Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Enzymatic demethylation of flavonoids

A flavonoid and alkoxy technology, applied in the field of enzymatic demethylation of flavonoids, can solve the problem of no prenylated phytoestrogens and the like

Active Publication Date: 2008-06-25
UNIV GENT
View PDF11 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Despite the wide industrial use of hops and hop extracts, there is no effective method for the production of biologically active prenylated phytoestrogens such as 8-PN from natural sources.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Enzymatic demethylation of flavonoids
  • Enzymatic demethylation of flavonoids
  • Enzymatic demethylation of flavonoids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] Example 1: Demethylation of isoxanthohumol (IX) using human fecal cultures.

[0096] Fecal samples were obtained from 12 healthy human subjects, aged between 20 and 35 years, indicated by A to L. None of the subjects had a history of gastrointestinal disease and had not taken antibiotics in the 3 months prior to sampling. A 20% (w / v) fecal slurry was prepared from fresh fecal samples by homogenizing the feces with phosphate buffered saline (0.1 M, pH 7) containing 1 g / l reducing agent sodium thioglycolate. Particulate matter was removed by centrifugation (1 min, 500xg). This supernatant is hereinafter referred to as "culture".

[0097] By culturing fecal cultures (10% (v / v)) under anaerobic conditions in Brain Heart Infusion medium (containing 0.5 g / l cysteine ​​hydrochloride) containing 25 mg / l isoxanthohumol, culture On day 8, the cultures from faecal samples A, B, C and D (hereinafter referred to as cultures A-D) were tested for their ability to degrade or conve...

Embodiment 2

[0106] Example 2. Use of microorganisms to produce compounds with 8-prenylnaringenin-type estrogen-like properties use of things

[0107] This example describes the ability of two known enteric anaerobes to convert IX to 8-PN.

[0108] Eubacterium limosum ATCC 8486 and Peptostreptococcus productus ATCC 27340 were obtained from the German Collection of Microorganisms and Cell Cultures (DSMZ, Braunschweig, Germany). E. limosum was co-cultured with 25 mg / l IX and 8-PN for 13 days in Brain Heart Infusion medium (containing 0.5 g / l cysteine ​​hydrochloride) under anaerobic conditions (Table 2). This strain is capable of converting IX to 8-PN. This strain did not further degrade 8-PN because all 8-PN added as a substrate could be recovered after 13 days of culture. These features markedly differ from the metabolic pathways observed in liver microsomes, where 8-PN is extensively further metabolized [Nikolic et al. (2005) J. of Mass Spectrom. 40, 289-299; Nikolic et al. (2004) ...

Embodiment 3

[0118] Example 3 Application of microorganisms capable of converting methylated prenyl flavonoids in fermentation.

[0119] A fed-batch fermentation experiment was designed to convert methylated prenylflavonoids under fermentative conditions using a Eubacterium limosum strain selected as described above. Fermentation in Braun Biostat M was carried out in a fermenter (2 L container), and 1.5 L of Brain Heart Infusion medium (containing 0.5 g / l cysteine ​​hydrochloride) was added thereto. Subsequently, the fermenter was autoclaved at 121 °C for 30 min. Before inoculation, the fermenter was flushed with a nitrogen flushing system for 1 h to create an anaerobic environment. Thereafter, in the fermenter, a 2-day-old E. limosum culture was introduced into the culture solution, and 25 mg / L of IX was added. Fermentations were carried out at 37°C for 2 weeks without pH control. From the first day, add 200ml of anaerobic Brain Heart Infusion medium (containing 0.5g / l cysteine ​​h...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses the demethylation of 5-methoxyflavonoids by bacterial enzymes, the use of these enzymes in the production of phytoestrogens in vitro, and in pharmaceutical compositions in combination with a source of methylated 5-methoxyprenylflavonoids.

Description

technical field [0001] The present invention relates to phytoestrogens and their preparation as well as pharmaceutical compounds and dietary supplements comprising such phytoestrogens. Background technique [0002] Hops (Humulus lupulus L.) have been used as the main ingredient in beer brewing for centuries, providing the bitterness and flavor of beer. In recent years, the plant has attracted increasing attention as a source of prenyl flavonoids, which are nonpolar isoprene compounds attached to one of the phenolic rings. Subclass of flavonoids with radical side chains. These are found in the lupus glands, found at the base of the bractlets inside the hop spikes on female plants. Of these prenyl flavonoids, two chalcones (xanthohumol (X) and desmethylxanthohumol (DMX)) and three flavanones (isoxanthohumol (IX), 8- Prenylnaringenin (8-PN) and 6-prenylnaringenin (6-PN) figure 2 ), is now receiving more attention for its potential health-promoting properties. X has been id...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/02
CPCC12P17/02A61P17/18A61P19/10A61P29/00
Inventor S·普斯赛米尔斯W·韦斯特雷特A·海瑞克D·德库克勒伊尔
Owner UNIV GENT
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com