Synthesis of feruloyl-myo-insitol derivatives and their inhibitory effects on phorbol ester-induced superoxide generation and Esptein-Barr virus activation.
We prepared 14 feruloyl-myo-inositol derivatives, and evaluated the relationships between their stereostructure and inhibitory activity toward the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced superoxide (O(2)(-)) generation. And further, their suppressive effect on the TPA-induced Epstein-Barr virus (EBV) activation was examined in order to estimate their anti-carcinogenic potentials. Among the derivatives tested, 1,6-O-bis[3-(4'-hydroxy-3'-methoxyphenyl)-2-propenoyl]-myo-inositol (6b) showed an excellent suppressive activity on the O(2)(-) generation at a concentration of 20 microM. For the suppressive effects on the EBV activation, 2,4,6-O-tris[3-(4'-hydroxy-3'-methoxyphenyl)-2-propenoyl]-myo-inositol 1,3,5-orthoformate (9b) showed the highest activity at a concentration of 100 microM among the derivatives tested. These results suggest that the inhibitory potencies of feruloyl-myo-inositol derivatives depend on the stereostructure of molecules rather than the hydrophobicity of molecules.
Hosoda
Asao
A
Industrial Technology Center of Wakayama Prefecture, 60 Ogura, 649-6261, Wakayama, Japan.
Nomura
Eisaku
E
Murakami
Akira
A
Koshimizu
Koichi
K
Ohigashi
Hajime
H
Mizuno
Kazuhiko
K
Taniguchi
Hisaji
H
D002460:Cell Line; D018922:HL-60 Cells; D004854:Herpesvirus 4, Human / Q000187:drug effects* / Q000254:growth & development / Q000502:physiology*; D006801:Humans; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D019255:NADPH Oxidases / Q000378:metabolism; D010703:Phorbol Esters / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000378:metabolism*; D014775:Virus Activation / Q000187:drug effects*
D010703:Phorbol Esters; D013481:Superoxides; D007294:Inositol; D019255:NADPH Oxidases