Toxicity and mutagenicity of molds of the Aspergillus glaucus group. Identification of physcion and three related anthraquinones as main toxic constituents from Aspergillus chevalieri

Polyphasic taxonomy of Aspergillus section Aspergillus (formerly Eurotium), and its occurrence in indoor environments and food

“…2013 (misidentified as A. effusus ), Chen et al. 2014 Aspergillus montevidensis , A. ruber Anthraquinones Catenarin, emodic acid, emodin (= parietin), erythroglaucin, fallacinol, physcion, questin (= emodin 8-O-methylether), questinol, rubrocristin, variecolorquinone A, (2S)-2,3-dihydroxypropyl-1,6,8-trihydroxy-3-methyl-9,10-dioxoanthracene-2-carboxylate, 3-O-(α-D-ribofuranosyl)questinol, 3-O-(α-D-ribofuranosyl)questin, rubrocristin, viocristin, isoviocristin, hydroxyviocristin, eurorubrin, asperinine A, B, ω-hydroxyemodin-5-merthyether, ω-hydroxyrubrocristin Anslow and Raistrick, 1940 , Bachmann et al., 1979 , Bachmann et al., 1982 , Anke et al., 1980a , Anke et al., 1980b , Fujimoto et al., 1999 , Engstrom et al., 1982 , Laatsch and Anke, 1982 , Arai et al., 1989 , Wang et al., 2006 (as Chaetomium globosum ), Smetanina et al., 2007 , Wang et al., 2007c (fungus misidentified as A. variecolor ), Du et al., 2008 , Wang et al., 2008 , Li et al., 2009 , Gomes et al., 2012 , Almeida et al., 2010 , Yan et al., 2012 , Du et al., 2014 , Micheluz et al., 2016 , Visagie et al., 2017 A. brunneus , A. chevalieri , A. cristatus , A. glaucus , A. intermedius , A. leucocarpus , A. mallochii , A. megasporus , A. neocarnoyi , A. niveoglaucus , A. pseudoglaucus , A. ruber , A. tonophilus (Citreorosein was reported from A. penicillioides by Micheluz et al. 2016 ) Asperflavins Anhydroasperflavin, asperflavin, asperflavin ribofuranoside, isoasperflavin Grove 1972a (misidentified as A. flavus ), Anke et al., 1978 , Fujimoto et al., 1999 , Li et al., 2006 (misidentified as Microsporum ), …”

“…2016 ) Asperflavins Anhydroasperflavin, asperflavin, asperflavin ribofuranoside, isoasperflavin Grove 1972a (misidentified as A. flavus ), Anke et al., 1978 , Fujimoto et al., 1999 , Li et al., 2006 (misidentified as Microsporum ), Smetanina et al., 2007 , Du et al., 2008 , Du et al., 2014 A. glaucus , A. pseudoglaucus , A. megasporus Isotorachrysones Isotorachrysone, isotarachrysone 6-O-α-D-ribofuranoside, 8-methoxy-3-methyl-1-naphthalenol-6-O-α-D-ribofuranoside, 8-methoxy-1-naphthalenol-6-O-α-D-ribofuranoside, (+)-variecolorquinone A, aspergiodiquinone Wang et al. 2007a (misidentified as A. variecolor ), Du et al., 2008 , Sun et al., 2013 A. glaucus Aspergiolides Aspergiolide A, B, C, D Du et al., 2007 , Du et al., 2008 , Du et al., 2011 , Sun et al., 2009 , Sun et al., 2013 , Tao et al., 2009 A. glaucus Eurotionones Eurotinone, variecolorquinone B, 2-methyleurotinone, 9-dehydroxyeurotinone, 2-O-methyl-9-dehydroxyeurotinone, 2-O-methyl-4-O-(α-D-ribofuranosyl)-9-dehydroxyeurotinone, all related to anthraquinones, (+) & (−) europhenol A Wang et al., 2007c , Li et al., 2009 , Yan et al., 2012 , Miyake et al., 2014 , Meng et al., 2016 A. ruber Bianthrons ( trans ) & ( cis )-emodin-physcion bianthrone, physcionanthrone (= physciondianthranol), physcion bianthrone (= physcion-dianthrone = physcion anthrone dimer), physcion-anthrone A (= physcion-9-anthrone), physcion anthrone B Ashley et al., 1939 , Bachmann et al., 1979 , Anke et al., 1980a , Anke et al., 1980b A. cristatus , A. chevalieri Asperentins ...…”

A survey of xerophilic Aspergillus from indoor environment, including descriptions of two new section Aspergillus species producing eurotium-like sexual states

“…Most notably, compounds from A. chevalieri were shown to be active against Plasmodium falciparum (malaria), Mycobacterium tuberculosis and cancer cell lines (Kanokmedhakul et al 2011), an antitumor compound was reported from A. cristatus (Almeida et al 2010), while many compounds are known to be antioxidants. They also produce mycotoxins, especially echinulin, flavoglaucin and physcion, which are toxic to animals (Ali et al 1989;Bachmann et al 1979;Cole and Cox 1981;Greco et al 2015;Nazar et al 1984;Rabie et al 1964;Semeniuk et al 1971;Slack et al 2009;Vesonder et al 1988), but toxicity has not been reported in humans. These species are not considered significant human pathogens, because most infections are superficial, with few cases of invasive infections known (de Hoog et al 2014).…”

Analysis of toxic anthraquinones and related compounds with a fused silica capillary column

“…Some conventional methods have been applied in the isolation of quinone derivatives from molds. Thin-layer chromatography was used to isolate three toxic anthraquinone derivatives from Aspergillus chevalieri [6]. Toxic naphthopyrones were isolated by column chromatography using silicic acid as a stationary phase and benzene as a mobile phase [A. Dihydroanthracenone derivatives were also isolated using column chromatography [8].…”