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25-HYDROXYATROTOSTERONE A

Year of first isolation: 1995
Formula:C28H46O8
Molecular weight:510
Occurence in plants:
Paxillus atrotomentosus [Fungi] » Images of Paxillus atrotomentosus Wikipedia: Paxillus atrotomentosus [Fungi]
Ajuga turkestanica [Lamiaceae (alt. Labiatae)] » Images of Ajuga turkestanica Wikipedia: Ajuga turkestanica [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
25-HYDROXYATROTOSTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC(CC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)O)O)C(C)(C)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]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC(C(C)(C)O)C)O)O)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@H](C(C)(C)O)C)O)O)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@@H](C(C)(C)O)C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID15839570
InChiKey
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FSNRQNKYLJDXMZ-APCZMLFGSA-N
InChIInChI=1S/C28H46O8/c1-14(24(2,3)34)9-22(33)27(6,35)21-7-8-28(36)16-11-17(29)15-10-18(30)19(31)12-25(15,4)23(16)20(32)13-26(21,28)5/h11,14-15,18-23,30-36H,7-10,12-13H2,1-6H3/t14-,15-,18+,19-,20+,21-,22+,23+,25-,26+,27+,28+/m0/s1

MASS SPECTRUM

FAB-MS m/z533 (M+Na)+ (2), 511 (M+H)+ (4), 493 (12), 475 (13), 457 (11), 439 (3), 387 (2), 379 (2), 373 (2), 362 (4), 345 (5), 317 (6), 299 (9), 281 (5), 249 (7), 225 (8), 213 (10), 197 (12), 181 (23), 157 (25), 113 (75), 93 (100), 83 (71), 69 (70), 57 (95)
HRESI-MS533.30800 [M+Na], expected 533.30849 for C28H46O8Na
ESI-MS m/z511 [M+H], 493 [MH-H2O], 475 [MH-2H2O], 457 [MH-3H2O], 439 [MH-4H2O]

CARBON NMR

PROTON NMR

CD3OD
0139.07
0268.94
0368.56
0433.28
0552.78
06206.72
07122.78
08165.70
0942.93
1039.90
1169.50
1243.75
13a
1484.95
1531.83
1621.61
1750.20
1818.85
1924.60
2077.96
2120.66
2277.88
2335.12
2444.42
2574.07
2628.19
2725.86
2816.89
D2O
0139.1
0269.3
0369.3
0433.7
0553.4
06210.4
07123.9
08167.6
0943.4
1040.7
1170.3
1243.9
1349.4
1486.6
1532.4
1622.0
1750.8
1819.7
1925.3
2080.2
2121.5
2276.1
2335.2
2442.0
2576.4
2627.3
2727.7
2815.1
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, 3.5)
03-He3.96 (q )
04-Ha1.78 (dt, 14.0, 13.2, 2.5)
04-He1.68 (dt, 14.0, 4.0, 2.5)
05-H2.34 (dd, 13.2, 4.0)
07-H5.80 (dd, 2.7, 0.8)
09-H3.14 (dd, 8.8, 2.7)
11-Ha4.10 (ddd, 10.5, 8.8, 6.0)
12-Ha2.21 (dd, 12.2, 10.5)
12-He2.15 (dd, 12.2, 6.0)
15-Ha1.95
15-Hb1.57
16-Ha2.00
16-Hb1.79
17-H2.42 (dd, 9.6, 8.6)
18-Me0.874 (s )
19-Me1.056 (s )
21-Me1.195 (s )
22-H3.47 (dd, 9.4, 2.0)
23-Ha1.86 (ddd, 14.4, 4.2, 2.0)
23-Hb1.05
24-H1.65 (dp, 4.2, 7.0, 7.0, 7.0, 7.0)
26-Me1.142 (s )
27-Me1.211 (s )
28-Me1.034 (d, 7.0)
D2O
01-Ha1.39 (t, 13)
01-He2.48 (dd, 13, 3.7)
02-Ha4.09 (m, w1/2 =11)
03-He4.09 (m, w1/2 =11)
04-Ha1.74
04-He1.79
05-H2.31
07-H5.98 (d, 2.6)
09-Ha3.13 (dd, 8.8, 3.6)
11-Ha4.23 (m, w1/2 =27, ddd, 10.8, 9, 6.1)
12-Ha2.05
12-He2.28 (dd, 12.7, 6)
15-Ha2.06
15-Hb1.65
16-Ha1.90*
16-Hb1.84*
17-H2.32 (m)
18-Me0.87 (s)
19-Me1.09 (s)
20-H 
21-Me1.26 (s)
22-H3.55 (d, 11)
23-Ha1.25
23-Hb1.52
24-Ha1.73
26-Me1.18 (s)
27-Me1.20 (s)
28-Me0.96 (d, 6.8)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3404 (OH), 1657 (cyclohexenone), 1054, 1072 (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 50.5 min (20E 31.7 min)
HPTLC 
TLC 
GLC 
HPLCRP-HPLC : column 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 41.1 min (20E 42.7 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.0 x 10-5M

REFERENCES

First isolationVOKÁČ, K. et al. (1995) 16th Conference on Isoprenoids, Prague, Abstracts, pp. 77-78 Search more
BioactivitiesHARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 Search more
IdentificationVOKÁČ, K. et al. (1998) Tetrahedron 54, 1657-1666 Search more
GeneralGUIBOUT, L. et al. (2015) Phytochemical Analysis 26, 293-300 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
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