Norathyriol (BioDeep_00000004195)

 

Secondary id: BioDeep_00000395924

human metabolite PANOMIX_OTCML-2023 blood metabolite natural product


代谢物信息卡片


1,3,6,7-TETRAHYDROXY-9H-XANTHEN-9-ONE

化学式: C13H8O6 (260.0321)
中文名称: 芒果苷元
谱图信息: 最多检出来源 Viridiplantae(plant) 85.15%

分子结构信息

SMILES: c1(cc(c2c(c1)oc1c(c2=O)cc(c(c1)O)O)O)O
InChI: InChI=1S/C13H8O6/c14-5-1-9(17)12-11(2-5)19-10-4-8(16)7(15)3-6(10)13(12)18/h1-4,14-17H

描述信息

A polyphenol metabolite detected in biological fluids [PhenolExplorer]

同义名列表

5 个代谢物同义名

1,3,6,7-TETRAHYDROXY-9H-XANTHEN-9-ONE; 1,3,6,7-Tetrahydroxyxanthoene; 1,3,6,7-Tetrahydroxyxanthone; Norathyriol; Norathyriol



数据库引用编号

18 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(2)

代谢反应

4 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(4)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

62 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。

亚细胞结构定位 关联基因列表
Cytoplasm 13 ABCB1, AKT1, ESR1, FDPS, MAPK1, PGAM1, PRKX, PTGS1, PTGS2, PTPN2, SIRT1, SREBF1, XDH
Peripheral membrane protein 3 ESR1, PTGS1, PTGS2
Endoplasmic reticulum membrane 4 PTGS1, PTGS2, SREBF1, UGT1A3
Nucleus 8 AKT1, ESR1, JUND, MAPK1, PRKX, PTPN2, SIRT1, SREBF1
cytosol 10 AKT1, ESR1, FDPS, MAPK1, PGAM1, PRKCQ, PTPN2, SIRT1, SREBF1, XDH
centrosome 1 MAPK1
nucleoplasm 9 AKT1, ESR1, FDPS, JUND, MAPK1, PRKX, PTPN2, SIRT1, SREBF1
RNA polymerase II transcription regulator complex 1 JUND
Cell membrane 3 ABCB1, AKT1, ESR1
Cytoplasmic side 1 ESR1
lamellipodium 1 AKT1
Multi-pass membrane protein 4 ABCB1, SLC22A6, SLC22A8, SREBF1
Golgi apparatus membrane 1 SREBF1
Synapse 1 MAPK1
cell cortex 1 AKT1
cell surface 1 ABCB1
glutamatergic synapse 1 AKT1
Golgi apparatus 3 ESR1, MAPK1, PTGS1
Golgi membrane 2 INS, SREBF1
lysosomal membrane 1 GAA
postsynapse 1 AKT1
Lysosome 1 GAA
plasma membrane 9 ABCB1, AKT1, ESR1, GAA, MAPK1, PRKCQ, PTPN2, SLC22A6, SLC22A8
Membrane 9 ABCB1, AKT1, ESR1, FDPS, GAA, PGAM1, PTPN2, SLC22A6, UGT1A3
apical plasma membrane 2 ABCB1, SLC22A8
basolateral plasma membrane 2 SLC22A6, SLC22A8
caveola 3 MAPK1, PTGS2, SLC22A6
extracellular exosome 6 ABCB1, GAA, PGAM1, PTGS1, SLC22A6, SLC22A8
Lysosome membrane 1 GAA
endoplasmic reticulum 4 PTGS2, PTPN2, SREBF1, UGT1A3
extracellular space 2 INS, XDH
lysosomal lumen 1 GAA
mitochondrion 2 MAPK1, SIRT1
protein-containing complex 5 AKT1, ESR1, PTGS2, SLC22A6, SREBF1
intracellular membrane-bounded organelle 2 GAA, PTGS1
Microsome membrane 2 PTGS1, PTGS2
chromatin silencing complex 1 SIRT1
Secreted 2 GAA, INS
extracellular region 4 GAA, INS, MAPK1, PGAM1
Single-pass membrane protein 1 UGT1A3
mitochondrial matrix 1 FDPS
transcription regulator complex 2 ESR1, JUND
centriolar satellite 1 PRKCQ
photoreceptor outer segment 1 PTGS1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 MAPK1
microtubule cytoskeleton 1 AKT1
nucleolus 1 SIRT1
Early endosome 1 MAPK1
cell-cell junction 1 AKT1
vesicle 1 AKT1
Apical cell membrane 1 ABCB1
heterochromatin 1 SIRT1
Cell junction, focal adhesion 1 MAPK1
Cytoplasm, cytoskeleton, spindle 1 MAPK1
focal adhesion 1 MAPK1
spindle 2 AKT1, MAPK1
Peroxisome 2 FDPS, XDH
sarcoplasmic reticulum 1 XDH
Nucleus, PML body 1 SIRT1
PML body 1 SIRT1
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
lateral plasma membrane 1 SLC22A8
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 2 PTGS2, SIRT1
nuclear outer membrane 1 PTGS2
Late endosome 1 MAPK1
neuron projection 2 PTGS1, PTGS2
ciliary basal body 1 AKT1
chromatin 4 ESR1, JUND, SIRT1, SREBF1
mitotic spindle 1 MAPK1
cytoskeleton 1 MAPK1
[Isoform 1]: Endoplasmic reticulum 1 PTPN2
Basolateral cell membrane 2 SLC22A6, SLC22A8
fibrillar center 1 SIRT1
nuclear envelope 2 SIRT1, SREBF1
Endomembrane system 2 PTGS1, PTPN2
endosome lumen 2 INS, PTPN2
Membrane, caveola 1 MAPK1
Cytoplasmic vesicle membrane 1 SREBF1
tertiary granule membrane 1 GAA
euchromatin 2 ESR1, SIRT1
pseudopodium 1 MAPK1
basal plasma membrane 1 SLC22A6
ficolin-1-rich granule lumen 2 MAPK1, PGAM1
secretory granule lumen 2 INS, PGAM1
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 INS, MAPK1, PTGS2
transcription repressor complex 1 JUND
transport vesicle 1 INS
azurophil granule membrane 1 GAA
azurophil granule lumen 1 MAPK1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
ER to Golgi transport vesicle membrane 1 SREBF1
endoplasmic reticulum-Golgi intermediate compartment 1 PTPN2
[Isoform 1]: Nucleus 1 ESR1
Basal cell membrane 1 SLC22A6
ficolin-1-rich granule membrane 1 GAA
external side of apical plasma membrane 1 ABCB1
eNoSc complex 1 SIRT1
rDNA heterochromatin 1 SIRT1
Cytoplasmic vesicle, COPII-coated vesicle membrane 1 SREBF1
transcription factor AP-1 complex 1 JUND
autolysosome lumen 1 GAA
[Sterol regulatory element-binding protein 1]: Endoplasmic reticulum membrane 1 SREBF1
[Processed sterol regulatory element-binding protein 1]: Nucleus 1 SREBF1
[Isoform SREBP-1aDelta]: Nucleus 1 SREBF1
[Isoform SREBP-1cDelta]: Nucleus 1 SREBF1
[SirtT1 75 kDa fragment]: Cytoplasm 1 SIRT1


文献列表

  • Nobuhiro Sasaki, Keiichirou Nemoto, Yuzo Nishizaki, Naoki Sugimoto, Keisuke Tasaki, Aiko Watanabe, Fumina Goto, Atsumi Higuchi, Ed Morgan, Takashi Hikage, Masahiro Nishihara. Identification and characterization of xanthone biosynthetic genes contributing to the vivid red coloration of red-flowered gentian. The Plant journal : for cell and molecular biology. 2021 09; 107(6):1711-1723. doi: 10.1111/tpj.15412. [PMID: 34245606]
  • Navneet Kishore, Pradeep Kumar, Karuna Shanker, Akhilesh Kumar Verma. Human disorders associated with inflammation and the evolving role of natural products to overcome. European journal of medicinal chemistry. 2019 Oct; 179(?):272-309. doi: 10.1016/j.ejmech.2019.06.034. [PMID: 31255927]
  • Hua Lin, Caixia Tu, Yanfen Niu, Fashuang Li, Lixian Yuan, Na Li, Aiping Xu, Lihui Gao, Ling Li. Dual actions of norathyriol as a new candidate hypouricaemic agent: uricosuric effects and xanthine oxidase inhibition. European journal of pharmacology. 2019 Jun; 853(?):371-380. doi: 10.1016/j.ejphar.2019.04.034. [PMID: 31009635]
  • Edwin Risky Sukandar, Sutin Kaennakam, Kitiya Rassamee, Taslim Ersam, Pongpun Siripong, Santi Tip-Pyang. Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra. Journal of natural products. 2019 05; 82(5):1312-1318. doi: 10.1021/acs.jnatprod.9b00046. [PMID: 30978023]
  • Dan Sun, Chun-Ze Zhang, Rui-Xue Ran, Yun-Feng Cao, Zuo Du, Zhi-Wei Fu, Chun-Ting Huang, Zhen-Ying Zhao, Wei-Hua Zhang, Zhong-Ze Fang. In Vitro Comparative Study of the Inhibitory Effects of Mangiferin and Its Aglycone Norathyriol towards UDP-Glucuronosyl Transferase (UGT) Isoforms. Molecules (Basel, Switzerland). 2017 Jun; 22(6):. doi: 10.3390/molecules22061008. [PMID: 28621744]
  • Jie Liu, Jianrun Zhang, Huailing Wang, Zhijun Liu, Cao Zhang, Zhenlei Jiang, Heru Chen. Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them. European journal of medicinal chemistry. 2017 Jun; 133(?):50-61. doi: 10.1016/j.ejmech.2017.03.068. [PMID: 28376372]
  • Xiaoting Tian, Yu Gao, Zhou Xu, Shan Lian, Yuanjie Ma, Xiaozhen Guo, Pei Hu, Zhixiong Li, Chenggang Huang. Pharmacokinetics of mangiferin and its metabolite-Norathyriol, Part 1: Systemic evaluation of hepatic first-pass effect in vitro and in vivo. BioFactors (Oxford, England). 2016 Sep; 42(5):533-544. doi: 10.1002/biof.1291. [PMID: 27130074]
  • Xiaoting Tian, Zhou Xu, Zhixiong Li, Yuanjie Ma, Shan Lian, Xiaozhen Guo, Pei Hu, Yu Gao, Chenggang Huang. Pharmacokinetics of mangiferin and its metabolite-norathyriol, Part 2: Influence of UGT, CYP450, P-gp, and enterobacteria and the potential interaction in Rhizoma Anemarrhenae decoction with timosaponin B2 as the major contributor. BioFactors (Oxford, England). 2016 Sep; 42(5):545-555. doi: 10.1002/biof.1290. [PMID: 27151461]
  • Yanfen Niu, Jia Liu, Hai-Yang Liu, Li-Hui Gao, Guo-Hua Feng, Xu Liu, Ling Li. Hypouricaemic action of mangiferin results from metabolite norathyriol via inhibiting xanthine oxidase activity. Pharmaceutical biology. 2016 Sep; 54(9):1680-6. doi: 10.3109/13880209.2015.1120322. [PMID: 26916555]
  • Hong Zhang, Dan-Dan Zhang, Yuan-Zhi Lao, Wen-Wei Fu, Shuang Liang, Qing-Hong Yuan, Ling Yang, Hong-Xi Xu. Cytotoxic and anti-inflammatory prenylated benzoylphloroglucinols and xanthones from the twigs of Garcinia esculenta. Journal of natural products. 2014 Jul; 77(7):1700-7. doi: 10.1021/np5003498. [PMID: 24960143]
  • Huihui Liu, Bin Wu, Guoyu Pan, Lei He, Zhixiong Li, Mingsong Fan, Longhai Jian, Mingcang Chen, Ke Wang, Chenggang Huang. Metabolism and pharmacokinetics of mangiferin in conventional rats, pseudo-germ-free rats, and streptozotocin-induced diabetic rats. Drug metabolism and disposition: the biological fate of chemicals. 2012 Nov; 40(11):2109-18. doi: 10.1124/dmd.112.045849. [PMID: 22859782]
  • Wei-ming Fu, Jin-fang Zhang, Hua Wang, Hong-sheng Tan, Wei-mao Wang, Shih-Chi Chen, Xiao Zhu, Tak-ming Chan, Ching-man Tse, Kwong-sak Leung, Gang Lu, Hong-xi Xu, Hsiang-fu Kung. Apoptosis induced by 1,3,6,7-tetrahydroxyxanthone in Hepatocellular carcinoma and proteomic analysis. Apoptosis : an international journal on programmed cell death. 2012 Aug; 17(8):842-51. doi: 10.1007/s10495-012-0729-y. [PMID: 22610480]
  • Jixia Li, Margarita Malakhova, Madhusoodanan Mottamal, Kanamata Reddy, Igor Kurinov, Andria Carper, Alyssa Langfald, Naomi Oi, Myoung Ok Kim, Feng Zhu, Carlos P Sosa, Keyuan Zhou, Ann M Bode, Zigang Dong. Norathyriol suppresses skin cancers induced by solar ultraviolet radiation by targeting ERK kinases. Cancer research. 2012 Jan; 72(1):260-70. doi: 10.1158/0008-5472.can-11-2596. [PMID: 22084399]
  • Huihui Liu, Ke Wang, Yihong Tang, Zhaolin Sun, Longhai Jian, Zhixiong Li, Bin Wu, Chenggang Huang. Structure elucidation of in vivo and in vitro metabolites of mangiferin. Journal of pharmaceutical and biomedical analysis. 2011 Jul; 55(5):1075-82. doi: 10.1016/j.jpba.2011.03.012. [PMID: 21466941]
  • He Zhong Jiang, Xiao Fang Quan, Wei Xi Tian, Jiang Miao Hu, Peng Cheng Wang, Sheng Zhuo Huang, Zhong Quan Cheng, Wen Juan Liang, Jun Zhou, Xiao Feng Ma, You Xing Zhao. Fatty acid synthase inhibitors of phenolic constituents isolated from Garcinia mangostana. Bioorganic & medicinal chemistry letters. 2010 Oct; 20(20):6045-7. doi: 10.1016/j.bmcl.2010.08.061. [PMID: 20817450]
  • Elisabetta Chieli, Nadia Romiti, Idania Rodeiro, Gabino Garrido. In vitro modulation of ABCB1/P-glycoprotein expression by polyphenols from Mangifera indica. Chemico-biological interactions. 2010 Aug; 186(3):287-94. doi: 10.1016/j.cbi.2010.05.012. [PMID: 20513373]
  • Neeraj K Sethiya, M B Patel, S H Mishra. Phytopharmacologic aspects of Canscora decussata Roem and Schult. Pharmacognosy reviews. 2010 Jan; 4(7):49-57. doi: 10.4103/0973-7847.65326. [PMID: 22228941]
  • Juliana Aparecida Severi, Zeila Pinheiro Lima, Hélio Kushima, Alba Regina Monteiro Souza Brito, Lourdes Campaner dos Santos, Wagner Vilegas, Clélia Akiko Hiruma-Lima. Polyphenols with antiulcerogenic action from aqueous decoction of mango leaves (Mangifera indica L.). Molecules (Basel, Switzerland). 2009 Mar; 14(3):1098-110. doi: 10.3390/molecules14031098. [PMID: 19305363]
  • Gabin Nselapi Louh, Alain Meli Lannang, Celine Djama Mbazoa, Jean Gustave Tangmouo, Justin Komguem, Paula Castilho, Fernande Ngounou Ngninzeko, Naz Qamar, David Lontsi, Muhammad Iqbal Choudhary, Beiban Luc Sondengam. Polyanxanthone A, B and C, three xanthones from the wood trunk of Garcinia polyantha Oliv. Phytochemistry. 2008 Feb; 69(4):1013-7. doi: 10.1016/j.phytochem.2007.10.002. [PMID: 18022654]
  • Hui Wang, Guan Ye, Chun-Hui Ma, Yi-Hong Tang, Ming-Song Fan, Zhi-Xiong Li, Cheng-Gang Huang. Identification and determination of four metabolites of mangiferin in rat urine. Journal of pharmaceutical and biomedical analysis. 2007 Dec; 45(5):793-8. doi: 10.1016/j.jpba.2007.07.019. [PMID: 17723287]
  • Jie Shen, Jun-Shan Yang. Two new xanthones from the stems of Garcinia cowa. Chemical & pharmaceutical bulletin. 2006 Jan; 54(1):126-8. doi: 10.1248/cpb.54.126. [PMID: 16394566]
  • Lien-Hoa D Nilar Nguyen, Ganpathi Venkatraman, Keng-Yeow Sim, Leslie J Harrison. Xanthones and benzophenones from Garcinia griffithii and Garcinia mangostana. Phytochemistry. 2005 Jul; 66(14):1718-23. doi: 10.1016/j.phytochem.2005.04.032. [PMID: 16173114]
  • J P Wang, S L Raung, L T Tsao, C N Lin. Evidence for the involvement of protein kinase C inhibition by norathyriol in the reduction of phorbol ester-induced neutrophil superoxide anion generation and aggregation. European journal of pharmacology. 1997 Oct; 336(1):81-8. doi: 10.1016/s0014-2999(97)01214-4. [PMID: 9384257]
  • J P Wang, S L Raung, C N Lin, C M Teng. Inhibitory effect of norathyriol, a xanthone from Tripterospermum lanceolatum, on cutaneous plasma extravasation. European journal of pharmacology. 1994 Jan; 251(1):35-42. doi: 10.1016/0014-2999(94)90440-5. [PMID: 7511107]