nepetin (BioDeep_00000229941)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy- (9CI)

化学式: C16H12O7 (316.0583)
中文名称: 泽兰黄酮, 6-甲氧基藤黄菌素
谱图信息: 最多检出来源 Viridiplantae(plant) 75.97%

分子结构信息

SMILES: c1(c(c(c2c(c1)oc(cc2=O)c1ccc(c(c1)O)O)O)OC)O
InChI: InChI=1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3

描述信息

Eupafolin, also known as 6-methoxy 5 or 734-tetrahydroxyflavone, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, eupafolin is considered to be a flavonoid lipid molecule. Eupafolin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Eupafolin can be found in common sage, lemon verbena, rosemary, and sesame, which makes eupafolin a potential biomarker for the consumption of these food products.
6-Methoxyluteolin is a natural product found in Eupatorium album, Eupatorium altissimum, and other organisms with data available.
See also: Arnica montana Flower (has part).
Nepetin (6-Methoxyluteolin) is a natural flavonoid isolated from Eupatorium ballotaefolium HBK with potent anti-inflammatory activities. Nepetin inhibits IL-6, IL-8 and MCP-1 secretion with IC50 values of 4.43 μM, 3.42 μM and 4.17 μM, respectively in ARPE-19 cells[1][2].
Nepetin (6-Methoxyluteolin) is a natural flavonoid isolated from Eupatorium ballotaefolium HBK with potent anti-inflammatory activities. Nepetin inhibits IL-6, IL-8 and MCP-1 secretion with IC50 values of 4.43 μM, 3.42 μM and 4.17 μM, respectively in ARPE-19 cells[1][2].

同义名列表

41 个代谢物同义名

Eupafolin; nepetin; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy- (9CI); 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-chromen-4-one; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4-chromenone; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-chromone; Flavone, 3,4,5,7-tetrahydroxy-6-methoxy- (8CI); Flavone, 3,4,5,7-tetrahydroxy-6-methoxy-; 5,7,3,4-Tetrahydroxy-6-methoxyflavone; 6-Methoxyluteolin; NCGC00163594-01; MEGxp0_000458; ACon1_000516; SMR000440634; ZINC01081536; MLS000877025; MLS000728561; AIDS-027676; AIDS027676; NSC 122416; ST5309235; NSC122416; 520-11-6; Methoxyluteolin; 2-[3,4-bis(oxidanyl)phenyl]-6-methoxy-5,7-bis(oxidanyl)chromen-4-one; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-1-benzopyran-4-one; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one #; 4H-1-Benzopyran-4-one,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one; 4-(4-Hydroxyphenyl)thiomorpholine1,1-dioxide; 5,7,3,4-TETRAHYDROXY-6-METHOXY FLAVONE; Flavone,4,5,7-tetrahydroxy-6-methoxy-; 6-methoxy 5,7,3,4-tetrahydroxyflavone; FHHSEFRSDKWJKJ-UHFFFAOYSA-N; ?6-METHOXYLUTEOLIN; UNII-I3O7LF3GED; I3O7LF3GED; Pedaltin; 2- (3,4-Dihydroxyphenyl) -5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one



数据库引用编号

18 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)

365 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


文献列表

  • Su Wu, Wenwei Ai, Lei Nie, Xiao Lu. Antidiabetic activity of eupafolin through peroxisome proliferator-activated receptor-gamma and PI3K/Akt signaling in Type 2 diabetic rats. Journal of biochemical and molecular toxicology. 2023 Aug; ?(?):e23463. doi: 10.1002/jbt.23463. [PMID: 37566541]
  • Shisong Jing, Xinran Ren, Li Wang, Xiangri Kong, Xingye Wang, Xiren Chang, Xuerui Guo, Yan Shi, Jiyu Guan, Tiedong Wang, Bingmei Wang, Wu Song, Yicheng Zhao. Nepetin reduces virulence factors expression by targeting ClpP against MRSA-induced pneumonia infection. Virulence. 2022 12; 13(1):578-588. doi: 10.1080/21505594.2022.2051313. [PMID: 35363605]
  • Wei-Horng Jean, Chih-Ta Huang, Jung-Hsuan Hsu, Kuan-Ming Chiu, Ming-Yi Lee, Jiann-Shing Shieh, Tzu-Yu Lin, Su-Jane Wang. Anticonvulsive and Neuroprotective Effects of Eupafolin in Rats Are Associated with the Inhibition of Glutamate Overexcitation and Upregulation of the Wnt/β-Catenin Signaling Pathway. ACS chemical neuroscience. 2022 05; 13(10):1594-1603. doi: 10.1021/acschemneuro.2c00227. [PMID: 35500294]
  • Ece Sevgi, Aydan Dag, Çağla Kızılarslan-Hançer, Sezen Atasoy, Belma Zengin Kurt, Öznur Aksakal. Evaluation of cytotoxic and antioxidant potential of Dittrichia viscosa (L.) Greuter used in traditional medicine. Journal of ethnopharmacology. 2021 Aug; 276(?):114211. doi: 10.1016/j.jep.2021.114211. [PMID: 34015367]
  • Zui Chen, Long Qiu Cheng. Eupafolin induces autophagy and apoptosis in B-cell non-Hodgkin lymphomas. The Journal of pharmacy and pharmacology. 2021 Mar; 73(2):241-246. doi: 10.1093/jpp/rgaa011. [PMID: 33793811]
  • Xingwang Chen, Zhijun Yao, Xian Peng, Long Wu, Huachu Wu, Yuantong Ou, Jianbo Lai. Eupafolin alleviates cerebral ischemia/reperfusion injury in rats via blocking the TLR4/NF‑κB signaling pathway. Molecular medicine reports. 2020 Dec; 22(6):5135-5144. doi: 10.3892/mmr.2020.11637. [PMID: 33173992]
  • Evelyn Saba, Young-Sil Lee, Won-Kyung Yang, Yuan Yee Lee, MinKi Kim, Su-Min Woo, KilSoo Kim, Young-Sam Kwon, Tae-Hwan Kim, Dongmi Kwak, Yang-Chun Park, Han Jae Shin, Chang Kyun Han, Jae-Wook Oh, Young Cheol Lee, Hyung-Sik Kang, Man Hee Rhee, Seung-Hyung Kim. Effects of a herbal formulation, KGC3P, and its individual component, nepetin, on coal fly dust-induced airway inflammation. Scientific reports. 2020 08; 10(1):14036. doi: 10.1038/s41598-020-68965-5. [PMID: 32820197]
  • Hao Zhang, Ming-Kun Chen, Ke Li, Cheng Hu, Min-Hua Lu, Jie Situ. Eupafolin nanoparticle improves acute renal injury induced by LPS through inhibiting ROS and inflammation. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Jan; 85(?):704-711. doi: 10.1016/j.biopha.2016.11.083. [PMID: 27923689]
  • Min Ae Han, Kyoung-Jin Min, Seon Min Woo, Bo Ram Seo, Taeg Kyu Kwon. Eupafolin enhances TRAIL-mediated apoptosis through cathepsin S-induced down-regulation of Mcl-1 expression and AMPK-mediated Bim up-regulation in renal carcinoma Caki cells. Oncotarget. 2016 Oct; 7(40):65707-65720. doi: 10.18632/oncotarget.11604. [PMID: 27582546]
  • Chiang-Wen Lee, Zih-Chan Lin, Lee-Fen Hsu, Jia-You Fang, Yao-Chang Chiang, Ming-Horng Tsai, Ming-Hsueh Lee, Shu-Yu Li, Stephen Chu-Sung Hu, I-Ta Lee, Feng-Lin Yen. Eupafolin ameliorates COX-2 expression and PGE2 production in particulate pollutants-exposed human keratinocytes through ROS/MAPKs pathways. Journal of ethnopharmacology. 2016 Aug; 189(?):300-9. doi: 10.1016/j.jep.2016.05.002. [PMID: 27180879]
  • Zih-Chan Lin, Chiang-Wen Lee, Ming-Horng Tsai, Horng-Huey Ko, Jia-You Fang, Yao-Chang Chiang, Chan-Jung Liang, Lee-Fen Hsu, Stephen Chu-Sung Hu, Feng-Lin Yen. Eupafolin nanoparticles protect HaCaT keratinocytes from particulate matter-induced inflammation and oxidative stress. International journal of nanomedicine. 2016; 11(?):3907-26. doi: 10.2147/ijn.s109062. [PMID: 27570454]
  • Chin-Chaun Chen, Ming-Wei Lin, Chan-Jung Liang, Shu-Huei Wang. The Anti-Inflammatory Effects and Mechanisms of Eupafolin in Lipopolysaccharide-Induced Inflammatory Responses in RAW264.7 Macrophages. PloS one. 2016; 11(7):e0158662. doi: 10.1371/journal.pone.0158662. [PMID: 27414646]
  • Hsin-Ching Sung, Chan-Jung Liang, Chiang-Wen Lee, Feng-Lin Yen, Chien-Yu Hsiao, Shu-Huei Wang, Ya-Fen Jiang-Shieh, Jaw-Shiun Tsai, Yuh-Lien Chen. The protective effect of eupafolin against TNF-α-induced lung inflammation via the reduction of intercellular cell adhesion molecule-1 expression. Journal of ethnopharmacology. 2015 Jul; 170(?):136-47. doi: 10.1016/j.jep.2015.04.058. [PMID: 25975517]
  • Horng-Huey Ko, Yao-Chang Chiang, Ming-Horng Tsai, Chan-Jung Liang, Lee-Fen Hsu, Shu-Yu Li, Moo-Chin Wang, Feng-Lin Yen, Chiang-Wen Lee. Eupafolin, a skin whitening flavonoid isolated from Phyla nodiflora, downregulated melanogenesis: Role of MAPK and Akt pathways. Journal of ethnopharmacology. 2014; 151(1):386-93. doi: 10.1016/j.jep.2013.10.054. [PMID: 24212072]
  • Ayumi Uehara, Tsukasa Iwashina. Flavonoids from the Japanese monotypic genus, Nipponanthemum. Natural product communications. 2012 Aug; 7(8):1005-6. doi: . [PMID: 22978216]
  • Sun-Yup Shim, Jeong-Ro Park, Dae-Seok Byun. 6-Methoxyluteolin from Chrysanthemum zawadskii var. latilobum suppresses histamine release and calcium influx via down-regulation of FcεRI α chain expression. Journal of microbiology and biotechnology. 2012 May; 22(5):622-7. doi: 10.4014/jmb.1111.11060. [PMID: 22561855]
  • Minpei Kuroda, Katsura Iwabuchi, Yoshihiro Mimaki. Chemical constituents of the aerial parts of Scutellaria lateriflora and their alpha-glucosidase inhibitory activities. Natural product communications. 2012 Apr; 7(4):471-4. doi: . [PMID: 22574444]
  • Shuangqing Wu, Qun Sun, Chunjun Chu, Jian Zhang. [Chemical constituents of Eupatorium lindleyanum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Apr; 37(7):937-40. doi: . [PMID: 22792793]
  • Wamidh H Talib, Musa H Abu Zarga, Adel M Mahasneh. Antiproliferative, antimicrobial and apoptosis inducing effects of compounds isolated from Inula viscosa. Molecules (Basel, Switzerland). 2012 Mar; 17(3):3291-303. doi: 10.3390/molecules17033291. [PMID: 22418930]
  • Maha M Salama, Zeinab A Kandil, Wafaa T Islam. Cytotoxic compounds from the leaves of Gaillardia aristata Pursh. growing in Egypt. Natural product research. 2012; 26(22):2057-62. doi: 10.1080/14786419.2011.606219. [PMID: 21846263]
  • Hyun Jung Shin, So Young Lee, Ju Sun Kim, Sanghyun Lee, Ran Joo Choi, Ha Sook Chung, Yeong Shik Kim, Sam Sik Kang. Sesquiterpenes and other constituents from Dendranthema zawadskii var. latilobum. Chemical & pharmaceutical bulletin. 2012; 60(3):306-14. doi: 10.1248/cpb.60.306. [PMID: 22382409]
  • Souheila Louaar, Amel Achouri, Mostefa Lefahal, Hocine Laouer, Kamel Medjroubi, Helmut Duddeck, Salah Akkal. Flavonoids from Algerian endemic Centaurea microcarpa and their chemotaxonomical significance. Natural product communications. 2011 Nov; 6(11):1603-4. doi: . [PMID: 22224272]
  • Mareike Maas, Alexandra M Deters, Andreas Hensel. Anti-inflammatory activity of Eupatorium perfoliatum L. extracts, eupafolin, and dimeric guaianolide via iNOS inhibitory activity and modulation of inflammation-related cytokines and chemokines. Journal of ethnopharmacology. 2011 Sep; 137(1):371-81. doi: 10.1016/j.jep.2011.05.040. [PMID: 21669270]
  • Kumaresan P Thirupathy, Asish Tulshkar, C Vijaya. Neuropharmacological activity of Lippia nodiflora Linn. Pharmacognosy research. 2011 Jul; 3(3):194-200. doi: 10.4103/0974-8490.85007. [PMID: 22022169]
  • Xiao-feng Jin, Yan-hua Lu, Dong-zhi Wei, Zheng-tao Wang. Chemical fingerprint and quantitative analysis of Salvia plebeia R.Br. by high-performance liquid chromatography. Journal of pharmaceutical and biomedical analysis. 2008 Sep; 48(1):100-4. doi: 10.1016/j.jpba.2008.05.027. [PMID: 18678457]
  • Nasim Sultana, A J Afolayan. A novel daucosterol derivative and antibacterial activity of compounds from Arctotis arctotoides. Natural product research. 2007 Aug; 21(10):889-96. doi: 10.1080/14786410601129606. [PMID: 17680499]
  • M Clavin, S Gorzalczany, A Macho, E Muñoz, G Ferraro, C Acevedo, V Martino. Anti-inflammatory activity of flavonoids from Eupatorium arnottianum. Journal of ethnopharmacology. 2007 Jul; 112(3):585-9. doi: 10.1016/j.jep.2007.04.007. [PMID: 17570627]
  • Filippo Cottiglia, Laura Casu, Leonardo Bonsignore, Mariano Casu, Costantino Floris, Silvio Sosa, Gianmario Altinier, Roberto Della Loggia. Topical anti-inflammatory activity of flavonoids and a new xanthone from Santolina insularis. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2005 Jan; 60(1-2):63-6. doi: 10.1515/znc-2005-1-212. [PMID: 15787246]
  • Sheng Lin, Yong-qing Xiao, Qi-wei Zhang, Ning-ning Zhang. [Studies on chemical constituents in bud of Artemisia scoparia (II)]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2004 Feb; 29(2):152-4. doi: . [PMID: 15719683]
  • Hasan Kirmizibekmez, Pinar Akbay, Otto Sticher, Ihsan Caliş. Iridoids from Globularia dumulosa. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2003 Mar; 58(3-4):181-6. doi: 10.1515/znc-2003-3-407. [PMID: 12710725]
  • So Ra Kim, Mi Jung Park, Mi Kyeong Lee, Sang Hyun Sung, Eun Jung Park, Jinwoong Kim, Sun Yeou Kim, Tae H Oh, George J Markelonis, Young Choong Kim. Flavonoids of Inula britannica protect cultured cortical cells from necrotic cell death induced by glutamate. Free radical biology & medicine. 2002 Apr; 32(7):596-604. doi: 10.1016/s0891-5849(02)00751-7. [PMID: 11909694]