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POLYPODINE B

Year of first isolation: 1967
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Polypodium vulgare [Polypodiaceae] » Images of Polypodium vulgare Wikipedia: Polypodium vulgare [Polypodiaceae]
Vitex megapotamica [Lamiaceae (alt. Labiatae)] » Images of Vitex megapotamica Wikipedia: Vitex megapotamica [Lamiaceae (alt. Labiatae)]
Helleborus genus [Ranunculaceae] » Images of Helleborus genus Wikipedia: Helleborus genus [Ranunculaceae]
Pfaffia iresinoides [Amaranthaceae] » Images of Pfaffia iresinoides Wikipedia: Pfaffia iresinoides [Amaranthaceae]
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: Leuzea carthamoides [Asteraceae]
Occurence in animals:
 
POLYPODINE B

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C1(CCC2C(C)(C(CCC(C)(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=C1C2CC[C@]2([C@]1(CC[C@@H]2[C@@]([C@@H](CCC(C)(C)O)O)(C)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)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN18069-14-2
PubChem CID441833
InChiKey
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GMFLGNRCCFYOKL-ACCCYTKYSA-N
InChIInChI=1S/C27H44O8/c1-22(2,32)9-8-20(30)25(5,33)19-7-11-26(34)16-12-21(31)27(35)14-18(29)17(28)13-24(27,4)15(16)6-10-23(19,26)3/h12,15,17-20,28-30,32-35H,6-11,13-14H2,1-5H3/t15-,17-,18+,19-,20+,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

FAB-MS m/zFAB (xenon): 587 (M+glycerol-H)-, 495 (M-H)
CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)478, 460, 442, 424, 361, 360, 344, 343, 99, 81
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0134.9
0268.1
0369.9
0436.1
0579.9
06201.0
07119.9
08167.0
0938.4
1044.8
1122.1
1232.2
1348.2
1484.1
1531.8
1621.4
1750.1
1818.0
1917.3
2076.9
2121.7
2277.7
2327.6
2442.3
2569.7
2630.1
2730.2
CD3OD
0136.2
0270.2
0368.4
0434.2
0580.3
06202.3
07120.6
08167.5
0939.0
1045.4
1122.5
1232.6
1348.6
1485.0
1531.7
1621.4
1750.4
1818.0
1917.0
2077.9
2121.0
2278.4
2327.3
2442.4
2571.3
2629.7
2728.9
C5D5N
01-Ha 
01-Hb 
02-Ha4.26 (br dt, 11.4, 4.0)
03-He4.15 (br s )
04-Ha 
04-He 
07-H6.25 (d , 2.2)
09-Ha3.62 (br t, 8.6)
11-Ha 
11-He 
12-Ha2.54 (dt, 12.6, 4.6)
12-He 
15-Ha 
15-Hb 
16-Ha2.43 (q, 10.2)
16-Hb 
17-H2.96 (t, 9)
18-Me1.19 (s )
19-Me1.13 (s )
21-Me1.57 (s )
22-H3.84 (br d, 9.2)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.35 (s )
27-Me1.35 (s )
CD3OD
01-Ha1.68
01-Hb1.78
02-Ha3.94
03-He3.99
04-Ha1.75
04-He2.08
07-H5.85 (d, 2.5)
09-Ha3.19 (m, w1/2=22)
11-Ha1.7
11-He1.8
12-Ha2.13
12-He1.88
15-Ha2.00
15-Hb1.60
16-Ha2.00
16-Hb1.75
17-H2.39 (m)
18-Me0.89 (s)
19-Me0.92 (s)
21-Me1.20 (s)
22-H3.33 (dd, 11, 2 )
23-Ha1.28
23-Hb1.66
24-Ha1.75-1.8
24-Hb1.45
26-Me1.19 (s)
27-Me1.19 (s)

PHYSICAL PROPERTIES

M.P.254-257°C
[α]D20 
IR (KBr) ν max (cm-1)3340 (OH), 1687 (chelated carbonyl), 1657, 1636
UV (EtOH) λ max (log ε)243 nm (4.11), 317 nm (2.07)

CHROMATOGRAPHY

TLCNP-TLC silica : Rf 0.33 (Me2CO) ; Rf 0.32 (CHCl3-EtOH 4:1) ; Rf 0.22 (CHCl3-EtOH 4:1) ; Rf 0.18 (EtOAc-MeOH-NH4OH 85:10:5) ; Rf 0.19 (CH2Cl2-EtOH 85:15) . RP-TLC on paraffin coated silica gel Rf 0.50 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.47 (MeOH-H2O 65:35)
GLCRet 7.5 min on 1.5% OV101 (0.9 m x 4.5 mm i.d.) at 285°C after silylation at 140°C for 60 h (heptakis-TMS ether) (E : 5.85 min)
RP-HPLC(Spherisorb-5ODS2) ACN-0.1% TFA in H2O (23:77), 1 ml.min-1, Ret. 5.8 min.
NP-HPLC(Zorbax-Sil) CH2Cl2-iPrOH-H2O (125:40:3), 1 ml.min-1, Ret. 11.3 min.

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.0 x 10-9M
Galleria mellonella in vivo assay: ED50 = 7.8 ug/g
Sarcophaga bullata in vivo assay: ED50 = 7.8 ug/g
Dermestes vulpinus in vivo assay: ED50 = 29.0 ug/g
Calliphora assay: 400% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationJIZBA, J. et al. (1967) Tetrahedron Lett. 5139-5143 Search more
IdentificationRIMPLER, H. et al. (1969) Tetrahedron Lett. 329-333 Search more
GeneralHARDMAN, R. et al. (1976) Phytochemistry 15, 1515-1516 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
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
IdentificationNISHIMOTO, N. et al. (1987) Phytochemistry 26, 2505-2507 Search more
GeneralWILSON, I.D. et al. (1988) In: Bioanalysis of Drugs and Metabolites (Eds. E. Reid, J. D. Robinson, I. D. Wilson), Plenum, pp. 313-320 Search more
IdentificationGIRAULT, J.-P. et al. (1988) Phytochemistry 27, 737-741 Search more
BioactivitiesSLÁMA, K. et al. (1993) Insect Biochem. Molec. Biol. 23, 181-185 Search more
IdentificationCOLL, J. et al. (1994) Tetrahedron 50, 7247-7252 Search more
Struct. analysisPIS, J. et al. (1994) Phytochemistry 37, 707-711 Search more
BioactivitiesHARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 Search more

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