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INTEGRISTERONE A 25-ACETATE

Year of first isolation: 1999
Formula:C29H46O9
Molecular weight:538
Occurence in plants:
Silene brahuica [Caryophyllaceae] » Images of Silene brahuica Wikipedia: Silene brahuica [Caryophyllaceae]
Occurence in animals:
 
INTEGRISTERONE A 25-ACETATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)OC(C)(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(C(C(C(C4)O)O)O)C)C)O)O)O
Isomeric SMILES
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[C@@H]1([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](CCC(C)(C)OC(=O)C)O)O)O)C)C)O » JSMol: View in 3D
IUPAC Name[(5R,6R)-5,6-dihydroxy-2-methyl-6-[(1S,2R,3R,5R,9R,10R,13R,14S,17S)-1,2,3,14-tetrahydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-2-yl] acetate
CAS-RN 
PubChem CID21592302
InChiKey
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QMXDANIONYZQEX-NAIDWPAJSA-N
InChIInChI=1S/C29H46O9/c1-15(30)38-25(2,3)10-9-22(33)28(6,36)21-8-12-29(37)17-13-19(31)18-14-20(32)23(34)24(35)27(18,5)16(17)7-11-26(21,29)4/h13,16,18,20-24,32-37H,7-12,14H2,1-6H3/t16-,18-,20+,21-,22+,23+,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)442 (M-CH3COOH - 2H2O)+ (5), 427 (3.5), 424 (3.5), 409 (3.5), 391 (4), 379 (23), 361 (100), 343 (60), 325 (41), 283 (39), 143 (41), 125 (44), 99 (44), 81 (96).
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0177.7
0270.0
0372.2
0433.3
0548.1
06205.5
07123.3
08166.9
0936.6
1045.5
1123.0
1233.6
1347.7
1485.7
1531.2
16 
1751.8
1819.5
1922.0
2078.5
2123.2
2279.1
2331.6
2440.9
2584.0
2627.7
2727.9
OAc172.0, 23.9
C5D5N
01-He4.3.1 (br, s)
02-Ha4.24 (br, s)
03-He4.31 (br, s)
04-Ha 
04-He 
05-H3.30 (m)
07-H6.27 (br, s)
09-Ha3.58 (m)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.96 (t, 9)
18-Me1.22 (s)
19-Me1.41 (s)
21-Me1.59 (s)
22-H3.83 (br, d, 9.8)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.41 (s)*
27-Me1.47 (s)*
O-Ac1.93 (s)

PHYSICAL PROPERTIES

M.P.198-200 °C
[α]D20 
IR (KBr) ν max (cm-1)3400 (OH), 1655 (cyclohexenone), 1730, 1244
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSADIKOV, Z.T. et al. (1999) Khim. Prir. Soedin. 492-493 Search more
GeneralSUKSAMRARN, A. et al. (2002) J. Nat. Prod. 65, 1194-1197 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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