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SENGOSTERONE

Year of first isolation: 1970
Formula:C29H44O9
Molecular weight:536
Occurence in plants:
Cyathula capitata [Amaranthaceae] » Images of Cyathula capitata Wikipedia: <br />
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Ajuga reptans [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans Wikipedia: <br />
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Occurence in animals:
 
SENGOSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1C(C(OC1=O)C)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)C)O)O)O
Isomeric SMILES
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C1[C@]2([C@@](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](O)C[C@@H]1[C@H](OC(=O)[C@H]1C)C)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]butyl]-3,5-dimethyloxolan-2-one
CAS-RN 
PubChem CID12442769
InChiKey
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YQCOGGGDJXBMBU-JIVHLSMOSA-N
InChIInChI=1S/C29H44O9/c1-14-16(15(2)38-24(14)34)10-22(32)27(5,35)21-7-9-28(36)18-11-23(33)29(37)13-20(31)19(30)12-26(29,4)17(18)6-8-25(21,28)3/h11,14-17,19-22,30-32,35-37H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19-,20+,21-,22+,25+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)518 (M-18)+ (4), 500 (10), 482 (4), 464 (2), 446 (1), 379 (2), 361 (14), 343 (24), 325 (17), 316 (9), 201 (M - 335) (5), 183 (8), 157 (M - 379) (18), 113 (13), 43 (100)
MS (thermospray) m/z (relat. intensity %)(MeOH:1M aq. HCO2NH4 3:7) 537 (M+H)+ (100), 536 (M)+ (80)

CARBON NMR

PROTON NMR

CDCl3/CD3OD
0134.5
0266.8
0368.4
0433.2
0578.4
06200.9
07118.6
08166.4
0937.3
1043.7
1143.7
1219.9
1330.8
1483.3
1530.8
1620.9
1748.5
1815.8
1916.7
2076.1
2119.3
2273.0
2332.8
2447.8
2542.0
26180.1
2714.9
2880.3
2918.7
C5D5N
01-Ha 
01-Hb 
02-Ha5.27
03-He4.10
04-Ha 
04-He 
07-H6.20 (d, 2)
09-Ha3.58 (ddd )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.21
19-Me1.13
21-Me1.56
22-H4.99 (dd )
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me--
27-Me1.36 (d, 7)
28-CH(Me)-4.11 (dq 7,6)
29-Me1.34 (d, 6)
CDCl3 (tri-OAc)
01-Ha 
01-Hb 
02-Ha 
03-He5.22
04-Ha 
04-He 
07-H5.95 (d 2)
09-Ha3.21 (ddd 2.8,10)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.85 (s )
19-Me0.93 (s )
21-Me1.25 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me 
27-Me1.28 (d )
28-CH(Me)- 
29-Me1.41 (d )

PHYSICAL PROPERTIES

M.P.159-161 °C
[α]D20+ 39.6° (c 0.69, pyridine)
IR (KBr) ν max (cm-1)3425 (OH), 1748 (?-lactone), 1670 (cyclohexenone)
UV (EtOH) λ max (log ε)241 (4.01)

CHROMATOGRAPHY

HPTLC 
TLCRf 0.15 (AcOEt-MeOH 10:1) (20E : 0.13); Rf 0.31 (CHCl3-MeOH 5:1) (20E 0.16)
GLC 
HPLCRP-HPLC, Column Spherisorb 5ODS2, 125x10 mm, flow-rate 3 ml.min-1, solvent iPrOH-H2O 9:91, 50°C.

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 9.0 x 10-8M
Sarcophaga assay: active

REFERENCES

First isolationHIKINO, H. et al. (1969) Tetrahedron Lett. (18), 1417-1420 Search more
GeneralHIKINO, H. et al. (1970) Tetrahedron 26, 887-898 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
GeneralCALGANO, M.P. et al. (1995) An. Quim. 90, 483-486 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more

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© Institut National de la Recherche Agronomique, Versailles, France
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