Ononin (BioDeep_00000003338)

 

Secondary id: BioDeep_00000230205, BioDeep_00000270227

natural product human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


3-(4-methoxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

化学式: C22H22O9 (430.1263762)
中文名称: 芒柄花苷
谱图信息: 最多检出来源 Viridiplantae(plant) 0.1%

分子结构信息

SMILES: c1(ccc2c(c1)occ(c2=O)c1ccc(cc1)OC)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)O
InChI: InChI=1S/C22H22O9/c1-28-12-4-2-11(3-5-12)15-10-29-16-8-13(6-7-14(16)18(15)24)30-22-21(27)20(26)19(25)17(9-23)31-22/h2-8,10,17,19-23,25-27H,9H2,1H3

描述信息

Widely distributed in the Leguminosae subfamily Papilionoideae, e.g. in Medicago sativa (alfalfa) and Trifolium subspecies Formononetin 7-glucoside is found in chickpea, soy bean, and pulses.
Ononin is found in chickpea. Ononin is widely distributed in the Leguminosae subfamily Papilionoideae, e.g. in Medicago sativa (alfalfa) and Trifolium species.
Acquisition and generation of the data is financially supported in part by CREST/JST.
IPB_RECORD: 381; CONFIDENCE confident structure
Ononin is an isoflavone that inhibits the growth of Pluchea lanceolata in soil.
Ononin is an isoflavone that inhibits the growth of Pluchea lanceolata in soil.

同义名列表

17 个代谢物同义名

3-(4-methoxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one; 3-(4-Methoxyphenyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one; 4-Methoxyisoflavone-7-O-beta-D-glucopyranoside; Formononetin 7-O-β-D-glucopyranoside; Formononetin 7-O-beta-D-glucopyranoside; Formononetin-7-O-beta-D-glucopyranoside; calycosin-7-O-beta-D-glucoside; Formononetin 7-O-glucoside; formononetin-7-O-glucoside; Formononetin-7-glucoside; Formononetin 7-glucoside; Formononetin glucoside; Ononoside; Ononin?; ononin; Formononetin 7-O-β-D-glucopyranoside; Ononin



数据库引用编号

40 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

278 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

  • Yi-Ming Zhang, Zhi-Ming Miao, Ya-Ping Chen, Zhang-Bo Song, Yang-Yang Li, Zhi-Wei Liu, Gu-Cheng Zhou, Jing Li, Liang-Liang Shi, Yan Chen, Shang-Zu Zhang, Xiaohui Xu, Jin-Peng He, Ju-Fang Wang, Li-Ying Zhang, Yong-Qi Liu. Ononin promotes radiosensitivity in lung cancer by inhibiting HIF-1α/VEGF pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Dec; 125(?):155290. doi: 10.1016/j.phymed.2023.155290. [PMID: 38308918]
  • Yu-Zhu Yang, Tao Wang, Qi-Lei Chen, Hu-Biao Chen, Qian-Song He, Ya-Zhou Zhang. Identification of the Metabolites of Both Formononetin in Rat Hepatic S9 and Ononin in Rat Urine Samples and Preliminary Network Pharmacology Evaluation of Their Main Metabolites. Molecules (Basel, Switzerland). 2023 Nov; 28(21):. doi: 10.3390/molecules28217451. [PMID: 37959870]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Liangliang Du, Douyun Zeng, Xian Hu, Xi Ren, Dazhi He. Ononin Relieves the Thyroid Cancer Progression through Targeting the Caspase 3 and CD274 Expression Levels. Biological & pharmaceutical bulletin. 2023; 46(8):1041-1048. doi: 10.1248/bpb.b22-00796. [PMID: 37532555]
  • Wan Xu, Feiye Zhou, Qin Zhu, Mengyao Bai, Tiancheng Luo, Libin Zhou, Ruyuan Deng. Calycosin-7-O-β-D-glucoside attenuates palmitate-induced lipid accumulation in hepatocytes through AMPK activation. European journal of pharmacology. 2022 Jun; 925(?):174988. doi: 10.1016/j.ejphar.2022.174988. [PMID: 35490724]
  • Jiao Guan, Liming Wang, Yuan Ji, Tianyi Zhang, Ye Sang, Sheng Chang, Bo Feng, Heyun Zhu. UHPLC-MS/MS Method for Quantifying Fangchinoline, Tetrandrine and Calycosin-7-O-β-D-Glucoside of Fangji Huangqi Decoction in Rat Plasma and Its Application to a Pharmacokinetic Study. Journal of chromatographic science. 2022 Jun; 60(5):458-464. doi: 10.1093/chromsci/bmab116. [PMID: 34734235]
  • Zhen Yang, Xiaoping Tan, Zhiqiang Zhang, Jing Han, Shenye Qu, Tianqiang Liu, Gaoxue Wang. Ononin: A candidate anti-parasitic drug isolated from Spatholobi caulis against infections of Dactylogyrus intermedius (Monogenea). Parasitology international. 2022 Jun; 88(?):102535. doi: 10.1016/j.parint.2021.102535. [PMID: 34995771]
  • Saveta G Mladenova, Martina S Savova, Andrey S Marchev, Claudio Ferrante, Giustino Orlando, Martin Wabitsch, Milen I Georgiev. Anti-adipogenic activity of maackiain and ononin is mediated via inhibition of PPARγ in human adipocytes. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 May; 149(?):112908. doi: 10.1016/j.biopha.2022.112908. [PMID: 35367764]
  • Fang Xu, Liang-Jun Zhao, Ting Liao, Zhao-Cong Li, Lei-Lei Wang, Pan-Yu Lin, Rui Jiang, Qing-Jun Wei. Ononin ameliorates inflammation and cartilage degradation in rat chondrocytes with IL-1β-induced osteoarthritis by downregulating the MAPK and NF-κB pathways. BMC complementary medicine and therapies. 2022 Jan; 22(1):25. doi: 10.1186/s12906-022-03504-5. [PMID: 35086536]
  • Kyung-Ran Park, Ji Eun Park, Bomi Kim, Il Keun Kwon, Jin Tae Hong, Hyung-Mun Yun. Calycosin-7-O-β-Glucoside Isolated from Astragalus membranaceus Promotes Osteogenesis and Mineralization in Human Mesenchymal Stem Cells. International journal of molecular sciences. 2021 Oct; 22(21):. doi: 10.3390/ijms222111362. [PMID: 34768792]
  • Bijay Kafle, Jan P A Baak, Cato Brede. Major bioactive chemical compounds in Astragali Radix samples from different vendors vary greatly. PloS one. 2021; 16(7):e0254273. doi: 10.1371/journal.pone.0254273. [PMID: 34234375]
  • Liyu Luo, Junyi Zhou, Haiyu Zhao, Miaoxuan Fan, Wenyuan Gao. The anti-inflammatory effects of formononetin and ononin on lipopolysaccharide-induced zebrafish models based on lipidomics and targeted transcriptomics. Metabolomics : Official journal of the Metabolomic Society. 2019 11; 15(12):153. doi: 10.1007/s11306-019-1614-2. [PMID: 31768751]
  • Yunru Yu, Zhenhao Li, Rui Guo, Jing Qian, Han Zhang, Junhua Zhang, Xiaoping Zhao, Shufang Wang, Yi Wang. Ononin, sec-O-β-d-glucosylhamaudol and astragaloside I: antiviral lead compounds identified via high throughput screening and biological validation from traditional Chinese medicine Zhongjing formulary. Pharmacological research. 2019 07; 145(?):104248. doi: 10.1016/j.phrs.2019.04.032. [PMID: 31082475]
  • Jiao Guan, Liming Wang, Jia Jin, Sheng Chang, Xiao Xiao, Bo Feng, Heyun Zhu. Simultaneous determination of calycosin-7-O-β-D-glucoside, cinnamic acid, paeoniflorin and albiflorin in rat plasma by UHPLC-MS/MS and its application to a pharmacokinetic study of Huangqi Guizhi Wuwu Decoction. Journal of pharmaceutical and biomedical analysis. 2019 Jun; 170(?):1-7. doi: 10.1016/j.jpba.2019.03.022. [PMID: 30897430]
  • Zhao-Guang Zheng, You-Hua Xu, Fang Liu, Ting-Ting Zhao, Rui-Xue Wang, Pei-Ying Huang, Ru-Shang Wang, An-Ping Yang, Quan Zhu. Screening bioactive components of Glycyrrhiza uralensis Fisch. with isolated perfused lung extraction and HPLC-ESI-MSn analysis. Journal of pharmaceutical and biomedical analysis. 2019 May; 169(?):127-132. doi: 10.1016/j.jpba.2019.03.007. [PMID: 30861404]
  • Ling He, Xiaoqian Shi, S W Seto, C Dennis, Heng Wang, Sheng Zhang, Weidong Chen, Jian Wang. Using 3D-UPLC-DAD and a new method-verification by adding mixture standard compounds to determine the fingerprint and eight active components of Naoluoxintong decoction. Journal of pharmaceutical and biomedical analysis. 2019 May; 169(?):60-69. doi: 10.1016/j.jpba.2018.12.046. [PMID: 30836247]
  • Jianqin Zhang, Xiaoli Xue, Yang Yang, Wen Ma, Yan Han, Xuemei Qin. Multiple biological defects caused by calycosin-7-O-β-d-glucoside in the nematode Caenorhabditis elegans are associated with the activation of oxidative damage. Journal of applied toxicology : JAT. 2018 06; 38(6):801-809. doi: 10.1002/jat.3588. [PMID: 29350786]
  • Li-Yu Luo, Miao-Xuan Fan, Hai-Yu Zhao, Ming-Xing Li, Xu Wu, Wen-Yuan Gao. Pharmacokinetics and Bioavailability of the Isoflavones Formononetin and Ononin and Their in Vitro Absorption in Ussing Chamber and Caco-2 Cell Models. Journal of agricultural and food chemistry. 2018 Mar; 66(11):2917-2924. doi: 10.1021/acs.jafc.8b00035. [PMID: 29504397]
  • Cha Zhang, Jia-Xing Zhang, Yi-Fan Xiong, Lu Lu, Ming-Qing Wang, Si-Ming Liu, Wei Xiao. [Screening active ingredients of Shenkangwan that regulate endothelial-mesenchymal transition of endothelial cells in vitro]. Nan fang yi ke da xue xue bao = Journal of Southern Medical University. 2018 Mar; 38(3):312-317. doi: . [PMID: 29643037]
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  • Fengyun Liao, Yingjiao Meng, Huazhu Zheng, Dongmei He, Xiao Shen, Jianye Yu, Yinai Wu, Lisheng Wang. Biospecific isolation and characterization of angiogenesis-promoting ingredients in Buyang Huanwu decoction using affinity chromatography on rat brain microvascular endothelial cells combined with solid-phase extraction, and HPLC-MS/MS. Talanta. 2018 Mar; 179(?):490-500. doi: 10.1016/j.talanta.2017.11.018. [PMID: 29310265]
  • 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]
  • Yang Liu, Jia Liu, Yu Wang, Ann Abozeid, Dong-Mei Tian, Xiao-Ning Zhang, Zhong-Hua Tang. The Different Resistance of Two Astragalus Plants to UV-B Stress is Tightly Associated with the Organ-specific Isoflavone Metabolism. Photochemistry and photobiology. 2018 01; 94(1):115-125. doi: 10.1111/php.12841. [PMID: 28881500]
  • Xian-Fei Zhang, Jun-Li Yang, Juan Chen, Yan-Ping Shi. Optimization of a Decoction Process for an Herbal Formula Using a Response Surface Methodology. Journal of AOAC International. 2017 Nov; 100(6):1776-1784. doi: 10.5740/jaoacint.17-0022. [PMID: 28534469]
  • Yaping Shao, Wen Zhang, Ling Tong, Jingyi Huang, Dongxiang Li, Wei Nie, Yan Zhu, Yunfei Li, Tao Lu. Simultaneous determination of eight bioactive components of Qishen Yiqi dripping pills in rat plasma using UFLC-MS/MS and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2017 Aug; 31(8):. doi: 10.1002/bmc.3941. [PMID: 28146302]
  • Xiao-Ling Wang, Fu-Rong Jiao, Meng Yu, Li-Bin Lin, Jian Xiao, Qiang Zhang, Le Wang, Dong-Zhu Duan, Gang Xie. Constituents with potent α-glucosidase inhibitory activity from Pueraria lobata (Willd.) ohwi. Bioorganic & medicinal chemistry letters. 2017 05; 27(9):1993-1998. doi: 10.1016/j.bmcl.2017.03.013. [PMID: 28343876]
  • 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]
  • Lin Li, Sihao Zheng, Josef A Brinckmann, Juan Fu, Rui Zeng, Linfang Huang, Shilin Chen. Chemical and genetic diversity of Astragalus mongholicus grown in different eco-climatic regions. PloS one. 2017; 12(9):e0184791. doi: 10.1371/journal.pone.0184791. [PMID: 28945770]
  • Jian Wu, Ying Xie, Zheng Xiang, Canjian Wang, Hua Zhou, Liang Liu. Simultaneous Determination of Multiple Components in Guanjiekang in Rat Plasma via the UPLC-MS/MS Method and Its Application in Pharmacokinetic Study. Molecules (Basel, Switzerland). 2016 Dec; 21(12):. doi: 10.3390/molecules21121732. [PMID: 27999285]
  • Liangliang Liu, Juan Leng, Xiai Yang, Liping Liao, Yin Cen, Aiping Xiao, Lei Ma. Rapid Screening and Identification of BSA Bound Ligands from Radix astragali Using BSA Immobilized Magnetic Nanoparticles Coupled with HPLC-MS. Molecules (Basel, Switzerland). 2016 Nov; 21(11):. doi: 10.3390/molecules21111471. [PMID: 27827956]
  • Xiao-ya Liu, Ji-ping Li, Xin-yue Chen, Ya-li Chen, Yan Hong, Shi-lan Feng. [Determination of eight active components in Radix Hedysari by HPLC and its cluster analysis]. Yao xue xue bao = Acta pharmaceutica Sinica. 2016 05; 51(5):786-91. doi: . [PMID: 29878726]
  • Jian-Qing Ruan, Shang Li, Ya-Ping Li, Wen-Jin Wu, Simon Ming-Yuen Lee, Ru Yan. The Presystemic Interplay between Gut Microbiota and Orally Administered Calycosin-7-O-β-D-Glucoside. Drug metabolism and disposition: the biological fate of chemicals. 2015 Oct; 43(10):1601-11. doi: 10.1124/dmd.115.065094. [PMID: 26101224]
  • Lotfi Ghribi, Pierre Waffo-Téguo, Stéphanie Cluzet, Axel Marchal, Jessica Marques, Jean-Michel Mérillon, Hichem Ben Jannet. Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L. Bioorganic & medicinal chemistry letters. 2015 Sep; 25(18):3825-30. doi: 10.1016/j.bmcl.2015.07.076. [PMID: 26248805]
  • Yue-Hua Jiang, Wei Sun, Wei Li, Hong-Zhen Hu, Le Zhou, Hui-Hui Jiang, Jing-Xin Xu. Calycosin-7-O-β-D-glucoside promotes oxidative stress-induced cytoskeleton reorganization through integrin-linked kinase signaling pathway in vascular endothelial cells. BMC complementary and alternative medicine. 2015 Sep; 15(?):315. doi: 10.1186/s12906-015-0839-5. [PMID: 26346982]
  • Xinyue Chen, Xiaoya Liu, Yali Chen, Yan Hong, Shilan Feng. [Spectrum-effect relationship on anti-hepatic fibrosis effect of Radix Hedysari]. Se pu = Chinese journal of chromatography. 2015 Apr; 33(4):413-8. doi: 10.3724/sp.j.1123.2014.12035. [PMID: 26292413]
  • Bingrui Liu, Kenneth T Kongstad, Sun Qinglei, Nils T Nyberg, Anna K Jäger, Dan Staerk. Dual high-resolution α-glucosidase and radical scavenging profiling combined with HPLC-HRMS-SPE-NMR for identification of minor and major constituents directly from the crude extract of Pueraria lobata. Journal of natural products. 2015 Feb; 78(2):294-300. doi: 10.1021/np5009416. [PMID: 25679337]
  • Rui Zhang, Shouyu Wang, Ming Lu, Zhen Zhang, Xiliang Tian, Decheng Lv. Simultaneous determination and pharmacokinetic study of three isoflavones from Trifolium pratense extract in rat plasma by LC-MS/MS. Biomedical chromatography : BMC. 2015 Feb; 29(2):210-9. doi: 10.1002/bmc.3261. [PMID: 24898405]
  • Xiao-Li Zhao, Ling Liu, Liu-Qing Di, Jun-Song Li, An Kang. [Studies on effects of calycosin-7-O-β-D-glucoside on prim-O-glucosylcimifugin and cimifugin in vivo pharmacokinetics]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Dec; 39(23):4669-74. doi: . [PMID: 25911821]
  • Xiao-hua Liu, Jian-bang Zhao, Long Guo, Ying-lai Yang, Fang Hu, Rui-juan Zhu, Shi-lan Feng. Simultaneous determination of calycosin-7-O-β-D-glucoside, ononin, calycosin, formononetin, astragaloside IV, and astragaloside II in rat plasma after oral administration of Radix Astragali extraction for their pharmacokinetic studies by ultra-pressure liquid chromatography with tandem mass spectrometry. Cell biochemistry and biophysics. 2014 Sep; 70(1):677-86. doi: 10.1007/s12013-014-9972-x. [PMID: 24782060]
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  • Shuping Fu, Yong Gu, Jian-Qin Jiang, Xi Chen, Mingjing Xu, Xingmiao Chen, Jiangang Shen. Calycosin-7-O-β-D-glucoside regulates nitric oxide /caveolin-1/matrix metalloproteinases pathway and protects blood-brain barrier integrity in experimental cerebral ischemia-reperfusion injury. Journal of ethnopharmacology. 2014 Aug; 155(1):692-701. doi: 10.1016/j.jep.2014.06.015. [PMID: 24930357]
  • Xuehui Sun, Pingping Zhang, Xiujun Wu, Qiong Wu, Mengmeng Zhang, Ye An, Guobing Shi. Simultaneous determination of calycosin-7-O-β-d-glucoside, calycosin, formononetin, astragaloside IV and schisandrin in rat plasma by LC-MS/MS: application to a pharmacokinetic study after oral administration of Shenqi Wuwei chewable tablets. Biomedical chromatography : BMC. 2014 Aug; 28(8):1118-25. doi: 10.1002/bmc.3128. [PMID: 24652759]
  • Wei Zhang, Shu Jiang, Da-Wei Qian, Er-Xin Shang, Han-Liang Guan, Hao Ren, Zhen-Hua Zhu, Jin-Ao Duan. [The interaction between ononin and human intestinal bacteria]. Yao xue xue bao = Acta pharmaceutica Sinica. 2014 Aug; 49(8):1162-8. doi: NULL. [PMID: 25322559]
  • Wei Zhang, Shu Jiang, Dawei Qian, Er-Xin Shang, Jin-Ao Duan. Analysis of interaction property of calycosin-7-O-β-D-glucoside with human gut microbiota. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jul; 963(?):16-23. doi: 10.1016/j.jchromb.2014.05.015. [PMID: 24922599]
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