Synthesis of Demethylxanthohumol, a New Potent Apoptosis-Inducing Agent from Hops

Abstract

Starting from commercially available phloracetophenone (= 1-(2,4,6-trihydroxyphenyl)ethanone), we synthesized demethylxanthohumol (4), a derivative of xanthohumol, devoid of 6'-O-methyl group. Both are prenylchalcones derived from hops (Humulus lupulus). The synthesis was accomplished by an aldol condensation between MOM-protected acetophenone 2 and MOM-protected benzaldehyde 3. The resulting demethylxanthohumol (4) displayed antiproliferative properties. Demethylxanthohumol (4) induced also apoptosis via the mitochondrial pathway in BJAB cells (Burkitt lymphoma cell line) and in primary lymphoblasts of childhood acute lymphoblastic leukemia (ALL).

Synthesis and DNA-binding properties of apoptosis-inducing cytotoxic half-sandwich rhodium(III) complexes with methyl-substituted polypyridyl ligands

“…The complex 8, which is inactive towards MCF-7 and HT-29 cells, was studied for comparison purposes. Necrotic cell death is characterized by an early release of lactate dehydrogenase (LDH), whereas apoptotic cells retain their membrane integrity and do not exhibit an early release of large intracellular proteins including LDH [37]. No significant LDH release was observed for non-adherent BJAB lymphoma cells (Burkitt-like lymphoma) following 3 h incubation periods with complexes 1 (Fig.…”

Structure–activity relationships and DNA binding properties of apoptosis inducing cytotoxic rhodium(III) polypyridyl complexes containing the cyclic thioether [9]aneS3

“…Cytotoxicity of 3 and 7 towards BJAB cells was measured by release of lactate dehydrogenase (LDH) as described previously [40]. After incubation with different concentrations of the complexes for 1 h or 3 h at 37°C, LDH released by BJAB cells was measured in the cell culture supernatants using the Cytotoxicity Detection Kit from Boehringer Mannheim Ò (Mannheim, Germany).…”

Synthesis of Four Natural Prenylflavonoids and Their Estrogen‐like Activities

“…Bavachin 1 and isobavachin 2 were synthesized using 2,4-dihydroxyacetophenone 5a as the starting material, which was prenylated with 3,3-dimethylallyl bromide, to furnish 6a and 6b, according to the reported method [13]. Compound 6c was achieved by treating 2,4,6-trihydroxyacetophenone 5c with 3,3-dimethylallyl bromide, according to the approach in the literature [22]. Selective methoxymethylation of 6a, 6b, and 6c with chloromethoxylmethyl ether and anhydrous K 2 CO 3 in dry acetone gave compounds 7a, 7b, and 7c, respectively.…”