C-ring cleavage of flavonoids by human intestinal bacteria.

Appl Environ Microbiol

Department of Pathology, St. Luke's-Roosevelt Hospital Center, New York, New York 10025.

Published: May 1989

Four hitherto undescribed Clostridium strains capable of cleaving the C ring of quercetin, kaempferol, and naringenin at C-3-C-4 were isolated from the fecal flora of humans. None of the strains cleaved catechin. C-ring fission occurred when the substrate was either in solution or in suspension. Mixed cultures of flavonoid-hydrolyzing bacteria, flavonoid-cleaving bacteria, and Escherichia coli, which was used to provide the anaerobic environment, rapidly metabolized rutin to 3,4-dihydroxyphenylacetic acid, indicating that the intestinal half-life of the biologically active aglycone is short. The cleaving strains shared many phenotypic characteristics, including their inability to ferment sugars, but they differed sufficiently to indicate that they represent different species.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC184277PMC
http://dx.doi.org/10.1128/aem.55.5.1203-1208.1989DOI Listing

Publication Analysis

Top Keywords

c-ring cleavage
4
cleavage flavonoids
4
flavonoids human
4
human intestinal
4
intestinal bacteria
4
bacteria hitherto
4
hitherto undescribed
4
undescribed clostridium
4
clostridium strains
4
strains capable
4

Similar Publications

Visible-Light-Antenna Ligand-Enabled Samarium-Catalyzed Reductive Transformations.

J Am Chem Soc

July 2024

Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.

Although divalent Sm reagents are some of the most important single-electron transfer reagents for reductive transformations, their catalytic applications are challenging. In this study, a bidentate phosphine oxide ligand substituted with 9,10-diphenylanthracene as a visible-light antenna was designed for Sm-catalyzed reduction reactions under mild reaction conditions. Pinacol coupling of aryl ketones and aldehydes was developed with 1 mol % of Sm catalyst and organic amine (DIPEA) as a sacrificial mild reductant.

View Article and Find Full Text PDF

Angucyclines are an important group of microbial natural products that display tremendous chemical diversity. Classical angucyclines are composed of a tetracyclic benz[]anthracene scaffold with one ring attached at an angular orientation. However, in atypical angucyclines, the polyaromatic aglycone is cleaved at A-, B-, or C-rings, leading to structural rearrangements and enabling further chemical variety.

View Article and Find Full Text PDF

Unravelling key enzymatic steps in C-ring cleavage during angucycline biosynthesis.

Commun Chem

December 2023

Department of Molecular Biotechnology, Institute of Biology, Leiden University, Sylviusweg 72, 2333BE, Leiden, The Netherlands.

Angucyclines are type II polyketide natural products, often characterized by unusual structural rearrangements through B- or C-ring cleavage of their tetracyclic backbone. While the enzymes involved in B-ring cleavage have been extensively studied, little is known of the enzymes leading to C-ring cleavage. Here, we unravel the function of the oxygenases involved in the biosynthesis of lugdunomycin, a highly rearranged C-ring cleaved angucycline derivative.

View Article and Find Full Text PDF

Flavan-3-ols are an important class of secondary metabolites in many plants. Their bioavailability and bioactivity are largely determined by the metabolism of intestinal microbiota. However, little is known about the intestinal bacteria involved in the metabolism of flavan-3-ols and the activities of the metabolites.

View Article and Find Full Text PDF

Identification of "missing links" in C- and D-ring cleavage of steroids by TA441.

Appl Environ Microbiol

October 2023

Environmental Molecular Biology Laboratory, RIKEN, Saitama, Japan.

TA441 is capable of aerobically degrading steroids through the aromatization and cleavage of the A- and B-rings, followed by D- and C-ring cleavage via β-oxidation. While most of the degradation steps have been previously characterized, a few intermediate compounds remained unidentified. In this study, we proposed that the cleavage of the D-ring at C13-17 required the ScdY hydratase, followed by C-ring cleavage via the ScdL1L2 transferase.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!