Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus).
The ethyl acetate soluble fraction of hops (Humulus lupulus) showed potent inhibitory activity on the production of nitric oxide (NO) induced by a combination of LPS and IFN-gamma. Four known prenylflavonoids (1-4) and a new prenylflavonoid (5), hulupinic acid (6), lupulone (7), and its six new derivatives (8-13) were isolated from the active fraction. The structures were determined on the basis of physiochemical properties and spectroscopic analysis. Their inhibitory activities on the production of NO in macrophage RAW 264.7 cells were examined.
Zhao
Feng
F
Central Laboratories for Key Technology, Kirin Brewery Co., Ltd., Yokohama-shi, Kanagawa 236-0004, Japan.
Watanabe
Yuki
Y
Nozawa
Hajime
H
Daikonnya
Akihiro
A
Kondo
Keiji
K
Kitanaka
Susumu
S
D000818:Animals; D002478:Cells, Cultured; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D027582:Humulus / Q000737:chemistry*; D007371:Interferon-gamma / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism*; D051379:Mice; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D019001:Nitric Oxide Synthase / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D052247:Nitric Oxide Synthase Type II; D019906:Nuclear Magnetic Resonance, Biomolecular; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D010946:Plants, Medicinal / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification
D004791:Enzyme Inhibitors; D005419:Flavonoids; D008070:Lipopolysaccharides; D013729:Terpenes; D009569:Nitric Oxide; D007371:Interferon-gamma; C008299:lupulon; D010696:Phloroglucinol; D019001:Nitric Oxide Synthase; D052247:Nitric Oxide Synthase Type II; C496317:Nos2 protein, mouse