TY - JOUR
T1 - Synthesis of demethylxanthohumol, a new potent apoptosis-inducing agent from hops
AU - Diller, Reinhard A.
AU - Riepl, Herbert M.
AU - Rose, Oliver
AU - Frias, Corazon
AU - Henze, Günter
AU - Prokop, Aram
PY - 2005
Y1 - 2005
N2 - 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).
AB - 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).
UR - http://www.scopus.com/inward/record.url?scp=27844508089&partnerID=8YFLogxK
U2 - 10.1002/cbdv.200590105
DO - 10.1002/cbdv.200590105
M3 - Review article
C2 - 17191934
AN - SCOPUS:27844508089
SN - 1612-1872
VL - 2
SP - 1331
EP - 1337
JO - Chemistry and Biodiversity
JF - Chemistry and Biodiversity
IS - 10
ER -