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

Vogel, Susanne and Heilmann, Joerg (2008) Synthesis, cytotoxicity, and antioxidative activity of minor prenylated chalcones from Humulus lupulus. JOURNAL OF NATURAL PRODUCTS, 71 (7). pp. 1237-1241. ISSN 0163-3864,

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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'-prenylchalconar-. ingenin (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 mu M). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.

Item Type: Article
Uncontrolled Keywords: CANCER-CELL-LINES; XANTHOHUMOL; FLAVONOIDS; L.; HOP; PRENYLFLAVONOIDS; ACTIVATION; APOPTOSIS; SURVIVAL; DEATH;
Subjects: 600 Technology > 615 Pharmacy
Divisions: Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann)
Depositing User: Dr. Gernot Deinzer
Date Deposited: 28 Oct 2020 11:05
Last Modified: 28 Oct 2020 11:05
URI: https://pred.uni-regensburg.de/id/eprint/30687

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