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J Nat Prod. 2008 Jul;71(7):1237-41. doi: 10.1021/np800188b. Epub 2008 Jul 9.

Synthesis, cytotoxicity, and antioxidative activity of minor prenylated chalcones from Humulus lupulus.

Author information

1
Institute of Pharmacy, University of Regensburg, Universitätsstrasse 31, 93053 Regensburg, Germany.

Abstract

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.

PMID:
18611049
DOI:
10.1021/np800188b
[Indexed for MEDLINE]

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