“…The isolated compounds were found to be members of the compound class azaphilones, a diverse group of compounds, such as the ones obtained from various Monascus species, i.e. the so-called Monascus pigments Tables 1 1 H and 13 C NMR shifts for (Gao et al 2013), including the newly described subclass atrorosins of which we recently reported nineteen new analogues (Isbrandt et al 2020). The exact biosynthetic pathway of these compounds have not been fully elucidated, although some work has been done in order to propose a possible route (Hajjaj et al 1999;Somoza et al 2012;Liu et al 2014;Woo et al 2015;Chen et al 2017;Tolborg et al 2017).…”
Section: Discussionmentioning
confidence: 99%
“…As we have recently discovered for the compound class atrorosins (Isbrandt et al 2020 ), the incorporation of nitrogen into the isochromene system can be done using various primary amine containing compounds (Tolborg et al 2020 ). We speculate that the nitrogen, and additional carbons and oxygen in 3 originate from a decarboxylated serine moiety, i.e.…”
Section: Discussionmentioning
confidence: 99%
“…The use of natural or naturally derived pigments for the food and cosmetics industry has in recent years been of increasing interest, and filamentous fungi have long been known to produce various colourful secondary metabolites. Several of such compounds exist within the class of azaphilones, such as atrorosins, a group of red pigments that we recently characterised (Isbrandt et al 2020 ). Azaphilones are common in the three large genera Aspergillus , Penicillium and Talaromyces (Osmanova et al 2010 ; Samson et al 2011 ; Romsdahl and Wang 2019 ).…”
Three new azaphilones, sassafrin E (1), sassafrin F (2), and sassafrinamine A (3), were isolated from the filamentous fungus Aspergillus neoglaber. The structures of the compounds were determined by nuclear magnetic resonance spectroscopy, and were found to be novel analogues of two already known compound classes; sassafrins and berkchaetoazaphilones. Sassafrin E and F were both oxygen containing, while sassafrinamine A additionally contained a nitrogen atom, originating from an aminoethanol moiety, as well as extensive conjugation resulting in an intense purple colour of the pure compound. The structure of sassafrin E was further confirmed using deuterium exchange experiments coupled with high-resolution tandem mass spectrometry.
“…The isolated compounds were found to be members of the compound class azaphilones, a diverse group of compounds, such as the ones obtained from various Monascus species, i.e. the so-called Monascus pigments Tables 1 1 H and 13 C NMR shifts for (Gao et al 2013), including the newly described subclass atrorosins of which we recently reported nineteen new analogues (Isbrandt et al 2020). The exact biosynthetic pathway of these compounds have not been fully elucidated, although some work has been done in order to propose a possible route (Hajjaj et al 1999;Somoza et al 2012;Liu et al 2014;Woo et al 2015;Chen et al 2017;Tolborg et al 2017).…”
Section: Discussionmentioning
confidence: 99%
“…As we have recently discovered for the compound class atrorosins (Isbrandt et al 2020 ), the incorporation of nitrogen into the isochromene system can be done using various primary amine containing compounds (Tolborg et al 2020 ). We speculate that the nitrogen, and additional carbons and oxygen in 3 originate from a decarboxylated serine moiety, i.e.…”
Section: Discussionmentioning
confidence: 99%
“…The use of natural or naturally derived pigments for the food and cosmetics industry has in recent years been of increasing interest, and filamentous fungi have long been known to produce various colourful secondary metabolites. Several of such compounds exist within the class of azaphilones, such as atrorosins, a group of red pigments that we recently characterised (Isbrandt et al 2020 ). Azaphilones are common in the three large genera Aspergillus , Penicillium and Talaromyces (Osmanova et al 2010 ; Samson et al 2011 ; Romsdahl and Wang 2019 ).…”
Three new azaphilones, sassafrin E (1), sassafrin F (2), and sassafrinamine A (3), were isolated from the filamentous fungus Aspergillus neoglaber. The structures of the compounds were determined by nuclear magnetic resonance spectroscopy, and were found to be novel analogues of two already known compound classes; sassafrins and berkchaetoazaphilones. Sassafrin E and F were both oxygen containing, while sassafrinamine A additionally contained a nitrogen atom, originating from an aminoethanol moiety, as well as extensive conjugation resulting in an intense purple colour of the pure compound. The structure of sassafrin E was further confirmed using deuterium exchange experiments coupled with high-resolution tandem mass spectrometry.
“…Natively, T. atroroseus produces a group of red pigments, called atrorosins. These pigments were first isolated, chemically characterised and described by the co‐founders of Chromologics in collaboration with the Natural Product Chemistry group from the Technical University of Denmark (DTU) [ 4‐5 ] . T. atroroseus was only sequenced a couple of years ago and the Chromologics team and researchers at DTU Bioengineering have already mapped the biosynthetic pathway of the pigments.Transitioning from traditional farming processes to modern biotechnological production strategies would eliminate many of the environmental challenges that are associated with agriculturally derived natural colourants.…”
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