Table 7.
Extrolites reported from Aspergillus section Aspergillus.1
| Biosynthetic family | Compounds | References | Producers |
|---|---|---|---|
| Cyclic dipeptides with a dimethylallyl group | LL-S-490β = N-a-acetylaszonalenine, rugulosuvine | Ellestad et al., 1973, Micheluz et al., 2016 | A. glaucus, A. pseudoglaucus |
| Deoxybrevianamides2 | Deoxybrevianamide E | Micheluz et al. 2016 | A. glaucus (& A penicillioides) |
| Stachybotryamides2 | Stachybotryamide | Micheluz et al. 2016 | A. glaucus |
| Tryprostatins2 | Tryprostatin B | Micheluz et al. 2016 | A. glaucus |
| Tenellins2 | Tenellin | Micheluz et al. 2016 | A. glaucus |
| Echinulins | Echinulin, dehydroechinulin, didehydroechinulin, preechinulin, L-alanyl-L-tryptophan anhydride, (L-valyl-L-tryptophan anhydride, cryptoechinulin G, neoechinulin, neoechinulin A, neoechinulin B (= E-10), neoechinulin C (= cryotoechinulin A = E-8), neoechinulin D, neoechinulin E = cryptoechinulin C, dihydroneoechinulin B, isoechinulin A, isoechinulin B, isoechinulin C, dihydroxyisoechinulin A, rubrumazine A, rubrumazine B, rubrumazine C, tardioxopiperazine A, tardioxopiperazine B, dehydrovariecolorin L, variecolorin A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, golmaneone, 12-demethyl-12-oxo-eurotechinulin A, B, alkaloid E-7, cristatumin A, cristatumin B, cristatumin C,3 cristatumin D, cristatumin E,3 critatumin F, eurocristatine3 | Quilico and Panazzi, 1943, Quilico and Cardini, 1950, Barbetta et al., 1969, Nakashima and Slater, 1971, Allen, 1972, Dossena et al., 1974, Cardillo et al., 1974, Cardillo et al., 1975, Marchelli et al., 1975, Nagasawa et al., 1975, Nagasawa et al., 1976, Hamasaki et al., 1976a, Hamasaki et al., 1976b, Stipanovic and Schroeder, 1976, Stipanovics et al., 1976, Inoue et al., 1977a, Marchelli et al., 1977, Gatti et al., 1978, Podojil et al., 1979, Fujimoto et al., 1999 (fungus was A. pseudoglaucus, misidentified as Microascus tardifaciens), Li et al., 2004a, Li et al., 2004b, Smetanina et al., 2007, Wang et al., 2007a, Wang et al., 2007b, Wang et al., 2007c, Li et al., 2008a, Li et al., 2008b, Slack et al., 2009, Almeida et al., 2010, Zhou et al., 2010 (misidentified as a Penicillium griseofulvum); Du et al., 2012, Gao et al., 2011, Gao et al., 2012a, Gomes et al., 2012, Yan et al., 2012, Gao et al., 2013 (misidentified as A. effusus), Wu et al., 2013, Miyake et al., 2014, Zou et al., 2014, Meng et al., 2015, Micheluz et al., 2016, Visagie et al., 2017 | A. brunneus, A. chevalieri, A. cristatus, A. glaucus, A. mallochii, A. megasporus, A. montevidensis, A. proliferans, A. pseudoglaucus, A. ruber (Arestricticins A, B, cristatin A and asperglaucide were reported from A. restrictus and A. penicillioides (Itabashi et al. 2006), indicating a strong relationship between species in sections Aspergillus and Restricti.) |
| Quinolone | Quinolactacin A1, Quinolactacin A2, Quinolactacin B | Visagie et al. 2017 | A. megasporus |
| Chimeric echinulins and auroglaucins | Cryptoechinulin B (= aurechinulin), (+) and (−)-cryptoechinulin D, 7-O-methylvariecolortide A, variecolortide A, (+) & (−) variecolortide B, (+) & (−) variecolortide C, (+) & (−) 7-isopentenylcryptoechinuline D, dihydrocryptoechinulin D, effusin A | Gatti et al., 1976, Inoue et al., 1977b, Li et al., 2010, Wang et al., 2007b (misidentified as A. variecolor); Kuttruff et al., 2011, Yan et al., 2012, Gao et al., 2012b (misidentified as A. effusus), Gao et al. 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), 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 | Asperentin (=cladosporin), cladosporin 8-O-methylether (= asperentin 8-O-methyl ether), aspyran, asperentin-6-O-methyl ether, 5′-hydroxy-asperentin-8-methyl ether, 5′-hydroxyasperentin, 4′-hydroxyasperentin, (isocladosporin), 6-O-α-D-ribosylasperentin, 6-O-α-D-ribosyl-8-O-methylasperentin, 5-hydroxyl-6-O-methylasperentin | Grove, 1972b, Grove, 1973, Cattel et al., 1973 (misidentified as A. flavus), Podojil et al., 1979, Fujimoto et al., 1999, Wang et al., 2006 (as Chaetomium globosum), Slack et al., 2009, Kimura et al., 2012, Wang et al., 2013 (as Cladosporium cladosporioides), Kozlovsky et al., 2014, Tang et al., 2014, Greco et al., 2015, Cochrane et al., 2016 (from Cladosporium cladosporioides) | A. chevalieri, A. montevidensis, A. proliferans, A. pseudoglaucus, A. ruber |
| Mycophenolic acids | 5,7-dihydroxy-4-methylphthalide, 6-farnesyl-5,7-dihydroxy-4-methylphthalide , mycophenolic acid | Grove, 1972a, Grove, 1972b (misidentified as A. flavus), Burkin and Kononenko, 2010, Gao et al., 2011, Gao et al., 2012a, Gao et al., 2012b, Séguin et al., 2014 | A. pseudoglaucus, A. ruber (traces of mycophenolic acid), A. montevidensis (traces of mycophenolic acid), A. chevalieri (traces of mycophenolic acid) |
| Pseurotins2 | Pseurotin A & D | Micheluz et al. 2016 | A. glaucus |
| Orsellinic acid derivatives | Cristatumside A | Du et al. 2014 | A. cristatus |
| Kotanins | Desmethylkotanin, kotanin | Büchi et al. 1971 | A. glaucus |
| Auroglaucins | Auroglaucin, flavoglaucin, dihydroauroglaucin, isodihydroauroglaucin, isotetrahydroauroglaucin (= dihydroflavoglaucin), chaetopyranin, 2-(2′,3-epoxy-1′,3-heptadienyl)-6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde, tetrahydroauroglaucin, (E)-2-(hept-1-enyl)-3-(hydroxymethyl)-5-(3-methylbut-2-enyl)benzene-1,4-diol, (E)-4-(hept-1-enyl)-7-(3-methylbut-2-enyl)-2,3-dihydrobenzofuran-2,5-diol, eurotirumin, 2-(2′,3-epoxy-1′-heptenyl)-6-hydroxy-5-(3″-methyl-2″-butenyl)benaldehyde, (E)-6-hydroxy-7-(3-methyl-2-butenyl)-2-(3-oxobut-1-enyl)chroman-5-carbaldehyde, 2-(1′,5′-heptadienyl)3,6-dihydroxy-5-(3″-methyl-2″butenyl)benzaldehyde, aspergentisyl A, B, aspergin | Gould and Raistrick, 1934, Ashley et al., 1939, Quilico et al., 1949, Birch, 1958, Inoue et al., 1977c, Hamasaki et al., 1980, Hamasaki et al., 1981, Ishikawa et al., 1984, Ishikawa et al., 1985, Li et al., 2006, Wang et al., 2006 (as Chaetomium globosum), Li et al., 2008a, Li et al., 2008b, Miyake et al., 2009, Slack et al., 2009, Almeida et al., 2010, Miyake et al., 2010a, Miyake et al., 2010b, Gao et al., 2011, Gao et al., 2012a, Gao et al., 2012b, Gao et al., 2013 (misidentified as A. effusus), Sun et al., 2013, Wu et al., 2013, Miyake et al., 2014, Visagie et al., 2017 | A. brunneus, A. glaucus, A. glaucus? (as Microsporum sp.), A. chevalieri, A. cristatus, A glaucus, A. montevidensis, A. mallochii, A. pseudoglaucus, A. ruber |
| Heveadrides | Epiheveadride, heveadride | Slack et al. 2009 | A. glaucus, A. montevidensis, A. ruber |
| Chaetoviridins | Chaetoviridin A | Micheluz et al. 2016 | A. glaucus |
| Eurocin | Eurocin | Oeemig et al. 2012 | A. montevidensis |
| Diterpene antibiotics | LL-S491β, LL-S491γ | Ellestad et al. 1972 | A. chevalieri |
| Asperglaucide | Asperglaucide | Cox et al. 1976 | A. glaucus |
| Hopane type triterpenoids | 2-Hydroxydiplopterol | Wang et al. 2009 (misidentified as A variecolor) | Aspergillus section Aspergillus species |
| Mycotoxin production by Aspergillus section Aspergillus strains checked but not confirmed in this study | |||
| Citrinin (produced by a contaminant?) | Li et al. 2006 | A. glaucus? (as Microsporum sp.) | |
| Aflatoxins (not produced) (Bachmann et al., 1979, Bachmann et al., 1982, Blaser et al., 1980, Varga et al., 2009) | Kulik and Holaday, 1966, Leitao et al., 1989, Jayraman and Kalyanasundaram, 1990, El-Kady et al., 1994, Ahmed et al., 2005, Fraga et al., 2007, Fraga et al., 2008 | A. chevalieri, A. intermedius, A. pseudoglaucus, A. ruber | |
| Sterigmatocystin (not produced) (Rank et al. 2011) | Schroeder and Kelton, 1975, Moubasher et al., 1977, Szebiotko et al., 1981, Karo and Hadlok, 1982, Soboleva and Kurmanov, 1984, El-Kady et al., 1994, Ahmed et al., 2005 | A. chevalieri, A. intermedius, A. montevidensis, A. pseudoglaucus, A. ruber | |
| Xanthocillin X (not produced) (Bachmann et al., 1979, Bachmann et al., 1982, Blaser et al., 1980) | Coveney et al. 1966 | A. glaucus | |
| Gliotoxin (not produced) (Bachmann et al., 1979, Bachmann et al., 1982, Blaser et al., 1980) | Wilkinson and Spilsbury, 1965, El-Kady et al., 1994 | A. chevalieri, A. intermedius, A. pseudoglaucus | |
| Ochratoxin A (not produced) (Bachmann et al., 1979, Bachmann et al., 1982, Blaser et al., 1980) | Chelkowski et al., 1987, El-Kady et al., 1994, Al-Julaifi, 2003 | A. glaucus, A. montevidensis, A. pseudoglaucus | |
1
Chevalone A-D, aszonapyrone A-B, eurochevalierine and CJ-12662 reported from Eurotium chevalieri were produced by a strain from Aspergillus section Fumigati (see Frisvad & Larsen 2016).
2
These compounds may have been produced by a strain of Aspergillus section Fumigati contaminating A. pseudoglaucus (Eurotium repens), as they have been found co-occurring in Aspergillus fumigatus (see Frisvad & Larsen 2016), but never in Aspergillus section Aspergillus.
3
Diketopiperazine dimers.