Derivates of azaphilone Monascus pigments

doi:10.1016/j.bcab.2016.12.014

Biocatalysis and Agricultural Biotechnology

Volume 9, January 2017, Pages 183-194

https://doi.org/10.1016/j.bcab.2016.12.014 Get rights and content

Abstract

Progress Research on Monascus pigments has been very rapidly, includes the discovery of new pigments and methods used for the isolation and identification of new pigments. Currently, nearly fifty seven new pigments have been found which are derivatives of the six main pigments that already exist. The process of discovery of new pigments can not be separated from the process which are carried out during fermentation or during the isolation. This review includes data from all fifty new pigments following chemical structure data, chemical formula, the level of water solubility, the value of Log P, Monascus strain, substrates used in the fermentation process and methode to identification. Data collected from various studies that have been done before, and added with some of the new data. The aim of this review is to give more comprehensive data about Monascus pigments.

Introduction

Monascus pigments (MPs) has long been used as a natural food colorants (natural food colorant), especially in some Asian countries such as South China. Monascus produce red yeast rice, which is rice fermented by a red Monascus sp. Angkak can be used to dye yoghurt, bacon, sausage, and for the preservative of fruits, vegetables, and fish products (Singgih and Julianti, 2015).

Monascus pigments (MPs) have many applications such as coloring agents in foodstuffs and texture industries, pharmacology, medicine and cosmetics (Mostafa and Abbady, 2014). Moreover, MPs have a range of biological activities, such as antimutagenic and anticancer properties (Hsu et al., 2011), antidiabetic effects (Shi and Pan, 2011; Lee et al., 2011) antimicrobial activities (Martlnková et al. 1995; Kim et al., 2006; Vedruscolo et al., 2014), potential anti obesity characteristics (Feng et al., 2012), and capable to producing antioxidants and dimerumic acid (Tseng et al., 2006, Yang et al., 2006, Pyo and Lee, 2007).

Monascus pigments are a group of fungal metabolites called azaphilones. The main pigments produced by Monascus sp, especially M. pilosus, M. ruber and M. purpureus, are six well-known compounds: two yellow pigment monascin and ankaflavin (Chen et al., 1969; Manchand and Whalley, 1973), two orange pigments rubropunctatin and monascorubrin (Chen et al., 1969), and two red pigments monascorubramine and rubropunctamine (Kumasaki et al., 1962; Sweeny et al., 1981).

In the past of decades, more than 57 azaphilone pigments from Monascus species have been identified and characterized including categories and structures, physicochemical properties, detection method, functions and molecular biology. (Feng et al., 2012) and biological activity (Patakova, 2013, Mostafa and Abbady, 2014).

Section snippets

Strain

More than twenty Monascus species are presented in the literature, however only certain species and strains of the fungus Monascus are used to produce MPs which include mainly M. argentinensis (Kim, 2010), M. anka (Shi et al., 2015), M. bakeri, M. floridanus (Vasilyeva et al., 2012), M. kaoliang (Lin and Lizuka, 1982; Cheng et al., 2015), M. lunispora, M. mayor, M. pilosus (Cheng et al., 2013; Wu et al., 2015), M. pubrigerus, M. purpureus (Rezael et al., 2011), M. ruber (Mostafa and Abbady, 2014

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Identification of Monascus pigments and citrinin in Sufu using a novel HPLC-MS/MS method
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Sufu is the traditional fermented soybean products in China. The aim of this study was to establish a rapid and sensitive method for the determination of 3 monascus pigments and citrinin in sufu, assess the content of them in sufu samples obtained from market. The extracted sufu samples were purified by optimized SPE methods: discard the first 1 mL of effluent and collect the rest for HPLC-MS/MS determination. Good linearities were obtained (r > 0.999) in the range of 0.05–10 μg L⁻¹ for citrinin, monascin and monascorubramin, and 0.05–10 mg L⁻¹ for monascorubrin. The method has been successfully applied to the identification of monascus pigments and citrinin in sufu samples, and the Spearman correlation analysis of the concentration was also performed, therefore fulfilling the requirements for mycotoxins analysis. Besides, according to the health risk assessment of citrinin, the health risk caused by intake of sufu was not significant, and the recommended safe sufu consumption rate was 211.0 g person⁻¹ day⁻¹. The established method was fast, sensitive and accurate, was suitable for the analysis of 3 monascus pigments and citrinin in sufu.
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Monascus pigments can potentially replace some synthetic pigments used in many fields, such as food (coloring agent, aroma & flavor enhancer, and condiment), texture, pharmacology, medicine and cosmetics (Mostafa & Abbady, 2014; Shi et al., 2015). It has many excellent properties, including antimicrobial activities, antidiabetic effects, antiobesity characteristics, etc (Feng et al., 2012; Pyo & Lee, 2007; Shi & Pan, 2011; Tseng, Yang, Chang, Lee, & Mau, 2006; Vendruscolo et al., 2016; Yang, Tseng, Lee, & Mau, 2006; Yuliana, Singgih, Julianti, & Blanc, 2017). The pigment will not only act as colorant but also can be used as antimicrobial agent, which can enhance the antimicrobial property of the CMC-monascus pigment inks.
In this study, carboxymethyl chitosan (CMC) based edible inks were prepared and the flexographic and screen printing properties of the inks were investigated. The water soluble carboxymethyl chitosan was prepared through a one-pot, environmental-friendly method in an alkali/urea mixture. The monascus pigment was then mixed with the carboxymethyl chitosan to obtain the inks. The inks showed good printing quality (e.g. pH, scratch resistance, optical density, contact angle and chromatic value) on coated paper after flexographic and screen printing. Also, the obtained inks, with excellent antibacterial activity against E. coli and S. aureus, demonstrated great printing effect on different substrates including different foods. We believe that this water soluble chitosan based edible inks may have potential applications in different food and medical packaging fields.
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Derivates of azaphilone Monascus pigments

Abstract

Introduction

Section snippets

Strain

Phytochem. Lett.

Food Chem.

Phytochemistry

Adv. Drug Deliv. Rev.

Food Chem.

Tetrahedron

Phytochemictry

Biocatal. Agric. Biotechnol.

Process Biochem.

Ind. Crops Prod.

LWT-Food Sci. Technol.

Food Chem.

Biol. Agric. Biotechnol.

LWT

Enzyme Microbiol. Technol.

Azaphilones, furanoisopthalides and amino acids from the extracts of Monascus pilosus-fermented rice (red mold rice) and their chemopreventive effects

J. Agric Food Chem.

Production oc citrinin by various species of Monascus

Biotechnol. Lett.

The structure of monascin

J. Chem. Soc. D.

New metabolite from the fungus Monascus kaoliang

Chem. Nat. Compd.

Comparative study of Monascus sanguines and Monascus purpureus for red pigments production under stress condition

Int. Food Res. J.

Submerged fermentation in wheat substrates for production of Monascus fermentation product and the role of citrinin contamination

Mutat. Res.

Monascus pigments

Appl. Microbiol. Biotechnol.

Effect of aeration condition on production of red pigments by Monascus purpureus growth on kpricly pear juice

Process Biochem.

A new series of coumarin derivates having monoamin oxidase inhibitory activity from Monascus anka

Chem. Pharm. Bull.

Monascus purpureus-fermented product and oral cancer: a review

Appl. Microbiol. Biotechnol.

Monaphilones A-C, three new antiproliferative azaphilone derivates from Monascus purpureus NTU 568

J. Agric Food Chem.

New bioactive orange pigments with yellow fluorescence from Monascus fermented dioscorea

J. Agric Food Chem.

Two new Monascus metabolites with strong blue fluorescence isolated from red yeast rice

J. Agric Food Chem.

Color characteristics of Monascus pigments derived by fermentation with various amino acids

J. Food Chem.