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.
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http://dx.doi.org/10.1128/aem.55.5.1203-1208.1989 | DOI Listing |
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 PDFACS Chem Biol
May 2024
Department of Life Technologies, University of Turku, FIN20014 Turku, Finland.
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 PDFCommun 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 PDFFood Funct
January 2024
College of Food Science and Technology, Huazhong Agricultural University, Wu Han 430000, China.
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 PDFAppl 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.
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