Microbial Sulfation of 8-Prenylnaringenin

Bartmańska, Agnieszka; Tronina, Tomasz; Huszcza, Ewa

doi:10.1515/znc-2013-5-609

Cited by 7 publications

(1 citation statement)

References 25 publications

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“…In addition to this bacterium, numerous fungi have been shown to be able to transform 8-PN [ 42 ]. Besides an oxygenated metabolite, which was also reported as a minor derivative of 8-PN in human liver microsomes [ 39 ], glucosylated, acyl-glucosylated, and sulfated fungi-generated metabolites have been identified [ 42 , 43 , 44 , 45 ].…”

Section: Pharmacokinetics Of 8-pnmentioning

confidence: 99%

The Potent Phytoestrogen 8-Prenylnaringenin: A Friend or a Foe?

Pohjanvirta

Nasri

2022

IJMS

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8-prenylnaringenin (8-PN) is a prenylated flavonoid, occurring, in particular, in hop, but also in other plants. It has proven to be one of the most potent phytoestrogens in vitro known to date, and in the past 20 years, research has unveiled new effects triggered by it in biological systems. These findings have aroused the hopes, expectations, and enthusiasm of a “wonder-drug” for a host of human diseases. However, the majority of 8-PN effects require such high concentrations that they cannot be reached by normal dietary exposure, only pharmacologically; thus, adverse impacts may also emerge. Here, we provide a comprehensive and up-to-date review on this fascinating compound, with special reference to the range of beneficial and untoward health consequences that may ensue from exposure to it.

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Section: Pharmacokinetics Of 8-pnmentioning

confidence: 99%

The Potent Phytoestrogen 8-Prenylnaringenin: A Friend or a Foe?

Pohjanvirta

Nasri

2022

IJMS

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Cascade biotransformation of dehydroepiandrosterone (DHEA) by Beauveria species

Kozłowska

Urbaniak

Hoc

et al. 2018

Sci Rep

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Beauveria bassiana is an entomopathogenic fungus used as a biological control agent. It is a well-known biocatalyst for the transformation of steroid compounds. Hydroxylations at the 7α or 11α position and oxidation to D-homo lactones are described in the literature. In our study, we examined the diversity of metabolism of five different B. bassiana strains and compared them to already known pathways. According to the literature, 7α and 11α-hydroxy derivatives as well as 3β,11α-dihydroxy-17a-oxa-D-homo-androst-5-en-17-one have been observed. Here we describe new DHEA metabolic pathways and two products not described before: 3β-hydroxy-17a-oxa-D-homo-androst-5-en-7,17-dione and 3β,11α-dihydroxyandrost-5-en-7,17-dione. We also used for the first time another species from this genus, Beauveria caledonica, for steroid transformation. DHEA was hydroxylated at the 7α, 7β and 11α positions and then reactions of oxidation and reduction leading to 3β,11α-dihydroxyandrost-5-en-7,17-dione were observed. All tested strains from the Beauveria genus effectively transformed the steroid substrate using several different enzymes, resulting in cascade transformation.

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Evolution of Chemical Diversity in Echinocandin Lipopeptide Antifungal Metabolites

Yue

Chen

et al. 2015

Eukaryot Cell

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The echinocandins are a class of antifungal drugs that includes caspofungin, micafungin, and anidulafungin. Gene clusters encoding most of the structural complexity of the echinocandins provided a framework for hypotheses about the evolutionary history and chemical logic of echinocandin biosynthesis. Gene orthologs among echinocandin-producing fungi were identified. Pathway genes, including the nonribosomal peptide synthetases (NRPSs), were analyzed phylogenetically to address the hypothesis that these pathways represent descent from a common ancestor. The clusters share cooperative gene contents and linkages among the different strains. Individual pathway genes analyzed in the context of similar genes formed unique echinocandinexclusive phylogenetic lineages. The echinocandin NRPSs, along with the NRPS from the inp gene cluster in Aspergillus nidulans and its orthologs, comprise a novel lineage among fungal NRPSs. NRPS adenylation domains from different species exhibited a one-to-one correspondence between modules and amino acid specificity that is consistent with models of tandem duplication and subfunctionalization. Pathway gene trees and Ascomycota phylogenies are congruent and consistent with the hypothesis that the echinocandin gene clusters have a common origin. The disjunct Eurotiomycete-Leotiomycete distribution appears to be consistent with a scenario of vertical descent accompanied by incomplete lineage sorting and loss of the clusters from most lineages of the Ascomycota. We present evidence for a single evolutionary origin of the echinocandin family of gene clusters and a progression of structural diversification in two fungal classes that diverged approximately 290 to 390 million years ago. Lineagespecific gene cluster evolution driven by selection of new chemotypes contributed to diversification of the molecular functionalities.

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Microbial Sulfation of 8-Prenylnaringenin

Cited by 7 publications

References 25 publications

The Potent Phytoestrogen 8-Prenylnaringenin: A Friend or a Foe?

The Potent Phytoestrogen 8-Prenylnaringenin: A Friend or a Foe?

Cascade biotransformation of dehydroepiandrosterone (DHEA) by Beauveria species

Evolution of Chemical Diversity in Echinocandin Lipopeptide Antifungal Metabolites

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