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

Chen, Wanping; Chen, Runfa; Liu, Qingpei; He, Yi; He, Kun; Ding, Xiaoli; Kang, Lijing; Guo, Xiaoxiao; Xie, Na; Zhou, Youxiang; Lu, Yuanyuan; Cox, Russell J.; Molnár, István; Li, Mu; Shao, Yanchun; Chen, Fusheng

doi:10.1039/c7sc00475c

Cited by 250 publications

(337 citation statements)

References 39 publications

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“…Based on their UV–Visible spectra, fluorescence spectra and mass spectra, Y1 was the reported intermediate azanigerone E (Zabala et al 2012; Chen et al 2017), and we concluded that the other compounds ( Y2 – Y4 ) were novel and had not been previously reported (Table 1; Fig. 2).…”

Section: Discussionmentioning

confidence: 60%

Rising temperature stimulates the biosynthesis of water-soluble fluorescent yellow pigments and gene expression in Monascus ruber CGMCC10910

et al. 2017

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Monascus species can produce secondary metabolites that have a polyketide structure. In this study, four types of extracellular water-soluble yellow pigments (Y1–Y4) were generated by submerged fermentation with Monascus ruber CGMCC 10910, of which Y3 and Y4 had strong yellow fluorescence. The composition of the pigment mixtures was closely related to the fermentation temperature. The dominating pigments changed from Y1 to Y3 and Y4 when fermentation temperature increased from 30 to 35 °C. Increasing the temperature to 35 °C changed the metabolic pathways of the pigments, which inhibited the biosynthesis of Y1 and enhanced the biosynthesis of Y3 and Y4. Moreover, the yield of Y1 reduced insignificantly, while the yields of Y3 and Y4 increased by 98.21 and 79.31% respectively under two-stage temperature fermentation condition. The expression levels of the relative pigment biosynthetic genes, such as MpFasA2, MpFasB2, MpPKS5, mppR1, mppB, and mppE, were up-regulated at 35 °C. The two-stage temperature strategy is a potential method for producing water-soluble Monascus yellow pigments with strong yellow fluorescence.Electronic supplementary materialThe online version of this article (doi:10.1186/s13568-017-0441-y) contains supplementary material, which is available to authorized users.

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Section: Discussionmentioning

confidence: 60%

Rising temperature stimulates the biosynthesis of water-soluble fluorescent yellow pigments and gene expression in Monascus ruber CGMCC10910

et al. 2017

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“…Monascus species have been used for centuries in the world, especially in China, Japan, and other Asian countries, for the production of many industrially-and medically-important compounds including Monascus pigments (MPs), monacolin K and so on [1][2][3][4][5]. Each species from the genus Monascus produces unique secondary metabolites, most of which are polyketides produced by the action of a mega enzyme known as polyketide synthase (PKS) [6].…”

Section: Introductionmentioning

confidence: 99%

Transfigured Morphology and Ameliorated Production of Six Monascus Pigments by Acetate Species Supplementation in Monascus ruber M7

Virk

Ramzan

Virk³

et al. 2020

Microorganisms

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Monascus species have been used for the production of many industrially and medically important metabolites, most of which are polyketides produced by the action of polyketide synthases that use acetyl-CoA and malonyl-CoA as precursors, and some of them are derived from acetate. In this study the effects of acetic acid, and two kinds of acetates, sodium acetate and ammonium acetate at different concentrations (0.1%, 0.25% and 0.5%) on the morphologies, biomasses, and six major Monascus pigments (MPs) of M. ruber M7 were investigated when M7 strain was cultured on potato dextrose agar (PDA) at 28 °C for 4, 8, 12 days. The results showed that all of the added acetate species significantly affected eight above-mentioned parameters. In regard to morphologies, generally the colonies transformed from a big orange fleecy ones to a small compact reddish ones, or a tightly-packed orange ones without dispersed mycelia with the increase of additives concentration. About the biomass, addition of ammonium acetate at 0.1% increased the biomass of M. ruber M7. With respect to six MPs, all acetate species can enhance pigment production, and ammonium acetate has the most significant impacts. Production of monascin and ankaflavin had the highest increase of 11.7-fold and 14.2-fold in extracellular contents at the 8th day when 0.1% ammonium acetate was supplemented into PDA. Intracellular rubropunctatin and monascorubrin contents gained 9.6 and 6.46-fold at the 8th day, when 0.1% ammonium acetate was added into PDA. And the extracellular contents of rubropunctamine and monascorubramine were raised by 1865 and 4100-fold at the 4th day when M7 grew on PDA with 0.5% ammonium acetate.

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“…in China. It was well known that there were three kinds of pigments in monascus pigments, orange (monascorubrin – C 23 H 26 O 5 and rubropunctatin – C 21 H 22 O 5 ), red (monascorubramine – C 23 H 27 NO 4 and rubropunctamine – C 21 H 23 NO 4 ), and yellow pigment (monascin – C 21 H 26 O 5 and ankaflavin – C 23 H 30 O 5 ) . Since traditional microbial isolation and pigment extraction were replaced by novel fermentation technology and genetic engineering techniques, there are, currently, nearly 57 new pigments which are derivatives of the six well‐known pigments that already exist .…”

Section: Introductionmentioning

confidence: 99%

A New Method to Purify Hydroxyl Monascus Red Pigment by Retrogradation of Both Pigments and Maize Amylopectin

Lian

Jiang

et al. 2019

Starch - Stärke

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In monascus red pigment (MRP) products, there exist many components such as polypeptides, amino acids, polysaccharide, and citrinin (toxin). The existence of those components lowers the purity of pigments and brings a great security problem. Hydroxyl MRP has been found in products of China and other countries. This paper presents a new method to isolate hydroxyl MRP by retrograded maize amylopectin (MA) and proposes the mechanism involved based on investigation of Xray‐diffraction, IR and 13C solid NMR spectra. The research results have shown that the optimum retrogradation parameters for purification of hydroxyl MRP are as follows: the ratio of pigments and MA is 1:1, autoclaving temperature 120 °C and time, 20 min, aging temperature 4 °C and time needed, 48 h. Most non‐pigment components without hydroxyls in the samples are dissolved in solution when retrograded MA containing MRP has been hydrolyzed by amylase with only MA and MRP left in the precipitatate. Such precipitation can redissolve in aqueous KOH to open hydrogen bond and the MA in solution can be distilled by ethanol in neutral pH, and then the purified pigments in solution can be concentrated and dried. Every 100 g MA can isolate 68.0 g MRP. The results of IR and 13C solid NMR have indicated that hydrogen bonds might form between C7 of pigment and C1 of MA, also, C10 of pigment and C3 or C2 of MA. Retrogradation is surely a simple, inexpensive, and valid method to isolate pigments with hydroxyl groups and citrinin.

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

Abstract: Each major step leading to the classical yellow, orange and red constituents of Monascus azaphilone pigments was defined.

Cited by 250 publications

References 39 publications

Rising temperature stimulates the biosynthesis of water-soluble fluorescent yellow pigments and gene expression in Monascus ruber CGMCC10910

Rising temperature stimulates the biosynthesis of water-soluble fluorescent yellow pigments and gene expression in Monascus ruber CGMCC10910

Transfigured Morphology and Ameliorated Production of Six Monascus Pigments by Acetate Species Supplementation in Monascus ruber M7

A New Method to Purify Hydroxyl Monascus Red Pigment by Retrogradation of Both Pigments and Maize Amylopectin

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