title: Humudifucol and Bioactive Prenylated Polyphenols from Hops (Humulus lupulus cv. "Cascade").
abstract: Humulus lupulus (hop plant) has long been used in traditional medicine as a sedative and antimicrobial agent. More recently, attention has been devoted to the phytoestrogenic activity of the plant extracts as well as to the anti-inflammatory and chemopreventive properties of the prenylated chalcones present. In this study, an Italian sample of H. lupulus cv. "Cascade" has been investigated and three new compounds [4-hydroxycolupulone (6), humudifucol (7) and cascadone (8)] have been purified and identified by means of NMR spectroscopy along with four known metabolites. Notably, humudifucol (7) is the first prenylated dimeric phlorotannin discovered in nature. Because structurally related phloroglucinols from natural sources were found previously to inhibit microsomal prostaglandin E2 synthase (mPGES)-1 and 5-lipoxygenase (5-LO), the isolated compounds were evaluated for their bioactivity against these pro-inflammatory target proteins. The prenylated chalcone xanthohumol inhibited both enzymes at low μM concentrations.
authors.affiliation: Department of Pharmacy, University of Naples Federico II , Via Montesano 49, 80131 Naples, Italy.
authors.forename: Martino
authors.initials: M
authors.lastname: Forino
authors.affiliation: Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Jena , Philosophenweg 14, D-07743 Jena, Germany.
authors.forename: Simona
authors.initials: S
authors.lastname: Pace
authors.affiliation: Department of Pharmacy, University of Naples Federico II , Via Montesano 49, 80131 Naples, Italy.
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Chianese
authors.affiliation: Department of Chemistry, University of Milan , Via Golgi 19, 20133 Milan, Italy.
authors.forename: Laura
authors.initials: L
authors.lastname: Santagostini
authors.affiliation: Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Jena , Philosophenweg 14, D-07743 Jena, Germany.
authors.forename: Markus
authors.initials: M
authors.lastname: Werner
authors.affiliation: Institute of Transfusion Medicine, University Hospital Jena , D-07743 Jena, Germany.
authors.forename: Christina
authors.initials: C
authors.lastname: Weinigel
authors.affiliation: Institute of Transfusion Medicine, University Hospital Jena , D-07743 Jena, Germany.
authors.forename: Silke
authors.initials: S
authors.lastname: Rummler
authors.affiliation: Department of Pharmaceutical Sciences, University of Milan , Via Mangiagalli 25, 20133 Milan, Italy.|Botanical Garden"G.E. Ghirardi" , Via Religione 25, 25088 Toscolano Maderno (BS), Italy.
authors.forename: Gelsomina
authors.initials: G
authors.lastname: Fico
authors.affiliation: Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Jena , Philosophenweg 14, D-07743 Jena, Germany.
authors.forename: Oliver
authors.initials: O
authors.lastname: Werz
authors.affiliation: Department of Pharmacy, University of Naples Federico II , Via Montesano 49, 80131 Naples, Italy.
authors.forename: Orazio
authors.initials: O
authors.lastname: Taglialatela-Scafati
mesh_terms: D001094:Arachidonate 5-Lipoxygenase; D047188:Chalcones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D005419:Flavonoids; D027582:Humulus / Q000737:chemistry*; D019746:Intramolecular Oxidoreductases / Q000037:antagonists & inhibitors; D007558:Italy; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D048789:Phytoestrogens / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D059808:Polyphenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D054876:Prenylation; D011427:Propiophenones; D000071876:Prostaglandin-E Synthases
chemical_list: D047188:Chalcones; D005419:Flavonoids; D048789:Phytoestrogens; D010936:Plant Extracts; D059808:Polyphenols; D011427:Propiophenones; C000610216:humudifucol; D001094:Arachidonate 5-Lipoxygenase; D019746:Intramolecular Oxidoreductases; D000071876:Prostaglandin-E Synthases; C104536:xanthohumol