Humudifucol and Bioactive Prenylated Polyphenols from Hops (Humulus lupulus cv. "Cascade")

J Nat Prod. 2016 Mar 25;79(3):590-7. doi: 10.1021/acs.jnatprod.5b01052. Epub 2016 Feb 26.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arachidonate 5-Lipoxygenase
  • Chalcones / chemistry
  • Chalcones / isolation & purification*
  • Chalcones / pharmacology*
  • Flavonoids
  • Humulus / chemistry*
  • Intramolecular Oxidoreductases / antagonists & inhibitors
  • Italy
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Phytoestrogens / chemistry
  • Phytoestrogens / isolation & purification*
  • Phytoestrogens / pharmacology*
  • Plant Extracts / chemistry
  • Plants, Medicinal / chemistry*
  • Polyphenols / chemistry
  • Polyphenols / isolation & purification*
  • Polyphenols / pharmacology*
  • Prenylation
  • Propiophenones
  • Prostaglandin-E Synthases

Substances

  • Chalcones
  • Flavonoids
  • Phytoestrogens
  • Plant Extracts
  • Polyphenols
  • Propiophenones
  • humudifucol
  • Arachidonate 5-Lipoxygenase
  • Intramolecular Oxidoreductases
  • Prostaglandin-E Synthases
  • xanthohumol