Eupatorin (BioDeep_00000230003)

 

Secondary id: BioDeep_00000178948

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


4H-1-Benzopyran-4-one, 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy- (9CI)

化学式: C18H16O7 (344.0895986)
中文名称: 3,5-二羟基-4,6,7-三甲氧基黄酮, 半齿泽兰素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(c(c(c2c(c1)oc(cc2=O)c1ccc(c(c1)O)OC)O)OC)OC
InChI: InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3

描述信息

Eupatorin is a trimethoxyflavone that is 6-hydroxyluteolin in which the phenolic hydogens at positions 4, 6 and 7 have been replaced by methyl groups. It has a role as a Brassica napus metabolite, an apoptosis inducer, a vasodilator agent, a calcium channel blocker, an anti-inflammatory agent, a P450 inhibitor and an antineoplastic agent. It is a dihydroxyflavone, a trimethoxyflavone and a polyphenol. It is functionally related to a 6-hydroxyluteolin.
Eupatorin is a natural product found in Eupatorium album, Eupatorium altissimum, and other organisms with data available.
A trimethoxyflavone that is 6-hydroxyluteolin in which the phenolic hydogens at positions 4, 6 and 7 have been replaced by methyl groups.
Eupatorin, a naturally occurring flavone, arrests cells at the G2-M phase of the cell cycle and induces apoptotic cell death involving activation of multiple caspases, mitochondrial release of cytochrome c and poly(ADP-ribose) polymerase cleavage[1].
Eupatorin, a naturally occurring flavone, arrests cells at the G2-M phase of the cell cycle and induces apoptotic cell death involving activation of multiple caspases, mitochondrial release of cytochrome c and poly(ADP-ribose) polymerase cleavage[1].

同义名列表

48 个代谢物同义名

4H-1-Benzopyran-4-one, 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-; 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-1-benzopyran-4-one; 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one; 5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6,7-dimethoxy-chromen-4-one; 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxychromen-4-one; Flavone, 3,5-dihydroxy-4,6,7-trimethoxy-; 3,5-dihydroxy-4,6,7-trimethoxy flavone; Flavone,5-dihydroxy-4,6,7-trimethoxy-; 3,5-dihydroxy-4,6,7-trimethoxyflavone; 5,3-Dihydroxy-6,7,4-trimethoxyflavone; 6-methoxyluteolin-4,7-dimethyl ether; 6-Methoxyluteolin 4,7-dimethyl ether; 4H-1-Benzopyran-4-one,7-dimethoxy-; Eupatorin, analytical standard; KLAOKWJLUQKWIF-UHFFFAOYSA-N; Eupatorin, >=97\\% (HPLC); 3,6,7-trimethoxyflavone; Spectrum5_000625; Spectrum2_000456; Spectrum4_001833; Eupatorin - 94\\%; UNII-3J474AV6MY; EUPATORIN [MI]; DivK1c_007019; KBio2_001517; Tox21_500799; KBio1_001963; KBio2_006653; KBio2_004085; ACon1_001351; Eupatorine; 3J474AV6MY; Eupatorin; 4H-1-Benzopyran-4-one, 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy- (9CI); 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4-chromenone; 5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6,7-dimethoxy-chromone; Flavone, 3,5-dihydroxy-4,6,7-trimethoxy- (8CI); SpecPlus_000923; Spectrum_001037; KBioSS_001517; KBioGR_002532; SPBio_000532; ZINC00001412; NSC 106402; ST5331588; NSC106402; 855-96-9; 5-Hydroxy-2- (3-hydroxy-4-methoxyphenyl) -6,7-dimethoxy-4H-1-benzopyran-4-one



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

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)

199 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

  • Zulfiqar Ali, Srivedavyasasri Radhakrishnan, Bharathi Avula, Amar G Chittiboyina, Jing Li, Charles Wu, Ikhlas A Khan. Eupatorin 3'-O-glucopyranoside, a trimethoxyflavonoid glucoside from the aerial parts of Salvia mellifera. Natural product research. 2023 Jan; 37(2):269-276. doi: 10.1080/14786419.2021.1969565. [PMID: 34435528]
  • Esther Della Nina Sahid, Josiane Clarice Claudino, Fernando Bombarda Oda, Flávio Alexandre Carvalho, André Gonzaga Dos Santos, Marcia A S Graminha, Leandro da Costa Clementino. Baccharis trimera (Less.) DC leaf derivatives and eupatorin activities against Leishmania amazonensis. Natural product research. 2022 Mar; 36(6):1599-1603. doi: 10.1080/14786419.2021.1887175. [PMID: 33586545]
  • Shih-Chung Yen, Liang-Chieh Chen, Han-Li Huang, Sin-Ting Ngo, Yi-Wen Wu, Tony Eight Lin, Tzu-Ying Sung, Ssu-Ting Lien, Hui-Ju Tseng, Shiow-Lin Pan, Wei-Jan Huang, Kai-Cheng Hsu. Investigation of Selected Flavonoid Derivatives as Potent FLT3 Inhibitors for the Potential Treatment of Acute Myeloid Leukemia. Journal of natural products. 2021 01; 84(1):1-10. doi: 10.1021/acs.jnatprod.0c00589. [PMID: 33393294]
  • Angela Bisio, Anna M Schito, Francesca Pedrelli, Ombeline Danton, Jakob K Reinhardt, Giulio Poli, Tiziano Tuccinardi, Thomas Bürgi, Francesco De Riccardis, Mauro Giacomini, Daniela Calzia, Isabella Panfoli, Gian Carlo Schito, Matthias Hamburger, Nunziatina De Tommasi. Antibacterial and ATP Synthesis Modulating Compounds from Salvia tingitana. Journal of natural products. 2020 04; 83(4):1027-1042. doi: 10.1021/acs.jnatprod.9b01024. [PMID: 32182064]
  • Akram Taleghani, Seyed Ahmad Emami, Zahra Tayarani-Najaran. Artemisia: a promising plant for the treatment of cancer. Bioorganic & medicinal chemistry. 2020 01; 28(1):115180. doi: 10.1016/j.bmc.2019.115180. [PMID: 31784199]
  • Nursyamirah Abd Razak, Swee Keong Yeap, Noorjahan Banu Alitheen, Wan Yong Ho, Chean Yeah Yong, Sheau Wei Tan, Wen Siang Tan, Kamariah Long. Eupatorin Suppressed Tumor Progression and Enhanced Immunity in a 4T1 Murine Breast Cancer Model. Integrative cancer therapies. 2020 Jan; 19(?):1534735420935625. doi: 10.1177/1534735420935625. [PMID: 32830560]
  • Melanie Deipenbrock, Andreas Hensel. Polymethoxylated flavones from Orthosiphon stamineus leaves as antiadhesive compounds against uropathogenic E. coli. Fitoterapia. 2019 Nov; 139(?):104387. doi: 10.1016/j.fitote.2019.104387. [PMID: 31678632]
  • Luya Li, Yuting Chen, Xue Feng, Jintuo Yin, Shenghao Li, Yupeng Sun, Lantong Zhang. Identification of Metabolites of Eupatorin in Vivo and in Vitro Based on UHPLC-Q-TOF-MS/MS. Molecules (Basel, Switzerland). 2019 Jul; 24(14):. doi: 10.3390/molecules24142658. [PMID: 31340434]
  • Vorapong Klungboonkrong, Buddhi P Lamsal, Singhanat Phoungchandang. Changes and degradation kinetics of some bioactive compounds in dried Orthosiphon aristatus (Java tea) leaves during elevated temperature storage. Journal of the science of food and agriculture. 2019 Jan; 99(2):933-940. doi: 10.1002/jsfa.9268. [PMID: 30009388]
  • Marco Martín González-Chávez, Cinthia Saraí Ramos-Velázquez, Roberto Serrano-Vega, Cuauhtemoc Pérez-González, Ernesto Sánchez-Mendoza, Salud Pérez-Gutiérrez. Anti-inflammatory activity of standardized dichloromethane extract of Salvia connivens on macrophages stimulated by LPS. Pharmaceutical biology. 2017 Dec; 55(1):1467-1472. doi: 10.1080/13880209.2017.1305423. [PMID: 28347190]
  • Emma Maldonado, Leonel Galicia, Ma Isabel Chávez, Simón Hernández-Ortega. neo-Clerodane Diterpenoids and Other Constituents of Salvia filipes. Journal of natural products. 2016 10; 79(10):2667-2673. doi: 10.1021/acs.jnatprod.6b00605. [PMID: 27679866]
  • Mun Fei Yam, Chu Shan Tan, Mariam Ahmad, Ruan Shibao. Mechanism of vasorelaxation induced by eupatorin in the rats aortic ring. European journal of pharmacology. 2016 Oct; 789(?):27-36. doi: 10.1016/j.ejphar.2016.06.047. [PMID: 27370961]
  • Yan Pan, Kai Hung Tiong, Badrul Amini Abd-Rashid, Zakiah Ismail, Rusli Ismail, Joon Wah Mak, Chin Eng Ong. In vitro effect of important herbal active constituents on human cytochrome P450 1A2 (CYP1A2) activity. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Oct; 21(12):1645-50. doi: 10.1016/j.phymed.2014.08.003. [PMID: 25442272]
  • Lei Chen, Young-Hwa Kang. Antioxidant and enzyme inhibitory activities of Plebeian herba (Salvia plebeia R. Br.) under different cultivation conditions. Journal of agricultural and food chemistry. 2014 Mar; 62(10):2190-7. doi: 10.1021/jf404570s. [PMID: 24422962]
  • Iva Dolečková, Lucie Rárová, Jiří Grúz, Magdaléna Vondrusová, Miroslav Strnad, Vladimír Kryštof. Antiproliferative and antiangiogenic effects of flavone eupatorin, an active constituent of chloroform extract of Orthosiphon stamineus leaves. Fitoterapia. 2012 Sep; 83(6):1000-7. doi: 10.1016/j.fitote.2012.06.002. [PMID: 22698713]
  • Mun Fei Yam, Elsnoussi Ali Hussin Mohamed, Lee Fung Ang, Li Pei, Yusrida Darwis, Roziahanim Mahmud, Mohd Zaini Asmawi, Rusliza Basir, Mariam Ahmad. A simple isocratic HPLC method for the simultaneous determination of sinensetin, eupatorin, and 3'-hydroxy-5,6,7,4'-tetramethoxyflavone in Orthosiphon stamineus extracts. Journal of acupuncture and meridian studies. 2012 Aug; 5(4):176-82. doi: 10.1016/j.jams.2012.05.005. [PMID: 22898066]
  • Peter Forgo, István Zupkó, Judit Molnár, Andrea Vasas, György Dombi, Judit Hohmann. Bioactivity-guided isolation of antiproliferative compounds from Centaurea jacea L. Fitoterapia. 2012 Jul; 83(5):921-5. doi: 10.1016/j.fitote.2012.04.006. [PMID: 22537643]
  • Mirka Laavola, Riina Nieminen, Mun Fei Yam, Amirin Sadikun, Mohd Zaini Asmawi, Rusliza Basir, Jukka Welling, Heikki Vapaatalo, Riku Korhonen, Eeva Moilanen. Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation. Planta medica. 2012 May; 78(8):779-86. doi: 10.1055/s-0031-1298458. [PMID: 22516932]
  • Anna-Leena Salmela, Jeroen Pouwels, Anu Kukkonen-Macchi, Sinikka Waris, Pauliina Toivonen, Kimmo Jaakkola, Jenni Mäki-Jouppila, Lila Kallio, Marko J Kallio. The flavonoid eupatorin inactivates the mitotic checkpoint leading to polyploidy and apoptosis. Experimental cell research. 2012 Mar; 318(5):578-92. doi: 10.1016/j.yexcr.2011.12.014. [PMID: 22227008]
  • Maria Graça Miguel, Maria Dulce Antunes. Is propolis safe as an alternative medicine?. Journal of pharmacy & bioallied sciences. 2011 Oct; 3(4):479-95. doi: 10.4103/0975-7406.90101. [PMID: 22219581]
  • Yan Pan, Badrul Amini Abd-Rashid, Zakiah Ismail, Rusli Ismail, Joon Wah Mak, Peter C K Pook, Hui Meng Er, Chin Eng Ong. In vitro effects of active constituents and extracts of Orthosiphon stamineus on the activities of three major human cDNA-expressed cytochrome P450 enzymes. Chemico-biological interactions. 2011 Mar; 190(1):1-8. doi: 10.1016/j.cbi.2011.01.022. [PMID: 21276781]
  • Philippe Rasoanaivo, Colin W Wright, Merlin L Willcox, Ben Gilbert. Whole plant extracts versus single compounds for the treatment of malaria: synergy and positive interactions. Malaria journal. 2011 Mar; 10 Suppl 1(?):S4. doi: 10.1186/1475-2875-10-s1-s4. [PMID: 21411015]
  • H Muhammad, M R Gomes-Carneiro, K S Poça, A C A X De-Oliveira, A Afzan, S A Sulaiman, Z Ismail, F J R Paumgartten. Evaluation of the genotoxicity of Orthosiphon stamineus aqueous extract. Journal of ethnopharmacology. 2011 Jan; 133(2):647-53. doi: 10.1016/j.jep.2010.10.055. [PMID: 21044879]
  • Yan Pan, Badrul Amini Abd-Rashid, Zakiah Ismail, Rusli Ismail, Joon Wah Mak, Peter C K Pook, Hui Meng Er, Chin Eng Ong. In vitro modulatory effects of Andrographis paniculata, Centella asiatica and Orthosiphon stamineus on cytochrome P450 2C19 (CYP2C19). Journal of ethnopharmacology. 2011 Jan; 133(2):881-7. doi: 10.1016/j.jep.2010.11.026. [PMID: 21093571]
  • Sau Har Lee, Indu Bala Jaganath, Seok Mui Wang, Shamala Devi Sekaran. Antimetastatic effects of Phyllanthus on human lung (A549) and breast (MCF-7) cancer cell lines. PloS one. 2011; 6(6):e20994. doi: 10.1371/journal.pone.0020994. [PMID: 21698198]
  • Mohammed A Alshawsh, Mahmood Ameen Abdulla, Salmah Ismail, Zahra A Amin. Hepatoprotective Effects of Orthosiphon stamineus Extract on Thioacetamide-Induced Liver Cirrhosis in Rats. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):103039. doi: 10.1155/2011/103039. [PMID: 21647311]
  • Siddig Ibrahim Abdelwahab, Syam Mohan, Manal Mohamed Elhassan, Nabil Al-Mekhlafi, Abdelbasit Adam Mariod, Ahmad Bustamam Abdul, Mahmood Ameen Abdulla, Khalid M Alkharfy. Antiapoptotic and Antioxidant Properties of Orthosiphon stamineus Benth (Cat's Whiskers): Intervention in the Bcl-2-Mediated Apoptotic Pathway. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):156765. doi: 10.1155/2011/156765. [PMID: 21234328]
  • Ahmad R Gohari, Soodabeh Saeidnia, Maryam Malmir, Abbass Hadjiakhoondi, Yousef Ajani. Flavones and rosmarinic acid from Salvia limbata. Natural product research. 2010 Dec; 24(20):1902-6. doi: 10.1080/14786411003766912. [PMID: 21108116]
  • Bence Csapi, Zsuzsanna Hajdú, István Zupkó, Agnes Berényi, Peter Forgo, Pál Szabó, Judit Hohmann. Bioactivity-guided isolation of antiproliferative compounds from Centaurea arenaria. Phytotherapy research : PTR. 2010 Nov; 24(11):1664-9. doi: 10.1002/ptr.3187. [PMID: 21031625]
  • Mun Fei Yam, Vuanghao Lim, Ibrahim Muhammad Salman, Omar Ziad Ameer, Lee Fung Ang, Noersal Rosidah, Muthanna Fawzy Abdulkarim, Ghassan Zuhair Abdullah, Rusliza Basir, Amirin Sadikun, Mohd Zaini Asmawi. HPLC and anti-inflammatory studies of the flavonoid rich chloroform extract fraction of Orthosiphon stamineus leaves. Molecules (Basel, Switzerland). 2010 Jun; 15(6):4452-66. doi: 10.3390/molecules15064452. [PMID: 20657453]
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