Biosynthesis of anthraquinone pigments in Dermocybe

Steglich, Wölfgang; Arnold, R.G.; Lösel, Walter; Reininger, W.

doi:10.1039/c39720000102

Cited by 25 publications

(12 citation statements)

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“…Two-dimensional TLC is a simple method for understanding the anthraquinone compositions in different species and comparing the species when there is prior knowledge concerning what to look for. In our experiments it was possible to locate the compounds which were previously observed in other studies [10,16,30]. Also, we could identify previously unknown compounds from C. vitiosus and C. semisanguineus.…”

Section: Yields Of Biocolorantssupporting

confidence: 55%

“…From the studies of Steglich and L€ osel [15] and Steglich et al [16], it is known that most of the anthraquinones in the Cortinarius fungi are bound to glycosides, whereas for dyeing and printing purposes, aglycones are more appropriate because of their minor solubility in water. To isolate the anthraquinone compounds from the fungal material as dye powder, a procedure containing enzymatic hydrolysis was used [9].…”

Section: Methodsmentioning

confidence: 99%

“…The dye uptake for polyester fabrics was high (>99%; Table 3). Clearly, the small size and the planar appearance of the natural anthraquinone dyes, as well as the similarity Table 2 Anthraquinone compounds in Cortinarius sanguineus, Cortinarius vitiosus and Cortinarius semisanguineus according to the twodimensional (2D) TLC separation ( Figure 5) and the references [16,30]. Compounds in C. sanguineus have been analysed by UV-vis and tandem mass spectroscopy and the results have been published in [10].…”

Section: Dyeing and Printingmentioning

confidence: 99%

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Fungal colorants in applications – focus on Cortinarius species

Räisänen

2018

Coloration Technology

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Secondary metabolites in fungi offer an interesting source of bio-based compounds that could be used as colorants in many applications. From a historical point of view, fungal natural dyes have been used more rarely than plant-based dyes. This paper investigates the potential of fungal colorants, using Cortinarius species as examples. In our research, fruiting bodies of the fungi Cortinarius sanguineus and Cortinarius semisanguineus were used as sources of anthraquinone dyestuffs. From 10 kg of fresh fruiting bodies, 60 g of anthraquinone powder was obtained, 6% of the dry weight content. The most abundant compounds were emodin, dermocybin and their glucosides, which formed over 90% of the total dyestuff amount. Pure emodin and dermocybin, as well as the crude water extract, were used for the dyeing and printing of natural and synthetic fibres. Conventional mordant techniques and high-temperature (HT) disperse dye techniques were applied, and light and washing fastness were tested according to International Organization for Standardization standards. Our experiments show that the yields of dye powders extracted from fungi are reasonable compared with the yields of, for example, madder (Rubia tinctorum). Natural anthraquinones produce strong and bright colours on several types of fibres. In particular, for HT disperse dyed polyester, the light and washing fastness properties were excellent. Anthraquinones are common in nature and there are many fungal species which produce them, so there are a variety of possibilities for growing fungi. The use of large-scale cultures is an interesting perspective for future biocolorant production.

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Section: Yields Of Biocolorantssupporting

confidence: 55%

Section: Methodsmentioning

confidence: 99%

Section: Dyeing and Printingmentioning

confidence: 99%

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Fungal colorants in applications – focus on Cortinarius species

Räisänen

2018

Coloration Technology

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“…S5 in the supplemental material) as well as chemical analysis of wildtype and enc mutant strains suggests that endocrocin is not spontaneously converted to emodin as suggested for the asperthecin cluster by Szewczyk et al (40). Indeed, a study in 1972 using labeled endocrocin did not find this compound to incorporate into emodin or other anthraquinones in the fungus Dermocybe sanguinea (36). These results suggest that although the asperthecin and endocrocin clusters share a high level of similarity in the organization of their biosynthetic genes, the distinct biosynthetic steps proposed to be catalyzed by EncC and AptC and the presence of EncD only in the endocrocin cluster contribute to the production of diverse metabolites from these two clusters.…”

Section: Discussionmentioning

confidence: 99%

Genome-Based Cluster Deletion Reveals an Endocrocin Biosynthetic Pathway in Aspergillus fumigatus

Lim

Hou

Chen

et al. 2012

Appl Environ Microbiol

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ABSTRACTEndocrocin is a simple anthraquinone frequently identified in extracts of numerous fungi. Several biosynthetic schemes for endocrocin synthesis have been hypothesized, but to date, no dedicated secondary metabolite gene cluster that produces this polyketide as its major metabolite has been identified. Here we describe our biosynthetic and regulatory characterization of the endocrocin gene cluster inAspergillus fumigatus. This is the first report of this anthraquinone in this species. The biosynthetic genes required for endocrocin production are regulated by the global regulator of secondary metabolism, LaeA, and encode an iterative nonreducing polyketide synthase (encA), a physically discrete metallo-β-lactamase type thioesterase (encB), and a monooxygenase (encC). Interestingly, the deletion of a gene immediately adjacent toencC, termedencDand encoding a putative 2-oxoglutarate-Fe(II) type oxidoreductase, resulted in higher levels of endocrocin production than in the wild-type strain, whereas overexpression ofencDeliminated endocrocin accumulation. We found that overexpression of theencAtranscript resulted in higher transcript levels ofencA-Dand higher production of endocrocin. We discuss a model of theenccluster as one evolutionary origin of fungal anthraquinones derived from a nonreducing polyketide synthase and a discrete metallo-β-lactamase-type thioesterase.

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“…The anthraquinones, endocrocin and emodin, are also formed through the polyketide pathway from nonaromatic precursors (29). Emodin could either originate from endocrocin by decarboxyIation or by a separate biosynthesis directly from polyacetates (36,37). A possible sequence of the transformations of emodin and endocrocin into other anthraquinones found in the E. echinulatum culture media is given in Fig.…”

Section: Mscussionmentioning

confidence: 99%

Anthraquinones and Phenols as Intermediates in the Formation of Dark‐Colored, Humic Acid‐Like Pigments by Eurotium echinulatum

Sáiz‐Jiménez¹,

Haider²,

Martin

1975

Soil Science Soc of Amer J

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EUrotiU711 echinulalum, a (ungus isolated (rom a vertisoJ in southcrn Spain, formcd humic acid-like pigments duriog growth in glucose-asparagine or gluoosc-NaNO;¡ media. After 6 to 7 days the phenols, orscllinic; ¡l·hydroxycinnamic, and p-hydroxyhcnzoic ncids, and the anthra<]uinones, cndocrocin, emodin, and physcion \Verc dctcctcd in the culture media. Upoo further dcvelopment of the mycclinJ mats additionaI aromatic compounds \Vere produccd and afte .. 4 to 6 wccks more than 50 different cther-extractahle phenoIs amI anthraquinoncs were detected. With further illcubation the nmounts and number oC these compounds dccreascd and pigment Cormation in the media increased. After 2 to 3 months the culture media were dark brown to black amI about 1 to 3.5 g/liter of polymer could be recovered upon acidification of the culture medium. Sodium amalgam rcduction of this polymer yielded numerous phcnols, anthraquinones, anthroncs, and possibly anthracene derivatives. Trcatment with sodium dithionite yieIded largely anthraquinones. The polymer contained 1 to 4.5% N depending upon the N source. From 50 to 60% of this N was released in the form of amino acids upon acid hydroIysis. With both asparagine and NaNO a as N sources the same amino acids were isoJated Crom ON Hel hydroIysates. Quantitatively, however, there were differences in the percentage distribution oC the amino acids. (24, 25. 26, 32). Jt is possibJe that the condensed hydrocarbons isolated either directly from the soil (5, 39) or upon zinc dust distilIation of humic acids (8.11, 13) mal' origina te by reduction of more highly condensed quinoid or phenolic structures. The fringelites of sea sediments discussed hy Blumer (4) and by Albrecht and Durisson (l) are dimeric anthraquinones with tetra-hydroxy-naphthodianthrone structures. They are derived from fossil crinoids and undergo a series of hydrations and dehydrations.For the present paper a study was made of anthraquinones -and phenols formed hy Eurotium echinulatum, a soil fungus isolated from a Vertizol in southern Spain. The linkage of these compounds into darkMcolored pigments similar to humic acid hy either phenolase or autoxidative polymerization proces.c;es in the culture medium and in the ceI1s during and after terminatíon of growth was followed. METHODSThe methods for cultivation and some properties of the darkcolored pigment have been described (22,23). The fungus was cultured in Czapek-Dox medium (20% glucose and 0.2% NaNO a ) or in glucose-asparagine medium (3% glucose and 0.5% asparagine) as described by Martin et al. (21). Growth and polymer formation was much better in the glucose~aspara gine medium. bu! the Czapek-Dox was preferred for monitoring the formation and transformation of phenols and anthraquinones. The phenols and anthraquinones were isolated from the culture media by acidification to pH 1.0 and extraction with peroxide-free ether. Concentrated cthcr extracts were spotted on thin layer silica gel (KGF 254. Fa, Merck, DarmstadO plates and chromatographed in two directions (9....

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Biosynthesis of anthraquinone pigments in Dermocybe

Cited by 25 publications

References 0 publications

Fungal colorants in applications – focus on Cortinarius species

Fungal colorants in applications – focus on Cortinarius species

Genome-Based Cluster Deletion Reveals an Endocrocin Biosynthetic Pathway in Aspergillus fumigatus

Anthraquinones and Phenols as Intermediates in the Formation of Dark‐Colored, Humic Acid‐Like Pigments by Eurotium echinulatum

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