Monascin (BioDeep_00000230043)

 

Secondary id: BioDeep_00000020191

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


2H-FURO(3,2-G)(2)BENZOPYRAN-2,9(3H)-DIONE, 3A,4,8,9A-TETRAHYDRO-9A-METHYL-3-(1-OXOHEXYL)-6-(1E)-1-PROPEN-1-YL-, (3S,3AR,9AR)-

化学式: C21H26O5 (358.17801460000004)
中文名称: 红曲素, 红曲
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 5.56%

分子结构信息

SMILES: CCCCCC(=O)C1C2CC3=C(COC(=C3)C=CC)C(=O)C2(OC1=O)C
InChI: InChI=1S/C21H26O5/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/h5,8,10,16,18H,4,6-7,9,11-12H2,1-3H3/b8-5+/t16-,18+,21-/m1/s1

描述信息

Monascin is an organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl and methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of carcinogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours. It has a role as an antineoplastic agent, a PPARgamma agonist, an antilipemic drug and a fungal metabolite. It is an organic heterotricyclic compound, a gamma-lactone, an alpha,beta-unsaturated ketone and a polyketide.
Monascin is a natural product found in Monascus kaoliang, Monascus purpureus, and Monascus pilosus with data available.
An organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl and methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of carcinogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours.

同义名列表

13 个代谢物同义名

2H-FURO(3,2-G)(2)BENZOPYRAN-2,9(3H)-DIONE, 3A,4,8,9A-TETRAHYDRO-9A-METHYL-3-(1-OXOHEXYL)-6-(1E)-1-PROPEN-1-YL-, (3S,3AR,9AR)-; (3S,3AR,9AR)-3A,4,8,9A-TETRAHYDRO-9A-METHYL-3-(1-OXOHEXYL)-6-(1E)-1-PROPEN-1-YL-2H-FURO(3,2-G)(2)BENZOPYRAN-2,9(3H)-DIONE; (3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-[(1E)-prop-1-en-1-yl]-3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione; (3S,3aR,9aR)-3-Hexanoyl-9a-methyl-6-((E)-prop-1-en-1-yl)-3a,4,8,9a-tetrahydro-2H-furo[3,2-g]isochromene-2,9(3H)-dione; (3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-[(E)-prop-1-enyl]-3,3a,4,8-tetrahydrofuro[3,2-g]isochromene-2,9-dione; Monascin, >=97.0\\% (HPLC); UNII-W74D2M37FX; MONASCOFLAVINE; Monascoflavin; MONASCIN [MI]; W74D2M37FX; Monascin; 3-hexanoyl-9a-methyl-6-[(1Z)-prop-1-en-1-yl]-2H,3H,3aH,4H,8H,9H,9aH-furo[3,2-g]isochromene-2,9-dione



数据库引用编号

9 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Mohamed Shaaban, Mohammad Magdy El-Metwally, Amal A I Mekawey, Ahmed B Abdelwahab, Maha M Soltan. Monascin and monascinol, azaphilonoid pigments from Mortierella polycephala AM1: in silico and in vitro targeting of the angiogenic VEGFR2 kinase. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2022 Jan; 77(1-2):11-19. doi: 10.1515/znc-2021-0095. [PMID: 34265877]
  • Jhao-Ru Lai, Ya-Wen Hsu, Tzu-Ming Pan, Chun-Lin Lee. Monascin and Ankaflavin of Monascus purpureus Prevent Alcoholic Liver Disease through Regulating AMPK-Mediated Lipid Metabolism and Enhancing Both Anti-Inflammatory and Anti-Oxidative Systems. Molecules (Basel, Switzerland). 2021 Oct; 26(20):. doi: 10.3390/molecules26206301. [PMID: 34684882]
  • Shufen Wu, Yue Sun, Di Chen, Huanhuan Liu, Zhenjing Li, Mianhua Chen, Changlu Wang, Lei Cheng, Qingbin Guo, Xin Peng. The noncovalent conjugations of human serum albumin (HSA) with MS/AK and the effect on anti-oxidant capacity as well as anti-glycation activity of Monascus yellow pigments. Food & function. 2021 Apr; 12(8):3692-3704. doi: 10.1039/d0fo03025b. [PMID: 33900309]
  • Shufen Wu, Xiaochan Wang, Yuxin Bao, Chuanying Zhang, Huanhuan Liu, Zhenjing Li, Mianhua Chen, Changlu Wang, Qingbin Guo, Xin Peng. Molecular insight on the binding of monascin to bovine serum albumin (BSA) and its effect on antioxidant characteristics of monascin. Food chemistry. 2020 Jun; 315(?):126228. doi: 10.1016/j.foodchem.2020.126228. [PMID: 31991257]
  • Chih-Fu Cheng, Tzu-Ming Pan. Monascus-fermented red mold dioscorea protects mice against alcohol-induced liver injury, whereas its metabolites ankaflavin and monascin regulate ethanol-induced peroxisome proliferator-activated receptor-γ and sterol regulatory element-binding transcription factor-1 expression in HepG2 cells. Journal of the science of food and agriculture. 2018 Mar; 98(5):1889-1898. doi: 10.1002/jsfa.8670. [PMID: 28902410]
  • Chun-Lin Lee, Ja-Yan Wen, Ya-Wen Hsu, Tzu-Ming Pan. The blood lipid regulation of Monascus-produced monascin and ankaflavin via the suppression of low-density lipoprotein cholesterol assembly and stimulation of apolipoprotein A1 expression in the liver. Journal of microbiology, immunology, and infection = Wei mian yu gan ran za zhi. 2018 Feb; 51(1):27-37. doi: 10.1016/j.jmii.2016.06.003. [PMID: 27422746]
  • Chih-Hui Lin, Tzu-Hsing Lin, Tzu-Ming Pan. Alleviation of metabolic syndrome by monascin and ankaflavin: the perspective of Monascus functional foods. Food & function. 2017 Jun; 8(6):2102-2109. doi: 10.1039/c7fo00406k. [PMID: 28608901]
  • Chih-Fu Cheng, Tzu-Ming Pan. Ankaflavin and Monascin Induce Apoptosis in Activated Hepatic Stellate Cells through Suppression of the Akt/NF-κB/p38 Signaling Pathway. Journal of agricultural and food chemistry. 2016 Dec; 64(49):9326-9334. doi: 10.1021/acs.jafc.6b03700. [PMID: 27960292]
  • Wei-Hsuan Hsu, Tzu-Ming Pan. A novel PPARgamma agonist monascin's potential application in diabetes prevention. Food & function. 2014 Jul; 5(7):1334-40. doi: 10.1039/c3fo60575b. [PMID: 24752777]
  • Wei-Hsuan Hsu, Ting-Hung Chen, Bao-Hong Lee, Ya-Wen Hsu, Tzu-Ming Pan. Monascin and ankaflavin act as natural AMPK activators with PPARα agonist activity to down-regulate nonalcoholic steatohepatitis in high-fat diet-fed C57BL/6 mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2014 Feb; 64(?):94-103. doi: 10.1016/j.fct.2013.11.015. [PMID: 24275089]
  • Bao-Hong Lee, Wei-Hsuan Hsu, Tao Huang, Yu-Yin Chang, Ya-Wen Hsu, Tzu-Ming Pan. Monascin improves diabetes and dyslipidemia by regulating PPARγ and inhibiting lipogenesis in fructose-rich diet-induced C57BL/6 mice. Food & function. 2013 Jun; 4(6):950-9. doi: 10.1039/c3fo60062a. [PMID: 23673903]
  • Chun-Lin Lee, Ja-Yan Wen, Ya-Wen Hsu, Tzu-Ming Pan. Monascus-fermented yellow pigments monascin and ankaflavin showed antiobesity effect via the suppression of differentiation and lipogenesis in obese rats fed a high-fat diet. Journal of agricultural and food chemistry. 2013 Feb; 61(7):1493-500. doi: 10.1021/jf304015z. [PMID: 23360447]
  • Bao-Hong Lee, Wei-Hsuan Hsu, Tao Huang, Yu-Ying Chang, Ya-Wen Hsu, Tzu-Ming Pan. Effects of monascin on anti-inflammation mediated by Nrf2 activation in advanced glycation end product-treated THP-1 monocytes and methylglyoxal-treated wistar rats. Journal of agricultural and food chemistry. 2013 Feb; 61(6):1288-98. doi: 10.1021/jf305067n. [PMID: 23331247]
  • Chun-Lin Lee, Yu-Ping Hung, Ya-Wen Hsu, Tzu-Ming Pan. Monascin and ankaflavin have more anti-atherosclerosis effect and less side effect involving increasing creatinine phosphokinase activity than monacolin K under the same dosages. Journal of agricultural and food chemistry. 2013 Jan; 61(1):143-50. doi: 10.1021/jf304346r. [PMID: 23237237]
  • Yeu-Ching Shi, Vivian Hsiu-Chuan Liao, Tzu-Ming Pan. Monascin from red mold dioscorea as a novel antidiabetic and antioxidative stress agent in rats and Caenorhabditis elegans. Free radical biology & medicine. 2012 Jan; 52(1):109-17. doi: 10.1016/j.freeradbiomed.2011.09.034. [PMID: 22041455]
  • Shen-Shih Chiang, Shang-Ping Chang, Tzu-Ming Pan. Osteoprotective effect of Monascus-fermented dioscorea in ovariectomized rat model of postmenopausal osteoporosis. Journal of agricultural and food chemistry. 2011 Sep; 59(17):9150-7. doi: 10.1021/jf201640j. [PMID: 21800902]
  • Chih-Pei Lin, Yun-Lian Lin, Po-Hsun Huang, Hui-Szu Tsai, Yung-Hsiang Chen. Inhibition of endothelial adhesion molecule expression by Monascus purpureus-fermented rice metabolites, monacolin K, ankaflavin, and monascin. Journal of the science of food and agriculture. 2011 Aug; 91(10):1751-8. doi: 10.1002/jsfa.4371. [PMID: 21445895]
  • Pey-Chyi Jou, Bing-Ying Ho, Ya-Wen Hsu, Tzu-Ming Pan. The effect of Monascus secondary polyketide metabolites, monascin and ankaflavin, on adipogenesis and lipolysis activity in 3T3-L1. Journal of agricultural and food chemistry. 2010 Dec; 58(24):12703-9. doi: 10.1021/jf103121c. [PMID: 21080714]
  • Chun-Lin Lee, Yi-Hsin Kung, Cheng-Lun Wu, Ya-Wen Hsu, Tzu-Ming Pan. Monascin and ankaflavin act as novel hypolipidemic and high-density lipoprotein cholesterol-raising agents in red mold dioscorea. Journal of agricultural and food chemistry. 2010 Aug; 58(16):9013-9. doi: 10.1021/jf101982v. [PMID: 20666456]
  • Toshihiro Akihisa, Harukuni Tokuda, Motohiko Ukiya, Ayaka Kiyota, Ken Yasukawa, Naoyuki Sakamoto, Yumiko Kimura, Takashi Suzuki, Junko Takayasu, Hoyoku Nishino. Anti-tumor-initiating effects of monascin, an azaphilonoid pigment from the extract of Monascus pilosus fermented rice (red-mold rice). Chemistry & biodiversity. 2005 Oct; 2(10):1305-9. doi: 10.1002/cbdv.200590101. [PMID: 17191930]