Anthraquinones and Derivatives from Marine-Derived Fungi: Structural Diversity and Selected Biological Activities

Fouillaud, Mireille; Venkatachalam, Mekala; Girard-Valenciennes, Emmanuelle; Caro, Yanis; Dufossé, Laurent

doi:10.3390/md14040064

Cited by 153 publications

(140 citation statements)

References 234 publications

(252 reference statements)

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“…Emodin ( 1 ), one of the most widely distributed anthraquinones, is found in various species of plants and fungi . It plays a crucial role as a biosynthetic precursor for many fungal metabolites such as the ergochromes ( Penicillium oxalicum ), xanthones ( Aspergillus versicolor ), monodictyphenone ( Aspergillus nidulans ), and bisanthraquinones ( Penicillium islandicum , Myrothecium verucaria , and Penicillium rugulosum ) .…”

Section: Figurementioning

confidence: 99%

Monomeric Dihydroanthraquinones: A Chemoenzymatic Approach and its (Bio)synthetic Implications for Bisanthraquinones

Saha

Mondal

Witte

et al. 2018

Chemistry A European J

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Modified bisanthraquinones are complex dimeric natural products containing a cage-like structural motif. For their biosynthesis, monomeric dihydroanthraquinones have been proposed as key intermediates despite not being isolated from natural sources or synthesized as of yet. Here, isolation and characterization of dihydroemodin, as well as dihydrolunatin, synthesized by a biomimetic and chemoenzymatic approach using NADPH-dependent polyhydroxyanthracence reductase (PHAR) from Cochliobolus lunatus followed by Pb(OAc) oxidation is reported. Subsequent dimerization through a hetero-Diels-Alder reaction of the dihydroemodin and dihydrolunatin resulted in (-)-flavoskyrin (68 %) and (-)-lunaskyrin (62 %), respectively. Pyridine treatment of (-)-flavoskyrin and (-)-lunaskyrin gave (-)-rugulosin and (-)-2,2'-epi-cytoskyrin A in 64 % and 60 % yield, respectively, through a cascade that involves two dimeric intermediates. Implications of the described synthesis for the biosynthesis of bisanthraquinones by a combination of enzymatic and spontaneous steps are discussed.

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Section: Figurementioning

confidence: 99%

Monomeric Dihydroanthraquinones: A Chemoenzymatic Approach and its (Bio)synthetic Implications for Bisanthraquinones

Saha

Mondal

Witte

et al. 2018

Chemistry A European J

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“…The bioproduction of colored and bioactive secondary metabolites from ascomycetous fungi has promising potential in various industrial fields from food coloring agents to drugs or even semiconductors and functional materials production, as the literature has been abundantly reporting . On top of their structural diversity, fungal pigments from the polyketide family (i.e., azaphilones, hydroxyanthraquinones, and naphthoquinones) demonstrated a wide range of potential applications as coloring agents in cosmetics, textile, leather, paper, animal feeds, food, and beverages industries.…”

Section: Introductionmentioning

confidence: 99%

Isolation of two novel purple naphthoquinone pigments concomitant with the bioactive red bikaverin and derivates thereof produced by Fusarium oxysporum

Lebeau¹,

Petit²,

Clerc³

et al. 2018

Biotechnology Progress

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Filamentous fungi have gained growing interest as sources of diverse pigmented secondary metabolites. Some specific polyketides from Ascomycetous species have demonstrated a wide range of industrial applications in food, cosmetic, textile, and in the design of pharmaceutical products. The formulation of recipes containing fungal polyketides has increased over recent years. Fusarium strains were proven useful to mankind in a variety of technologies. Nevertheless, there is still need of new isolates of Fusarium for use in emerging and already existing fields. In this article, we report the concomitant production of the bioactive red bikaverin along with two novel purple pigments by the phytopathogenic Fusarium oxysporum LCP531 strain isolated from soil. In literature, the production of purple pigment had only been described in cultures of Fusarium Fujikuroi, Fusarium verticillioides, and Fusarium graminearum. The production of these naphthoquinonic pigments, their distribution (either produced in mycelia or excreted in liquid medium) and their chemical profiles were investigated with respect to nutrient composition. The pigments were extracted by using a pressurized liquid extraction method, monitored by colorimetric analysis and characterized by HPLC‐DAD chromatography. To our knowledge, this is the first report of these two novel wild‐type purple naphtoquinones pigments along with bikaverin, where additionally, the culture conditions were put into perspective to optimize fermentation cultures and extraction process accordingly to the pigment/biomolecule desired. These colored naphthoquinones should be promising fungal functional compounds which could be expected to have a place of choice, along with other antibacterial, antifungal, antiviral, anticancer, and antineoplastic derivatives. © 2018 American Institute of Chemical Engineers Biotechnol. Prog., 35: e2738, 2019

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“…The choice of AQS instead of anthraquinone was made due to solubility concerns, as anthraquinone by itself has poor solubility in aqueous solution . With naturally‐occurring anthraquinone groups found in marine biology, there are multiple forms of anthraquinone derivatives and analogues that marine organisms synthesize that are soluble . Similarly, protoporphyrin IX has poor solubility in water but has soluble derivatives that are important for terrestrial biology – such as heme and other metal ion complexes.…”

Section: Resultsmentioning

confidence: 99%

Electrochemistry for Life Detection on Ocean Worlds

et al. 2020

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All forms of terrestrial life include cellular machinery to transform and regulate chemical energy flow through electron‐transfer pathways reliant upon key classes of biological redox molecules; life that evolved elsewhere, presumably, would possess a similar possibly overlapping set of energy‐management molecules. A second set of universal processes in terrestrial biology encompasses enzymatic change to add or remove functional groups, such as phosphate moieties, to biomolecules for a variety of purposes, from managing energy flow to tuning protein function; electrochemical assays can detect such enzymes. Thus, measurement of biological redox activity is a promising means to search for two major classes of life indicators as a component of future exploration missions to the “ocean worlds” of our solar system, those bodies that support substantial liquid oceans. Here, we assay a representative set of life‐critical redox molecules in synthetic seawater (SW) using electrochemical techniques. We also appropriate a well‐developed electrochemical assay that indicates the presence of phosphatase(s) by comparing the redox signatures of a substrate for, and the product of, the enzymatic process. We report measured limits of detection in SW as low as 10 nM for naturally occurring redox molecules and 3.1 aM for alkaline phosphatase over a 60‐minute period, demonstrating the promise and sensitivity of electrochemical sensors as effective life‐detection tools for future ocean worlds missions.

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Anthraquinones and Derivatives from Marine-Derived Fungi: Structural Diversity and Selected Biological Activities

Cited by 153 publications

References 234 publications

Monomeric Dihydroanthraquinones: A Chemoenzymatic Approach and its (Bio)synthetic Implications for Bisanthraquinones

Monomeric Dihydroanthraquinones: A Chemoenzymatic Approach and its (Bio)synthetic Implications for Bisanthraquinones

Isolation of two novel purple naphthoquinone pigments concomitant with the bioactive red bikaverin and derivates thereof produced by Fusarium oxysporum

Electrochemistry for Life Detection on Ocean Worlds

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