Synthesis, cytotoxicity, and antioxidative activity of minor prenylated chalcones from Humulus lupulus.
The minor hop ( Humulus lupulus) chalcones 3'-geranylchalconaringenin (3), 5'-prenylxanthohumol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1'',2''-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3'-geranyl-6'-O-methylchalconaringenin (2), 3'-methylflavokawin (6), and 2'-O-methyl-3'-prenylchalconaringenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC 50 values comparable to xanthohumol (8.2-19.2 microM). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.
Vogel
Susanne
S
Institute of Pharmacy, University of Regensburg, Universitätsstrasse 31, 93053 Regensburg, Germany.
Heilmann
Jörg
J
D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005419:Flavonoids; D006367:HeLa Cells; D006801:Humans; D027582:Humulus / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D011427:Propiophenones / Q000494:pharmacology*
D000975:Antioxidants; D047188:Chalcones; D005419:Flavonoids; D011427:Propiophenones; C104536:xanthohumol