Pomiferin, histone deacetylase inhibitor isolated from the fruits of Maclura pomifera.

The major constituents from the fruits of Maclura pomifera are the prenylated isoflavones, osajin (1) and pomiferin (2). Their structures were elucidated using NMR spectroscopic techniques and mass spectrometric analysis. Compound 2 showed potential inhibitory activity in histone deacetylase (HDAC) enzyme assay. It also exhibited growth inhibitory activity on five human tumor cell lines and more sensitive inhibitory activity on the HCT-15 colon tumor cell line. Further structure-activity relationships of position 3 on ring B from aromatic ring will be reported in due course.

[1]  Thomas Beckers,et al.  Histone Deacetylase Inhibitors Suppress the Inducibility of Nuclear Factor-κB by Tumor Necrosis Factor-α Receptor-1 Down-regulation , 2006 .

[2]  H. W. Lee,et al.  Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin. , 2000, Cancer research.

[3]  A. Vitali,et al.  Two isoflavones and a flavone from the fruits of Maclura pomifera , 1994 .

[4]  N. Maggiano,et al.  Inhibitory effect of quercetin on primary ovarian and endometrial cancers and synergistic activity with cis‐diamminedichloroplatinum(II) , 1993, Gynecologic oncology.

[5]  Vigushin Dm,et al.  Targeted histone deacetylase inhibition for cancer therapy. , 2004 .

[6]  R A Rifkind,et al.  Suberoylanilide hydroxamic acid, an inhibitor of histone deacetylase, suppresses the growth of prostate cancer cells in vitro and in vivo. , 2000, Cancer research.

[7]  Silvio Massa,et al.  3-(4-Aroyl-1-methyl-1H-2-pyrrolyl)-N-hydroxy-2-alkylamides as a new class of synthetic histone deacetylase inhibitors. 1. Design, synthesis, biological evaluation, and binding mode studies performed through three different docking procedures. , 2003, Journal of medicinal chemistry.

[8]  B. Havsteen,et al.  The biochemistry and medical significance of the flavonoids. , 2002, Pharmacology & therapeutics.

[9]  M. Murakoshi,et al.  Cancer prevention by antioxidants , 2004, BioFactors.

[10]  M. Yoshida,et al.  Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylase. , 1993, The Journal of biological chemistry.

[11]  E. Middleton,et al.  Antiproliferative effects of citrus flavonoids on a human squamous cell carcinoma in vitro. , 1991, Cancer letters.

[12]  I. Kawamura,et al.  FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. III. Antitumor activities on experimental tumors in mice. , 1994, The Journal of antibiotics.

[13]  J. Muselík,et al.  Antioxidative and EROD activities of osajin and pomiferin. , 2004, Fitoterapia.

[14]  Silvio Massa,et al.  Histone deacetylation in epigenetics: An attractive target for anticancer therapy , 2005, Medicinal research reviews.

[15]  R. Dixon,et al.  Prenylated flavonoids from Maclura pomifera , 1998 .

[16]  Vigushin Dm,et al.  Histone deacetylase inhibitors in cancer treatment. , 2002 .

[17]  R. Nijveldt,et al.  Accurate prediction of xanthine oxidase inhibition based on the structure of flavonoids. , 2002, European journal of pharmacology.