea sensibilis Wikipedia: <br />
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Pfaffia iresinoides [Amaranthaceae] » Images of Pfaffia iresinoides Wikipedia: <br />
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Pfaffia paniculata [Amaranthaceae] » Images of Pfaffia paniculata Wikipedia: <br />
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Polypodium vulgare [fern] » Images of Polypodium vulgare Wikipedia: <br />
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Occurence in animals:
 
PTEROSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
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)([C@H](O)C[C@@H](C(C)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,5-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN18089-44-6
PubChem CID441836
InChiKey
[ ChemIDPlus: search ]
UMMBJCYNGLCGEF-OAUIFJKNSA-N
InChIInChI=1S/C27H44O7/c1-14(2)18(28)12-23(32)26(5,33)22-7-9-27(34)16-10-19(29)17-11-20(30)21(31)13-24(17,3)15(16)6-8-25(22,27)4/h10,14-15,17-18,20-23,28,30-34H,6-9,11-13H2,1-5H3/t15-,17-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)480, 462, 444, 426, 408, 363 (M-117), 345, 328, 117, 99, 81
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0137.7
0268.1
0368.0
0432.4
0551.3
06203.8
07121.6
08166.3
0934.3
1038.6
1121.0
1231.9
1348.0
1484.1
1531.6
1621.4
1749.9
1817.9
1924.4
2076.8
2121.6
2277.4
2335.7
2476.7
2533.8
2617.0
2719.5
C5D5N
01-Ha 
01-Hb 
02-Ha4.16 (br dt, 11.8, 3.4)
03-He4.22 (br s )
04-Ha 
04-He 
05-H3.02 (dd, 13.0, 4.3)
07-H6.25 (d, 2.2)
09-Ha3.58 (br t, 9.2)
11-Ha 
11-He 
12-Ha2.60 (dt, 13.0, 5.0)
12-He 
15-Ha 
15-Hb 
16-Ha2.47 (q, 10.4)
16-Hb 
17-H2.94 (t, 9.2)
18-Me1.21 (s ) 1.18*
19-Me1.06 (s ) 1.05*
21-Me1.59 (s ) 1.54*
22-H4.12 (br d, 10.6)
23-Ha 
23-Hb 
24-H3.94 (dt, 9.0, 4.0)
26-Me1.003 (d, 6.6) 1.00*
27-Me1.006 (d, 6.6) 1.00*

PHYSICAL PROPERTIES

M.P.229-230 °C
[α]D20+ 7.4° (c ; MeOH)
IR (KBr) ν max (cm-1)3420 (OH), 1650 (cyclohexenone)
UV (EtOH) λ max (log ε)243 (?)

CHROMATOGRAPHY

HPTLC 
TLCsilicagel plates, Rf 0.54 (CHCl3-MeOH-H2O, 13:7:2)
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-9M
Sarcophaga assay: highly active

REFERENCES

First isolationTAKEMOTO, T. et al. (1967) Chem. Pharm. Bull. 15, 1816 Search more
GeneralTAKEMOTO, T. et al. (1968) Tetrahedron Lett. 375-378 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
GeneralNISHIMOTO, N. et al. (1988) Phytochemistry 27, 1665-1668 Search more
GeneralNISHIMOTO, N. et al. (1988) Phytochemistry 26, 2505-2507 Search more
IdentificationCOLL, J. et al. (1994) Tetrahedron 50, 7247-7252 Search more
BioactivitiesDINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 Search more
GeneralLI, J. et al. (2010) Planta Med. 76(6): 635-639 Search more

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