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Pigments of Higher Fungi: a Review

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Pigments of Higher Fungi: a Review Czech J. Food Sci. Vol. 29, 2011, No. 2: 87–102 Pigments of Higher Fungi: A Review Jan VELÍŠEK and Karel CEJPEK Department of Food Chemistry and Analysis, Faculty of Food and Biochemical Technology, Institute of Chemical Technology in Prague, Prague, Czech Republic Abstract Velíšek J., Cejpek K. (2011): Pigments of higher fungi – a review. Czech J. Food Sci., 29: 87–102. This review surveys the literature dealing with the structure of pigments produced by fungi of the phylum Basidiomycota and also covers their significant colourless precursors that are arranged according to their biochemical origin to the shikimate, polyketide and terpenoid derived compounds. The main groups of pigments and their leucoforms include simple benzoquinones, terphenylquinones, pulvinic acids, and derived products, anthraquinones, terpenoid quinones, benzotropolones, compounds of fatty acid origin and nitrogen-containing pigments (betalains and other alkaloids). Out of three orders proposed, the concern is only focused on the orders Agaricales and Boletales and the taxonomic groups (incertae sedis) Cantharellales, Hymenochaetales, Polyporales, Russulales, and Telephorales that cover most of the so called higher fungi often referred to as mushrooms. Included are only the European species that have generated scientific interest due to their attractive colours, taxonomic importance and distinct biological activity. Keywords: higher fungi; Basidiomycota; mushroom pigments; mushroom colour; pigment precursors Mushrooms inspired the cuisines of many cul- carotenoids and other terpenoids are widespread tures (notably Chinese, Japanese and European) only in some species of higher fungi. Many of the for centuries and many species were used in folk pigments of higher fungi are quinones or similar medicine for thousands of years. However, lit- conjugated structures that are mostly classified ac- tle is known that mushrooms were a commonly cording to the perceived biosynthetic pathways, re- used textile dye before the invention of synthetic flecting their structure, to pigments derived from (i) dyes because of the vast range of vivid and rich the shikimate (chorismate) pathway, (ii) the acetate- colours achievable (Mussak & Bechtold 2009). malonate (polyketide) pathway, (iii) the mevalonate The chromophores of mushroom dyes contain a (terpenoid) pathway, and (iv) pigments containing variety of fascinating organic compounds. Their nitrogen. Several review articles covering the litera- pigmentation may vary with the age and some ture published from its inception during the latter undergo distinctive colour changes on bruising; half of the 19th century to the end of 2009 have been therefore, the colours of mushrooms are one of already published (Gill & Steglich 1987; Gill the essential features used in their identification. 1994, 1996, 1999, 2003; Hanson 2008a,b; Räisänen Furthermore, the pigments of mushrooms may 2009; Zhou & Liu 2010). protect the organism from UV damage and bacte- The shikimate pathway provides a route to the rial attack or play a role as insect attractants. essential amino acids phenylalanine, tyrosine and Mushrooms do not contain the pigments that tryptophan via the central intermediates shikimic dominate in higher plant colours. Chlorophylls and and chorismic acids. Phenylalanine and tyrosine are anthocyanins are not present in fungi at all; betalains, precursors for a wide range of compounds includ- Partly supported by the Ministry of Education, Youth and Sports of the Czech Republic, Project No. MSM 6046137305. 87 Vol. 29, 2011, No. 2: 87–102 Czech J. Food Sci. ing arylpyruvic, cinnamic and benzoic acids that (anthranol, anthrone, anthrahydroquinone, and represent the building blocks for many pigments of oxanthrone derivatives) that may occur in the form higher fungi. Condensation of two arylpyruvic acid of various glycosides. Many natural anthraquinones yields red to brown terphenylquinones and related are oligomers formed by coupling of two or more orange to red grevillins. Diarylcyclopentenones, anthraquinone molecules. These oligomers further responsible for the colour changes in some bruised differ in the points through which monomers are mushrooms, are formed by ring contractions of attached and may have more than one polymor- terphenylquinones while oxidative cleavage of the phic form (Velíšek et al. 2007, 2008; Velíšek & hydroxyquinone ring in terphenylquinones and Cejpek 2008). Styrylpyrones are biosynthesised rearrangement of thus formed intermediates results by a combined shikimate and polyketide pathway, in a series of yellow and orange lactones known as which otherwise yields various terpenoids includ- pulvinic (pulvic) acids. Their decarboxylation yields ing carotenoids. the yellow pulvinones that can be oxidised and fur- Various pigments and other fungi constituents ther transformed to a number of structurally related show important biological activities (antioxidative, products. Reduction of cinnamic acids affords the free radical scavenging, anticarcinogenic, immu- corresponding alcohols that are the building blocks nomodulatory, antiviral, and antibacterial) that of benzotropolone pigments. Tyrosine, hydroxy- have generated intensive research interest (Steg- lated to 3,4-dihydroxyphenylalanine (DOPA), is lich 1981; Calìa et al. 2003; Liu 2006; Medicinal the precursor of the red-violet betacyanins and the Mushrooms 2008; Schüffler & Anke 2009). orange-yellow betaxanthins. Both amino acids and The taxonomy of the kingdom Fungi (the subking- their transformation products can be converted via dom Dikarya) is in a state of constant flux; therefore, quinones into the heterogeneous dark pigments the most recent 2007 classification adopted by a melanins by the enzymatic browning reactions coalition of mycologists was used (Thorna et al. (oxidations and polymerisations). Tryptophan is 2007; MycoBank 2010). Out of seven phyla (divisions) transformed to hydroxyanthranilic acids that be- proposed, the concern of this review only deals with come the precursor of phenoxazines and other ni- the phylum Basidiomycota (“club fungi”)1 (subphy- trogen-containing pigments. Benzoquinones can be lum Agaricomycotina, class Agaromycetes, subclass synthesised from very different starting substances Agaromycetidae) that covers most of the so called “high- and via different biochemical pathways, e.g. using er fungi” often referred to as “mushrooms”growing benzoic acids produced in the shikimate pathway. in Europe. The referred pigments, not reviewed up Terpenoid quinones are formed by combination of to now, are arranged according to the mushroom the shikimate pathway with the mevalonate path- orders. Many other pigments were identified in way. The polyketide pathway yields either aromatic fungi indigenous to Australasia. ketides or fatty acids. For the aromatic ketides, the growing chain stabilises by cyclization reactions and partial reduction, whereas for fatty acids, the 1 Agaricales carbonyl groups of the chain are reduced before attachment of the next C2 group. Products of this The genera Agaricus L., Leucoagarius Locq. ex pathway include tetra-, hepta-, octa- and higher Singer and Macrolepiota Singer of the Agaricaceae, ketides and compounds of fatty acid origin. Fungi including the common mushroom A. bisporus (J.E. contain a range of pigments of octaketide origin Lange) Imbach (now cultivated in at least 70 coun- (e.g. anthraquinones) that are based on the anthra- tries around the world), contain the glutamic acid 9,10-quinone skeleton with both rings substituted. derived hydrazine agaritine (1) that may be enzy- In many cases, anthraquinones are found in fungi matically oxidised at the C-4 hydroxymethyl group as the corresponding colourless reduced forms to the corresponding formyl and carboxyl deriva- 1The clade containing Ascomycota and Basidiomycota is classified as subkingdom Dikarya. The phylum Ascomycota (“sac fungi”) covers some higher fungi (belonging to the subdivision Pezizomycotina, class Pezizomycetes, subclass Penzizomycodidae, order Pezizales), such as the true morel (Morchella Dill. ex Pers., Morchellaceae), the false morel (Gyromitra Fr., Discinaceae) and the truffle (Tuber P. Micheli ex F.H. Wigg., Tuberaceae). Their pigments have been stud- ied only sporadically; the black pigments of the black truffle T. melanosporum are polymeric allomelanins of polyketide origin (DE ANGELIS et al. 1996). 88 O O H H O N COOH N COOHN N H N N N N N N N COOH N H H N N H H N HO NHHO2 NH H H 2 O O Czech HJ.O Food Sci. NH2 ȱ O Vol. 29, 2011,ȱ No. 2: 87–102ȱ ȱ 1.ȱagaritineȱȱ 1.ȱagaritineȱȱ 2.ȱagariconeȱȱ ȱ 2.ȱagariconeȱȱ 1. agaritine 2. agaricone O O HO HO O O O O O OH OH H HO H N N OH N COOHN O COOH N COOHN COOH N N N N N N H H COOH H H H H HO NH HO 2 N NH2 NHO2 NH2 H O NH NH ȱ NH ȱ ȱ ȱ ȱ ȱ ȱ ȱ 2 NH 1.ȱagaritineȱȱ 1.ȱagaritineȱȱ 3.ȱJȬglutamyl2.ȱagariconeȬ4Ȭhydroxybenzeneȱȱȱ 3.2.ȱJȱȬagariconeȱglutamylȬȱȱ4Ȭhydroxybenzeneȱ 4.ȱ2ȬhydroxyȬ4Ȭimino4.Ȭȱȱ2ȬhydroxyȬ4ȬiminocyclohexaȬ2,5Ȭdienoneȱȱ 3. γ-glutamyl-4-hydroxybenzȱȱ ene 4. 2-hydroxy-4-iminocyclohexa-2,5ȱȱȱȱ-dienonecyclohexaȬ2,5Ȭdienoneȱȱ O O COOH HO HO O O OH OH COOH - HOOC COO- COO O – COOH COOH – - HOOC COO COO O COO + O + + N N + - – O N O H H COO + O + N + N N N COO NH2 +NH2 N O – O N N NH N NH N COO ȱ ȱ ȱ O ȱ COOH OH O COOH 3.ȱJȬglutamylȬ4Ȭhydroxybenzene3.ȱJȬglutamylȬ4ȱȬhydroxybenzeneȱ 4.ȱ2Ȭhydroxy4.ȱ2OȬȬhydroxyH4ȬiminoȬȱȬ4ȬiminocyclohexaȬ2,5Ȭdienoneȱȱ ȱȱ ȱȱȱȱcyclohexaȬ2,5Ȭdienoneȱȱ HOOCN COOH HOOCN COOH HOOCCOOH N COOH HOOC N COOH H H H HOOC N COOH HOOC - N COHOH HOOC N COOH HOOC
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