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CASTASTERONE

Year of first isolation: 1982
Formula:C28H48O5
Molecular weight:464
Occurence in plants:
Castanea (chestnut tree) insect galls [Fagaceae] » Images of Castanea (chestnut tree) insect galls Wikipedia: Castanea (chestnut tree) insect galls [Fagaceae]
Occurence in animals:
 
CASTASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(C)C(C(C(C)C1CCC2C1(CCC3C2CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O
Isomeric SMILES
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C1[C@]2([C@H](C[C@@H]([C@@H]1O)O)C(=O)CC1[C@@H]2CC[C@]2(C1CC[C@@H]2[C@H](C)[C@H]([C@@H](C(C(C)C)C)O)O)C)C » JSMol: View in 3D
IUPAC Name(2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-2,3-dihydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
CAS-RN80736-41-0
PubChem CID133534
InChiKey
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VYUIKSFYFRVQLF-YLNAYWRASA-N
InChInChI=1S/C28H48O5/c1-14(2)15(3)25(32)26(33)16(4)18-7-8-19-17-11-22(29)21-12-23(30)24(31)13-28(21,6)20(17)9-10-27(18,19)5/h14-21,23-26,30-33H,7-13H2,1-6H3/t15-,16-,17-,18+,19-,20-,21+,23-,24+,25+,26+,27+,28+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)403 (0.4), 385 (0.3), 393 (3), 375 (2), 357 (2), 364 (100), 363 (35), 362 (36), 346 (42), 345 (59), 327 (36), 315 (7), 305 (5), 287 (17), 269 (10), 263 (11), 245 (13), 227 (5), 155 (5).
HR-MS 
FAB-MS m/z465 (M+1)+, 447 (M+1-18), 429, 393, 364

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
28 
CDCl3
01-Ha 
01-Hb 
02-H3.77 (br, w1/2=23)
03-H4.06 (br, w1/2= 8)
04-Ha 
04-He 
05-H2.69 (dd, 13, 4)
07-Ha 
07-Hb 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.69 (s )
19-Me0.76 (s )
22-H3.56 (d, 9)*
23-H3.72 (d, 9)*
24-Ha 
24-Hb 
25-H 
Me'0.85 (d )
Me''0.91 (d )
Me'''0.95 (d )
Me''''0.97 (d )

PHYSICAL PROPERTIES

M.P.259-261°C
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC on silicaRf 0.38 (CHCl3-EtOH 6:1)
GLCGLC-MS of bismethane-boronate
HPLCNP-HPLC, Partisil 5 (CHCl3-iPrOH, gradient); RP-HPLC, Develosil ODS-3 (ACN-H2O 1:1)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = >10-3M

REFERENCES

First isolationYOKOTA, T. et al. (1982) Tetrahedron Lett., 1275-1278 Search more
GeneralSUZUKI, Y. et al. (1985) Agric. Biol. Chem. 49, 49-54 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 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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