Literature DB >> 34921328

Azaphilone alkaloids: prospective source of natural food pigments.

Lujie Liu1,2, Zhilong Wang3.   

Abstract

Azaphilone, biosynthesized by polyketide synthase, is a class of fungal metabolites. In this review, after brief introduction of the natural azaphilone diversity, we in detail discussed azaphilic addition reaction involving conversion of natural azaphilone into the corresponding azaphilone alkaloid. Then, setting red Monascus pigments (a traditional food colorant in China) as example, we presented a new strategy, i.e., interfacing azaphilic addition reaction with living microbial metabolism in a one-pot process, to produce azaphilone alkaloid with a specified amine residue (red Monascus pigments) during submerged culture. Benefit from the red Monascus pigments with a specified amine residue, the influence of primary amine on characteristics of the food colorant was highlighted. Finally, the progress for screening of alternative azaphilone alkaloids (production from interfacing azaphilic addition reaction with submerged culture of Talaromyces sp. or Penicillium sp.) as natural food colorant was reviewed. KEY POINTS: • Azaphilic addition reaction of natural azaphilone is biocompatible • Red Monascus pigment is a classic example of azaphilone alkaloids • Azaphilone alkaloids are alterative natural food colorant.
© 2021. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.

Entities:  

Keywords:  Azaphilic addition reaction; Azaphilone; Azaphilone alkaloid; Food colorant; Red Monascus pigments

Mesh:

Substances:

Year:  2021        PMID: 34921328     DOI: 10.1007/s00253-021-11729-6

Source DB:  PubMed          Journal:  Appl Microbiol Biotechnol        ISSN: 0175-7598            Impact factor:   4.813


  49 in total

1.  Sclerotiorine, C(20)H(20)O(5)Cl, a chlorine-containing metabolic product of Penicillium sclerotiorum van Beyma.

Authors:  T P Curtin; J Reilly
Journal:  Biochem J       Date:  1940-11       Impact factor: 3.857

2.  Water-soluble fluorescent red colorant production by Talaromyces amestolkiae.

Authors:  Fernanda de Oliveira; Danielle Biscaro Pedrolli; Maria Francisca Simas Teixeira; Valéria de Carvalho Santos-Ebinuma
Journal:  Appl Microbiol Biotechnol       Date:  2019-06-24       Impact factor: 4.813

3.  Variations in Monascus pigment characteristics and biosynthetic gene expression using resting cell culture systems combined with extractive fermentation.

Authors:  Gong Chen; Qi Bei; Tao Huang; Zhenqiang Wu
Journal:  Appl Microbiol Biotechnol       Date:  2017-11-02       Impact factor: 4.813

4.  Synthesis of azaphilone-based chemical libraries.

Authors:  Mathieu Achard; Aaron B Beeler; John A Porco
Journal:  ACS Comb Sci       Date:  2012-02-24       Impact factor: 3.784

5.  Production and Identification of N-Glucosylrubropunctamine and N-Glucosylmonascorubramine from Monascus ruber and Occurrence of Electron Donor-Acceptor Complexes in These Red Pigments.

Authors:  H Hajjaj; A Klaebe; M O Loret; T Tzedakis; G Goma; P J Blanc
Journal:  Appl Environ Microbiol       Date:  1997-07       Impact factor: 4.792

6.  Genetic localization and in vivo characterization of a Monascus azaphilone pigment biosynthetic gene cluster.

Authors:  Bijinu Balakrishnan; Suman Karki; Shih-Hau Chiu; Hyun-Ju Kim; Jae-Won Suh; Bora Nam; Yeo-Min Yoon; Chien-Chi Chen; Hyung-Jin Kwon
Journal:  Appl Microbiol Biotechnol       Date:  2013-03-17       Impact factor: 4.813

7.  Orange, red, yellow: biosynthesis of azaphilone pigments in Monascus fungi.

Authors:  Wanping Chen; Runfa Chen; Qingpei Liu; Yi He; Kun He; Xiaoli Ding; Lijing Kang; Xiaoxiao Guo; Nana Xie; Youxiang Zhou; Yuanyuan Lu; Russell J Cox; István Molnár; Mu Li; Yanchun Shao; Fusheng Chen
Journal:  Chem Sci       Date:  2017-04-24       Impact factor: 9.825

8.  Talaromyces atroroseus, a new species efficiently producing industrially relevant red pigments.

Authors:  Jens C Frisvad; Neriman Yilmaz; Ulf Thrane; Kasper Bøwig Rasmussen; Jos Houbraken; Robert A Samson
Journal:  PLoS One       Date:  2013-12-19       Impact factor: 3.240

9.  Hybridorubrins A-D: Azaphilone Heterodimers from Stromata of Hypoxylon fragiforme and Insights into the Biosynthetic Machinery for Azaphilone Diversification.

Authors:  Kevin Becker; Sebastian Pfütze; Eric Kuhnert; Russell J Cox; Marc Stadler; Frank Surup
Journal:  Chemistry       Date:  2020-12-10       Impact factor: 5.236

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