Glycitein (BioDeep_00000001345)

 

Secondary id: BioDeep_00000384946

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one; 7,4-Dihydroxy-6-methoxyisoflavone; Glycetein; Glycitein; Glycitin aglycon

化学式: C16H12O5 (284.0684702)
中文名称: 黄豆黄素, 黄豆黄素
谱图信息: 最多检出来源 Homo sapiens(blood) 0.08%

分子结构信息

SMILES: c1(c(cc2c(c1)occ(c2=O)c1ccc(cc1)O)OC)O
InChI: InChI=1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

描述信息

Glycitein is a methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4. It has been isolated from the mycelia of the fungus Cordyceps sinensis. It has a role as a plant metabolite, a phytoestrogen and a fungal metabolite. It is a methoxyisoflavone and a 7-hydroxyisoflavone. It is functionally related to an isoflavone.
Glycitein is a natural product found in Psidium guajava, Ammopiptanthus mongolicus, and other organisms with data available.
Glycitein is a soy isoflavone. It is a minor component in most soy products. Its role of reducing low-density lipoprotein cholesterol is not clear. Glycitein is metabolized by human gut microorganisms and may follow metabolic pathways similar to other soy isoflavones (PMID: 12011578; 16248547). Glycitein is a biomarker for the consumption of soy beans and other soy products.
Isoflavone present in soya foods (inc. tofu, miso); potential nutriceutical [DFC]. Glycitein is a biomarker for the consumption of soy beans and other soy products. Glycitein is found in many foods, some of which are miso, soy bean, soy milk, and soy sauce.
A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4. It has been isolated from the mycelia of the fungus Cordyceps sinensis.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
Glycitein is a soy isoflavone used to study apoptosis and antioxidant.
Glycitein is a soy isoflavone used to study apoptosis and antioxidant.

同义名列表

20 个代谢物同义名

7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one; 7,4-Dihydroxy-6-methoxyisoflavone; Glycetein; Glycitein; Glycitin aglycon; 7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one; 7,4 inverted exclamation mark -Dihydroxy-6 methoxyisoflavone;Glycetein; 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-; Glycitein, United States Pharmacopeia (USP) Reference Standard; 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one; 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one; 4-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-chromen-7-one; 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-chromen-4-one; 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4H-one; 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one; GLYCITEIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]; 4,7-Dihydroxy-6-methoxyisoflavone; 7,4-Dihydroxy-6-methoxyisoflavone; Glycitein, analytical standard; Glycitein, >=97\\% (HPLC); GLYCITEIN [USP-RS]; UNII-92M5F28TVF; 92M5F28TVF; Glycitein; Glycetein



数据库引用编号

21 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(3)

BioCyc(0)

PlantCyc(0)

代谢反应

28 个相关的代谢反应过程信息。

Reactome(28)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

23 个相关的物种来源信息

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

  • Tao Xiang, Weibiao Jin. Mechanism of glycitein in the treatment of colon cancer based on network pharmacology and molecular docking. Lifestyle genomics. 2022 Sep; ?(?):. doi: 10.1159/000527124. [PMID: 36183698]
  • Na Dong, Zhilong Yang. Glycitein exerts neuroprotective effects in Rotenone-triggered oxidative stress and apoptotic cell death in the cellular model of Parkinson's disease. Acta biochimica Polonica. 2022 Jun; 69(2):447-452. doi: 10.18388/abp.2020_5963. [PMID: 35691030]
  • Sarah M Jung, Ella H Haddad, Amandeep Kaur, Rawiwan Sirirat, Alice Y Kim, Keiji Oda, Sujatha Rajaram, Joan Sabaté. A Non-Probiotic Fermented Soy Product Reduces Total and LDL Cholesterol: A Randomized Controlled Crossover Trial. Nutrients. 2021 Feb; 13(2):. doi: 10.3390/nu13020535. [PMID: 33562090]
  • Kai Uchida, Yuji Sawada, Koji Ochiai, Muneo Sato, Jun Inaba, Masami Yokota Hirai. Identification of a Unique Type of Isoflavone O-Methyltransferase, GmIOMT1, Based on Multi-Omics Analysis of Soybean under Biotic Stress. Plant & cell physiology. 2020 Dec; 61(11):1974-1985. doi: 10.1093/pcp/pcaa112. [PMID: 32894761]
  • Minsu Kim, Seowoo Im, Yoon Keun Cho, Cheoljun Choi, Yeonho Son, Doyoung Kwon, Young-Suk Jung, Yun-Hee Lee. Anti-Obesity Effects of Soybean Embryo Extract and Enzymatically-Modified Isoquercitrin. Biomolecules. 2020 09; 10(10):. doi: 10.3390/biom10101394. [PMID: 33008006]
  • Amritha Johny, Lada Ivanova, Tone-Kari Knutsdatter Østbye, Christiane Kruse Fæste. Biotransformation of phytoestrogens from soy in enzymatically characterized liver microsomes and primary hepatocytes of Atlantic salmon. Ecotoxicology and environmental safety. 2020 Jul; 197(?):110611. doi: 10.1016/j.ecoenv.2020.110611. [PMID: 32294595]
  • Yae Rim Choi, Jaewon Shim, Min Jung Kim. Genistin: A Novel Potent Anti-Adipogenic and Anti-Lipogenic Agent. Molecules (Basel, Switzerland). 2020 Apr; 25(9):. doi: 10.3390/molecules25092042. [PMID: 32349444]
  • Young Sung Jung, Ye-Jin Kim, Aaron Taehwan Kim, Davin Jang, Mi-Seon Kim, Dong-Ho Seo, Tae Gyu Nam, Chan-Su Rha, Cheon-Seok Park, Dae-Ok Kim. Enrichment of Polyglucosylated Isoflavones from Soybean Isoflavone Aglycones Using Optimized Amylosucrase Transglycosylation. Molecules (Basel, Switzerland). 2020 Jan; 25(1):. doi: 10.3390/molecules25010181. [PMID: 31906359]
  • You Jin Lim, Bora Lim, Hae Yeong Kim, Soon-Jae Kwon, Seok Hyun Eom. Deglycosylation patterns of isoflavones in soybean extracts inoculated with two enzymatically different strains of lactobacillus species. Enzyme and microbial technology. 2020 Jan; 132(?):109394. doi: 10.1016/j.enzmictec.2019.109394. [PMID: 31731960]
  • Vikas Kumar, A Aneesh Kumar, Vinod Joseph, Vipin Mohan Dan, Abdul Jaleel, T R Santhosh Kumar, Chandrasekharan C Kartha. Untargeted metabolomics reveals alterations in metabolites of lipid metabolism and immune pathways in the serum of rats after long-term oral administration of Amalaki rasayana. Molecular and cellular biochemistry. 2020 Jan; 463(1-2):147-160. doi: 10.1007/s11010-019-03637-1. [PMID: 31595424]
  • Shuhong Dai, Mingfang Pan, Hani S El-Nezami, Jennifer M F Wan, M F Wang, Olivier Habimana, Jetty C Y Lee, Jimmy C Y Louie, Nagendra P Shah. Effects of Lactic Acid Bacteria-Fermented Soymilk on Isoflavone Metabolites and Short-Chain Fatty Acids Excretion and Their Modulating Effects on Gut Microbiota. Journal of food science. 2019 Jul; 84(7):1854-1863. doi: 10.1111/1750-3841.14661. [PMID: 31206699]
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  • Pilar Gaya, Abel Sánchez-Jiménez, Ángela Peirotén, Margarita Medina, José Maria Landete. Incomplete metabolism of phytoestrogens by gut microbiota from children under the age of three. International journal of food sciences and nutrition. 2018 May; 69(3):334-343. doi: 10.1080/09637486.2017.1353955. [PMID: 28728453]
  • Marijana Tucak, Daniela Horvat, Tihomir Cupic, Goran Krizmanic, Vesna Tomas, Marija Ravlic, Svetislav Popovic. Forage Legumes as Sources of Bioactive Phytoestrogens for Use in Pharmaceutics: A Review. Current pharmaceutical biotechnology. 2018; 19(7):537-544. doi: 10.2174/1389201019666180730165917. [PMID: 30062960]
  • Yu-Hsuan Hsiao, Sheng-Yang Hsia, Yin-Ching Chan, Jung-Feng Hsieh. Complex Coacervation of Soy Proteins, Isoflavones and Chitosan. Molecules (Basel, Switzerland). 2017 Jun; 22(6):. doi: 10.3390/molecules22061022. [PMID: 28632187]
  • Michaela Kopečná-Zapletalová, Kristýna Krasulová, Pavel Anzenbacher, Petr Hodek, Eva Anzenbacherová. Interaction of isoflavonoids with human liver microsomal cytochromes P450: inhibition of CYP enzyme activities. Xenobiotica; the fate of foreign compounds in biological systems. 2017 Apr; 47(4):324-331. doi: 10.1080/00498254.2016.1195028. [PMID: 27312150]
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  • Yoshie Nagata, Yukiko Sugiyama, Fumimasa Fukuta, Akio Takayanagi, Naoya Masumori, Taiji Tsukamoto, Hiroshi Akasaka, Hirofumi Ohnishi, Shigeyuki Saitoh, Tetsuji Miura, Kaoru Moriyama, Hirokazu Tsuji, Hideyuki Akaza, Mitsuru Mori. Relationship of serum levels and dietary intake of isoflavone, and the novel bacterium Slackia sp. strain NATTS with the risk of prostate cancer: a case-control study among Japanese men. International urology and nephrology. 2016 Sep; 48(9):1453-60. doi: 10.1007/s11255-016-1335-7. [PMID: 27262851]
  • Huihua Qu, Baoping Qu, Xueqian Wang, Yue Zhang, Jinjun Cheng, Wenhao Zeng, Shuchen Liu, Qingguo Wang, Yan Zhao. Rapid, sensitive separation of the three main isoflavones in soybean using immunoaffinity chromatography. Journal of separation science. 2016 Mar; 39(6):1195-201. doi: 10.1002/jssc.201501052. [PMID: 26813984]
  • Yan Zhang, Sam K C Chang. Isoflavone Profiles and Kinetic Changes during Ultra-High Temperature Processing of Soymilk. Journal of food science. 2016 Mar; 81(3):C593-9. doi: 10.1111/1750-3841.13236. [PMID: 26814612]
  • Joanna M Redmon, Binu Shrestha, Rosario Cerundolo, Michael H Court. Soy isoflavone metabolism in cats compared with other species: urinary metabolite concentrations and glucuronidation by liver microsomes. Xenobiotica; the fate of foreign compounds in biological systems. 2016; 46(5):406-15. doi: 10.3109/00498254.2015.1086038. [PMID: 26366946]
  • Yeming Chen, Sam K C Chang. Macronutrients, Phytochemicals, and Antioxidant Activity of Soybean Sprout Germinated with or without Light Exposure. Journal of food science. 2015 Jun; 80(6):S1391-8. doi: 10.1111/1750-3841.12868. [PMID: 25916398]
  • Y J Hu, K G Gao, C T Zheng, Z J Wu, X F Yang, L Wang, X Y Ma, A G Zhou, Z J Jiang. Effect of dietary supplementation with glycitein during late pregnancy and lactation on antioxidative indices and performance of primiparous sows. Journal of animal science. 2015 May; 93(5):2246-54. doi: 10.2527/jas.2014-7767. [PMID: 26020321]
  • Kwang-Pil Ko, Cheong-Sik Kim, Younjhin Ahn, Seon-Joo Park, Yeon-Jeong Kim, Jae Kyung Park, Young-Khi Lim, Keun-Young Yoo, Sung Soo Kim. Plasma isoflavone concentration is associated with decreased risk of type 2 diabetes in Korean women but not men: results from the Korean Genome and Epidemiology Study. Diabetologia. 2015 Apr; 58(4):726-35. doi: 10.1007/s00125-014-3463-x. [PMID: 25533387]
  • Marina C Nemitz, Francini K J Yatsu, Juliana Bidone, Letícia S Koester, Valquiria L Bassani, Cássia V Garcia, Andreas S L Mendez, Gilsane L von Poser, Helder F Teixeira. A versatile, stability-indicating and high-throughput ultra-fast liquid chromatography method for the determination of isoflavone aglycones in soybeans, topical formulations, and permeation assays. Talanta. 2015 Mar; 134(?):183-193. doi: 10.1016/j.talanta.2014.10.062. [PMID: 25618656]
  • Seiko Otokozawa, Ryoichi Tanaka, Hiroshi Akasaka, Eiki Ito, Sumiyo Asakura, Hirofumi Ohnishi, Shigeyuki Saito, Tetsuji Miura, Tsuyoshi Saito, Mitsuru Mori. Associations of Serum Isoflavone, Adiponectin and Insulin Levels with Risk for Epithelial Ovarian Cancer: Results of a Case-control Study. Asian Pacific journal of cancer prevention : APJCP. 2015; 16(12):4987-91. doi: 10.7314/apjcp.2015.16.12.4987. [PMID: 26163627]
  • Vera van der Velpen, Anouk Geelen, Peter C H Hollman, Evert G Schouten, Pieter van 't Veer, Lydia A Afman. Isoflavone supplement composition and equol producer status affect gene expression in adipose tissue: a double-blind, randomized, placebo-controlled crossover trial in postmenopausal women. The American journal of clinical nutrition. 2014 Nov; 100(5):1269-77. doi: 10.3945/ajcn.114.088484. [PMID: 25332325]
  • V van der Velpen, P C Hollman, M van Nielen, E G Schouten, M Mensink, P Van't Veer, A Geelen. Large inter-individual variation in isoflavone plasma concentration limits use of isoflavone intake data for risk assessment. European journal of clinical nutrition. 2014 Oct; 68(10):1141-7. doi: 10.1038/ejcn.2014.108. [PMID: 24939433]
  • Hiroko Yonemoto-Yano, Motohiro Maebuchi, Kensuke Fukui, Shinichi Tsuzaki, Kiyoharu Takamatsu, Mariko Uehara. Malonyl isoflavone glucosides are chiefly hydrolyzed and absorbed in the colon. Journal of agricultural and food chemistry. 2014 Mar; 62(10):2264-70. doi: 10.1021/jf404378r. [PMID: 24524651]
  • Masum Akond, Shiming Liu, Stella K Kantartzi, Khalid Meksem, Nacer Bellaloui, David A Lightfoot, Jiazheng Yuan, Dechun Wang, My Abdelmajid Kassem. Quantitative trait loci for seed isoflavone contents in 'MD96-5722' by 'Spencer' recombinant inbred lines of soybean. Journal of agricultural and food chemistry. 2014 Feb; 62(7):1464-8. doi: 10.1021/jf4040173. [PMID: 24499298]
  • Marie-Pierre Artigot, Mathieu Baes, Jean Daydé, Monique Berger. Expression of flavonoid 6-hydroxylase candidate genes in normal and mutant soybean genotypes for glycitein content. Molecular biology reports. 2013 Jul; 40(7):4361-9. doi: 10.1007/s11033-013-2526-2. [PMID: 23695494]
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  • Svitlana Shinkaruk, Marlène Durand, Valérie Lamothe, Allison Carpaye, Amandine Martinet, Philippe Chantre, Sébastien Vergne, Xavier Nogues, Nicholas Moore, Catherine Bennetau-Pelissero. Bioavailability of glycitein relatively to other soy isoflavones in healthy young Caucasian men. Food chemistry. 2012 Dec; 135(3):1104-11. doi: 10.1016/j.foodchem.2012.03.135. [PMID: 22953831]
  • Xianglan Zhang, Yu-Tang Gao, Gong Yang, Honglan Li, Qiuyin Cai, Yong-Bing Xiang, Bu-Tian Ji, Adrian A Franke, Wei Zheng, Xiao-Ou Shu. Urinary isoflavonoids and risk of coronary heart disease. International journal of epidemiology. 2012 Oct; 41(5):1367-75. doi: 10.1093/ije/dys130. [PMID: 22927214]
  • T Y Tai, K S Tsai, S T Tu, J S Wu, C I Chang, C L Chen, N S Shaw, H Y Peng, S Y Wang, C H Wu. The effect of soy isoflavone on bone mineral density in postmenopausal Taiwanese women with bone loss: a 2-year randomized double-blind placebo-controlled study. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA. 2012 May; 23(5):1571-80. doi: 10.1007/s00198-011-1750-7. [PMID: 21901480]
  • Djordje Malenčić, Jelena Cvejić, Jegor Miladinović. Polyphenol content and antioxidant properties of colored soybean seeds from central Europe. Journal of medicinal food. 2012 Jan; 15(1):89-95. doi: 10.1089/jmf.2010.0329. [PMID: 21861721]
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  • Supanimit Teekachunhatean, Sujitra Techatoei, Noppamas Rojanasthein, Maleeya Manorot, Chaichan Sangdee. Influence of fructooligosaccharide on pharmacokinetics of isoflavones in postmenopausal women. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):783802. doi: 10.1155/2012/783802. [PMID: 22611432]
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