Monascustin, an Unusual γ-Lactam from Red Yeast Rice

Wei, Wendi; Lin, Sheng; Chen, Minghua; Liu, Tianxi; Wang, Ali; Li, Jinjie; Guo, Qing‐Lan; Shang, Xiao-Ya

doi:10.1021/acs.jnatprod.6b00493

Cited by 25 publications

(9 citation statements)

References 30 publications

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“…Nine other compounds, including peroxymonascuspyrone 84 , α-tocospiro A 85 , spathulenol 86 (Cheng et al, 2010a), monascodilone 87 (Wild et al, 2002a; Wild et al, 2002b), monascustin 88 (Wei et al, 2017), N- cis -feruloylmethoxytyramine 89 (Cheng et al, 2013), monaspurpurone 90 , p -nitrophenol 91 (Cheng et al, 2010b), and 1-dotriacontanol 92 (Tan, 2015), were isolated from RYR. The chemical structures of these compounds are shown in Figure 6 .…”

Section: Chemistrymentioning

confidence: 99%

Red Yeast Rice: A Systematic Review of the Traditional Uses, Chemistry, Pharmacology, and Quality Control of an Important Chinese Folk Medicine

Zhu

Fang-yuan

et al. 2019

Front. Pharmacol.

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Red yeast rice (RYR), a Chinese traditional folk medicine produced by the fermentation of cooked rice kernels with a Monascaceae mold, Monascus purpureus, has long been used to treat blood circulation stasis, indigestion, diarrhea, and limb weakness in East Asian countries. This article provides a systematic review of the traditional uses, chemistry, biological activities, and toxicology of RYR to highlight its future prospects in the field of medicine. The literature reviewed for this article was obtained from the Web of Science, Elsevier, SciFinder, PubMed, CNKI, ScienceDirect, and Google Scholar, as well as Ph.D. and M.Sc. dissertations, published prior to July 2019. More than 101 chemical constituents have been isolated from RYR, mainly consisting of monacolins, pigments, organic acids, sterols, decalin derivatives, flavonoids, polysaccharides, and other compounds. Crude extracts of RYR, as well as its isolated compounds, possess broad pharmacological properties with hypolipidemic, anti-atherosclerotic, anti-cancer, neurocytoprotective, anti-osteoporotic, anti-fatigue, anti-diabetic, and anti-hypertensive activities. However, further studies are needed to characterize its diverse chemical constituents and the toxicological actions of the main bioactive compounds. New pharmacological trials addressing the overlooked traditional uses of RYR, such as in the treatment of indigestion and diarrhea, are required.

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Section: Chemistrymentioning

confidence: 99%

Red Yeast Rice: A Systematic Review of the Traditional Uses, Chemistry, Pharmacology, and Quality Control of an Important Chinese Folk Medicine

Zhu

Fang-yuan

et al. 2019

Front. Pharmacol.

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“…Fr.10 was purified by silica gel column using a step gradient elution with petroleum ether-EtOAc (10:0-0:10) to get 12 subfractions (Fr.10-1-Fr. [10][11][12]. HPLC purification of Fr.10-2 with a solvent system CH 3…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…In Asia, Monascus fermented rice has been used as a traditional medicine for centuries and as a healthy food to improve the color and delicacy of meat, fish and soybean products [7]. Monascus species can produce chemodiverse secondary metabolites including monascus pigments, monacolins, azaphilones, furanoisophthalides, amino acids, γ-lactams, pyranoindole alkaloids, benzenoids, furans, fatty acids and other structural types [8][9][10][11][12]. Some metabolites display various biological activities, such as anticancer, antibacterial, anti-inflammatory, antioxidative, enzyme inhibitor, antihypertensive and reducing plasma cholesterol activities [13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Monarubins A–C from the Marine Shellfish-Associated Fungus Monascus ruber BB5

et al. 2020

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Three new compounds, monarubins A–C (1, 6 and 13), together with ten known compounds, including four alkaloids (2–5), two isocoumarins (7 and 8) and four polyketides (9–12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid (3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3-sec-buthylpyrazine (4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B (6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC50 values of 1.72 and 0.71 μΜ, respectively; lunatinin (7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC50 values of 9.60, 7.12 and 28.12 μΜ, respectively.

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“…have been used in food fermentation in Asian countries, such as China, Japan, and The Korean Peninsula, for nearly 2,000 years (Chen et al, 2015; Kim et al, 2016; Rahayu et al, 2017). At present, their fermented products, such as red fermented rice (RFR), also called red yeast rice, Anka , Hongqu , red koji, and red mold rice, are widely used as food coloring, fermentation starters and food supplements worldwide (Chen et al, 2015; Yu et al, 2015; Wei et al, 2017; Derosa et al, 2018; Luo et al, 2018), because Monascus spp. can produce various useful secondary metabolites (SMs), mainly including Monascus pigments (MPs), monacolin K (MK) and γ-amino butyric acid (Feng et al, 2012; Huang et al, 2013; Patakova, 2013; Diana et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Effects of Different G-Protein α-Subunits on Growth, Development and Secondary Metabolism of Monascus ruber M7

et al. 2019

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Strains of Monascus filamentous fungal species have been used to produce fermented foods in Asian countries, such as China, Japan, and The Korean Peninsula, for nearly 2,000 years. At present, their fermented products are widely used as food additives and nutraceutical supplements worldwide owing to their production of beneficial secondary metabolites. Heterotrimeric G-protein signaling pathways participate in regulating multiple biological processes in fungi. Previously, we identified three Monascus ruber M7 G-protein α subunits (Mga1–3) and demonstrated that Mga1 can regulate growth, reproduction and some secondary metabolites’ production. Here, we systematically analyzed and compared the roles of mga 1–3 by combining single- and double-gene(s) knockouts and their transcriptomic data. First, mga 2 and mga 3 knock-out mutants and pairwise combinations of mga 1–3 deletion strains were generated. Then the changes in growth, development and the main secondary metabolites, Monascus pigments and citrinin, in these mutants were systematically compared with M. ruber M7. Moreover, RNA-Seq analyses of these mutants were performed. All three Gα subunits worked together to regulate biological processes in M. ruber M7, with Mga1 playing a major role, while Mga2 and Mga3 playing supplemental roles. According to the existing literatures which we can find, gene knock-out mutants of the pairwise combination of mga 1–3 and their transcriptome analysis are first reported in this study. The current results have clearly demonstrated the functional division of Mga1–3 in M. ruber M7, and could provide a deeper understanding of the effects of different Gα subunits on growth, development and secondary metabolism in other filamentous fungi.

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Monascustin, an Unusual γ-Lactam from Red Yeast Rice

Cited by 25 publications

References 30 publications

Red Yeast Rice: A Systematic Review of the Traditional Uses, Chemistry, Pharmacology, and Quality Control of an Important Chinese Folk Medicine

Red Yeast Rice: A Systematic Review of the Traditional Uses, Chemistry, Pharmacology, and Quality Control of an Important Chinese Folk Medicine

Monarubins A–C from the Marine Shellfish-Associated Fungus Monascus ruber BB5

Effects of Different G-Protein α-Subunits on Growth, Development and Secondary Metabolism of Monascus ruber M7

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