Irilone (BioDeep_00000008107)

 

Secondary id: BioDeep_00000270151, BioDeep_00000862582

human metabolite PANOMIX_OTCML-2023 blood metabolite natural product


代谢物信息卡片


9-Hydroxy-7-(4-hydroxyphenyl)-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one, 9ci

化学式: C16H10O6 (298.047736)
中文名称: 德鸢尾素
谱图信息: 最多检出来源 Homo sapiens(blood) 4.11%

分子结构信息

SMILES: c12c(c(c3c(c1)occ(c3=O)c1ccc(cc1)O)O)OCO2
InChI: InChI=1S/C16H10O6/c17-9-3-1-8(2-4-9)10-6-20-11-5-12-16(22-7-21-12)15(19)13(11)14(10)18/h1-6,17,19H,7H2

描述信息

Irilone is found in herbs and spices. Irilone is a constituent of Trifolium pratense (red clover).
Constituent of Trifolium pratense (red clover). Irilone is found in tea and herbs and spices.

同义名列表

6 个代谢物同义名

9-Hydroxy-7-(4-hydroxyphenyl)-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one, 9ci; 9-Hydroxy-7-(4-hydroxyphenyl)-8H-1,3-dioxolo[4,5-g]-1-benzopyran-8-one; 9-hydroxy-7-(4-hydroxyphenyl)-2H,8H-[1,3]dioxolo[4,5-g]chromen-8-one; 5,4-Dihydroxy-6,7-methylenedioxyisoflavone; Irolone; Irilone



数据库引用编号

17 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)

47 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

  • Sandra Ochensberger, Fabian Alperth, Božena Mitić, Olaf Kunert, Stefanie Mayer, Maria Ferreira Mourão, Ivana Turek, Simon Vlad Luca, Krystyna Skalicka-Woźniak, Željan Maleš, Dario Hruševar, Ivan Duka, Franz Bucar. Phenolic compounds of Iris adriatica and their antimycobacterial effects. Acta pharmaceutica (Zagreb, Croatia). 2019 Dec; 69(4):673-681. doi: 10.2478/acph-2019-0037. [PMID: 31639092]
  • Gonzalo R Malca Garcia, J Brent Friesen, Yang Liu, Dejan Nikolić, David C Lankin, James B McAlpine, Shao-Nong Chen, Guido F Pauli. Preparation of DESIGNER extracts of red clover (Trifolium pratense L.) by centrifugal partition chromatography. Journal of chromatography. A. 2019 Nov; 1605(?):360277. doi: 10.1016/j.chroma.2019.05.057. [PMID: 31307793]
  • Jung-Ho Lee, Matthew Dean, Julia R Austin, Joanna E Burdette, Brian T Murphy. Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling. Journal of natural products. 2018 09; 81(9):1962-1967. doi: 10.1021/acs.jnatprod.8b00131. [PMID: 30199256]
  • Yannan Li, Jing Ning, Yan Wang, Chao Wang, Chengpeng Sun, Xiaokui Huo, Zhenlong Yu, Lei Feng, Baojing Zhang, Xiangge Tian, Xiaochi Ma. Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicology letters. 2018 Sep; 294(?):27-36. doi: 10.1016/j.toxlet.2018.05.008. [PMID: 29753067]
  • Xiafen Xu, Xinhui Li, Xianrui Liang. Application of ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry in identification of three isoflavone glycosides and their corresponding metabolites. Rapid communications in mass spectrometry : RCM. 2018 Feb; 32(3):262-268. doi: 10.1002/rcm.8038. [PMID: 29222826]
  • Sabrin R M Ibrahim, Gamal A Mohamed, Mohamed F Zayed, Samir A Ross. 8-Hydroxyirilone 5-methyl ether and 8-hydroxyirilone, new antioxidant and α-amylase inhibitors isoflavonoids from Iris germanica rhizomes. Bioorganic chemistry. 2017 02; 70(?):192-198. doi: 10.1016/j.bioorg.2016.12.010. [PMID: 28069265]
  • João C M Barreira, Tatiana Visnevschi-Necrasov, Eugénia Nunes, Sara C Cunha, Graça Pereira, M Beatriz P P Oliveira. Medicago spp. as potential sources of bioactive isoflavones: Characterization according to phylogenetic and phenologic factors. Phytochemistry. 2015 Aug; 116(?):230-238. doi: 10.1016/j.phytochem.2015.04.011. [PMID: 25982842]
  • Anne Scheffler, Annette E Albrecht, Harald L Esch, Leane Lehmann. Mutagenic potential of the isoflavone irilone in cultured V79 cells. Toxicology letters. 2015 Apr; 234(2):81-91. doi: 10.1016/j.toxlet.2015.02.013. [PMID: 25703823]
  • Stefanie Lutter, Katja Schmalbach, Harald L Esch, Leane Lehmann. The isoflavone irilone contributes to the estrogenic potential of dietary supplements containing red clover. Archives of toxicology. 2014 Feb; 88(2):309-21. doi: 10.1007/s00204-013-1114-5. [PMID: 23982890]
  • B Roger, V Jeannot, X Fernandez, S Cerantola, J Chahboun. Characterisation and quantification of flavonoids in Iris germanica L. and Iris pallida Lam. resinoids from Morocco. Phytochemical analysis : PCA. 2012 Sep; 23(5):450-5. doi: 10.1002/pca.1379. [PMID: 22213588]
  • Sabrin R M Ibrahim, Gamal A Mohamed, Nawal M Al-Musayeib. New constituents from the rhizomes of Egyptian Iris germanica L. Molecules (Basel, Switzerland). 2012 Mar; 17(3):2587-98. doi: 10.3390/molecules17032587. [PMID: 22388969]
  • Tayyab A Mansoor, Rita M Ramalho, Xuan Luo, Cátia Ramalhete, Cecília M P Rodrigues, Maria-José U Ferreira. Isoflavones as apoptosis inducers in human hepatoma HuH-7 cells. Phytotherapy research : PTR. 2011 Dec; 25(12):1819-24. doi: 10.1002/ptr.3498. [PMID: 21495101]
  • Yuan-Yuan Zhang, Qi Wang, Lian-Wen Qi, Xiao-Ying Qin, Min-Jian Qin. Characterization and determination of the major constituents in Belamcandae Rhizoma by HPLC-DAD-ESI-MS(n). Journal of pharmaceutical and biomedical analysis. 2011 Sep; 56(2):304-14. doi: 10.1016/j.jpba.2011.05.040. [PMID: 21715119]
  • Annett Braune, Ronald Maul, Nils Helge Schebb, Sabine E Kulling, Michael Blaut. The red clover isoflavone irilone is largely resistant to degradation by the human gut microbiota. Molecular nutrition & food research. 2010 Jul; 54(7):929-38. doi: 10.1002/mnfr.200900233. [PMID: 19998384]
  • Guo-Rong Wang, Wen-Zhao Tang, Qing-Qiang Yao, Hao Zhong, Yong-Jun Liu. New flavonoids with 2BS cell proliferation promoting effect from the seeds of Trigonella foenum-graecum L. Journal of natural medicines. 2010 Jul; 64(3):358-61. doi: 10.1007/s11418-010-0407-8. [PMID: 20349151]
  • Ronald Maul, Sabine E Kulling. Absorption of red clover isoflavones in human subjects: results from a pilot study. The British journal of nutrition. 2010 Jun; 103(11):1569-72. doi: 10.1017/s0007114509993564. [PMID: 20067656]
  • Nighat Nazir, Surrinder Koul, Mushtaq Ahmad Qurishi, Subhash Chander Taneja, Sheikh Fayaz Ahmad, Beenish Khan, Sarang Bani, Ghulam Nabi Qazi. Immunomodulatory activity of isoflavones isolated from Iris germanica (Iridaceae) on T-lymphocytes and cytokines. Phytotherapy research : PTR. 2009 Mar; 23(3):428-33. doi: 10.1002/ptr.2683. [PMID: 19003948]
  • Han-Qing Chen, Xi-Jin Wang, Zheng-Yu Jin, Xue-Ming Xu, Jian-Wei Zhao, Zheng-Jun Xie. Protective effect of isoflavones from Trifolium pratense on dopaminergic neurons. Neuroscience research. 2008 Oct; 62(2):123-30. doi: 10.1016/j.neures.2008.07.001. [PMID: 18675857]
  • Ronald Maul, Nils Helge Schebb, Sabine E Kulling. Application of LC and GC hyphenated with mass spectrometry as tool for characterization of unknown derivatives of isoflavonoids. Analytical and bioanalytical chemistry. 2008 May; 391(1):239-50. doi: 10.1007/s00216-008-1884-4. [PMID: 18317741]
  • B Klejdus, J Vacek, L Benesová, J Kopecký, O Lapcík, V Kubán. Rapid-resolution HPLC with spectrometric detection for the determination and identification of isoflavones in soy preparations and plant extracts. Analytical and bioanalytical chemistry. 2007 Dec; 389(7-8):2277-85. doi: 10.1007/s00216-007-1606-3. [PMID: 17899029]
  • Daniela Rigano, Carmen Formisano, Armando Grassia, Gianluca Grassia, Angela Perrone, Sonia Piacente, Maria Luisa Vuotto, Felice Senatore. Antioxidant flavonoids and isoflavonoids from rhizomes of Iris pseudopumila. Planta medica. 2007 Jan; 73(1):93-6. doi: 10.1055/s-2006-957071. [PMID: 17315314]
  • Rong Tsao, Yousef Papadopoulos, Raymond Yang, J Chris Young, Ken McRae. Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages. Journal of agricultural and food chemistry. 2006 Aug; 54(16):5797-805. doi: 10.1021/jf0614589. [PMID: 16881680]
  • Qingli Wu, Mingfu Wang, James E Simon. Determination of isoflavones in red clover and related species by high-performance liquid chromatography combined with ultraviolet and mass spectrometric detection. Journal of chromatography. A. 2003 Oct; 1016(2):195-209. doi: 10.1016/j.chroma.2003.08.001. [PMID: 14601839]
  • Eckhard Wollenweber, Jan Frederik Stevens, Karin Klimo, Jutta Knauft, Norbert Frank, Clarissa Gerhäuser. Cancer chemopreventive in vitro activities of isoflavones isolated from Iris germanica. Planta medica. 2003 Jan; 69(1):15-20. doi: 10.1055/s-2003-37030. [PMID: 12567273]
  • Atta-Ur-Rahman, Shama Nasim, Irfan Baig, Ismat Ara Jahan, Bilge Sener, Ilkay Orhan, Muhammad Iqbal Choudhary. Isoflavonoid glycosides from the rhizomes of Iris germanica. Chemical & pharmaceutical bulletin. 2002 Aug; 50(8):1100-2. doi: 10.1248/cpb.50.1100. [PMID: 12192144]
  • Bernard Blaise Messanga, Samuel Fon Kimbu, Beibam Luc Sondengam, Bernard Bodo. Triflavonoids of Ochna calodendron. Phytochemistry. 2002 Feb; 59(4):435-8. doi: 10.1016/s0031-9422(01)00414-9. [PMID: 11830163]