Luteolin 7-methyl ether (BioDeep_00000017278)

 

Secondary id: BioDeep_00000000833, BioDeep_00000270489, BioDeep_00000270530

human metabolite PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one, 9CI

化学式: C16H12O6 (300.06338519999997)
中文名称: 羟基芫花素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 14.29%

分子结构信息

SMILES: c1(cc(c2c(c1)oc(cc2=O)c1ccc(c(c1)O)O)O)OC
InChI: InChI=1S/C16H12O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-7,17-19H,1H3

描述信息

Luteolin 7-methyl ether is a member of flavonoids and an ether. It is a conjugate acid of a luteolin-5-olate 7-methyl ether.
7-O-Methylluteolin is a natural product found in Verbascum lychnitis, Salvia hypoleuca, and other organisms with data available.
Luteolin 7-methyl ether is found in common sage. Luteolin 7-methyl ether is isolated from Salvia officinalis (sage).
Isolated from Salvia officinalis (sage). Luteolin 7-methyl ether is found in tea, herbs and spices, and common sage.
Hydroxygenkwanin (7-O-Methylluteolin), a natural flavonoid compound, is one of the main components of Lilac Daphne. Hydroxygenkwanin has anti-oxidant ability, anti-glioma ability and anticancer effect[1][2].
Hydroxygenkwanin (7-O-Methylluteolin), a natural flavonoid compound, is one of the main components of Lilac Daphne. Hydroxygenkwanin has anti-oxidant ability, anti-glioma ability and anticancer effect[1][2].

同义名列表

17 个代谢物同义名

2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one, 9CI; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-; 4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-; 2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one; 2-(3,4-Dihydroxyphenyl)-5-Hydroxy-7-Methoxy-4h-1-Chromen-4-One; 2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one; 2-(3,4-Dihydroxy-phenyl)-5-hydroxy-7-methoxy-chromen-4-one; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-chromen-4-one; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychromen-4-one; 5,3,4-Trihydroxy-7-methoxyflavone; Luteolin 7-methyl ether; 7-O-Methylluteolin; 3-hydroxygenkwanin; Hydroxygenkwanin; MEGxp0_000798; ACon1_000842; 6B5



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

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Plant Reactome(0)

INOH(0)

PlantCyc(0)

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40 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

  • Yan-Qing Li, Megumi Murakami, Yang-Hui Huang, Tai-Ho Hung, Shun-Ping Wang, Yu-Shan Wu, Suresh V Ambudkar, Chung-Pu Wu. Hydroxygenkwanin Improves the Efficacy of Cytotoxic Drugs in ABCG2-Overexpressing Multidrug-Resistant Cancer Cells. International journal of molecular sciences. 2022 Oct; 23(21):. doi: 10.3390/ijms232112763. [PMID: 36361555]
  • Xinli Dong, Yanhua Wang, Hua Zhuang, Gang An. Hydroxygenkwanin suppresses proliferation, invasion and migration of osteosarcoma cells via the miR‑320a/SOX9 axis. Molecular medicine reports. 2022 Oct; 26(4):. doi: 10.3892/mmr.2022.12815. [PMID: 35929504]
  • Chin-Chuan Chen, Chi-Yuan Chen, Shu-Fang Cheng, Tzong-Ming Shieh, Yann-Lii Leu, Wen-Yu Chuang, Kuang-Ting Liu, Shir-Hwa Ueng, Yin-Hwa Shih, Li-Fang Chou, Tong-Hong Wang. Hydroxygenkwanin Increases the Sensitivity of Liver Cancer Cells to Chemotherapy by Inhibiting DNA Damage Response in Mouse Xenograft Models. International journal of molecular sciences. 2021 Sep; 22(18):. doi: 10.3390/ijms22189766. [PMID: 34575923]
  • Yann-Lii Leu, Tong-Hong Wang, Chih-Ching Wu, Kuo-Yen Huang, Yu-Wen Jiang, Yi-Chiung Hsu, Chi-Yuan Chen. Hydroxygenkwanin Suppresses Non-Small Cell Lung Cancer Progression by Enhancing EGFR Degradation. Molecules (Basel, Switzerland). 2020 Feb; 25(4):. doi: 10.3390/molecules25040941. [PMID: 32093124]
  • Li-Fang Chou, Chi-Yuan Chen, Wan-Hua Yang, Chin-Chuan Chen, Junn-Liang Chang, Yann-Lii Leu, Miaw-Jene Liou, Tong-Hong Wang. Suppression of Hepatocellular Carcinoma Progression through FOXM1 and EMT Inhibition via Hydroxygenkwanin-Induced miR-320a Expression. Biomolecules. 2019 12; 10(1):. doi: 10.3390/biom10010020. [PMID: 31877715]
  • Yi Tao, Dandan Su, Weidong Li, Baochang Cai. Pharmacokinetic comparisons of six components from raw and vinegar-processed Daphne genkwa aqueous extracts following oral administration in rats by employing UHPLC-MS/MS approaches. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Mar; 1079(?):34-40. doi: 10.1016/j.jchromb.2018.02.005. [PMID: 29428673]
  • Ning Chen, Pei-Pei Miao, Chang-E Guo, Hong-Ying Chen, Peng-Kai Ma, Hong-Pin Li, Hong-Yu Zhu, Xing Gao, Yu-Jie Zhang. [In vitro effects of Genkwa Flos chloroform extract on activity of human liver microsomes UGTs and UGT1A1]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2016 Sep; 41(17):3296-3302. doi: 10.4268/cjcmm20161729. [PMID: 28920386]
  • Pei-Pei Miao, Yuan-Yuan Zhao, Qing Miao, Chang-E Guo, Hong-Ying Chen, Ning Chen, Yu-Jie Zhang, Shuang-Cheng Ma. [Inhibitory effect of different species of hydroxygenkwanin on UGTs and UGT1A1 activities]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2016 Feb; 41(3):504-508. doi: 10.4268/cjcmm20160324. [PMID: 28868871]
  • Lin Li, Fang-zhou Yin, Tu-lin Lu, Hong-yue Guan, Bao-chang Cai. [Fingerprint of Vinegar Processed Genkwa Flos Based on Improving Euclidean Distance]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Jun; 38(6):1168-71. doi: . [PMID: 26762055]
  • Savio S Elo Manga, Anastasie E Tih, Bintou Abderamane, Raphael T Ghogomu, Alain Blond, Bernard Bodo. Flavonoid glycosides and their p-coumaroyl esters from Campylospermum calanthum leaves. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2012 May; 67(5-6):233-43. doi: 10.1515/znc-2012-5-601. [PMID: 22888527]
  • Jian-Xin Chen, Shen-Hui Huang, Ying Wang, Meng Shao, Wen-Cai Ye. [Studies on the chemical constituents from Lobelia chinensis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2010 Nov; 33(11):1721-4. doi: ". [PMID: 21434431]
  • Rong-hua Liu, Chong-ye Mei, Feng Shao, Gang Ren, Hui-lian Huang, Shi-sheng Chen, Wu-liang Yang. [Studies on the chemical constituents from Daphne tangutica]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Dec; 32(12):1846-7. doi: . [PMID: 20432900]
  • Wenwen Jiang, Junping Kou, Zhi Zhang, Boyang Yu. The effects of twelve representative flavonoids on tissue factor expression in human monocytes: structure-activity relationships. Thrombosis research. 2009 Dec; 124(6):714-20. doi: 10.1016/j.thromres.2009.04.010. [PMID: 19604541]
  • Cai-Fang Wang, Rao-Rao Li, Lan-Lan Huang, Li-Qun Zhong, Si-Tong Yuan. [Studies on chemical constituents of Daphne genkwa]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Apr; 32(4):508-11. doi: . [PMID: 19645232]
  • An-Shen Lin, Chia-Rong Lin, Ying-Chi Du, Tilo Lübken, Michael Y Chiang, I-Hsiao Chen, Chin-Chung Wu, Tsong-Long Hwang, Shu-Li Chen, Ming-Hong Yen, Fang-Rong Chang, Yang-Chang Wu. Acasiane A and B and farnesirane A and B, diterpene derivatives from the roots of Acacia farnesiana. Planta medica. 2009 Feb; 75(3):256-61. doi: 10.1055/s-0028-1112201. [PMID: 19101886]
  • Yan Feng, Xiao-Ming Li, Xiao-Juan Duan, Bin-Gui Wang. Iridoid glucosides and flavones from the aerial parts of Avicennia marina. Chemistry & biodiversity. 2006 Jul; 3(7):799-806. doi: 10.1002/cbdv.200690082. [PMID: 17193312]
  • Naoto Osaki, Takashi Koyano, Thaworn Kowithayakorn, Masahiko Hayashi, Kanki Komiyama, Masami Ishibashi. Sesquiterpenoids and plasmin-inhibitory flavonoids from Blumea balsamifera. Journal of natural products. 2005 Mar; 68(3):447-9. doi: 10.1021/np049622e. [PMID: 15787457]
  • Brenda Modak, M Leonor Contreras, Fernando González-Nilo, René Torres. Structure-antioxidant activity relationships of flavonoids isolated from the resinous exudate of Heliotropium sinuatum. Bioorganic & medicinal chemistry letters. 2005 Jan; 15(2):309-12. doi: 10.1016/j.bmcl.2004.10.081. [PMID: 15603945]
  • Supinya Tewtrakul, Hirotsugu Miyashiro, Norio Nakamura, Masao Hattori, Takuya Kawahata, Toru Otake, Tomokazu Yoshinaga, Tamio Fujiwara, Tanomjit Supavita, Supreeya Yuenyongsawad, Pranee Rattanasuwon, Sukanya Dej-Adisai. HIV-1 integrase inhibitory substances from Coleus parvifolius. Phytotherapy research : PTR. 2003 Mar; 17(3):232-9. doi: 10.1002/ptr.1111. [PMID: 12672152]
  • Kayoko Miura, Hiroe Kikuzaki, Nobuji Nakatani. Antioxidant activity of chemical components from sage (Salvia officinalis L.) and thyme (Thymus vulgaris L.) measured by the oil stability index method. Journal of agricultural and food chemistry. 2002 Mar; 50(7):1845-51. doi: 10.1021/jf011314o. [PMID: 11902922]
  • C R Ji. [Determination of hydroxygenkwanin in the leaves of Daphne genkwa]. Zhong yao tong bao (Beijing, China : 1981). 1986 Jul; 11(7):43-4. doi: ". [PMID: 2948707]