Pigments Of Fungi Research Articles

Pigments of Fungi. Part 71. Austrocolorins A1(I) and B1(II): Atropisomeric 10,10′‐Linked Dihydroanthracenones from an Australian Dermocybe sp.

ChemInformVolume 35, Issue 36 Organic Dyes Pigments of Fungi. Part 71. Austrocolorins A1(I) and B1(II): Atropisomeric 10,10′-Linked Dihydroanthracenones from an Australian Dermocybe sp. Karren Beattie, Karren Beattie Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorCatherine Elsworth, Catherine Elsworth Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorMelvyn Gill, Melvyn Gill Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorNives M. Milanovic, Nives M. Milanovic Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorDeddi Prima-Putra, Deddi Prima-Putra Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorEvelin Raudies, Evelin Raudies Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this author Karren Beattie, Karren Beattie Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorCatherine Elsworth, Catherine Elsworth Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorMelvyn Gill, Melvyn Gill Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorNives M. Milanovic, Nives M. Milanovic Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorDeddi Prima-Putra, Deddi Prima-Putra Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorEvelin Raudies, Evelin Raudies Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this author First published: 11 August 2004 https://doi.org/10.1002/chin.200436175Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume35, Issue36September 7, 2004 RelatedInformation

Pigments of Fungi. Part 69. Total Synthesis of (R)‐Ochratoxin α (I) and the Formal Total Synthesis of Ochratoxin A (II).

ChemInformVolume 33, Issue 45 p. 201-201 Natural Products Pigments of Fungi. Part 69. Total Synthesis of (R)-Ochratoxin α (I) and the Formal Total Synthesis of Ochratoxin A (II). Christoph D. Donner, Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorMelvyn Gill, Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this author Christoph D. Donner, Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this authorMelvyn Gill, Sch. Chem., Univ. Melbourne, Melbourne, Victoria 3010, AustraliaSearch for more papers by this author First published: 19 May 2010 https://doi.org/10.1002/chin.200245201Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume33, Issue45November 12, 2002Pages 201-201 RelatedInformation

Effect of volatiles from bacteria and yeast on the growth and pigmentation of sapstain fungi

Sapstain fungi affect the appearance of wood due to colonisation by pigmented hyphae but without producing significant strength losses. This is due to the production of melanin in the fungal cell walls of the staining fungi. Any biological control strategy targeted against this type of deterioration would therefore be considered successful if it inhibited either fungal growth or pigment production. Previous work has established that specific bacterial and yeast isolates selected on the basis of agar screening studies could significantly reduce levels of staining in wood block tests. This paper presents the results of a study to examine the role of volatile organic compounds (VOCs) produced by four bacterial and three yeast isolates on the growth and pigment production by a range of five sapstain fungi on three media types. VOCs from three of the four bacterial strains tested completely inhibited growth of the five target sapstain fungi but only when the antagonists were grown on tryptone soya media. When antagonists were grown on either malt agar or a low nutrient medium levels of inhibition were either significantly reduced or non-existent. Yeast antagonists generally produced lower levels of growth inhibition than the bacteria but a Williopsis mrakii isolate gave 100% inhibition of three of the five sapstain fungi. Production of inhibitory VOCs was highly dependent on the specific antagonist as well as its growth substrate and all five sapstain fungi showed varying sensitivities to the VOCs produced. Not all fungi were inhibited, growth of O. piliferum and A. pullulans being stimulated by the VOCs from antagonists but only when grown under low nutrient conditions. In some instances, where growth was only slightly reduced, the level of pigmentation of the sapstain colony was significantly reduced compared with corresponding controls. The implications of this work for the biological control of sapstain fungi are discussed.

Pigments of Fungi. LXIX. Total Synthesis of (R)-Ochratoxin α and the Formal Total Synthesis of Ochratoxin

(R)-Ochratoxin α, the monochiral carboxylic acid component of the biologically active dipeptide ochratoxin A, is synthesized for the first time over nine steps from (R)-propylene oxide. The method constitutes a versatile and general route to functionalized dihydroisocoumarins.

ChemInform Abstract: Pigments of Fungi. Part 59. Synthesis of (1S,3S)- (I) and (1R,3R)-Austrocortilutein and (1S,3S)-Austrocortirubin (II) from Citramalic Acid.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Pigments of Fungi. LXIII. Synthesis of (1S,3R)- and (1R,3S)-Austrocortilutein and the Enantiomeric Purity of Austrocortilutein in some Australian Dermocybe Toadstools

The naturally occurring tetrahydroanthraquinones (1S,3R)- and (1R,3S)-austrocortilutein (1b) and (1d), respectively, are synthesized for the first time in enantiomerically pure form by Diels–Alder cycloaddition between the functionalized butadiene derivative (4) and the corresponding monochiral trans-1,3-dihydroxy-1,2,3,4- tetrahydro-5,8-naphthoquinone (5a) or (5b), themselves derived from citramalic acid. Separation of the four stereoisomeric austrocortiluteins by using h.p.l.c. over a chiral stationary phase reveals that the enantiomeric purity of the (1S,3S)- and (1R,3R)-quinones (1a) and (1c) varies from species to species whereas the (1S,3R)-isomer (1b) is, in the five cases examined, enantiomerically pure.

Pigments of Fungi. LXVI. The Gentiobiosides of (R)- and (S)-Torosachrysone from Australian Toadstools and Methods for Assaying the Enantiomeric Purity of Natural Torosachrysone

The diastereoisomeric 8-O--b-gentiobiosides (2) and (10) of (S)- and (R)-torosachrysone (1) and (11), respectively, are isolated in admixture to varying degrees from toadstools belonging to the genera Cortinarius and Dermocybe. (R)-Torosachrysone (11) is characterized for the first time from a fungus and spectroscopic and chromatographic methods are described that show that torosachrysone, as it occurs in several fungi, is anisochiral and its stereochemical composition is species-dependent.

Pigments of Fungi. LIX. Synthesis of (1S,3S)- and (1R,3R)-Austrocortilutein and (1S,3S)-Austrocortirubin from Citramalic Acid

The naturally occurring tetrahydroanthraquinone (1S,3S)-austrocortilutein (1) is synthesized for the first time in enantiomerically pure form by Diels–Alder cycloaddition between the functionalized butadiene derivative (8) and the chiral 1,3-dihydroxy-1,2,3,4-tetrahydro-5,8-naphthoquinone (9), the latter being derived from (R)-citramalic acid (3). The natural products (1S,3S)-austrocortirubin (2) and (1R,3R)-austrocortilutein (5) were also prepared for the first time by using the same strategy.

ChemInform Abstract: Pigments of Fungi. Part 51. Structure and Stereochemistry of Coupled Pre‐Anthraquinones of the Pseudophlegmacin Type from Australian Toadstools Belonging to the Genus Dermocybe.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Pigments of Fungi. LXII. (1S,3R)-Austrocortirubin: Isolation from the Fungus Dermocybe splendida and Synthesis from (S)-Citramalic Acid

(1S,3R)-Austrocortirubin (3), a new naturally occurring red tetrahydroanthraquinone, is isolated from the ethanol extract of the fungus Dermocybe splendida and its structure and stereochemistry are deduced by spectroscopic and chemical methods and are confirmed by synthesis from (S)-citramalic acid (10).

Pigments of fungi. Part 51.1 Structure and stereochemistry of coupled pre-anthraquinones of the pseudophlegmacin type from Australian toadstools belonging to the genus Dermocybe

(3′R,P)-Anhydropseudophlegmacin-9,10-quinone 6′,8′-di-O-methyl ether 4 and the corresponding 1,6′,8′-tri-O-methyl ether 5 are isolated together with the atropisomeric green pigments austroviridin B 10 and austroviridin A 11 from the fruiting bodies of indigenous Australian toadstools belonging to the genus Dermocybe. The structures of these pigments are determined by spectroscopic methods, while their absolute configurations are established from the respective CD spectra and by reductive cleavage of 5 to a mixture of (R)-torosachrysone 8-O-methyl ether 12 and emodin 1-O-methyl ether 14.

Pigments of Fungi. LII Anisochiral Flavomannin 6,6′,8-Tri-O-methyl Ether from an Australian Dermocybe Toadstool

Flavomannin 6,6′,8-tri-O-methyl ether occurs in the fruiting bodies of the Australian toadstool Dermocybe sp. WAT 24274 as an anisochiral mixture of the (3S,3′S,P)- and (3R,3′R,M)-enantiomers (5) and (7), respectively, in which the former predominates to the extent of 50% e.e. The structure of the natural product is determined by spectroscopic methods and the absolute configuration and enantiomeric purity are deduced from the c.d. spectrum and by chemical degradation of the natural product to a mixture of stereoisomeric dihydroanthracenones that has been analysed by chiral h.p.l.c.

Pigments of Fungi. LV. The Absolute Configuration of Dermocanarin 4 and the Structure and Stereochemistry of the Dermocanarins 5, 6, 8 and 9 from Australian Toadstools Belonging to the Genus Cortinarius

The stereochemistry in the dihydroanthracenone ring of dermocanarin 4 (1) is defined as (S) by incorporation of the gentiobioside (2) of (S)-[6-OMe- 13 C]torosachrysone into the dihydroanthracenone ring of dermocanarin 4 by fruiting bodies of Cortinarius sinapicolor. In addition, the new dermocanarins 5 (3), 6 (4), 8 (5) and 9 (6) are isolated from two other indigenous toadstools belonging to Cortinarius and their structure and stereochemistry are deduced from the respective spectroscopic data and by comparison with dermocanarin 4 (1).

ChemInform Abstract: Pigments of Fungi. Part 48. Clavorubin (Ia) from Two Australasian Toadstools of the Genus Cortinarius and the X‐Ray Crystal Structure of the Methyl Ester of 6‐O‐Methylclavorubin (Ib).

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Pigments of Fungi. Part 47. Cardinalic Acid, a New Anthraquinone Carboxylic Acid from the New Zealand Toadstool Dermocybe cardinalis and the Synthesis and X‐Ray Crystal Structure of Methyl 1,7,8‐Tri‐O‐methylcardinalate.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Pigments of Fungi. Part 44. Synthesis of Differentially Protected Chiral Pentane‐1,3,5‐triol Derivatives; Confirmation of the Absolute Configuration of Naturally Occurring 3‐Acetoxy‐2,3‐dihydropiptoporic Acid.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Pigments of Fungi. XLVII. Cardinalic Acid, a New Anthraquinone Carboxylic Acid from the New Zealand Toadstool Dermocybe cardinalis and the Synthesis and X-Ray Crystal Structure of Methyl 1,7,8-Tri-O-methylcardinalate

Cardinalic acid (1,7,8-trihydroxy-6-methoxy-3-methyl-9,10-dioxoanthracene-2-carboxylic acid) (4) and the known anthraquinone carboxylic acids endocrocin (1), dermolutein (2) and cinnalutein (3) have been isolated from the New Zealand toadstool Dermocybe cardinalis. Methyl 1,7,8-tri-O-methylcardinalate (5) has been prepared both by permethylation of the natural product (4) and from 2,6-dichloro-1,4-benzoquinone by two consecutive regioselective Diels–Alder cycloaddition reactions. A single-crystal X-ray structure analysis of the ester (5) corroborates the structure of the natural product (4) and confirms the outcome of both cycloaddition reactions.

Pigments of Fungi. XLVIII Clavorubin from Two Australasian Toadstools of the Genus Cortinarius and the X-Ray Crystal Structure of the Methyl Ester of 6-O-Methylclavorubin

Clavorubin (1,5,6,8-tetrahydroxy-3-methyl-9,10-dioxoanthracene-2-carboxylic acid) (1), previously known only from the ascomycetious rye fungus Claviceps purpurea (‘ergot’), has been isolated from the fruit bodies of two Australasian basidiomycetes belonging to the genus Cortinarius and characterized by spectroscopic and chemical methods. A single-crystal X-ray structure analysis of the methyl ester (4) of 6-O-methylclavorubin establishes unequivocally, for the first time, the structure of the natural product.

Pigments of Fungi. XLVI. New Dimeric Dihydroanthracenones of the Flavomannin Type from an Australian Toadstool of the Genus Dermocybe

cis,cis-4,4′-Dihydroxyflavomannin 6,6′-di-O-methyl ether A (4), 10,10′-dihydroxy-4,4′-dioxoflavomannin 6,6′-di-O-methyl ether A (6) and 4′,10-dihydroxy-4-oxoanhydroflavomannin-9′,10′-quinone 6,6′-di-O-methyl ether A (7), new coupled dihydroanthracenones, and bierythroglaucin (8), a novel dimeric anthraquinone, have been isolated along with emodin (9) and citreorosein (ω-hydroxyemodin) (10) from the purple-brown fruit bodies of the Australian Dermocybe sp. WAT 21566. The structures and relative stereochemistry of the new natural products (4) and (6)–(8) are deduced by spectroscopic and chemical methods.

Pigments of Fungi. XLIV Synthesis of Differentially Protected Chiral Pentane-1,3,5-triol Derivatives; Confirmation of the Absolute Configuration of Naturally Occurring 3-Acetoxy-2,3-dihydropiptoporic Acid

(R)-1-t-Butyldimethylsilyloxy-5-phenylmethoxypentan-3-ol (25), prepared in 68% yield and >99·9% enantiomeric excess over six steps from commercially available but-3-yn-1-ol by Katsuki-Sharpless epoxidation, was converted by way of its 3-methoxymethyl ether (30) into both enantiomers (6) and (11) of methyl 3,5-diacetoxypentanoate. Direct comparison of these substances with the ester derived by oxidative degradation of the fungus pigment 3-acetoxy-2,3-dihydropiptoporic acid (1) confirmed the (R) absolute configuration of the natural product. Some new chemistry of the differentially protected chiral triols (12) and (30) is described.