Monascuspiloin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-05173 |
| CAS | 1011244-19-1 |
| Molecular Weight | 360.44 |
| Molecular Formula | C21H28O5 |
| Purity | ≥95% by HPLC |
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Description
Monascuspiloin is a fungal metabolite isolated from M. pilosus M93-fermented rice. It induces endoplasmic reticulum stress and autophagy in PC3 prostate cancer cells. It is a moderately potent inhibitor of HMG-CoA reductase and has potent anti-androgen activity.
Specification
| Synonyms | Monascinol; (3S,3aR,9aR)-3-(1-hydroxyhexyl)-9a-methyl-6-((E)-prop-1-en-1-yl)-3a,4,8,9a-tetrahydro-2H-furo[3,2-g]isochromene-2,9(3H)-dione |
| Storage | Store at -20°C |
| IUPAC Name | (3S,3aR,9aR)-3a,4,8,9a-tetrahydro-3-(1-hydroxyhexyl)-9a-methyl-6-(1E)-1-propen-1-yl-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione |
| Canonical SMILES | C[C@]12[C@@](CC3=C(COC(/C=C/C)=C3)C2=O)([H])[C@@H]([C@H](O)CCCCC)C(O1)=O |
| InChI | InChI=1S/C21H28O5/c1-4-6-7-9-17(22)18-16-11-13-10-14(8-5-2)25-12-15(13)19(23)21(16,3)26-20(18)24/h5,8,10,16-18,22H,4,6-7,9,11-12H2,1-3H3/b8-5+/t16-,17-,18+,21-/m1/s1 |
| InChI Key | GNZJIIUXMNGZCY-IDIMIXOQSA-N |
Properties
| Appearance | Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 577.9±50.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in DMSO, Methanol |
Reference Reading
1. Monascuspiloin from Monascus-Fermented Red Mold Rice Alleviates Alcoholic Liver Injury and Modulates Intestinal Microbiota
Li Wu, Kangxi Zhou, Ziyi Yang, Jiayi Li, Guimei Chen, Qi Wu, Xucong Lv, Wenlin Hu, Pingfan Rao, Lianzhong Ai, Li Ni Foods. 2022 Sep 30;11(19):3048. doi: 10.3390/foods11193048.
Monascus-fermented red mold rice (RMR) has excellent physiological efficacy on lipid metabolism and liver function. This study investigated the ameliorative effects of monascuspiloin (MP) from RMR on alcoholic liver injury in mice, and further clarified its mechanism of action. Results showed that MP intervention obviously ameliorated lipid metabolism and liver function in mice with over-drinking. In addition, dietary MP intervention reduced liver MDA levels and increased liver CAT, SOD, and GSH levels, thus alleviating liver oxidative stress induced by excessive drinking. 16S rRNA amplicon sequencing showed that MP intervention was beneficial to ameliorate intestinal microbiota dysbiosis by elevating the proportion of norank_f_Lachnospiraceae, Lachnoclostridium, Alistipes, Roseburia, Vagococcus, etc., but decreasing the proportion of Staphylococcus, norank_f_Desulfovibrionaceae, Lachnospiraceae_UCG-001, Helicobacter, norank_f_Muribaculaceae, unclassified_f_Ruminococcaceae, etc. Additionally, correlation network analysis indicated that the key intestinal bacterial taxa intervened by MP were closely related to some biochemical parameters of lipid metabolism, liver function, and oxidative stress. Moreover, liver metabolomics analysis revealed that dietary MP supplementation significantly regulated the levels of 75 metabolites in the liver, which were involved in the synthesis and degradation of ketone bodies, taurine, and hypotaurine metabolism, and other metabolic pathways. Furthermore, dietary MP intervention regulated gene transcription and protein expression associated with hepatic lipid metabolism and oxidative stress. In short, these findings suggest that MP mitigates alcohol-induced liver injury by regulating the intestinal microbiome and liver metabolic pathway, and thus can serve as a functional component to prevent liver disease.
2. Monascuspiloin induces apoptosis and autophagic cell death in human prostate cancer cells via the Akt and AMPK signaling pathways
Rong-Jane Chen, Chin-Ming Hung, Yen-Lin Chen, Ming-Der Wu, Gwo-Fang Yuan, Ying-Jan Wang J Agric Food Chem. 2012 Jul 25;60(29):7185-93. doi: 10.1021/jf3016927. Epub 2012 Jul 13.
Monascus pigments have been reported to possess anticancer effects in various cancer cells; however, the molecular mechanisms of their anticancer properties remain largely unknown. Monascuspiloin is an analogue of the Monascus pigment monascin, and its anticancer growth activity against human prostate cancer cells was evaluated using in vitro and in vivo models. Monascuspiloin effectively inhibits the growth of both androgen-dependent LNCaP and androgen-independent PC-3 human prostate cancer cells. Monascuspiloin preferentially induces apoptosis in LNCaP cells by attenuating the PI3K/Akt/mTOR pathway. In androgen-independent PC-3 cells, monascuspiloin induces G2/M arrest and autophagic cell death by an AMPK-dependent pathway. Induction of autophagy in PC-3 cells further sensitizes cells to apoptosis induced by monascuspiloin. Monascuspiloin inhibits tumor growth in nude mice bearing PC-3 xenografts through induction of apoptosis and autophagy. This study is the first to demonstrate that monascuspiloin has therapeutic potential for the treatment of both androgen-dependent and -independent human prostate cancers.
3. Effect of a Monascus sp. Red Yeast Rice Extract on Germination of Bacterial Spores
Marketa Husakova, Michaela Plechata, Barbora Branska, Petra Patakova Front Microbiol. 2021 May 24;12:686100. doi: 10.3389/fmicb.2021.686100. eCollection 2021.
The pink-red color of traditional sausages (cured meat) is the result of nitrite addition and the formation of nitrosomyoglobin. However, the pleasant color of processed meat products is a side effect of nitrite addition while the main anticipated goal is to suppress the germination of clostridial spores. The fungus Monascus is known as a producer of oligoketide pigments, which are used in Asian countries, especially in China, for coloring foods, including meat products. Although, different biological activities of Monascus pigments have been tested and confirmed in many studies, their effect on germination of bacterial spores has never been investigated. This study is focused on testing the activity of red yeast rice (RYR) extract, containing monascin, rubropunctatin, rubropunctamine complexes and monascuspiloin as the main pigments, on germination of Clostridium and Bacillus spores. It was found that addition of nitrite alone, at the permitted concentration, had no effect on spore germination. However, the combined effects of nitrite with NaCl, tested after addition of pickling salt, was efficient in inhibiting the germination of C. beijerinckii spores but had no effect on B. subtilis spores. In contrast, total suppression of C. beijerinckii spore germination was reached after addition of RYR extract to the medium at a concentration of 2% v/v. For B. subtilis, total inhibition of spore germination was observed only after addition of 4% v/v RYR extract to the medium containing 1.3% w/w NaCl.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
