Daphneolone

Two new compounds with cytotoxic activity on the human melanoma A375-S2 cells from Daphne giraldii callus cells.[Pubmed:23106433]

J Asian Nat Prod Res. 2012;14(11):1020-6.

Four compounds were isolated from Daphne giraldii callus cells, and their structures were characterized as daphnenone (1), daphnolon (2), R-( - )-1-(4'-hydroxyphenyl)-3-hydroxy-5-phenyl-1,5-pentandione (3), and S-(+)-Daphneolone-4'-O-beta-d-glucoside (4) on the basis of MS, NMR spectrographic analysis, and chemical methods. All of the four compounds possessed C6-C5-C6 carbon skeleton, and among them, 3 and 4 were two new compounds. In activity screening test, compounds 1, 2, 3, and 4 showed different degrees of cytotoxic activity against the tumor cells of human melanoma A375-S2 by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium hydrobromide method, with IC(50) values of 29.8, 51.0, 41.0, and 150.0 muM, respectively. Furthermore, we found the important target which could explain the cytotoxic mechanism of the four compounds by using autodock 4.0, a structure-guided discovery approach, and the important residues CYS532, GLY534, and SER535 of B-Raf kinase have been discovered.

Lead optimization and insecticidal activity of analogues of daphneolone isolated from Stellera chamaejasme L.[Pubmed:17575567]

Pest Manag Sci. 2007 Sep;63(9):928-34.

Starting from the chemical structure of the botanical aphicides 1,5-diphenyl-1-pentanone and 1,5-diphenyl-2-penten-1-one, extracted from Stellera chamaejasme L., the authors designed and synthesized a series of novel compounds following the concept of bioisosterism. Their structures were established on the basis of (1)H NMR and GC-MS spectra, and the insecticidal activities of the compounds were evaluated against Aphis gossypii Glover. The results demonstrated that the substitution of a heterocycle for the phenyl ring was favourable. Thus, further modification of compound 2n, containing a furan ring, which showed excellent activity (LC(50) = 0.85 g L(-1)), is of some promise.