Alpinetin (BioDeep_00000229864)

 

Secondary id: BioDeep_00000175937

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-5-methoxy-2-phenyl-, (2S)-

化学式: C16H14O4 (270.0892044)
中文名称: 山姜素, 山姜素
谱图信息: 最多检出来源 Viridiplantae(plant) 0.71%

分子结构信息

SMILES: C1(O)=CC2OC(C3C=CC=CC=3)CC(=O)C=2C(OC)=C1
InChI: InChI=1S/C16H14O4/c1-19-14-7-11(17)8-15-16(14)12(18)9-13(20-15)10-5-3-2-4-6-10/h2-8,13,17H,9H2,1H3

描述信息

Alpinetin is a phytochemical isolated from a variety of plants including those of the genus Alpinia.[1] It is going through tests to see if it is a vasorelaxant.[2]

Alpinetin is a natural product found in Alpinia blepharocalyx, Alnus firma, and other organisms with data available.
Alpinetin is a flavonoid isolated from cardamom and has anti-inflammatory activity. Alpinetin inhibits lipopolysaccharide (LPS)-induced inflammation, activates PPAR-γ, activates Nrf2, and inhibits TLR4 expression to protect LPS-induced renal injury[1][2].
Alpinetin is a flavonoid isolated from Alpinia katsumadai Hayata, activates activates PPAR-γ, with potent anti-inflammatory activity[1].
Alpinetin is a flavonoid isolated from Alpinia katsumadai Hayata, activates activates PPAR-γ, with potent anti-inflammatory activity[1].

同义名列表

21 个代谢物同义名

Alpinetin; 4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-5-methoxy-2-phenyl-, (2S)-; 4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-7-HYDROXY-5-METHOXY-2-PHENYL-, (S)-; (2S)-7-Hydroxy-5-methoxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one; (2S)-2,3-DIHYDRO-7-HYDROXY-5-METHOXY-2-PHENYL-4H-1-BENZOPYRAN-4-ONE; (2S)-7-hydroxy-5-methoxy-2-phenyl-2,3-dihydrochromen-4-one; (2S)-7-hydroxy-5-methoxy-2-phenyl-chroman-4-one; (S)-7-Hydroxy-5-methoxy-2-phenylchroman-4-one; (2s)-7-hydroxy-5-methoxyflavanone; (S)-7-Hydroxy-5-methoxyflavanone; 5-Methoxy-7-hydroxyflavanone; 7-hydroxy-5-methoxyflavanone; 5-O-Methylpinocembrin; UNII-SX3EL59QD8; Alpinetin, (S)-; Alpinetin,(S); n-Propylether; (-)-alpinetin; (S)-ALPINETIN; SX3EL59QD8; (S) -2,3-Dihydro-7-hydroxy-5-methoxy-2-phenyl-4H-1-benzopyran-4-one



数据库引用编号

86 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)

3 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

  • Shining Xiao, Yu Zhang, Zihao Liu, Anan Li, Weilai Tong, Xu Xiong, Jiangbo Nie, Nanshan Zhong, Guoqing Zhu, Jiaming Liu, Zhili Liu. Alpinetin inhibits neuroinflammation and neuronal apoptosis via targeting the JAK2/STAT3 signaling pathway in spinal cord injury. CNS neuroscience & therapeutics. 2023 04; 29(4):1094-1108. doi: 10.1111/cns.14085. [PMID: 36627822]
  • Yuanyuan Chen, Chuan Yang, Mi Zou, Dan Wang, Ruilin Sheng, Meng Zhan, Qi Chen, Wenqin Yang, Xiao Liu, Shijun Xu. Inhibiting mitochondrial inflammation through Drp1/HK1/NLRP3 pathway: A mechanism of alpinetin attenuated aging-associated cognitive impairment. Phytotherapy research : PTR. 2023 Feb; ?(?):. doi: 10.1002/ptr.7767. [PMID: 36772986]
  • Yang Lu, Juan Liu, Jiaqi Tong, Chenxiao Zhang, Yi Duan, Xiaoli Song, Yongling Lu, Lishuang Lv. Dual effects of cardamonin/alpinetin and their acrolein adducts on scavenging acrolein and the anti-bacterial activity from Alpinia katsumadai Hayata as a spice in roasted meat. Food & function. 2022 Jul; 13(13):7088-7097. doi: 10.1039/d2fo00100d. [PMID: 35697027]
  • Doudou Dong, Yun Zhang, Hui He, Yuan Zhu, Hailong Ou. Alpinetin inhibits macrophage infiltration and atherosclerosis by improving the thiol redox state: Requirement of GSk3β/Fyn-dependent Nrf2 activation. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2022 04; 36(4):e22261. doi: 10.1096/fj.202101567r. [PMID: 35332570]
  • Yang Lu, Juan Liu, Anqi Tong, Yongling Lu, Lishuang Lv. Interconversion and Acrolein-Trapping Capacity of Cardamonin/Alpinetin and Their Metabolites In Vitro and In Vivo. Journal of agricultural and food chemistry. 2021 Oct; 69(40):11926-11936. doi: 10.1021/acs.jafc.1c04373. [PMID: 34587738]
  • Zhiheng Zhu, Renyue Hu, Jidan Li, Xiaoxiao Xing, Jianxin Chen, Qi Zhou, Jingjun Sun. Alpinetin exerts anti-inflammatory, anti-oxidative and anti-angiogenic effects through activating the Nrf2 pathway and inhibiting NLRP3 pathway in carbon tetrachloride-induced liver fibrosis. International immunopharmacology. 2021 Jul; 96(?):107660. doi: 10.1016/j.intimp.2021.107660. [PMID: 33862553]
  • Jie Pan, Sanyang Chen, Wenzhi Guo, Shengli Cao, Xiaoyi Shi, Jiakai Zhang, Huapeng Zhang, Shuijun Zhang. Alpinetin protects against hepatic ischemia/reperfusion injury in mice by inhibiting the NF-κB/MAPK signaling pathways. International immunopharmacology. 2021 Jun; 95(?):107527. doi: 10.1016/j.intimp.2021.107527. [PMID: 33743314]
  • Shasha Hou, Qi Yuan, Chunru Cheng, Zhigang Zhang, Bingran Guo, Xiaxia Yuan. Alpinetin delays high-fat diet-aggravated lung carcinogenesis. Basic & clinical pharmacology & toxicology. 2021 Mar; 128(3):410-418. doi: 10.1111/bcpt.13540. [PMID: 33259132]
  • Yukun Liu, Kang Wang, Qaunrui Feng, Yongsheng Zhang, Chuntao Wang, Qinxin Liu, Xinghua Liu, Xiang Wang, Wei Gao, Xiangjun Bai, Zhanfei Li, Yuchang Wang. Alpinetin Attenuates Persistent Inflammation, Immune Suppression, and Catabolism Syndrome in a Septic Mouse Model. Journal of immunology research. 2021; 2021(?):9998517. doi: 10.1155/2021/9998517. [PMID: 34285925]
  • Xiangsheng Zhao, Shihui Zhang, Dan Liu, Meihua Yang, Jianhe Wei. Analysis of Flavonoids in Dalbergia odorifera by Ultra-Performance Liquid Chromatography with Tandem Mass Spectrometry. Molecules (Basel, Switzerland). 2020 Jan; 25(2):. doi: 10.3390/molecules25020389. [PMID: 31963485]
  • Jieying Qiu, Hongyu Wu, Feng Feng, Xiaoying He, Caihong Wang, Shenghui Chu, Zheng Xiang. Metabolic Profiling of Alpinetin in Rat Plasma, Urine, Bile and Feces after Intragastric Administration. Molecules (Basel, Switzerland). 2019 Sep; 24(19):. doi: 10.3390/molecules24193458. [PMID: 31554153]
  • Tong-Gang Liu, Kai-Hui Sha, Li-Guo Zhang, Xian-Xian Liu, Fang Yang, Jin-Ying Cheng. Protective effects of alpinetin on lipopolysaccharide/d-Galactosamine-induced liver injury through inhibiting inflammatory and oxidative responses. Microbial pathogenesis. 2019 Jan; 126(?):239-244. doi: 10.1016/j.micpath.2018.11.007. [PMID: 30414839]
  • Weijian Ye, Xiaoji Lin, Youting Zhang, Youxiao Xu, Rui Sun, Congcong Wen, Xianqin Wang, Shihui Bao, Ruijie Chen. Quantification and pharmacokinetics of alpinetin in rat plasma by UHPLC-MS/MS using protein precipitation coupled with dilution approach to eliminate matrix effects. Journal of pharmaceutical and biomedical analysis. 2018 Apr; 152(?):242-247. doi: 10.1016/j.jpba.2017.12.046. [PMID: 29433096]
  • Yong Zhou, Yin-Lu Ding, Jian-Liang Zhang, Peng Zhang, Jin-Qing Wang, Zhao-Hua Li. Alpinetin improved high fat diet-induced non-alcoholic fatty liver disease (NAFLD) through improving oxidative stress, inflammatory response and lipid metabolism. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Jan; 97(?):1397-1408. doi: 10.1016/j.biopha.2017.10.035. [PMID: 29156529]
  • Zhen-Ran Wang, Yang Li, Bo Tang. [Protection Mechanism of Alpinetin on Pulmonary Microvascular Endothelial Cells Injury]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 2017 04; 37(4):476-479. doi: ". [PMID: 30650509]
  • Ibrahim Malami, Ahmad Bustamam Abdul, Rasedee Abdullah, Nur Kartinee Bt Kassim, Rozita Rosli, Swee Keong Yeap, Peter Waziri, Imaobong Christopher Etti, Muhammad Bashir Bello. Crude Extracts, Flavokawain B and Alpinetin Compounds from the Rhizome of Alpinia mutica Induce Cell Death via UCK2 Enzyme Inhibition and in Turn Reduce 18S rRNA Biosynthesis in HT-29 Cells. PloS one. 2017; 12(1):e0170233. doi: 10.1371/journal.pone.0170233. [PMID: 28103302]
  • Xingsi Liang, Bin Zhang, Quan Chen, Jing Zhang, Biao Lei, Bo Li, Yangchao Wei, Run Zhai, Zhiqing Liang, Songqing He, Bo Tang. The mechanism underlying alpinetin-mediated alleviation of pancreatitis-associated lung injury through upregulating aquaporin-1. Drug design, development and therapy. 2016; 10(?):841-50. doi: 10.2147/dddt.s97614. [PMID: 26966354]
  • Zhengming Jiang, Haiqiang Sang, Xin Fu, Ying Liang, Ling Li. Alpinetin enhances cholesterol efflux and inhibits lipid accumulation in oxidized low-density lipoprotein-loaded human macrophages. Biotechnology and applied biochemistry. 2015 Nov; 62(6):840-7. doi: 10.1002/bab.1328. [PMID: 25496323]
  • Yi Huang, Li-shan Zhou, Li Yan, Juan Ren, Dai-xing Zhou, Shu-Sheng Li. Alpinetin inhibits lipopolysaccharide-induced acute kidney injury in mice. International immunopharmacology. 2015 Oct; 28(2):1003-8. doi: 10.1016/j.intimp.2015.08.002. [PMID: 26321118]
  • Ke Hu, Yu Yang, Qiuyun Tu, Yingquan Luo, Ruoting Ma. Alpinetin inhibits LPS-induced inflammatory mediator response by activating PPAR-γ in THP-1-derived macrophages. European journal of pharmacology. 2013 Dec; 721(1-3):96-102. doi: 10.1016/j.ejphar.2013.09.049. [PMID: 24104193]
  • Haijin Chen, Xiaodong Mo, Jinlong Yu, Zonghai Huang. Alpinetin attenuates inflammatory responses by interfering toll-like receptor 4/nuclear factor kappa B signaling pathway in lipopolysaccharide-induced mastitis in mice. International immunopharmacology. 2013 Sep; 17(1):26-32. doi: 10.1016/j.intimp.2013.04.030. [PMID: 23669335]
  • Bo Tang, Jian Du, Jingwen Wang, Guang Tan, Zhenming Gao, Zhongyu Wang, Liming Wang. Alpinetin suppresses proliferation of human hepatoma cells by the activation of MKK7 and elevates sensitization to cis-diammined dichloridoplatium. Oncology reports. 2012 Apr; 27(4):1090-6. doi: 10.3892/or.2011.1580. [PMID: 22159816]
  • Mee-Young Lee, Chang-Seob Seo, Jin-Ah Lee, In-Sik Shin, Su-Jeong Kim, HeyKyung Ha, Hyeun-Kyoo Shin. Alpinia katsumadai H(AYATA) seed extract inhibit LPS-induced inflammation by induction of heme oxygenase-1 in RAW264.7 cells. Inflammation. 2012 Apr; 35(2):746-57. doi: 10.1007/s10753-011-9370-0. [PMID: 21830094]
  • Jian Du, Bo Tang, Jingwen Wang, Hongtao Sui, Xueli Jin, Liming Wang, Zhongyu Wang. Antiproliferative effect of alpinetin in BxPC-3 pancreatic cancer cells. International journal of molecular medicine. 2012 Apr; 29(4):607-12. doi: 10.3892/ijmm.2012.884. [PMID: 22246103]
  • Xu-Dong Cao, Zhi-Shan Ding, Fu-Sheng Jiang, Xing-Hong Ding, Jian-Zhen Chen, Su-Hong Chen, Gui-Yuan Lv. Antitumor constituents from the leaves of Carya cathayensis. Natural product research. 2012; 26(22):2089-94. doi: 10.1080/14786419.2011.628174. [PMID: 22007794]
  • Meixia Huo, Na Chen, Gefu Chi, Xue Yuan, Shuang Guan, Hongyu Li, Weiting Zhong, Weixiao Guo, Lanan Wassy Soromou, Ruijie Gao, Hongsheng Ouyang, Xuming Deng, Haihua Feng. Traditional medicine alpinetin inhibits the inflammatory response in Raw 264.7 cells and mouse models. International immunopharmacology. 2012 Jan; 12(1):241-8. doi: 10.1016/j.intimp.2011.11.017. [PMID: 22178196]
  • Guowen Zhang, Nan Zhao, Xing Hu, Jiao Tian. Interaction of alpinetin with bovine serum albumin: Probing of the mechanism and binding site by spectroscopic methods. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2010 Aug; 76(3-4):410-7. doi: 10.1016/j.saa.2010.04.009. [PMID: 20427226]
  • Yongnian Ni, Shuangshuang Wang, Serge Kokot. Spectrometric study of the interaction between alpinetin and bovine serum albumin using chemometrics approaches. Analytica chimica acta. 2010 Mar; 663(2):139-46. doi: 10.1016/j.aca.2010.01.053. [PMID: 20206002]
  • Xiu-Qin Wang, Xiao-Jiang Yang, Jiao-She Li. [Studies on chemical constituents of alpinia katsumadai]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 Jun; 31(6):853-5. doi: ". [PMID: 18998568]
  • Guo-Wen Zhang, An-Ping Wang, Ting Jiang. [Studies on the interaction between alpinetin and human serum albumin by fluorescence spectroscopy]. Guang pu xue yu guang pu fen xi = Guang pu. 2008 Apr; 28(4):908-12. doi: NULL. [PMID: 18619327]
  • Wenying He, Ying Li, Chunxia Xue, Zhide Hu, Xingguo Chen, Fenling Sheng. Effect of Chinese medicine alpinetin on the structure of human serum albumin. Bioorganic & medicinal chemistry. 2005 Mar; 13(5):1837-45. doi: 10.1016/j.bmc.2004.11.038. [PMID: 15698801]
  • Yu-Juan Li, Guan-Hua Du. Effects of alpinetin on rat vascular smooth muscle cells. Journal of Asian natural products research. 2004 Jun; 6(2):87-92. doi: 10.1080/1028602031000135558. [PMID: 15008454]