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PAXILLOSTERONE 20,22-p-HYDROXYBENZYLIDENE ACETAL

Year of first isolation: 1995
Formula:C35H50O9
Molecular weight:614
Occurence in plants:
Paxillus atrotomentosus [Fungi] » Images of Paxillus atrotomentosus Wikipedia: Paxillus atrotomentosus [Fungi]
Occurence in animals:
 
PAXILLOSTERONE 20,22-p-HYDROXYBENZYLIDENE ACETAL

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(C)(CC1C(OC(O1)C2=CC=C(C=C2)O)(C)C3CCC4(C3(CC(C5C4=CC(=O)C6C5(CC(C(C6)O)O)C)O)C)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1C2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@@]1([C@@H](C[C@@](C(C)C)(C)O)OC(O1)c1ccc(cc1)O)C)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-17-[(4R,5R)-5-(2-hydroxy-2,3-dimethylbutyl)-2-(4-hydroxyphenyl)-4-methyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID15839568
InChiKey
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CCUHDLIIVDDRTB-LAPRSRFCSA-N
InChIInChI=1S/C35H50O9/c1-18(2)33(5,41)17-28-34(6,44-30(43-28)19-7-9-20(36)10-8-19)27-11-12-35(42)22-14-23(37)21-13-24(38)25(39)15-31(21,3)29(22)26(40)16-32(27,35)4/h7-10,14,18,21,24-30,36,38-42H,11-13,15-17H2,1-6H3/t21-,24+,25-,26+,27-,28+,29+,30?,31-,32+,33?,34+,35+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)(M)+ (0), 456 (1), 438 (3), 423 (2), 420 (1), 413 (3), 404 (2), 395 (3), 354 (7), 342 (10), 337 (6), 326 (14), 299 (21), 281 (10), 157 (26), 139 (19), 121 (96), 107 (30), 87 (70), 69 (68), 55 (68), 43 (100)
FAB-MS m/z (relative intensity %)637 (M+Na)+ (3), 615 (M+H)+ (2), 597 (2), 475 (7), 457 (5), 439 (3), 422 (8), 400 (20), 391 (4), 383 (2), 355 (4), 345 (2), 327 (3), 312 (6), 299 (4), 284 (4), 263 (7), 250 (7), 188 (17), 121 (39), 109 (61), 92 (36), 83 (42), 69 (72), 55 (100)
HR-MS(M+H)+, found 615.7342, calc. 615.7439

CARBON NMR

PROTON NMR

CD3OD
0139.09
0268.96
0368.58
0433.31
0552.79
06206.71
07122.89
08165.32
0942.92
1039.88
1169.44
1243.43
13a
1485.04
1531.84
1622.67
1750.72
1818.54
1924.62
2085.73
2123.52
2281.30
2339.38
2475.23
2539.55
2618.17
2717.52
2822.13
C6H4-OH131.22, 129.45 (2), 115.86 (2), 159.39
O-CH-O105.26
CD3OD
01-Ha1.38 (dd, 13.0, 12.0)
01-He2.59 (dd, 13.0, 4.2)
02-Ha4.01 (ddd, 12.0, 4.2, 3.3)
03-He3.95 (q )
04-Ha1.79 (dt, 14.2, 13.2, 2.5)
04-He1.69 (dt, 14.2, 4.0, 3.5)
05-H2.34 (dd, 13.2, 4.0)
07-H5.82 (dd, 2.7, 0.8)
09-H3.15 (dd, 9.0, 2.7)
11-He4.10 (ddd,10.8, 9.0, 6.0)
12-Ha2.22 (dd, 12.2, 10.8)
12-He2.14 (dd, 12.2, 6.0)
15-Ha~ 2.05
15-Hb1.63 (m )
16-Ha~ 2.05
16-Hb~ 2.05
17-H2.42 (dd, 9.0, 8.5)
18-Me0.871 (s )
19-Me1.051 (s )
21-Me1.280 (s )
22-H4.18 (d, 9.4)
23-Ha1.80 (dd, 14.8, 9.4)
23-Hb1.56 (bd, 14.8)
25-H1.74 (h, 6.8)
26-Me0.968 (d, 6.8)
27-Me0.934 (d, 6.8)
28-Me1.135 (s )
C6H4-OH6.77 (m ), 7.29 (m )
O-CH-O5.73 (s )

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3409 (OH), 1657 (cyclohexenone), 1617, 1518 (C=C), 1102 (C-O
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

NP-HPLCcolumn Silasorb 600 (4 x 250 mm), flow-rate 0.8 ml.min-1, solvent Et2O-CH3CN-H2O (780:190: 30), Ret 20.3 min (20E 31.7 min)
HPTLC 
TLC 
GLC 
RP-HPLCcolumn Separon SIX C18 (4 x 250 mm), solvent MeOH-H2O, linear gradient 10 to 70 % MeOH in 50 min, flow-rate 0.6 ml.min-1, Ret 57.2 min (20E 42.7 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 3.0 x 10-7M

REFERENCES

BioactivitiesHARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 Search more
First isolationVOKÁČ, K. et al. (1998) Phytochemistry 49, 2109-2114 Search more
GeneralVOKÁČ, K. et al. (1998) Tetrahedron 54, 1657-1666 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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