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POLYPORUSTERONE B

Year of first isolation: 1992
Formula:C28H44O6
Molecular weight:476
Occurence in plants:
Polyporus umbellatus [Fungi] » Images of Polyporus umbellatus Wikipedia: Polyporus umbellatus [Fungi]
Occurence in animals:
 
POLYPORUSTERONE B

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(=C)CC(C(C)(C1CCC2(C1(CCC3C2=CC(=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)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC(=C)C(C)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methyl-5-methylideneheptan-2-yl]-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 CID15168041
InChiKey
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OQDKHYZVFZGSRC-DWJOQFFMSA-N
InChIInChI=1S/C28H44O6/c1-15(2)16(3)11-24(32)27(6,33)23-8-10-28(34)18-12-20(29)19-13-21(30)22(31)14-25(19,4)17(18)7-9-26(23,28)5/h12,15,17,19,21-24,30-34H,3,7-11,13-14H2,1-2,4-6H3/t17-,19-,21+,22-,23-,24+,25+,26+,27+,28+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
FD-MS m/z499 [M+Na]+, 477 [M+1]+, 476 [M]+, 363 [M-C7H13O]+, 113 [C7H13O]+, base peak.
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0137.9
0267.8
0367.8
0432.3
0551.2
06202.4
07121.1
08165.3
0934.4
1038.5
1121.1
1221.4
1347.9
1483.7
1531.9
1631.6
1749.7
1817.8
1924.4
2076.5
2121.3
2274.3
2337.1
2436.0
2529.6
2616.1
2715.8
2821.2
C5D5N
01-Ha 
01-Hb 
02-Ha4.18 (br d, 11.2)
03-He4.24 (br s )
04-Ha 
04-He 
05-H 
07-H6.28 (d, 2.5)
09-Ha3.61 (m )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.94 (dd, 9.4, 9.0)
18-Me1.25 (s )
19-Me1.09 (s )
21-Me1.59 (s )
22-H3.93 (br d, 9.5)
23-Ha 
23-Hb 
24-H1.88 (m )
25-H1.45 (septed, 6.2)
26-Me0.88 (d, 6.1)
27-Me0.87 (d, 6.4)
28-Me0.76 (d, 6.8)

PHYSICAL PROPERTIES

M.P.250 °C
[α]D20+ 56.1 ° (c 0.46; EtOH)
IR (KBr) ν max (cm-1)3300 (OH), 1650 (C=O), 803 (C=CH2)
UV (EtOH) λ max (log ε)241 (4.05)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC, Column Inertsil ODS (20x250 mm), 30% THF in water, flow-rate 10 ml.min-1 Ret. 12.3 min

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 2.1 x 10-9M

REFERENCES

First isolationOHSAWA, T. et al. (1992) Chem. Pharm. Bull. 40, 143-147 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

see Important notice
© 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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