Scutellarein (BioDeep_00000229882)

 

Secondary id: BioDeep_00000003711, BioDeep_00000861685

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(2S)-2,3-dihydro-5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

化学式: C15H10O6 (286.047736)
中文名称: 野黄芩黄素, 黄岑配基, 高黄芩素, 金黄紫碱, 野黄芩素, 野黄芩素 也叫金黄紫 碱
谱图信息: 最多检出来源 Viridiplantae(plant) 0.41%

分子结构信息

SMILES: c1(c(c(c2c(c1)oc(cc2=O)c1ccc(cc1)O)O)O)O
InChI: InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)11-5-9(17)13-12(21-11)6-10(18)14(19)15(13)20/h1-6,16,18-20H

描述信息

Scutellarein is flavone substituted with hydroxy groups at C-4, -5, -6 and -7. It has a role as a metabolite. It is functionally related to an apigenin. It is a conjugate acid of a scutellarein(1-).
Scutellarein is a natural product found in Scoparia dulcis, Artemisia douglasiana, and other organisms with data available.
Flavone substituted with hydroxy groups at C-4, -5, -6 and -7.
Scutellarein, also known as 6-hydroxyapigenin or 4,5,6,7-tetrahydroxyflavanone, is a member of the class of compounds known as flavones. Flavones are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, scutellarein is considered to be a flavonoid lipid molecule. Scutellarein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Scutellarein can be synthesized from apigenin. Scutellarein is also a parent compound for other transformation products, including but not limited to, scutellarin, 4,6-dihydroxy-5,7-dimethoxyflavone, and 6-hydroxy-4,5,7-trimethoxyflavone. Scutellarein is a bitter tasting compound found in mexican oregano and sweet orange, which makes scutellarein a potential biomarker for the consumption of these food products. Scutellarein is a flavone that can be found in Scutellaria lateriflora and other members of the genus Scutellaria, as well as the fern Asplenium belangeri .
Scutellarein is a natural flavonoid compound with anti-inflammatory effects.
Scutellarein is a natural flavonoid compound with anti-inflammatory effects.

同义名列表

25 个代谢物同义名

(2S)-2,3-dihydro-5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 4H-1-Benzopyran-4-one, 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-; 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-1-benzopyran-4-one; 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one; 5,6,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one; 6-Hydroxyapigenin;4,5,6,7-Tetrahydroxyflavone; 4,5,6,7-tetrahydroxy-flavanone; 4,5,6,7-tetrahydroxyflavanone; 5,6,7,4-Tetrahydroxyflavone; 4,5,6,7-tetrahydroxyflavone; Scutellarein, >=98\\% (HPLC); 6-HYDROXYPELARGIDENON-1465; SCUTELLAREIN [WHO-DD]; 6-hydroxynaringenin; 6-hydroxy-apigenin; 6-hydroxyapigenin; SCUTELLAREIN [MI]; Isocarthamidin; Scutellarein; SCUTELLARTLN; carthamidin; 6,7-Dimethylscutellarein; 5,6,7-Trihydroxy-2- (4-hydroxyphenyl) -4H-1-benzopyran-4-one; 4',5,6,7-Tetrahydroxyflavone



数据库引用编号

27 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)

158 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

  • Guangjun Yu, Yichun Shi, Shiqin Cong, Chengxun Wu, Jing Liu, Yanghui Zhang, Hongyan Liu, Xiuxiu Liu, Haixing Deng, Zhenghuai Tan, Yong Deng. Synthesis and evaluation of butylphthalide-scutellarein hybrids as multifunctional agents for the treatment of Alzheimer's disease. European journal of medicinal chemistry. 2024 Feb; 265(?):116099. doi: 10.1016/j.ejmech.2023.116099. [PMID: 38160618]
  • Lu Liu, Yunsen Zhang, Lun Wang, Yue Liu, Hongqing Chen, Qiongying Hu, Chunguang Xie, Xianli Meng, Xiaofei Shen. Scutellarein alleviates chronic obstructive pulmonary disease through inhibition of ferroptosis by chelating iron and interacting with arachidonate 15-lipoxygenase. Phytotherapy research : PTR. 2023 Oct; 37(10):4587-4606. doi: 10.1002/ptr.7928. [PMID: 37353982]
  • Yujing Wang, Liaoxi Tan, Kejun Jiao, Chu Xue, Qinglian Tang, Shan Jiang, Younan Ren, Hao Chen, Tarek Mohamed Abd El-Aziz, Khalid N M Abdelazeem, Ye Yu, Fang Zhao, Michael X Zhu, Zhengyu Cao. Scutellarein attenuates atopic dermatitis by selectively inhibiting transient receptor potential vanilloid 3 channels. British journal of pharmacology. 2022 10; 179(20):4792-4808. doi: 10.1111/bph.15913. [PMID: 35771623]
  • Min Yeong Park, Sang Eun Ha, Hun Hwan Kim, Pritam Bhagwan Bhosale, Abuyaseer Abusaliya, Se Hyo Jeong, Joon-Suk Park, Jeong Doo Heo, Gon Sup Kim. Scutellarein Inhibits LPS-Induced Inflammation through NF-κB/MAPKs Signaling Pathway in RAW264.7 Cells. Molecules (Basel, Switzerland). 2022 Jun; 27(12):. doi: 10.3390/molecules27123782. [PMID: 35744907]
  • Ivana M P Violante, Carlos A Carollo, Larissa I Silva, Adna Q C Oliveira, Flavia C Pardinho, Walmir Silva Garcez, Fernanda R Garcez, Ruberlei Godinho de Oliveira, Karuppusamy Arunachalam, Domingos Tabajara de Oliveira Martins. Cytotoxicity and antibacterial activity of scutellarein and carajurone-enriched fraction obtained from the hydroethanolic extract of the leaves of Fridericia chica (Bonpl.) L.G. Lohmann. Natural product research. 2021 Dec; 35(23):5287-5293. doi: 10.1080/14786419.2020.1753050. [PMID: 32290696]
  • Dong Liu, Cuijie Zhang, Min Hu, Kangle Su. Scutellarein relieves the death and inflammation of tubular epithelial cells in ischemic kidney injury by degradation of COX-2 protein. International immunopharmacology. 2021 Dec; 101(Pt A):108193. doi: 10.1016/j.intimp.2021.108193. [PMID: 34619498]
  • Dongni Ji, Jianhua Li, Fanglin Xu, Yuhong Ren, Yong Wang. Improve the Biosynthesis of Baicalein and Scutellarein via Manufacturing Self-Assembly Enzyme Reactor In Vivo. ACS synthetic biology. 2021 05; 10(5):1087-1094. doi: 10.1021/acssynbio.0c00606. [PMID: 33880917]
  • Venu Venkatarame Gowda Saralamma, Preethi Vetrivel, Ho Jeong Lee, Seong Min Kim, Sang Eun Ha, Rajeswari Murugesan, Eun Hee Kim, Jeong Doo Heo, Gon Sup Kim. Comparative proteomic analysis uncovers potential biomarkers involved in the anticancer effect of Scutellarein in human gastric cancer cells. Oncology reports. 2020 09; 44(3):939-958. doi: 10.3892/or.2020.7677. [PMID: 32705238]
  • Yuanzhi Li, Jundong Wang, Sen Zhong, Jun Li, Weiliang Du. Scutellarein inhibits the development of colon cancer via CDC4‑mediated RAGE ubiquitination. International journal of molecular medicine. 2020 Apr; 45(4):1059-1072. doi: 10.3892/ijmm.2020.4496. [PMID: 32124957]
  • Hou-da Zhu, Pan Tian, Liang-Jun Guan, Liang-Mian Chen, Xiao-Qian Liu, Hui-Min Gao, Zhi-Min Wang. [Analysis and structural identification of relevant substances in Breviscapine for Injection]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2020 Mar; 45(6):1350-1356. doi: 10.19540/j.cnki.cjcmm.20200207.309. [PMID: 32281347]
  • Yiguang Lin, Nina Ren, Siyu Li, Ming Chen, Peng Pu. Novel anti-obesity effect of scutellarein and potential underlying mechanism of actions. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Sep; 117(?):109042. doi: 10.1016/j.biopha.2019.109042. [PMID: 31228804]
  • Jianhua Li, Chenfei Tian, Yuhui Xia, Ishmael Mutanda, Kaibo Wang, Yong Wang. Production of plant-specific flavones baicalein and scutellarein in an engineered E. coli from available phenylalanine and tyrosine. Metabolic engineering. 2019 03; 52(?):124-133. doi: 10.1016/j.ymben.2018.11.008. [PMID: 30496827]
  • He-Min Li, Ting Gu, Wen-Yu Wu, Shao-Peng Yu, Tian-Yuan Fan, Yue Zhong, Nian-Guang Li. Synthesis and Biological Evaluation of Scutellarein Alkyl Derivatives as Preventing Neurodegenerative Agents with Improved Lipid Soluble Properties. Medicinal chemistry (Shariqah (United Arab Emirates)). 2019; 15(7):771-780. doi: 10.2174/1573406414666181015143551. [PMID: 30324887]
  • Lin Shi, Yi Wu, Dian Liang Lv, Lei Feng. Scutellarein selectively targets multiple myeloma cells by increasing mitochondrial superoxide production and activating intrinsic apoptosis pathway. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Jan; 109(?):2109-2118. doi: 10.1016/j.biopha.2018.09.024. [PMID: 30551468]
  • Nourah Zoman Alzoman, Hadir Mohamed Maher, Hessa Al-Showiman, Ghada Ahmed Fawzy, Areej Mohammad Al-Taweel, Shagufta Perveen, Rasool Bakhsh Tareen, Ruba Mahmoud Al-Sabbagh. CE-DAD Determination of Scutellarein and Caffeic Acid in Abelia triflora Crude Extract. Journal of chromatographic science. 2018 Sep; 56(8):746-752. doi: 10.1093/chromsci/bmy042. [PMID: 29750262]
  • Siying Chen, Mei Li, Yueting Li, Hejia Hu, Ying Li, Yong Huang, Lin Zheng, Yuan Lu, Jie Hu, Yanyu Lan, Aimin Wang, Yongjun Li, Zipeng Gong, Yonglin Wang. A UPLC-ESI-MS/MS Method for Simultaneous Quantitation of Chlorogenic Acid, Scutellarin, and Scutellarein in Rat Plasma: Application to a Comparative Pharmacokinetic Study in Sham-Operated and MCAO Rats after Oral Administration of Erigeron breviscapus Extract. Molecules (Basel, Switzerland). 2018 Jul; 23(7):. doi: 10.3390/molecules23071808. [PMID: 30037063]
  • François Chassagne, Mohamed Haddad, Aurélien Amiel, Chiobouaphong Phakeovilay, Chanthanom Manithip, Geneviève Bourdy, Eric Deharo, Guillaume Marti. A metabolomic approach to identify anti-hepatocarcinogenic compounds from plants used traditionally in the treatment of liver diseases. Fitoterapia. 2018 Jun; 127(?):226-236. doi: 10.1016/j.fitote.2018.02.021. [PMID: 29477305]
  • Guanghui Ni, Yanling Tang, Minxin Li, Yuefeng He, Gaoxiong Rao. Synthesis of Scutellarein Derivatives with a Long Aliphatic Chain and Their Biological Evaluation against Human Cancer Cells. Molecules (Basel, Switzerland). 2018 Feb; 23(2):. doi: 10.3390/molecules23020310. [PMID: 29389889]
  • Lin You, Hong Zhu, Chun Wang, Fang Wang, Yongjun Li, Yan Li, Yonglin Wang, Bin He. Scutellarin inhibits Hela cell growth and glycolysis by inhibiting the activity of pyruvate kinase M2. Bioorganic & medicinal chemistry letters. 2017 12; 27(24):5404-5408. doi: 10.1016/j.bmcl.2017.11.011. [PMID: 29157862]
  • V F Kulikovskii, E T Zhilyakova, O O Novikov, D I Pisarev, N V Prokushchenko, L L Ivanova. Study of Sedative Tea Phytocomplex within the Framework of Studies Aimed at Creation of a Rectal Dosage Form with Antihistaminic Effect. Bulletin of experimental biology and medicine. 2017 Oct; 163(6):753-756. doi: 10.1007/s10517-017-3896-6. [PMID: 29063320]
  • Yelin Kang, Bong-Gyu Kim, Sunghoon Kim, Youngshim Lee, Youngdae Yoon. Inhibitory potential of flavonoids on PtdIns(3,4,5)P3 binding with the phosphoinositide-dependent kinase 1 pleckstrin homology domain. Bioorganic & medicinal chemistry letters. 2017 02; 27(3):420-426. doi: 10.1016/j.bmcl.2016.12.051. [PMID: 28049590]
  • Xiaoxuan Tian, Lianying Chang, Guangyin Ma, Taiyi Wang, Ming Lv, Zhilong Wang, Liping Chen, Yuefei Wang, Xiumei Gao, Yan Zhu. Delineation of Platelet Activation Pathway of Scutellarein Revealed Its Intracellular Target as Protein Kinase C. Biological & pharmaceutical bulletin. 2016; 39(2):181-91. doi: 10.1248/bpb.b15-00511. [PMID: 26581323]
  • Hao Tang, Zhi-Hao Shi, Nian-Guang Li, Yu-Ping Tang, Qian-Ping Shi, Ze-Xi Dong, Peng-Xuan Zhang, Jin-Ao Duan. Investigation on the interactions of scutellarin and scutellarein with bovine serum albumin using spectroscopic and molecular docking techniques. Archives of pharmacal research. 2015 Oct; 38(10):1789-801. doi: 10.1007/s12272-014-0541-z. [PMID: 25577334]
  • Yearam Jung, Soon Young Shin, Yeonjoong Yong, Hyeryoung Jung, Seunghyun Ahn, Young Han Lee, Yoongho Lim. Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships. Chemical biology & drug design. 2015 May; 85(5):574-85. doi: 10.1111/cbdd.12445. [PMID: 25298094]
  • Zhipei Sang, Xiaoming Qiang, Yan Li, Wen Yuan, Qiang Liu, Yikun Shi, Wei Ang, Youfu Luo, Zhenghuai Tan, Yong Deng. Design, synthesis and evaluation of scutellarein-O-alkylamines as multifunctional agents for the treatment of Alzheimer's disease. European journal of medicinal chemistry. 2015 Apr; 94(?):348-66. doi: 10.1016/j.ejmech.2015.02.063. [PMID: 25778991]
  • Hao Tang, Yuping Tang, Nian-Guang Li, Hang Lin, Weixia Li, Qianping Shi, Wei Zhang, Pengxuan Zhang, Zexi Dong, Minzhe Shen, Ting Gu, Jin-Ao Duan. Comparative Metabolomic Analysis of the Neuroprotective Effects of Scutellarin and Scutellarein against Ischemic Insult. PloS one. 2015; 10(7):e0131569. doi: 10.1371/journal.pone.0131569. [PMID: 26147971]
  • Kasumi Nakamura, Jia-Hua Yang, Eiji Sato, Naoyuki Miura, Yi-Xin Wu. Effects of Hydroxy Groups in the A-Ring on the Anti-proteasome Activity of Flavone. Biological & pharmaceutical bulletin. 2015; 38(6):935-40. doi: 10.1248/bpb.b15-00018. [PMID: 25810454]
  • Xiao Yang, Xiaoqing Miao, Fangrui Cao, Shang Li, Nana Ai, Qi Chang, Simon M Y Lee, Ying Zheng. Nanosuspension development of scutellarein as an active and rapid orally absorbed precursor of its BCS class IV glycoside scutellarin. Journal of pharmaceutical sciences. 2014 Nov; 103(11):3576-3584. doi: 10.1002/jps.24149. [PMID: 25187229]
  • Xin Wang, Hongjun Xia, Youping Liu, Feng Qiu, Xin Di. Simultaneous determination of three glucuronide conjugates of scutellarein in rat plasma by LC-MS/MS for pharmacokinetic study of breviscapine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Aug; 965(?):79-84. doi: 10.1016/j.jchromb.2014.06.013. [PMID: 24999248]
  • Qing Liu, Qi-Ming Yang, Hai-Jun Hu, Li Yang, Ying-Bo Yang, Gui-Xin Chou, Zheng-Tao Wang. Bioactive diterpenoids and flavonoids from the aerial parts of Scoparia dulcis. Journal of natural products. 2014 Jul; 77(7):1594-600. doi: 10.1021/np500150f. [PMID: 24955889]
  • Guang-You Ma, Yun-Feng Cao, Cui-Min Hu, Zhong-Ze Fang, Xiao-Yu Sun, Mo Hong, Zhi-Tu Zhu. Comparison of inhibition capability of scutellarein and scutellarin towards important liver UDP-glucuronosyltransferase (UGT) isoforms. Phytotherapy research : PTR. 2014 Mar; 28(3):382-6. doi: 10.1002/ptr.4990. [PMID: 23620377]
  • Z Shu-Yao, J Hong, L Chao-Xian, Z Zhi-Wei, Xin Dai-Shan, C Lei. In vitro evidence of possible influence of scutellarein towards bile acids' metabolism. African health sciences. 2013 Sep; 13(3):556-9. doi: 10.4314/ahs.v13i3.4. [PMID: 24250288]
  • Yun-Ze Yin, Rui-Shan Wang, Ri-Dao Chen, Li-Rui Qiao, Lin Yang, Chun-Mei Wang, Jun-Gui Dai. [Chemical constituents from cell suspension cultures of Cudrania tricuspidata]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Dec; 37(24):3734-7. doi: . [PMID: 23627169]
  • Chunying Gao, Hongjian Zhang, Zitao Guo, Tiangeng You, Xiaoyan Chen, Dafang Zhong. Mechanistic studies on the absorption and disposition of scutellarin in humans: selective OATP2B1-mediated hepatic uptake is a likely key determinant for its unique pharmacokinetic characteristics. Drug metabolism and disposition: the biological fate of chemicals. 2012 Oct; 40(10):2009-20. doi: 10.1124/dmd.112.047183. [PMID: 22822035]
  • Jing Xu, Li Yang, Shu-Juan Zhao, Zheng-Tao Wang, Zhi-Bi Hu. An efficient way from naringenin to carthamidine and isocarthamidine by Aspergillus niger. World journal of microbiology & biotechnology. 2012 Apr; 28(4):1803-6. doi: 10.1007/s11274-011-0934-9. [PMID: 22805963]
  • Vivian Chen, Richard E Staub, Scott Baggett, Ramesh Chimmani, Mary Tagliaferri, Isaac Cohen, Emma Shtivelman. Identification and analysis of the active phytochemicals from the anti-cancer botanical extract Bezielle. PloS one. 2012; 7(1):e30107. doi: 10.1371/journal.pone.0030107. [PMID: 22272282]
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  • Xiaoyan Chen, Liang Cui, Xiaotao Duan, Bin Ma, Dafang Zhong. Pharmacokinetics and metabolism of the flavonoid scutellarin in humans after a single oral administration. Drug metabolism and disposition: the biological fate of chemicals. 2006 Aug; 34(8):1345-52. doi: 10.1124/dmd.106.009779. [PMID: 16714374]
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