Synthesis and biological activity of fungal metabolite, 4-hydroxy-3-(3'-methyl-2'-butenyl)-benzoic acid.
4-Hydroxy-3-(3'-methyl-2'-butenyl)-benzoic acid (HMBA) was previously isolated from Curvularia sp. KF119 as a cell-cycle inhibitor. However, the present study used a novel and practical synthetic method to prepare a large quantity of HMBA. The synthetic HMBA was found to inhibit the cell-cycle progression of HeLa cells with a comparable potency to the natural fungal metabolite. The inhibition of the cell-cycle progression by the synthetic HMBA involved both the activation of p21(WAFI) and the inhibition of cyclin Dl expression in the cells. Consequently, this new synthetic procedure provides an easy and convenient way to produce or manipulate the original fungal metabolite.
Kim
Jin Hye
JH
Chemical Genomics Laboratory, Department of Biotechnology, College ofEngineering, Yonsei University, Seoul 120-749, Korea.
Kwon
Ho Jeong
HJ
D001203:Ascomycota / Q000378:metabolism*; D001709:Biotechnology / Q000379:methods*; D002453:Cell Cycle / Q000187:drug effects*; D016193:G1 Phase / Q000187:drug effects; D006367:HeLa Cells / Q000187:drug effects; D006801:Humans; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016196:S Phase / Q000187:drug effects
D062385:Hydroxybenzoates