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STACHYSTERONE C

Year of first report:1970
Formula:C27H42O6
Molecular weight:462
Occurence in plants:
Stachyurus praecox [Stachyuraceae] » Images of Stachyurus praecox Wikipedia: <br />
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Occurence in animals:
 
STACHYSTERONE C

MASS SPECTRUM

FAB-MS (relative intensity %)463 [M+H]+ (54), 445 (29 463 [M+H]+ (54), 445 (29), 427 (6).
CI-MS (NH3) m/z480 (MH + NH3)+, 463 (MH)+, 445, 429, 427, 380 (M-C22-C27 + NH3)+, 363, 347, 345
EI-MS m/z (relative intensity %)462 (M)+, 444 (M-18), 363 (25), 345 (74), 327 (25), 99 (C22-C27; 9), 81 (23), 69 (C23-C27; 49), 43 (100).
HR-MS444.2863 (M-18), calculated 444.2874

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 
C5D5N
01-Ha 
01-Hb 
02-Ha4.17 (m)
03-He4.24 (br s)
04-Ha 
04-He 
05-H3.02 (dd 13.2, 3.5)
07-H6.25 (d 2.1)
09-Ha3.60 (m)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.95 (t 9.3)
18-Me1.21 (s)
19-Me1.07 (s)
21-Me1.59 (s)
22-H3.89 (dd 9.7, 1.5)
23-Ha 
23-Hb 
24-H5.55 (br t 7)
26-Me1.59 (s)
27-Me1.63 (s)

PHYSICAL PROPERTIES

M.P.225-227 ░C
[α]D20+ 43 ░ (c ; dioxane)
IR (KBr) ν max (cm-1)3414, 2926, 1647, 1445, 1382, 1116, 1056, 875
UV (EtOH) λ max (log ε)242 (4.02)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.4 x 10-8M
Sarcophaga assay: highly active
Drosophila melanogaster BII cell assay: EC50 = 7.5 x 10-9M

REFERENCES

First isolationIMAI, S. et al. (1970) J. Chem. Soc., Chem. Commun. 352-353 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
GeneralPIS, J. et al. (1995) Steroids 60, 188-194 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more
BioactivitiesDINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 Search more
SynthesisYINGYONGNARONGKUL, B.-E. et al. (2005) Steroids 70, 636-644 Search more

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© UniversitÚ 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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