Synthesis of demethylxanthohumol, a new potent apoptosis-inducing agent from hops

Reinhard A. Diller, Herbert M. Riepl, Oliver Rose, Corazon Frias, Günter Henze, Aram Prokop

Research output: Contribution to journalReview articlepeer-review

31 Scopus citations

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 lymophoma cell line) and in primary lymphoblasts of childhood acute lymphoblastic leukemia (ALL).

Original languageEnglish
Pages (from-to)1331-1337
Number of pages7
JournalChemistry and Biodiversity
Volume2
Issue number10
DOIs
StatePublished - 2005

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