Eriodictyol (BioDeep_00000270214)

Main id: BioDeep_00000000303

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(S) -2- (3,4-Dihydroxyphenyl) -2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one

化学式: C15H12O6 (288.06338519999997)
中文名称: 圣草酚
谱图信息: 最多检出来源 Homo sapiens(urine) 1.43%

分子结构信息

SMILES: C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC(=C(C=C3)O)O
InChI: InChI=1S/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2

描述信息

Constituent of the leaves and branches of Phyllanthus emblica (emblic). Eriodictyol 7-(6-coumaroylglucoside) is found in fruits.
Annotation level-1
Eriodictyol is a flavonoid isolated from the Chinese herb, with antioxidant and anti-inflammatory activity. Eriodictyol induces Nrf2 signaling pathway. Eriodictyol is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 18 nM.
Eriodictyol is a flavonoid isolated from the Chinese herb, with antioxidant and anti-inflammatory activity. Eriodictyol induces Nrf2 signaling pathway. Eriodictyol is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 18 nM.

同义名列表

16 个代谢物同义名

Eriodictyol 7-(6-coumaroylglucoside); Eriodictyol; (2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one; (2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chroman-4-one; (2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-chromanone; (2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-4-one; (S)-3,4,5,7-Tetrahydroxyflavanone; ZINC00058117; 74565_FLUKA; CHEBI:28412; 552-58-9; C05631; ERD; (S) -2- (3,4-Dihydroxyphenyl) -2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one; 3,4,5,7-Tetrahydroxyflavanone; Huazhongilexone



数据库引用编号

54 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(8)

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)

161 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

  • Anna Balykina, Lidia Naida, Kürsat Kirkgöz, Viacheslav O Nikolaev, Ekaterina Fock, Michael Belyakov, Anastasiia Whaley, Andrei Whaley, Valentina Shpakova, Natalia Rukoyatkina, Stepan Gambaryan. Antiplatelet Effects of Flavonoid Aglycones Are Mediated by Activation of Cyclic Nucleotide-Dependent Protein Kinases. International journal of molecular sciences. 2024 Apr; 25(9):. doi: 10.3390/ijms25094864. [PMID: 38732081]
  • Mingyu Yue, Mengsu Liu, Song Gao, Xuefeng Ren, Shenghu Zhou, Yijian Rao, Jingwen Zhou. High-Level De Novo Production of (2S)-Eriodictyol in Yarrowia Lipolytica by Metabolic Pathway and NADPH Regeneration Engineering. Journal of agricultural and food chemistry. 2024 Feb; 72(8):4292-4300. doi: 10.1021/acs.jafc.3c08861. [PMID: 38364826]
  • Hanna Marie Schilbert, Mareike Busche, Vania Sáez, Andrea Angeli, Bernd Weisshaar, Stefan Martens, Ralf Stracke. Generation and characterisation of an Arabidopsis thaliana f3h/fls1/ans triple mutant that accumulates eriodictyol derivatives. BMC plant biology. 2024 Feb; 24(1):99. doi: 10.1186/s12870-024-04787-1. [PMID: 38331743]
  • Patricia Magadán-Corpas, Suhui Ye, Álvaro Pérez-Valero, Patrick L McAlpine, Paula Valdés-Chiara, Jesús Torres-Bacete, Juan Nogales, Claudio J Villar, Felipe Lombó. Optimized De Novo Eriodictyol Biosynthesis in Streptomyces albidoflavus Using an Expansion of the Golden Standard Toolkit for Its Use in Actinomycetes. International journal of molecular sciences. 2023 May; 24(10):. doi: 10.3390/ijms24108879. [PMID: 37240225]
  • Xiaokai Wang, Jun Chen, Hongyan Tie, Wei Tian, Yanli Zhao, Luying Qin, Siyan Guo, Qiufang Li, Chen Bao. Eriodictyol regulated ferroptosis, mitochondrial dysfunction, and cell viability via Nrf2/HO-1/NQO1 signaling pathway in ovarian cancer cells. Journal of biochemical and molecular toxicology. 2023 Apr; ?(?):e23368. doi: 10.1002/jbt.23368. [PMID: 37020356]
  • Sa Guo, Nan Xing, Gelin Xiang, Yi Zhang, Shaohui Wang. Eriodictyol: a review of its pharmacological activities and molecular mechanisms related to ischemic stroke. Food & function. 2023 Feb; 14(4):1851-1868. doi: 10.1039/d2fo03417d. [PMID: 36757280]
  • Jianbo He, Hongjuan Fu, Cancan Li, Zhihui Deng, Hui Chang. Eriodictyol inhibits breast carcinogenesis by targeting circ_0007503 and repressing PI3K/Akt pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jul; 102(?):154159. doi: 10.1016/j.phymed.2022.154159. [PMID: 35580441]
  • Sameh S Elhady, Elsayed A Ibrahim, Marwa S Goda, Mohamed S Nafie, Hanan Samir, Reem M Diri, Abdulrahman M Alahdal, Ama Kyeraa Thomford, Alaa El Gindy, Ghada M Hadad, Jihan M Badr, Reda F A Abdelhameed. GC-MS/MS Quantification of EGFR Inhibitors, β-Sitosterol, Betulinic Acid, (+) Eriodictyol, (+) Epipinoresinol, and Secoisolariciresinol, in Crude Extract and Ethyl Acetate Fraction of Thonningia sanguinea. Molecules (Basel, Switzerland). 2022 Jun; 27(13):. doi: 10.3390/molecules27134109. [PMID: 35807354]
  • Lin Li, Wen-Jun Li, Xiang-Ru Zheng, Qing-Long Liu, Qian Du, Yu-Jie Lai, Song-Qing Liu. Eriodictyol ameliorates cognitive dysfunction in APP/PS1 mice by inhibiting ferroptosis via vitamin D receptor-mediated Nrf2 activation. Molecular medicine (Cambridge, Mass.). 2022 01; 28(1):11. doi: 10.1186/s10020-022-00442-3. [PMID: 35093024]
  • Muhammad Farrukh Nisar, Tiantian Liu, Mei Wang, Shida Chen, Li Chang, Vega Widya Karisma, Weixu, Qingchun Diao, Mei Xue, Xueyong Tang, Charareh Pourzand, Jing Yang, Julia Li Zhong. Eriodictyol protects skin cells from UVA irradiation-induced photodamage by inhibition of the MAPK signaling pathway. Journal of photochemistry and photobiology. B, Biology. 2022 Jan; 226(?):112350. doi: 10.1016/j.jphotobiol.2021.112350. [PMID: 34785489]
  • Javier Fernández, Blanca Silván, Rodrigo Entrialgo-Cadierno, Claudio J Villar, Raffaele Capasso, José Antonio Uranga, Felipe Lombó, Raquel Abalo. Antiproliferative and palliative activity of flavonoids in colorectal cancer. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 Nov; 143(?):112241. doi: 10.1016/j.biopha.2021.112241. [PMID: 34649363]
  • Jianli Liu, Zhijun Yang, Ye Cheng, Qiong Wu, Yin He, Qijiu Li, Xiangyu Cao. Eriodictyol and naringenin inhibit the formation of AGEs: An in vitro and molecular interaction study. Journal of molecular recognition : JMR. 2020 01; 33(1):e2814. doi: 10.1002/jmr.2814. [PMID: 31637788]
  • Yongkun Lv, Monireh Marsafari, Mattheos Koffas, Jingwen Zhou, Peng Xu. Optimizing Oleaginous Yeast Cell Factories for Flavonoids and Hydroxylated Flavonoids Biosynthesis. ACS synthetic biology. 2019 11; 8(11):2514-2523. doi: 10.1021/acssynbio.9b00193. [PMID: 31622552]
  • Wei Li, Tae In Kim, Ji Hye Kim, Hwan-Suck Chung. Immune Checkpoint PD-1/PD-L1 CTLA-4/CD80 are Blocked by Rhus verniciflua Stokes and its Active Compounds. Molecules (Basel, Switzerland). 2019 Nov; 24(22):. doi: 10.3390/molecules24224062. [PMID: 31717574]
  • Jia-Xuan Xia, Bin-Bin Zhao, Jun-Feng Zan, Ping Wang, Lin-Lin Chen. Simultaneous determination of phenolic acids and flavonoids in Artemisiae Argyi Folium by HPLC-MS/MS and discovery of antioxidant ingredients based on relevance analysis. Journal of pharmaceutical and biomedical analysis. 2019 Oct; 175(?):112734. doi: 10.1016/j.jpba.2019.06.031. [PMID: 31330286]
  • Anam Qadir Khan, Zhonghua Li, Muhammad Mahmood Ahmed, Pengcheng Wang, Xianlong Zhang, Lili Tu. Eriodictyol can modulate cellular auxin gradients to efficiently promote in vitro cotton fibre development. BMC plant biology. 2019 Oct; 19(1):443. doi: 10.1186/s12870-019-2054-x. [PMID: 31651240]
  • Miroslav Novakovic, Iris Djordjevic, Nina Todorovic, Snezana Trifunovic, Boban Andjelkovic, Boris Mandic, Milka Jadranin, Ivan Vuckovic, Vlatka Vajs, Slobodan Milosavljevic, Vele Tesevic. New aurone epoxide and auronolignan from the heartwood of Cotinus coggygria Scop. Natural product research. 2019 Oct; 33(19):2837-2844. doi: 10.1080/14786419.2018.1508141. [PMID: 30513208]
  • YingChun Liu, XiaoNing Yan. Eriodictyol inhibits survival and inflammatory responses and promotes apoptosis in rheumatoid arthritis fibroblast-like synoviocytes through AKT/FOXO1 signaling. Journal of cellular biochemistry. 2019 09; 120(9):14628-14635. doi: 10.1002/jcb.28724. [PMID: 31009103]
  • Shoib Ahmad Baba, Nasheeman Ashraf. Functional characterization of flavonoid 3'-hydroxylase, CsF3'H, from Crocus sativus L: Insights into substrate specificity and role in abiotic stress. Archives of biochemistry and biophysics. 2019 05; 667(?):70-78. doi: 10.1016/j.abb.2019.04.012. [PMID: 31054842]
  • Aleksandra Golonko, Tomasz Pienkowski, Renata Swislocka, Ryszard Lazny, Marek Roszko, Wlodzimierz Lewandowski. Another look at phenolic compounds in cancer therapy the effect of polyphenols on ubiquitin-proteasome system. European journal of medicinal chemistry. 2019 Apr; 167(?):291-311. doi: 10.1016/j.ejmech.2019.01.044. [PMID: 30776692]
  • Eun-Young Kwon, Myung-Sook Choi. Dietary Eriodictyol Alleviates Adiposity, Hepatic Steatosis, Insulin Resistance, and Inflammation in Diet-Induced Obese Mice. International journal of molecular sciences. 2019 Mar; 20(5):. doi: 10.3390/ijms20051227. [PMID: 30862092]
  • Katherina Garcia Vanegas, Arésu Bondrup Larsen, Michael Eichenberger, David Fischer, Uffe Hasbro Mortensen, Michael Naesby. Indirect and direct routes to C-glycosylated flavones in Saccharomyces cerevisiae. Microbial cell factories. 2018 Jul; 17(1):107. doi: 10.1186/s12934-018-0952-5. [PMID: 29986709]
  • Grant Quiller, Ángel Mérida-Ortega, Stephen J Rothenberg, Mariano E Cebrián, A Jay Gandolfi, Francisco Franco-Marina, Lizbeth López-Carrillo. Dietary flavonoids improve urinary arsenic elimination among Mexican women. Nutrition research (New York, N.Y.). 2018 07; 55(?):65-71. doi: 10.1016/j.nutres.2018.04.012. [PMID: 29914629]
  • Abdul Hameed, Rahman M Hafizur, Nusrat Hussain, Sayed Ali Raza, Mujeeb Rehman, Sajda Ashraf, Zaheer Ul-Haq, Faisal Khan, Ghulam Abbas, M Iqbal Choudhary. Eriodictyol stimulates insulin secretion through cAMP/PKA signaling pathway in mice islets. European journal of pharmacology. 2018 Feb; 820(?):245-255. doi: 10.1016/j.ejphar.2017.12.015. [PMID: 29229531]
  • Francis A Armah, Isaac K Amponsah, Abraham Y Mensah, Rita A Dickson, Paul A Steenkamp, Ntakadzeni E Madala, Christian K Adokoh. Leishmanicidal activity of the root bark of Erythrophleum Ivorense (Fabaceae) and identification of some of its compounds by ultra-performance liquid chromatography quadrupole time of flight mass spectrometry (UPLC-QTOF-MS/MS). Journal of ethnopharmacology. 2018 Jan; 211(?):207-216. doi: 10.1016/j.jep.2017.09.030. [PMID: 28970156]
  • Li-Ping Huang, Bo Yan, Min Hou, Meng-Sheng Sun, Kun He, Yang Guan, Li-Hua Yao, Mao-Fu Zhou. [Study on Material Basis and Mechanism of Erzhi Wan prevent Alzheimer's disease by network pharmacology]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 Nov; 42(21):4211-4217. doi: 10.19540/j.cnki.cjcmm.20170905.008. [PMID: 29271163]
  • Zhaoyu Wang, Yao Lan, MingHao Chen, Cailing Wen, Yanxian Hu, Zhongqiu Liu, Ling Ye. Eriodictyol, Not Its Glucuronide Metabolites, Attenuates Acetaminophen-Induced Hepatotoxicity. Molecular pharmaceutics. 2017 09; 14(9):2937-2951. doi: 10.1021/acs.molpharmaceut.7b00345. [PMID: 28654297]
  • Yuyan Liang, Hai Niu, Limei Ma, Dan Du, Li Wen, Qing Xia, Wen Huang. Eriodictyol 7‑O‑β‑D glucopyranoside from Coreopsis tinctoria Nutt. ameliorates lipid disorders via protecting mitochondrial function and suppressing lipogenesis. Molecular medicine reports. 2017 Aug; 16(2):1298-1306. doi: 10.3892/mmr.2017.6743. [PMID: 28627652]
  • Vladimir Chobot, Franz Hadacek, Gert Bachmann, Wolfram Weckwerth, Lenka Kubicova. Pro- and Antioxidant Activity of Three Selected Flavan Type Flavonoids: Catechin, Eriodictyol and Taxifolin. International journal of molecular sciences. 2016 Nov; 17(12):. doi: 10.3390/ijms17121986. [PMID: 27898046]
  • Leo-Paul Tisserant, Jane Hubert, Michelle Lequart, Nicolas Borie, Nicolas Maurin, Serge Pilard, Philippe Jeandet, Aziz Aziz, Jean-Hugues Renault, Jean-Marc Nuzillard, Christophe Clément, Michèle Boitel-Conti, Eric Courot. 13C NMR and LC-MS Profiling of Stilbenes from Elicited Grapevine Hairy Root Cultures. Journal of natural products. 2016 11; 79(11):2846-2855. doi: 10.1021/acs.jnatprod.6b00608. [PMID: 27933900]
  • Fangming Song, Lin Zhou, Jinmin Zhao, Qian Liu, Mingli Yang, Renxiang Tan, Jun Xu, Ge Zhang, Julian M W Quinn, Jennifer Tickner, Yuanjiao Huang, Jiake Xu. Eriodictyol Inhibits RANKL-Induced Osteoclast Formation and Function Via Inhibition of NFATc1 Activity. Journal of cellular physiology. 2016 09; 231(9):1983-93. doi: 10.1002/jcp.25304. [PMID: 26754483]
  • Wenzhu Wang, Haigang Li, Jintao Yu, Michael Hong, Jing Zhou, Lin Zhu, Yang Wang, Min Luo, Zian Xia, Zeng-Jin Yang, Tao Tang, Ping Ren, Xi Huang, Jian Wang. Protective Effects of Chinese Herbal Medicine Rhizoma drynariae in Rats After Traumatic Brain Injury and Identification of Active Compound. Molecular neurobiology. 2016 09; 53(7):4809-20. doi: 10.1007/s12035-015-9385-x. [PMID: 26334614]
  • Paula S Ferreira, Luis C Spolidorio, John A Manthey, Thais B Cesar. Citrus flavanones prevent systemic inflammation and ameliorate oxidative stress in C57BL/6J mice fed high-fat diet. Food & function. 2016 Jun; 7(6):2675-81. doi: 10.1039/c5fo01541c. [PMID: 27182608]
  • Cheng-zhen Li, Hai-hong Jin, Hong-xin Sun, Zhong-zhe Zhang, Jia-xin Zheng, Shu-hua Li, Seong-ho Han. Eriodictyol attenuates cisplatin-induced kidney injury by inhibiting oxidative stress and inflammation. European journal of pharmacology. 2016 Feb; 772(?):124-30. doi: 10.1016/j.ejphar.2015.12.042. [PMID: 26723515]
  • Mai Yamashita, Motofumi Kumazoe, Yuki Nakamura, Yeong Seon Won, Jaehoon Bae, Shuya Yamashita, Hirofumi Tachibana. The Combination of Green Tea Extract and Eriodictyol Inhibited High-Fat/High-Sucrose Diet-Induced Cholesterol Upregulation Is Accompanied by Suppression of Cholesterol Synthesis Enzymes. Journal of nutritional science and vitaminology. 2016; 62(4):249-256. doi: 10.3177/jnsv.62.249. [PMID: 27725410]
  • J Andrew Jones, Shannon M Collins, Victoria R Vernacchio, Daniel M Lachance, Mattheos A G Koffas. Optimization of naringenin and p-coumaric acid hydroxylation using the native E. coli hydroxylase complex, HpaBC. Biotechnology progress. 2016 Jan; 32(1):21-5. doi: 10.1002/btpr.2185. [PMID: 26488898]
  • Yingzhan Tang, Junhong Ling, Peng Zhang, Xiangrong Zhang, Na Zhang, Wenli Wang, Jiayuan Li, Ning Li. Potential therapeutic agents for circulatory diseases from Bauhinia glauca Benth.subsp. pernervosa. (Da Ye Guan Men). Bioorganic & medicinal chemistry letters. 2015 Aug; 25(16):3217-20. doi: 10.1016/j.bmcl.2015.05.089. [PMID: 26096681]
  • Liyi Yang, Kimberly F Allred, Linda Dykes, Clinton D Allred, Joseph M Awika. Enhanced action of apigenin and naringenin combination on estrogen receptor activation in non-malignant colonocytes: implications on sorghum-derived phytoestrogens. Food & function. 2015 Mar; 6(3):749-55. doi: 10.1039/c4fo00300d. [PMID: 25553799]
  • Gustavo Costa, Susana González-Manzano, Ana González-Paramás, Isabel Vitória Figueiredo, Celestino Santos-Buelga, Maria Teresa Batista. Flavan hetero-dimers in the Cymbopogon citratus infusion tannin fraction and their contribution to the antioxidant activity. Food & function. 2015 Mar; 6(3):932-7. doi: 10.1039/c5fo00042d. [PMID: 25652784]
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  • Saijie Zhu, Junjun Wu, Guocheng Du, Jingwen Zhou, Jian Chen. Efficient synthesis of eriodictyol from L-tyrosine in Escherichia coli. Applied and environmental microbiology. 2014 May; 80(10):3072-80. doi: 10.1128/aem.03986-13. [PMID: 24610848]
  • Qingtao Liu, Long Liu, Jingwen Zhou, Hyun-Dong Shin, Rachel R Chen, Catherine Madzak, Jianghua Li, Guocheng Du, Jian Chen. Biosynthesis of homoeriodictyol from eriodictyol by flavone 3'-O-methyltransferase from recombinant Yarrowia lioplytica: Heterologous expression, biochemical characterization, and optimal transformation. Journal of biotechnology. 2013 Sep; 167(4):472-8. doi: 10.1016/j.jbiotec.2013.07.025. [PMID: 23906843]
  • Sae-Jin Park, Yong-Hyeon Lee, Kwang Ho Lee, Tack-Joong Kim. Effect of eriodictyol on the development of atopic dermatitis-like lesions in ICR mice. Biological & pharmaceutical bulletin. 2013; 36(8):1375-9. doi: 10.1248/bpb.b13-00296. [PMID: 23902981]
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