title: 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).
authors.affiliation: Institute of Technology for Biogenic Resources, Technical University of Munich, Petersgasse 18, D-94315 Straubing.
authors.forename: Reinhard A
authors.initials: RA
authors.lastname: Diller
authors.forename: Herbert M
authors.initials: HM
authors.lastname: Riepl
authors.forename: Oliver
authors.initials: O
authors.lastname: Rose
authors.forename: Corazon
authors.initials: C
authors.lastname: Frias
authors.forename: Günter
authors.initials: G
authors.lastname: Henze
authors.forename: Aram
authors.initials: A
authors.lastname: Prokop
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects*; D045744:Cell Line, Tumor; D006801:Humans; D027582:Humulus / Q000737:chemistry*; D015394:Molecular Structure; D011427:Propiophenones / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D011427:Propiophenones; C517884:demethylxanthohumol