-
Journal of the American Chemical Society Dec 2019Generation of reactive intermediates and interception of these fleeting species under physiological conditions is a common strategy employed by Nature to build molecular...
Generation of reactive intermediates and interception of these fleeting species under physiological conditions is a common strategy employed by Nature to build molecular complexity. However, selective formation of these species under mild conditions using classical synthetic techniques is an outstanding challenge. Here, we demonstrate the utility of biocatalysis in generating -quinone methide intermediates with precise chemoselectivity under mild, aqueous conditions. Specifically, α-ketoglutarate-dependent non-heme iron enzymes, CitB and ClaD, are employed to selectively modify benzylic C-H bonds of -cresol substrates. In this transformation, biocatalytic hydroxylation of a benzylic C-H bond affords a benzylic alcohol product which, under the aqueous reaction conditions, is in equilibrium with the corresponding -quinone methide. -Quinone methide interception by a nucleophile or a dienophile allows for one-pot conversion of benzylic C-H bonds into C-C, C-N, C-O, and C-S bonds in chemoenzymatic cascades on preparative scale. The chemoselectivity and mild nature of this platform is showcased here by the selective modification of peptides and chemoenzymatic synthesis of the chroman natural product (-)-xyloketal D.
Topics: Indolequinones; Molecular Structure; Monascus; Nonheme Iron Proteins; Penicillium; Stereoisomerism
PubMed: 31840992
DOI: 10.1021/jacs.9b10474 -
Journal of Clinical Biochemistry and... Sep 2021Monascus pigment is derived from red-mold rice fermented by monascus purpureus and utilized as a natural coloring agent and natural food additive in East Asia. Monascus...
Monascus pigment is derived from red-mold rice fermented by monascus purpureus and utilized as a natural coloring agent and natural food additive in East Asia. Monascus pigment works as a radical scavenger. Some antioxidant combine cancer chemo-therapy to protect normal tissue because chemotherapy induce side effect for normal tissue. This combination therapy can attenuate the cytotoxicity of anti-cancer drugs by antioxidants effects. However, the effect of this combination therapy for cancer cells dose not investigate enough. In this study, we investigated the combination effect of anti-oxidants and anti-cancer drugs. We selected an anti-oxidant as monascus pigment and following four anti-cancer drugs: doxorubicin, tamoxifen, paclitaxicel, and cyclophosphamide. Combination treatment with monascus pigment and cyclophosphamide enhanced the cytotoxicity of cyclophosphamide. Moreover, this combination treatment accelerated apoptosis. The spot on TLC assay board of the monascus pigment and cyclophosphamide mixture is different from the spot of monascus pigment alone and cyclophosphamide alone. The interaction between monascus pigment and cyclo-phosphamide can produce some cytotoxicity compounds or accelerate intracellular cyclophosphamide accumulation. Hence, we concluded that the interaction of both cyclophosphamide and monascus pigment involved enhancement of cyclophosphamide cytotoxicity.
PubMed: 34616104
DOI: 10.3164/jcbn.20-197 -
Foods (Basel, Switzerland) Jul 2023In order to study the effects and mechanism of Monascus on the quality of hairtail surimi, high-throughput sequencing technology, headspace solid-phase...
In order to study the effects and mechanism of Monascus on the quality of hairtail surimi, high-throughput sequencing technology, headspace solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC/MS), and electronic nose techniques were used to investigate the changes in the quality, microbial diversity, and volatile flavor compounds of Monascus-fermented hairtail surimi (MFHS) during fermentation. The results showed that the total volatile basic nitrogen (TVB-N) index of hairtail surimi fermented by Monascus for 0-5 h met the requirements of the national standard. Among them, the 1 h group showed the best gel quality, which detected a total of 138 volatile substances, including 20 alcohols, 7 aldehydes, 12 olefins, 4 phenols, 12 alkanes, 8 ketones, 15 esters, 6 acids, 16 benzenes, 4 ethers, and 8 amines, as well as 26 other compounds. In addition, the dominant fungal microorganisms in the fermentation process of MFHS were identified, and a Spearman correlation analysis showed that 16 fungal microorganisms were significantly correlated with the decrease in fishy odor substances in the fermented fish and that 8 fungal microorganisms were significantly correlated with the increase in aromatic substances after fermentation. In short, Monascus fermentation can eliminate and reduce the fishy odor substances in hairtail fish, increase and improve the aromatic flavor, and improve the quality of hairtail surimi gel. These findings are helpful for revealing the mechanism of the quality formation of fermented surimi and provide guidance for the screening of starter culture in the future.
PubMed: 37569159
DOI: 10.3390/foods12152891 -
Journal of Food Science May 2024Pear residue, a byproduct of pear juice extraction, is rich in soluble sugar, vitamins, minerals, and cellulose. This study utilized Monascus anka in liquid fermentation...
Pear residue, a byproduct of pear juice extraction, is rich in soluble sugar, vitamins, minerals, and cellulose. This study utilized Monascus anka in liquid fermentation to extract dietary fiber (DF) from pear residue, and the structural and functional characteristics of the DF were analyzed. Soluble DF (SDF) content was increased from 7.9/100 g to 12.6 g/100 g, with a reduction of average particle size from 532.4 to 383.0 nm by fermenting with M. anka. Scanning electron microscopy and infrared spectroscopic analysis revealed more porous and looser structures in Monascus pear residue DF (MPDF). Water-, oil-holding, and swelling capacities of MPDF were also enhanced. UV-visible spectral analysis showed that the yield of yellow pigment in Monascus pear residue fermentation broth (MPFB) was slightly higher than that in the Monascus blank control fermentation broth. The citrinin content in MPFB and M. anka seed broth was 0.90 and 0.98 ug/mL, respectively. Therefore, liquid fermentation with M. anka improved the structural and functional properties of MPDF, suggesting its potential as a functional ingredient in food.
PubMed: 38778561
DOI: 10.1111/1750-3841.17114 -
Journal of Food and Drug Analysis Mar 2023Red mold rice (RMR) is a traditional Chinese medicine prepared using Monascus fermentation. Monascus ruber ( pilosus) and Monascus purpureus have a long history of use...
Red mold rice (RMR) is a traditional Chinese medicine prepared using Monascus fermentation. Monascus ruber ( pilosus) and Monascus purpureus have a long history of use as food and medicine. As an economically important starter culture, the relationship between the taxonomy of Monascus and production capabilities of secondary metabolites is crucial for the Monascus food industry. In this study, monacolin K, monascin, ankaflavin, and citrinin production by M. purpureus and M. ruber were genomically and chemically investigated. Our findings suggest that M. purpureus can produce monascin and ankaflavin in a correlated manner, whereas M. ruber produces monascin with minimum ankaflavin. M. purpureus is capable of producing citrinin; however, it is unlikely able to produce monacolin K. In contrast, M. ruber produces monacolin K, but not citrinin. We suggest that the current monacolin K content-related regulation of Monascus food should be revised, and labeling of Monascus species should be considered.
Topics: Monascus; Fermentation; Lovastatin; Oryza
PubMed: 37224553
DOI: 10.38212/2224-6614.3438 -
Food & Function Jun 2017The metabolites of Monascus with multiple benefits are popular subjects for the development of functional foods. The yellow pigments, monascin and ankaflavin, which are... (Review)
Review
The metabolites of Monascus with multiple benefits are popular subjects for the development of functional foods. The yellow pigments, monascin and ankaflavin, which are the constituent metabolites of M. purpureus, M. pilosus and M. ruber, are becoming the focus of research on Monascus. Monascin and ankaflavin are azaphilone compounds with similar structures that exhibit multiple beneficial effects including anti-inflammation, anti-oxidation, anti-diabetes, immunomodulation, attenuation of Alzheimer's disease risk factor, and anti-tumorigenic effects. Monascin and ankaflavin not only possess pleiotropic bioactivities, but are also more potent than monacolin K in lowering lipid levels and have lower toxicity. Monascin and ankaflavin act as the activators of PPARγ agonist/Nrf-2 that subsequently ameliorate metabolic syndrome. Following the intensive exploration of Monascus bioactivities in recent years, the focus of research on Monascus-functional foods has shifted from whole fermented products/extracts to specific bioactive compounds. Therefore, the production of monascin and ankaflavin is an important topic with respect to Monascus-functional foods. Although several genomic studies have paved the way for understanding the production of secondary metabolites in Monascus, efforts are still required to effectively manipulate the biosynthesis of secondary metabolites with genetic engineering and/or culture techniques.
Topics: Animals; Fermentation; Flavins; Functional Food; Heterocyclic Compounds, 3-Ring; Humans; Metabolic Syndrome; Monascus
PubMed: 28608901
DOI: 10.1039/c7fo00406k -
Journal of Fungi (Basel, Switzerland) Feb 2022is used widely in Asian countries and produces various biologically active metabolites, such as Monascus pigments (MPs) and monacolin K (MK). In this study, the effect...
is used widely in Asian countries and produces various biologically active metabolites, such as Monascus pigments (MPs) and monacolin K (MK). In this study, the effect of γ-heptalactone on secondary metabolites and mycelial growth during M1 fermentation was investigated. After the addition of 50 μM γ-heptalactone, the yields of MPs (yellow, orange, and red) reached maxima, increased by 115.70, 141.52, and 100.88%, respectively. The 25 μM γ-heptalactone groups showed the highest yield of MK was increased by 62.38% compared with that of the control. Gene expression analysis showed that the relative expression levels of MPs synthesis genes (, , , , , , , and /) were significantly upregulated after γ-heptalactone treatment. The relative expression levels of MK synthesis genes (, , , and ) were significantly affected. The mycelium samples treated with γ-heptalactone exhibited more folds and swelling than that in the samples of the control group. This study confirmed that the addition of γ-heptalactone has the potential to induce yields of MPs and MK, and promote the expression of biosynthesis genes, which may be related to the transformation of mycelial morphology in .
PubMed: 35205931
DOI: 10.3390/jof8020179 -
Biotechnology Advances Nov 2020There has been an increased interest in replacing synthetic colorants by colorants obtained from natural sources, especially microbial pigments. Monascus pigments have... (Review)
Review
There has been an increased interest in replacing synthetic colorants by colorants obtained from natural sources, especially microbial pigments. Monascus pigments have been used as natural colorings and food additives in Asia for centuries but have raised toxicity issues. Recently, Talaromyces/Penicillium species have been recognized as potential strains to produce natural pigments similar to those produced by Monascus species. To date, it has not been published a literature compilation about the research and development activity of Talaromyces/Penicillium pigments. Developing a new bioprocess requires several steps, from an initial concept to a practical and feasible application. Industrial applications of fungal pigments will depend on: (i) characterization of the molecules to assure a safe consumption, (ii) stability of the pigments to the processing conditions required by the products where they will be incorporated, (iii) optimizing process conditions to achieve high yields, iv) implementing an efficient product recovery and (v) scale-up of the bioprocess. The above aspects have been reviewed in detail to evaluate the feasibility of reaching a commercial scale of the pigments produced by Talaromyces/Penicillium. Finally, the biological activities of the pigments and their potential applications are discussed.
Topics: Asia; Biotechnology; Penicillium; Pigments, Biological; Talaromyces
PubMed: 32682871
DOI: 10.1016/j.biotechadv.2020.107601 -
Studies in Mycology Mar 2017The genus was described by van Tieghem (1884) to accommodate and , two species with non-ostiolate ascomata. Species delimitation in the genus is still mainly based on...
The genus was described by van Tieghem (1884) to accommodate and , two species with non-ostiolate ascomata. Species delimitation in the genus is still mainly based on phenotypic characters, and taxonomic studies that include sequence data are limited. The genus is of economic importance. Species are used in fermented Asian foods as food colourants (e.g. 'red rice' (ang-kak, angka)) and found as spoilage organisms, and recently was found to be essential in the lifecycle of stingless bees. In this study, a polyphasic approach was applied combining morphological characters, ITS, LSU, β-tubulin, calmodulin and RNA polymerase II second largest subunit sequences and extrolite data, to delimit species and to study phylogenetic relationships in . Furthermore, 30 isolates from honey, pollen and nests of stingless bees in Brazil were included. Based on this polyphasic approach, the genus is resolved in nine species, including three new species associated with stingless bees ( sp. nov., sp. nov., sp. nov., , , , , , ), and split in two new sections (section sect. nov., section sect. nov.). Phylogenetic analysis showed that the xerophile does not belong in and monophyly in is restored with the transfer of to ( comb. nov.). A list of accepted and excluded and species is given, together with information on (ex-)types cultures and barcode sequence data.
PubMed: 28539687
DOI: 10.1016/j.simyco.2017.04.001 -
Journal of Fungi (Basel, Switzerland) Jul 2021species are asexually or sexually reproduced homothallic fungi that can produce a red colorant, specifically the so-called red yeast rice or Anka, which is used as a...
species are asexually or sexually reproduced homothallic fungi that can produce a red colorant, specifically the so-called red yeast rice or Anka, which is used as a food ingredient in Asia. Traditional experiences of using for treating indigestion, enhancing blood circulation, and health remedies motivate us to investigate and repurpose -fermented products. Here, two new 5-cyclopenta[]pyridine type azaphilones, 5,6-monaspurpyridine A () and 5,6-monaspurpyridine A (), two new xanthonoids, monasxanthones A and B ( and ), one new naphthalenone, monasnaphthalenone (), and one new azaphilone, monapurpurin (), along with two known compounds were isolated from the 70% EtOH extract of a citrinin-free domesticated strain BCRC 38110. The phytochemical properties of the xanthonoid and naphthalenone components were first identified from sp. differently from the representative ingredients of polyketide-derived azaphilones. UVB-induced cell viability loss and reactive oxygen species (ROS) overproduction in human keratinocytes were attenuated by monascuspirolide B () and ergosterol peroxide (), indicating their photoprotective potentials. Ergosterol peroxide () decreased the melanin contents and tyrosinase activities of mouse melanocytes, depending on the concentration, suggesting their anti-melanogenic effects. In conclusion, six new and two known compounds were isolated from BCRC 38110, and two of them exhibited dermal protective activities. The results revealed the novel potential of for developing natural cosmeceutics against skin photoaging.
PubMed: 34436158
DOI: 10.3390/jof7080619