Mpp7 controls regioselective Knoevenagel condensation during the biosynthesis of Monascus azaphilone pigments

Balakrishnan, Bijinu; Chen, Chien-Chi; Pan, Tzu‐Ming; Kwon, Hyung‐Jin

doi:10.1016/j.tetlet.2014.01.090

Cited by 51 publications

(48 citation statements)

References 20 publications

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“…A MpigE ‐deleted mutant of M. ruber yielded 4 types of yellow pigments but very few red pigments, suggesting that MpigE may be involved in the conversion of different pigment compositions (Liu and others ). Targeted inactivation of the mpp7 gene (the homolog of MpigN ) in M. pilosus resulted in the abolition of the main pigment components, and it was proposed that Mpp7 assists in regioselective Knoevenagel aldol condensation during pigment biosynthesis (Balakrishnan and others ). The product profile of mppF (the homolog of MpigO ), mppA (the homolog of MpigC ), and mppC (the homolog of MpigE ) mutants of M. purpureus substantiate that MppA‐mediated ω‐2 ketoreduction is a prerequisite for the synthesis of the pyranoquinone bicyclic core of the Monascus pigments and MppC activity determines the regioselectivity of the spontaneous Knoevenagel condensation (Balakrishnan and others ).…”

Section: Monascus Molecular Biology a New Breakthrough (From The Latmentioning

confidence: 99%

Edible Filamentous Fungi from the Species Monascus: Early Traditional Fermentations, Modern Molecular Biology, and Future Genomics

Chen

Zhou

et al. 2015

Comp Rev Food Sci Food Safe

192

154

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Monascus spp. are filamentous fungi famous for their fermented products, especially red mold rice (RMR), a traditional fermented food in East Asian areas with a very long edible history documented back to the Han dynasty (BC 202-AD 220) in China. Nowadays, RMR and its related products involve a very large industry from artisanal traditional fermentations to food companies to medicine manufacturers, which are distributed worldwide. Modern studies have shown that Monascus spp. are able to produce abundant beneficial secondary metabolites, such as monacolins (cholesterollowering agents), γ -amino butyric acid (an antihypertensive substance), dimerumic acid (an antioxidant), and pigments (food-grade colorants), and some strains can also secrete citrinin, a nephrotoxic metabolite. Monascus-related studies have received much attention because of their wide applications. However, to our knowledge, no systematic review on the progress of Monascus research has ever been published. In this review, the progress of research on Monascus is summarized into 3 stages: Monascus fermentation, Monascus molecular biology, and Monascus genomics. This review covers the past history, current status, and future direction of Monascus research, contributing to a comprehensive understanding of Monascus research progress.

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Section: Monascus Molecular Biology a New Breakthrough (From The Latmentioning

confidence: 99%

Edible Filamentous Fungi from the Species Monascus: Early Traditional Fermentations, Modern Molecular Biology, and Future Genomics

Chen

Zhou

et al. 2015

Comp Rev Food Sci Food Safe

192

154

View full text Add to dashboard Cite

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“…The synthesis of the new red pigments might be partly same to that of monasfluol in Ref. [20]. The identification of the newly genes to control synthesis of monascus red pigments in Monascus ruber M7 will help us to know the mystery of Monascus metabolism [21,22].…”

Section: Chemical Structure Of the New Monascus Red Pigmentmentioning

confidence: 99%

Two new monascus red pigments produced by Shandong Zhonghui Food Company in China

Lian

Liu

Dong

et al. 2014

Eur Food Res Technol

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“…We previously identified MAz biosynthetic gene clusters in Monascus pilosus (Balakrishnan et al 2013) and M. purpureus (Balakrishnan et al 2014a) (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

“…2). Subsequent gene knockout studies in M. purpureus led us to the isolation of MAz biosynthetic intermediates, helping us to elucidate the biosynthetic pathway (Balakrishnan et al 2013;2014a;2014b;Bijinu et al 2014;Balakrishnan et al 2017a;2017b) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

“…The acyltransferase MppB then decorates the resulting intermediate with a 3-oxo-acyl moiety that is generated by MpFAS2 (Balakrishnan et al 2014b). It has also been proposed that subsequent modifications by Mpp7 and MppC generate a hypothetical intermediate (MAz-INT) that then enters into either a reductive (yellow MAz) or an oxidative (orange MAz) pathway (Balakrishnan et al 2014a;Bijinu et al 2014) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

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Selective production of red azaphilone pigments in a Monascus purpureus mppDEG deletion mutant

Balakrishnan

Lim

Hwang

et al. 2017

JABC

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The Monascus azaphilone (MAz) pigment is a wellknown food colorant that has yellow, orange and red components. The structures of the yellow and orange MAz differ by two hydride reductions, with yellow MAz being the reduced form. Orange MAz can be non-enzymatically converted to red MAz in the presence of amine derivatives. It was previously demonstrated that mppE and mppG are involved in the biosynthesis of yellow and orange MAz, respectively. However, ΔmppE and ΔmppG knockout mutants maintained residual production of yellow and orange MAz, respectively. In this study, we deleted the region encompassing mppD, mppE and mppG in M. purpureus and compared the phenotype of the resulting mutant (ΔmppDEG) with that of an mppD knockout mutant (ΔmppD). It was previously reported that the ΔmppD strain retained the ability to produce MAz but at approximately 10% of the level observed in the wildtype strain. A chemical analysis demonstrated that the ΔmppDEG strain was still capable of producing both yellow and orange MAz, suggesting the presence of minor MAz route(s) not involving mppE or mppG. Unexpectedly, the ΔmppDEG strain was observed to accumulate fast-eluting pigments in a reverse phase high-performance liquid chromatography analysis. A LC-MS analysis identified these pigments as ethanolamine derivatives of red MAz, which had been previously identified in an mppE knockout mutant that produces high amounts of orange MAz.Although the underlying mechanism is largely unknown, this study has yielded an M. purpureus strain that selectively accumulates red MAz.

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Mpp7 controls regioselective Knoevenagel condensation during the biosynthesis of Monascus azaphilone pigments

Cited by 51 publications

References 20 publications

Edible Filamentous Fungi from the Species Monascus: Early Traditional Fermentations, Modern Molecular Biology, and Future Genomics

Edible Filamentous Fungi from the Species Monascus: Early Traditional Fermentations, Modern Molecular Biology, and Future Genomics

Two new monascus red pigments produced by Shandong Zhonghui Food Company in China

Selective production of red azaphilone pigments in a Monascus purpureus mppDEG deletion mutant

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