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PubMed2005

Characterization of an hyperpigmenting mutant of Monascus purpureus IB1: identification of two novel pigment chemical structures.

Monascus purpureus IB1 produces about 50-fold higher levels of azaphilone pigments than M. purpureus NRRL1596. Differently pigmented mutants were obtained from M. purpureus IB1 by nitrosoguanidine treatment. A highly pigmented strain, M. purpureus HP14, was found to lack the formation of the classical yellow and orange azaphilones and was found to produce only about 10% of the red azaphilone pigments. The intense color was associated with novel pigments as shown by high-performance liquid chromatography (HPLC). The addition of hexanoic acid to M. purpureus IB1 resulted in higher volumetric and specific red pigment productivity, but in a complete absence of the classical orange azaphilones, while the classical yellow and red azaphilone pigments were severely reduced; new peaks corresponding to less hydrophobic pigments were found in hexanoic-supplemented cultures by HPLC. Purification of pigments from hexanoic-supplemented cultures showed the presence of five new pigments as indicated by the absorption spectra and HPLC analysis. Two of them, R3 and Y3, were characterized by nuclear magnetic resonance as 9-hexanoyl-3-(2-hydroxypropyl)-6a-methyl-9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione and 4-[2,4-dihydroxy-6-(3-hydroxybutanethioyloxy)-3-methylphenyl]-3,4-dihydroxy-3,6-dimethylheptanoic acid. These pigments were also found to be present in cultures of the high-producing mutant M. purpureus HP14. These new pigments are less hydrophobic than the classical azaphilones and may have better properties as natural colorants in the food industry.

Chromatography, High Pressure Liquid↗
PubMed2006

Optimization of nutrient parameters for lovastatin production by Monascus purpureus MTCC 369 under submerged fermentation using response surface methodology.

Lovastatin, an inhibitor of HMG-CoA reductase, was produced by submerged fermentation using Monascus purpureus MTCC 369. Five nutritional parameters screened using Plackett-Burman experimental design were optimized by Box-Behnken factorial design of response surface methodology for lovastatin production in shake flask cultures. Maximum lovastatin production of 351 mg/l were predicted in medium containing 29.59 g/l dextrose, 3.86 g/l NH4Cl, 1.73 g/l KH2PO4, 0.86 g/l MgSO4 x 7H2O, and 0.19 g/l MnSO4 x H2O using response surface plots and point prediction tool of DESIGN EXPERT 7.0 (Statease, USA) software.

Culture Media↗
PubMed2006

Isolation and characterization of dihydromonacolin-MV from Monascus purpureus for antioxidant properties.

The methanolic extract of Monascus purpureus cultivated by solid-state fermentation on rice showed strong 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity and better yield as compared to other polarity based extracted fractions. It was selected for further purification of the antioxidant. The activity-guided repeated fractionation of methanolic extract on a silica gel column chromatography yielded a compound that exhibited strong antioxidant activity. Based on the spectroscopic analysis by UV, IR, 1H NMR, 13C NMR, 2D-HSQCT NMR, and MS, the antioxidant isolated was elucidated as a derivative of dihydromonacolin-K, where the ester group is 2-methyl propionate, designated as dihydromonacolin-MV. The DPPH radical was significantly scavenged by the dihydromonacolin-MV (IC50 20+/-1 microg ml-1). The dihydromonacolin-MV showed strong inhibition of lipid peroxidation in a liposome model with an IC50 value of 5.71+/-0.38 microg ml-1 and superoxide radical scavenging activity with an IC50 value of 163.97+/-2.68 microg ml-1.

Antioxidants↗
PubMed2003

Expression of pigmentation genes following electroporation of albino Monascus purpureus.

A UV-induced albino strain of Monascus purpureus was subjected to electroporation in the presence of genomic DNA from a wild-type red strain of the fungus. Eight colonies expressed color after several weeks of growth. The growth rates of all eight color variants were significantly greater than the recipient and donor strains under some culture conditions. Spectrophotometric analysis of the pigments extracted from the color variants revealed the pigments had absorbance spectra different from the DNA donor strain. These color variants may have resulted from transformation with wild-type DNA, mutation reversion, or activation of alternative pathway(s)-i.e., new mutations-that resulted in pigment production.

Biotechnology↗
PubMed2004

Purification and characterization of a high molecular mass serine carboxypeptidase from Monascus pilosus.

Two serine carboxypeptidases, MpiCP-1 and MpiCP-2, were purified to homogeneity from Monascus pilosus IFO 4480. MpiCP-1 is a homodimer with a native molecular mass of 125 kDa composed of two identical subunits of 61 kDa, while MpiCP-2 is a high mass homooligomer with a native molecular mass of 2,263 kDa composed of about 38 identical subunits of 59 kDa. This is unique among carboxypeptidases and distinguishes MpiCP-2 as the largest known carboxypeptidase. The two purified enzymes were both acidic glycoproteins. MpiCP-1 has an isoelectric point of 3.7 and a carbohydrate content of 11%, while for MpiCP-2 these values were 4.0 and 33%, respectively. The optimum pH and temperature were around 4.0 and 50 degrees C for MpiCP-1, and 3.5 and 50 degrees C for MpiCP-2. MpiCP-1 was stable over a broad range of pH between 2.0 and 8.0 at 37 degrees C for 1 h, and up to 55 degrees C for 15 min at pH 6.0, but MpiCP-2 was stable in a narrow range of pH between 5.5 and 6.5, and up to 50 degrees C for 15 min at pH 6.0. Phenylmethylsulfonylfluoride strongly inhibited MpiCP-1 and completely inhibited MpiCP-2, suggesting that they are both serine carboxypeptidases. Of the substrates tested, benzyloxycarbonyl-L: -tyrosyl-L: -glutamic acid (Z-Tyr-Glu) was the best for both enzymes. The Km, Vmax, Kcat and Kcat/Km values of MpiCP-1 for Z-Tyr-Glu at pH 4.0 and 37 degrees C were 1.33 mM, 1.49 mM min(-1), 723 s(-1) and 545 mM(-1) s(-1), and those of MpiCP-2 at pH 3.5 and 37 degrees C were 1.55 mM, 1.54 mM min(-1), 2,039 s(-1) and 1,318 mM(-1) s(-1), respectively.

Carboxypeptidases↗
PubMed2005

Debittering effect of Monascus carboxypeptidase during the hydrolysis of soybean protein.

The actions of pepsin and the admixture of pepsin and Monascus pilosus carboxypeptidase 1 (MpiCP-1) on the hydrolysis of soybean protein were studied. The results showed that the pepsin hydrolyzate of soybean protein was much more bitter and contained relatively smaller amounts of total free amino acids than the hydrolyzate obtained with the admixture of pepsin and MpiCP-1. In addition, hydrophilic and hydrophobic amino acids were present in almost equal proportions in the pepsin hydrolyzate, while mainly hydrophobic amino acids made up the hydrolyzate obtained with the admixture of pepsin and MpiCP-1. These results suggest that MpiCP-1 suppresses and reverses the development of the bitterness taste that results from the pepsin hydrolysis of soybean protein by releasing mainly hydrophobic amino acids from the C-termini of the bitter components.

Carboxypeptidases↗
PubMed2005

Macrophage-stimulating activity of exo-biopolymer from cultured rice bran with Monascus pilosus.

To find a new use of rice bran, five fungi were examined for the production of exo-biopolymer with macrophage-stimulating activity from rice bran. Among the exo-biopolymers produced from the cultures, Monascus pilosus had the most potent macrophage stimulating activity in a liquid culture rather than in a solid culture. In order to improve the yield of exo-biopolymer with macrophage-stimulating activity, a suitable medium for exo-biopolymer was tested in submerged culture of M. pilosus. The highest amount of exo-biopolymer (13.9 mg/mL) was obtained in a medium containing rice bran as an only carbon source followed by media with additional maltose and sucrose (13.8 and 13.7 mg/mL, respectively). The addition of peptone resulted in the production of high amount of exo-biopolymer (15.1 mg/mL), meanwhile the addition of ammonium chloride resulted in 264.0 microg/mL of glucosamine content. Among eight different kinds of inorganic salts tested, potassium phosphate (0.1%) was the most effective inorganic salt for the mycelial growth and exo-biopolymer production. Therefore the optimal medium composition was as follows (g/L): 20 g of rice bran, 5 g of peptone, and 1 g of KH2PO4. The optimal culture pH and time for mycelial growth and exo-biopolymer production was pH 5.0 and 25 degrees C, respectively. The maximum exo-biopolymer (20.1 mg/mL) was observed at the fourth day of cultivation. Exo-biopolymer, a crude polysaccharide fraction, mainly contained neutral sugar (81.8%) with considerable amounts of uronic acid (18.2%). Component sugar analysis showed that the active fraction consisted mainly of arabinose, galactose, glucose, which was digested from starch of rice bran during cultivation, and uronic acid (molar ratio; 0.8:1.0:0.7:0.8).

Animals↗
PubMed2006

Solid-state fermentation for the production of Monascus pigments from jackfruit seed.

The aim of the present work was to investigate the feasibility of jackfruit seed powder as a substrate for the production of pigments by Monascus purpureus in solid-state fermentation (SSF). A pigment yield of 25ODUnits/g dry fermented substrate was achieved by employing jackfruit seed powder with optimized process parameters such as 50% initial moisture content, incubation temperature 30 degrees C, 9x10(4)spores/g dry substrate inoculum and an incubation period of seven days. The color of the pigments was stable over a wide range of pH, apparently due to the buffering nature of the substrate, which could be a significant point for its scope in food applications. To the best of our knowledge this is the first report on pigment production using jackfruit seed powder in solid-state fermentation (SSF).

Artocarpus↗
PubMed2006

Effect of monascus pigment derivatives on the electrophoretic mobility of bacteria, and the cell adsorption and antibacterial activities of pigments.

Various amino acid derivatives of monascus pigments were synthesized. The effects of pigment derivatives on the pigment adsorption ratio, electrophoretic mobility (EPM) of bacterial cells, and antibacterial activity were investigated under varying conditions of pigment type, pigment concentration, pH, and ionic strength. Two hydrophobic and two hydrophilic derivatives were selected as model pigments. There was a close relationship between the antimicrobial activity and the pigment adsorption ratio. Against Escherichia coli, the hydrophobic L-Tyr and L-Phe derivatives (log P = 3.18 and 3.57) exhibited high antimicrobial activities (MIC = 8 and 16 mg/L) and high cellular adsorption ratios (9.6 and 10.9 mg/L). The hydrophilic L-Glu and L-Asn derivatives (log P = 1.40 and 0.47) exhibited low activities (MIC = 64 and 128 mg/L) and low adsorption ratios (4.7 and 4.0 mg/L). The electrophoretic mobility of 11 different bacteria varied between -1.93 x 10(-8) and -1.19 x 10(-8) m(2) V(-1) s(-1) regardless of Gram(+) or Gram(-). The L-Phe derivative showed low MIC values (high antimicrobial activities) against bacteria with a high electrophoretic mobility. A positive linearity between the pigment adsorption ratio and the electrophoretic mobility was established. When the four pigment derivatives were added to E. coli solutions, the electrophoretic mobility of cells in all cases sharply increased with an increasing pigment concentration. The mobility value was high for hydrophobic pigment derivatives in descending order of L-Phe (0.8 x 10(-8) m(2) V(-1) s(-1)), L-Tyr (0.68 x 10(-8) m(2) V(-1) s(-1)), L-Glu (0.46 x 10(-8) m(2) V(-1) s(-1)), and L-Asn (0.44 x 10(-8) m(2) V(-1) s(-1)). Additional adsorption of the hydrophobic derivatives probably occurred due to a hydrophobic interaction between the pigment and the pigment-coated cells. The electrophoretic mobility decreased gradually with an increasing pH and/or ionic strength with both addition and no addition of the pigment derivatives. The pattern of change of the pigment adsorption ratio under varying pH and/or ionic strength values was similar to the pattern for electrophoretic mobility.

Adsorption↗
PubMed2005

Antihyperlipidaemic effect of a Monascus purpureus brand dietary supplement on a large sample of subjects at low risk for cardiovascular disease: a pilot study.

OBJECTIVES: We planned to carry out a pilot study to evaluate the efficacy and safety as an antihypercholesterolemic agent of a brand dietary supplement made of Monascus purpureus titrated extract, octacosanols and niacin on 111 Caucasian patients with low cardiovascular disease risk (<20% by Framingham algorithms), comparing them with the antihypercholesterolemic effect of a low dosage of Pravastatin on 20 subjects with similar risk profile. RESULTS: In our study, the tested dietary supplement determined a significant decrease of Total Cholesterol (TC), Low Density Lipoprotein Cholesterol (LDL-C), and Triglycerides (TG) in moderately hypercholesterolemic subjects without clinically relevant change in liver and muscular toxicity markers. The reduction of LDL-C reached the 20%, and it is similar to that obtained with a well-known effective statin like Pravastatin. CONCLUSIONS: Further long-term and double blind evaluation have to be carried out before to infer the observed results, however it appears that the studied dietary supplements could be a safe and efficacious antihypercholesterolemic agent for patients at low risk for cardiovascular diseases.

Adult↗
PubMed2005

A validated stability-indicating HPLC with photodiode array detector (PDA) method for the stress tests of Monascus purpureus-fermented rice, red yeast rice.

A stability-indicating reversed phase high-performance liquid chromatography (RP-HPLC) with photodiode array (PDA) detection method was developed and validated for the assay of monacolin series compounds including monacolin K, L, J and their hydroxyl acid forms as well as dehydroxymonacolin K simultaneously in Monascus purpureus-fermented rice, red yeast rice. Well-resolved peaks of seven main compounds of monacolin family were profiled on a C(18) reverse-phase column using a linear gradient of 0.1% trifluoroacetic acid and acetonitrile as the mobile phase, and the detection wavelength was set at 237nm. The method was validated with respect to specificity, chromatographic parameters, linearity, precision, accuracy, limits of detection and quantitation. The stability stress testing for fermented red yeast rice powder was carried out to show the effects of high temperature (80 degrees C), high humidity at room temperature (92.5% RH, 25 degrees C), high humidity at high temperature (75% RH, 60 degrees C) and light (sunlight) in solid state. The results exhibited that monacolins decreased significantly under the conditions of high humidity at high temperature (75% RH, 60 degrees C) and sunlight. Monacolin K and its hydroxyl acid form would be dehydrolyzed and turned to dehydromonacolin K at high temperature (80 degrees C) while the monacolin K, J and L would be transformed into their corresponding hydroxyl acid forms under the condition of high humidity (92.5% RH, 25 degrees C). The indication is that monacolins in red yeast rice powder are light-sensitive and thermal-sensitive. Therefore, it has been suggested that the preparations containing monacolins be stored in the place of cool and lightproof. The proposed degradation pathways were discussed as well. The multi-components assay for stability of botanical products could provide much more information than the normal marker-orientation method.

Chromatography, High Pressure Liquid↗
PubMed2006

Quantitative analysis of lovastatin in capsule of Chinese medicine monascus by capillary zone electrophoresis with UV-vis detector.

A capillary zone electrophoresis (CZE) method was developed for the quantitative analysis of lovastatin (Lvt) in capsule of monascus-Chinese medicine. Lvt in the capsule was separated using an electrolyte system consisting of 16% ethanol (v/v) in 60 mM Gly-sodium hydroxide buffer, pH 10.5, 16 kV applied voltage, 238 nm detection wavelength with a capillary of 51 cm x 75 microm i.d (43 cm to detector). Under the optimized conditions, the linear response of Lvt concentration ranges from 4.0 to 240 microg/mL with high correlation coefficient (r=0.9998, n=9), the limits of detection (LOD) and quantification (LOQ) for Lvt are 0.73 and 2.42 microg/mL, the precision values (expressed as R.S.D.) of intra-day and inter-day are 1.40-2.12% and 1.47-3.88%, respectively. The recoveries of the analyte at three concentration levels are 90.28-100.71%. The developed method can be well used for the quantification of Lvt in the drug in commercial formulations.

Buffers↗
PubMed2003

Color characteristics of monascus pigments derived by fermentation with various amino acids.

Various pigment colors were produced by Monascus fermentations with separate addition of 20 amino acids. The color characteristics and structures of the pigment derivatives were investigated. When each amino acid was added to the fermentation broth as a precursor, pigment extracts with different hue and chroma values were obtained depending on the content ratios of yellow, orange, and red colors in the fermentation broth. The yellow and orange pigments were identical regardless of amino acid addition. The red compounds varied on the basis of the type of amino acid added. LC-MS and (1)H and (13)C NMR structural analyses confirmed that the derivative pigments contained the moieties of the added amino acids. L, a, and b values of the CIELAB color system for the derivative pigments were measured. Values of hue and chroma were then calculated. The colors of the derivative pigments were in the range of orangish red to violet red. The hydrophilicities/hydrophobicities of the derivative pigments could be predicted from their log P values, which were estimated using computer programs.

Amino Acids↗
PubMed2003

Aqueous extract of Monascus purpureus M9011 prevents and reverses fructose-induced hypertension in rats.

This study aimed to determine the antihypertensive and metabolic effects of an aqueous extract of Monascus purpureus M9011 on fructose-induced hypertensive rats. After dietary feeding of fructose for 2 weeks, the rats exhibited significantly higher systolic blood pressure (SBP), mean arterial pressure (MAP), and plasma insulin and triglyceride levels, but lower insulin sensitivity than those in control rats on regular diet. The intragastric loading of fructose-fed rats with M9011 containing gamma-aminobutyric acid (GABA, 1 mg.kg(-)(1).day(-)(1)) prevented the development of fructose-induced hypertension. After fructose-induced hypertension had been established, intragastric loading of M9011 reversed the elevated blood pressure to normal level. Administration of pure GABA at the same dose as that contained in M9011 failed to prevent or reverse hypertension due to fructose consumption. Chronic M9011 treatment significantly suppressed the fructose-induced elevation in total cholesterol levels and enhanced the recovery of high-density lipoprotein cholesterol/total cholesterol ratio. However, M9011 treatment did not alter insulin sensitivity or the plasma levels of insulin, glucose, and triglyceride in fructose-fed and control rats. The present results suggest that M9011 is a novel, potent, food-based antihypertensive agent with the capability to improve long-term control of cholesterol metabolism in rats and may be of importance in clinical application for the hypertensive diabetic population.

Animals↗
PubMed2005

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

Six azaphilones, monascin (1), ankaflavin (2), rubropunctatin (3), monascorburin (4), rubropunctamine (5), and monascorburamine (6), two furanoisophthalides, xanthomonasin A (7) and xanthomonasin B (8), and two amino acids, (+)-monascumic acid (9) and (-)-monascumic acid (10), isolated from the extracts of Monascus pilosus-fermented rice (red-mold rice) were evaluated for their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice, on the induction of Epstein-Barr virus early antigen (EBV-EA) by TPA in Raji cells, and on the activation of (+/-)-(E)-methyl-2[(E)-hydroxy-imino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitric oxide (NO) donor. Among the compounds tested, seven compounds (1-6 and 10) on TPA-induced inflammation, and six compounds (1, 3-5, 9, and 10) on EBV-EA activation, exhibited potent inhibitory effects. All of the compounds tested showed moderate inhibitory effects on NOR 1 activation.

Animals↗
PubMed2004

Odor-active headspace components in fermented red rice in the presence of a monascus species.

Headspace components from rice and agar with (experimental) and without (control) inoculation with a Monascus spp. were investigated. Kinetics studies were carried out. Using rice as a substrate, 10 and 19 compounds were found for the control and the experimental groups, respectively, at day 14. Experimental group compounds were composed mainly of alcohols, ketones, and esters, whereas control group compounds were composed of aldehydes and ketones. With agar as a substrate, only five and three components were found in the control and experimental groups, respectively. Five alcohols, four esters, two ketones, and one furan with odor activity values (OAV) >1 dominated the overall flavor of the product. With liquid inoculation, the first six components with high OAVs were in the following order: 3-methyl-1-butanol (17) > ethanol (14) > ethyl acetate (10) > 2-methyl-1-propanol (15) > ethyl butanoate (11) > 3-methylbutyl acetate (13). Kinetic studies showed that most compounds reached their maximum concentrations at 10-12 days. Many compounds identified in the model red rice were reported in commercial red sufus, and several appeared to contribute solely by red rice.

Fermentation↗
PubMed2005

Enhanced photostability of monascus pigments derived with various amino acids via fermentation.

The photostability of 18 amino acid derivatives from monascus pigment was tested under various physical and chemical conditions. Under sunlight, the half-life of derivatives was increased to 1.45-5.58 h, corresponding to a 6-25-fold improvement over a control red pigment (0.22 h). The degradation of pigment derivatives followed a first-order reaction, and the pigment stability increased with an increasing concentration while it decreased with both an increase and decrease in pH from 7. The stabilities of derivatives decreased in descending order in hexane, ethanol, propanol, methanol, ethyl ether, distilled water, chloroform, and acetonitrile. Pigment stability under UV light (365 nm) showed a pattern similar to stability after exposure to sunlight. After 30 days of incubation at 30 degrees C, more than 80% of the initial derivative contents remained while only 29% of the control red remained. The differences in degradation patterns that control red gradually changed to brown whereas the phenylalanine derivative remained a weak red were confirmed by HPLC analysis.

Amino Acids↗
PubMed2004

(+)- and (-)-syn-2-isobutyl-4-methylazetidine-2,4-dicarboxylic acids from the extract of Monascus pilosus-fermented rice (red-mold rice).

The structures of two enantiomeric azetidine-type amino acids isolated from the n-butanol-soluble fraction of the 70% ethanol extract of red-mold rice fermented with Monascus pilosus were established to be (+)- [1; (+)-monascumic acid] and (-)-syn-2-isobutyl-4-methylazetidine-2,4-dicarboxylic acids [2; (-)-monascumic acid] based on spectroscopic methods.

Dicarboxylic Acids↗