Tectorigenin (BioDeep_00000003822)

 

Secondary id: BioDeep_00000270755, BioDeep_00000862580

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-

化学式: C16H12O6 (300.0634)
中文名称: 鸢尾黄素, 射干苷元, 鸢尾苷
谱图信息: 最多检出来源 Viridiplantae(plant) 46.54%

Reviewed

Last reviewed on 2024-08-20.

Cite this Page

Tectorigenin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/tectorigenin (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000003822). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: c1(c(c(c2c(c1)occ(c2=O)c1ccc(cc1)O)O)OC)O
InChI: InChI=1S/C16H12O6/c1-21-16-11(18)6-12-13(15(16)20)14(19)10(7-22-12)8-2-4-9(17)5-3-8/h2-7,17-18,20H,1H3

描述信息

Tectorigenin is a methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 5, 7 and 4 respectively. It has a role as an anti-inflammatory agent and a plant metabolite. It is a member of 7-hydroxyisoflavones and a methoxyisoflavone. It is functionally related to an isoflavone.
Tectorigenin is a natural product found in Iris milesii, Dalbergia sissoo, and other organisms with data available.
Tectorigenin is an isoflavone from Pueraria thunbergiana, which induces differentiation and apoptosis in cancer cells. (NCI)
Tectorigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from leopard lily (Belamcanda chinensis) or Pueraria thunbergiana.
A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 5, 7 and 4 respectively.
C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor
A polyphenol metabolite detected in biological fluids [PhenolExplorer]
C471 - Enzyme Inhibitor > C1017 - Glucuronidase Inhibitor
Tectorigenin is a plant isoflavonoid originally isolated from the dried flower of Pueraria lobate Benth.
Tectorigenin is a plant isoflavonoid originally isolated from the dried flower of Pueraria lobate Benth.

同义名列表

22 个代谢物同义名

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-; 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one; 3-(4-hydroxyphenyl)-6-methoxy-5,7-bis(oxidanyl)chromen-4-one; 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one; 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-6-methoxy-chromen-4-one; 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one; 5-18-05-00311 (Beilstein Handbook Reference); ISOFLAVONE, 4,5,7-TRIHYDROXY-6-METHOXY-; 4,5,7-trihydroxy-6-methoxyisoflavone; 5,7,4-Trihydroxy-6-methoxyisoflavone; 4,5,7-Trihydroxy-6-methoxyisoflavone; Tectorigenin, analytical standard; TECTORIGENIN [MI]; Tectorigenine; DivK1c_006241; KBio1_001185; KBio2_006377; KBio2_003809; KBio2_001241; Tectorigenin; R0U; Tectorigenin



数据库引用编号

23 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)

119 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 12 AKR1B1, BCL2, CASP9, CAT, MAPK8, NLRP3, PIK3CA, PPARG, PTGS1, PTGS2, TLR4, TNFSF11
Peripheral membrane protein 3 GORASP1, PTGS1, PTGS2
Endosome membrane 1 TLR4
Endoplasmic reticulum membrane 3 BCL2, PTGS1, PTGS2
Nucleus 7 BCL2, CASP9, ESR2, MAPK8, MMP2, NLRP3, PPARG
cytosol 8 AKR1B1, BCL2, CASP9, CAT, MAPK8, NLRP3, PIK3CA, PPARG
nucleoplasm 4 AKR1B1, ESR2, MAPK8, PPARG
RNA polymerase II transcription regulator complex 1 PPARG
Cell membrane 3 TLR4, TNF, TNFSF11
Cytoplasmic side 1 GORASP1
lamellipodium 1 PIK3CA
Golgi apparatus membrane 2 GORASP1, NLRP3
Synapse 1 MAPK8
cell surface 2 TLR4, TNF
Golgi apparatus 2 GORASP1, PTGS1
Golgi membrane 3 GORASP1, INS, NLRP3
neuronal cell body 1 TNF
Cytoplasm, cytosol 1 NLRP3
plasma membrane 5 MMP2, PIK3CA, TLR4, TNF, TNFSF11
Membrane 5 BCL2, CAT, NLRP3, TLR4, TNFSF11
axon 2 CCK, MAPK8
caveola 1 PTGS2
extracellular exosome 4 AKR1B1, CAT, MMP9, PTGS1
endoplasmic reticulum 3 BCL2, NLRP3, PTGS2
extracellular space 8 AKR1B1, CCK, IL6, INS, MMP2, MMP9, TNF, TNFSF11
perinuclear region of cytoplasm 3 PIK3CA, PPARG, TLR4
intercalated disc 1 PIK3CA
mitochondrion 7 AKR1B1, BCL2, CASP9, CAT, ESR2, MMP2, NLRP3
protein-containing complex 4 BCL2, CASP9, CAT, PTGS2
intracellular membrane-bounded organelle 4 CAT, ESR2, PPARG, PTGS1
Microsome membrane 2 PTGS1, PTGS2
Single-pass type I membrane protein 1 TLR4
Secreted 5 CCK, IL6, INS, NLRP3, TNFSF11
extracellular region 9 CAT, CCK, IL6, INS, MMP2, MMP9, NLRP3, TNF, TNFSF11
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 1 CAT
photoreceptor outer segment 1 PTGS1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 TLR4, TNF
Secreted, extracellular space, extracellular matrix 1 MMP9
Early endosome 1 TLR4
recycling endosome 1 TNF
Single-pass type II membrane protein 2 TNF, TNFSF11
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 CAT
cis-Golgi network 1 GORASP1
extracellular matrix 1 MMP2
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 2 MMP2, MMP9
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
sarcomere 1 MMP2
receptor complex 2 PPARG, TLR4
neuron projection 2 PTGS1, PTGS2
chromatin 2 ESR2, PPARG
phagocytic cup 2 TLR4, TNF
Endomembrane system 2 NLRP3, PTGS1
endosome lumen 1 INS
microtubule organizing center 1 NLRP3
myelin sheath 1 BCL2
lipopolysaccharide receptor complex 1 TLR4
ficolin-1-rich granule lumen 2 CAT, MMP9
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 IL6, INS, PTGS2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
tertiary granule lumen 1 MMP9
transport vesicle 1 INS
[Isoform 1]: Secreted, extracellular space, extracellular matrix 1 MMP2
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
apoptosome 1 CASP9
[Isoform 2]: Cytoplasm 1 TNFSF11
[Tumor necrosis factor ligand superfamily member 11, soluble form]: Secreted 1 TNFSF11
basal dendrite 1 MAPK8
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
BAD-BCL-2 complex 1 BCL2
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
caspase complex 1 CASP9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Juan Rong, Fei Fu, Chenxia Han, Yaling Wu, Qing Xia, Dan Du. Tectorigenin: A Review of Its Sources, Pharmacology, Toxicity, and Pharmacokinetics. Molecules (Basel, Switzerland). 2023 Aug; 28(15):. doi: 10.3390/molecules28155904. [PMID: 37570873]
  • Yuan Wang, Ming-Ming Yuan, Jing Zhou, Xiao-Han Zheng, Chong-Jun Yuan, Shuai Chen, Sen Luo, Lei Zhang. [Anti-herpes simplex virus type Ⅰ of tectorigenin derivative and effect on Toll-like receptors in vitro]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Aug; 47(16):4428-4435. doi: 10.19540/j.cnki.cjcmm.20220216.401. [PMID: 36046872]
  • Ruiqian Duan, Kai Huang, Xiao Guan, Sen Li, Ji'an Xia, Meng Shen, Zhu Sun, Zhiquan Yu. Tectorigenin ameliorated high-fat diet-induced nonalcoholic fatty liver disease through anti-inflammation and modulating gut microbiota in mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2022 Jun; 164(?):112948. doi: 10.1016/j.fct.2022.112948. [PMID: 35390440]
  • Juanjuan Zhu, Yuan Wen, Qiuling Zhang, Fei Nie, Mingliang Cheng, Xueke Zhao. The monomer TEC of blueberry improves NASH by augmenting tRF-47-mediated autophagy/pyroptosis signaling pathway. Journal of translational medicine. 2022 03; 20(1):128. doi: 10.1186/s12967-022-03343-5. [PMID: 35287671]
  • Jianchun Li, Jieke Yang, Bingwen Zhu, Junming Fan, Qiongdan Hu, Li Wang. Tectorigenin protects against unilateral ureteral obstruction by inhibiting Smad3-mediated ferroptosis and fibrosis. Phytotherapy research : PTR. 2022 Jan; 36(1):475-487. doi: 10.1002/ptr.7353. [PMID: 34964161]
  • Xiong Qian, Qi Xiao, Zongqi Li. Tectorigenin regulates migration, invasion, and apoptosis in dexamethasone-induced human airway epithelial cells through up-regulating miR-222-3p. Drug development research. 2021 11; 82(7):959-968. doi: 10.1002/ddr.21795. [PMID: 33543488]
  • Li Yao, Meili Yang, Juanli Zhang, Fei Wang, Qing Liu, Xiaojun Xie, Zhuo Liu, Qiang Guo, Hang Su, Jiemin Zhai, Jianbo He, Sha Xue, Zhengguo Qiu. Tectorigenin attenuates the OGD/R-induced HT-22 cell damage through regulation of the PI3K/AKT and the PPARγ/NF-κB pathways. Human & experimental toxicology. 2021 Aug; 40(8):1320-1331. doi: 10.1177/0960327121993213. [PMID: 33588632]
  • Jiaqing Xiang, Guangyan Yang, Chuanrui Ma, Lingling Wei, Han Wu, Wei Zhang, Xiuhua Tao, Lingyun Jiang, Zhen Liang, Lin Kang, Shu Yang. Tectorigenin alleviates intrahepatic cholestasis by inhibiting hepatic inflammation and bile accumulation via activation of PPARγ. British journal of pharmacology. 2021 06; 178(12):2443-2460. doi: 10.1111/bph.15429. [PMID: 33661551]
  • Ganesan Divya, Abhishek Albert, Abdel Nasser B Singab, Iriny M Ayoub, Eman Al-Sayed, Eldho Paul, Kumarriah Manoharan, Luciano Saso, Govindan Sadasivam Selvam. Renoprotective effect of tectorigenin glycosides isolated from Iris spuria L. (Zeal) against hyperoxaluria and hyperglycemia in NRK-49Fcells. Natural product research. 2021 Mar; 35(6):1029-1034. doi: 10.1080/14786419.2019.1613396. [PMID: 31135219]
  • Youpeng Wang, Weichao Jing, Wanying Qu, Zhiwei Liu, Di Zhang, Xiaoyu Qi, Lujia Liu. Tectorigenin inhibits inflammation and pulmonary fibrosis in allergic asthma model of ovalbumin-sensitized guinea pigs. The Journal of pharmacy and pharmacology. 2020 Jul; 72(7):956-968. doi: 10.1111/jphp.13271. [PMID: 32314371]
  • Etta Y Liu, Zoey X Zheng, Brody Z Zheng, Yingjie Xia, Maggie S Guo, Tina T Dong, Karl W K Tsim. Tectorigenin, an isoflavone aglycone from the rhizome of Belamcanda chinensis, induces neuronal expression of erythropoietin via accumulation of hypoxia-inducible factor-1α. Phytotherapy research : PTR. 2020 Jun; 34(6):1329-1337. doi: 10.1002/ptr.6599. [PMID: 31845440]
  • He-Hsiung Cheng, Wei-Zhe Liang, Wei-Chuan Liao, Chun-Chi Kuo, Lyh-Jyh Hao, Chiang-Ting Chou, Chung-Ren Jan. Investigation of effect of tectorigenin (O-methylated isoflavone) on Ca2+ signal transduction and cytotoxic responses in canine renal tubular cells. The Chinese journal of physiology. 2020 Mar; 63(2):60-67. doi: 10.4103/cjp.cjp_14_20. [PMID: 32341231]
  • Shu Yang, Chuanrui Ma, Han Wu, Hao Zhang, Fengyi Yuan, Guangyan Yang, Qi Yang, Lijing Jia, Zhen Liang, Lin Kang. Tectorigenin attenuates diabetic nephropathy by improving vascular endothelium dysfunction through activating AdipoR1/2 pathway. Pharmacological research. 2020 03; 153(?):104678. doi: 10.1016/j.phrs.2020.104678. [PMID: 32014572]
  • Dongjin Noh, Jin Gyu Choi, Young Bae Lee, Young Pyo Jang, Myung Sook Oh. Protective effects of Belamcandae Rhizoma against skin damage by ameliorating ultraviolet-B-induced apoptosis and collagen degradation in keratinocytes. Environmental toxicology. 2019 Dec; 34(12):1354-1362. doi: 10.1002/tox.22836. [PMID: 31436008]
  • Lingjian Zhang, Yalei Zhao, Linxiao Fan, Kai Xu, Feiyang Ji, Zhongyang Xie, Xiaoxi Ouyang, Daxian Wu, Lanjuan Li. Tectorigenin protects against experimental fulminant hepatic failure by regulating the TLR4/mitogen-activated protein kinase and TLR4/nuclear factor-κB pathways and autophagy. Phytotherapy research : PTR. 2019 Apr; 33(4):1055-1064. doi: 10.1002/ptr.6299. [PMID: 30701601]
  • Dongjin Noh, Jin Gyu Choi, Eugene Huh, Myung Sook Oh. Tectorigenin, a Flavonoid-Based Compound of Leopard Lily Rhizome, Attenuates UV-B-Induced Apoptosis and Collagen Degradation by Inhibiting Oxidative Stress in Human Keratinocytes. Nutrients. 2018 Dec; 10(12):. doi: 10.3390/nu10121998. [PMID: 30562977]
  • Danka Bukvički, Miroslav Novaković, Nurunajah Ab Ghani, Petar D Marin, Yoshinori Asakawa. Secondary metabolites from endemic species Iris adriatica Trinajstić ex Mitić (Iridaceae). Natural product research. 2018 Aug; 32(15):1849-1852. doi: 10.1080/14786419.2017.1402309. [PMID: 29126369]
  • Linwen Zeng, Shaofeng Yuan, Jianliang Shen, Ming Wu, Liangming Pan, Xiangdong Kong. Suppression of human breast cancer cells by tectorigenin through downregulation of matrix metalloproteinases and MAPK signaling in vitro. Molecular medicine reports. 2018 03; 17(3):3935-3943. doi: 10.3892/mmr.2017.8313. [PMID: 29359782]
  • Ge Zhan, Leiqing Pan, Kang Tu, Shunshan Jiao. Antitumor, Antioxidant, and Nitrite Scavenging Effects of Chinese Water Chestnut (Eleocharis dulcis) Peel Flavonoids. Journal of food science. 2016 Oct; 81(10):H2578-H2586. doi: 10.1111/1750-3841.13434. [PMID: 27603811]
  • Yu Guo, Ya-Hong Chen, Zhi-Hua Cheng, Huo-Niu Ou-Yang, Cong Luo, Zhi-Lin Guo. Tectorigenin inhibits osteosarcoma cell migration through downregulation of matrix metalloproteinases in vitro. Anti-cancer drugs. 2016 07; 27(6):540-6. doi: 10.1097/cad.0000000000000362. [PMID: 26991068]
  • Nóra Gampe, András Darcsi, Szilvia Lohner, Szabolcs Béni, László Kursinszki. Characterization and identification of isoflavonoid glycosides in the root of Spiny restharrow (Ononis spinosa L.) by HPLC-QTOF-MS, HPLC-MS/MS and NMR. Journal of pharmaceutical and biomedical analysis. 2016 May; 123(?):74-81. doi: 10.1016/j.jpba.2016.01.058. [PMID: 26874257]
  • Min Yang, Xiaolin Yang, Jinmeng An, Wei Xiao, Zhenzhong Wang, Wenzhe Huang, Zhonglin Yang, Fei Li. Comparative pharmacokinetic profiles of tectorigenin in rat plasma by UPLC-MS/MS after oral administration of Iris tectorum Maxim extract and pure tectoridin. Journal of pharmaceutical and biomedical analysis. 2015 Oct; 114(?):34-41. doi: 10.1016/j.jpba.2015.05.005. [PMID: 26004225]
  • Ziming Shi, Guozhe Zhang, Lizhu Zhao, Shen Wang, Yoshihiro Kano, Dan Yuan. Excretion of tectorigenin in rat urine orally administrated at different dosages by ultra-performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry. European journal of drug metabolism and pharmacokinetics. 2015 Sep; 40(3):255-66. doi: 10.1007/s13318-014-0202-0. [PMID: 24789580]
  • Astrid Hasibeder, Vivek Venkataramani, Paul Thelen, Heinz-Joachim Radzun, Stefan Schweyer. Phytoestrogens regulate the proliferation and expression of stem cell factors in cell lines of malignant testicular germ cell tumors. International journal of oncology. 2013 Nov; 43(5):1385-94. doi: 10.3892/ijo.2013.2060. [PMID: 23969837]
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  • Shen Wang, Tianxing Gong, Jing Lu, Yoshihiro Kano, Dan Yuan. Simultaneous determination of tectorigenin and its metabolites in rat plasma by ultra performance liquid chromatography/quadrupole time-of-flight mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Aug; 933(?):50-8. doi: 10.1016/j.jchromb.2013.06.009. [PMID: 23872519]
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  • Ting Han, Gang Cheng, Ying Liu, Hong Yang, Yu-Tao Hu, Wen Huang. In vitro evaluation of tectoridin, tectorigenin and tectorigenin sodium sulfonate on antioxidant properties. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Feb; 50(2):409-14. doi: 10.1016/j.fct.2011.10.066. [PMID: 22079309]
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  • Wei-dong Zhang, Wan-jun Yang, Xiao-juan Wang, Yi Gu, Rong Wang. Simultaneous determination of tectorigenin, irigenin and irisflorentin in rat plasma and urine by UHPLC-MS/MS: application to pharmacokinetics. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Dec; 879(31):3735-41. doi: 10.1016/j.jchromb.2011.10.022. [PMID: 22071270]
  • 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]
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