Atrorosins: a new subgroup of Monascus pigments from Talaromyces atroroseus

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Abstract

A new series of azaphilone pigments named atrorosins have been isolated from the filamentous fungus Talaromyces atroroseus. Atrorosins have a similar azaphilone scaffold as the orange Monascus pigment PP-O, with a carboxylic acid group at C-1, but are unique by their incorporation of amino acids into the isochromene system. Despite that the atrorosin precursor PP-O, during fermentation, was initially produced as two isomers (3:2, cis:trans ratio), the atrorosins were surprisingly almost exclusively (99.5%) produced as the cis-form, possibly due to steric interactions with the incorporated amino acid. When grown on complex media, a whole range of atrorosins is produced, whereas individual atrorosins can be produced selectively during fermentation by supplementing with the desired primary amine-containing compound.
Original languageEnglish
JournalApplied Microbiology and Biotechnology
Pages (from-to)1-8
Number of pages8
ISSN0175-7598
DOIs
Publication statusPublished - 2019

Keywords

  • Talaromyces
  • Azaphilone
  • Monascus pigments
  • Structural elucidation

Cite this

@article{731c47ed04cd4bce811460b2f5ee3bdb,
title = "Atrorosins: a new subgroup of Monascus pigments from Talaromyces atroroseus",
abstract = "A new series of azaphilone pigments named atrorosins have been isolated from the filamentous fungus Talaromyces atroroseus. Atrorosins have a similar azaphilone scaffold as the orange Monascus pigment PP-O, with a carboxylic acid group at C-1, but are unique by their incorporation of amino acids into the isochromene system. Despite that the atrorosin precursor PP-O, during fermentation, was initially produced as two isomers (3:2, cis:trans ratio), the atrorosins were surprisingly almost exclusively (99.5{\%}) produced as the cis-form, possibly due to steric interactions with the incorporated amino acid. When grown on complex media, a whole range of atrorosins is produced, whereas individual atrorosins can be produced selectively during fermentation by supplementing with the desired primary amine-containing compound.",
keywords = "Talaromyces, Azaphilone, Monascus pigments, Structural elucidation",
author = "Thomas Isbrandt and Gerit Tolborg and {\O}dum, {Anders Sebastian Rosenkrans} and Mhairi Workman and Larsen, {Thomas Ostenfeld}",
year = "2019",
doi = "10.1007/s00253-019-10216-3",
language = "English",
pages = "1--8",
journal = "Applied Microbiology and Biotechnology",
issn = "0175-7598",
publisher = "Springer",

}

TY - JOUR

T1 - Atrorosins: a new subgroup of Monascus pigments from Talaromyces atroroseus

AU - Isbrandt, Thomas

AU - Tolborg, Gerit

AU - Ødum, Anders Sebastian Rosenkrans

AU - Workman, Mhairi

AU - Larsen, Thomas Ostenfeld

PY - 2019

Y1 - 2019

N2 - A new series of azaphilone pigments named atrorosins have been isolated from the filamentous fungus Talaromyces atroroseus. Atrorosins have a similar azaphilone scaffold as the orange Monascus pigment PP-O, with a carboxylic acid group at C-1, but are unique by their incorporation of amino acids into the isochromene system. Despite that the atrorosin precursor PP-O, during fermentation, was initially produced as two isomers (3:2, cis:trans ratio), the atrorosins were surprisingly almost exclusively (99.5%) produced as the cis-form, possibly due to steric interactions with the incorporated amino acid. When grown on complex media, a whole range of atrorosins is produced, whereas individual atrorosins can be produced selectively during fermentation by supplementing with the desired primary amine-containing compound.

AB - A new series of azaphilone pigments named atrorosins have been isolated from the filamentous fungus Talaromyces atroroseus. Atrorosins have a similar azaphilone scaffold as the orange Monascus pigment PP-O, with a carboxylic acid group at C-1, but are unique by their incorporation of amino acids into the isochromene system. Despite that the atrorosin precursor PP-O, during fermentation, was initially produced as two isomers (3:2, cis:trans ratio), the atrorosins were surprisingly almost exclusively (99.5%) produced as the cis-form, possibly due to steric interactions with the incorporated amino acid. When grown on complex media, a whole range of atrorosins is produced, whereas individual atrorosins can be produced selectively during fermentation by supplementing with the desired primary amine-containing compound.

KW - Talaromyces

KW - Azaphilone

KW - Monascus pigments

KW - Structural elucidation

U2 - 10.1007/s00253-019-10216-3

DO - 10.1007/s00253-019-10216-3

M3 - Journal article

C2 - 31802169

SP - 1

EP - 8

JO - Applied Microbiology and Biotechnology

JF - Applied Microbiology and Biotechnology

SN - 0175-7598

ER -