(E,E)-Piperlonguminine (BioDeep_00000017441)

 

Secondary id: BioDeep_00000616131, BioDeep_00000860666

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds


代谢物信息卡片


(Z,2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienimidic acid

化学式: C16H19NO3 (273.13648639999997)
中文名称: 荜茇宁
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 9.09%

分子结构信息

SMILES: CC(C)CNC(=O)C=CC=CC1=CC2=C(C=C1)OCO2
InChI: InChI=1S/C16H19NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h3-9,12H,10-11H2,1-2H3,(H,17,18)/b5-3+,6-4+

描述信息

(E,E)-Piperlonguminine is a member of benzodioxoles.
Piperlonguminine is a natural product found in Piper amalago, Piper retrofractum, and other organisms with data available.
(E,E)-Piperlonguminine is found in herbs and spices. (E,E)-Piperlonguminine is an alkaloid from Piper longum (long pepper) and other Piper specie
Alkaloid from Piper longum (long pepper) and other Piper subspecies (E,E)-Piperlonguminine is found in herbs and spices.
Piperlonguminine is an alkaloid amide isolated from the Piper species. Piperlonguminine shows various biological properties, including anti-inflammatory, antitumor, neuroprotective, anti-platelet, anti-melanogenic, antifungal and antibacterial activities[1][2][3][4].
Piperlonguminine is an alkaloid amide isolated from the Piper species. Piperlonguminine shows various biological properties, including anti-inflammatory, antitumor, neuroprotective, anti-platelet, anti-melanogenic, antifungal and antibacterial activities[1][2][3][4].

同义名列表

22 个代谢物同义名

(Z,2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienimidic acid; (2E,4E)-5-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienimidate; 2,4-Pentadienamide, 5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (2E,4E)-; (2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide; 2,4-Pentadienamide, 5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (E,E)-; (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide; (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N-isobutylpenta-2,4-dienamide; (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-isobutyl-penta-2,4-dienamide; (2E,4E)-5-(1,3-Benzodioxol-5-yl)-N-isobutyl-2,4-pentadienamide; 5-BENZO[1,3]DIOXOL-5-YL-N-(2-METHYLPROPYL)PENTA-2,4-DIENAMIDE; (E,E)-Piperlonguminine; AIF; CE0; MS2Dec; Piperamide, N-isobutyl-; Piperlonguminine [INCI]; (E,E)-Piperlonguminine; N-Isobutylpiperamide; piperlonguminine; Piperlonguminin; UNII-HN39MC8KIO; Piperlongumine; HN39MC8KIO; 5-(1,3-benzodioxol-5-yl)-n-(2-methylpropyl)penta-2,4-dienamide; Piperlonguminine



数据库引用编号

15 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)

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

  • Wickneswaran Ishaniya, Chezhiyan Sumithaa, Muthuraman Subramani, Aswathy Karanath-Anilkumar, Ganesh Munuswamy-Ramanujam, Arumugam Madan Kumar, Saravanakumar Rajendran, Mani Ganeshpandian. Polydiacetylene/lipid-coated red-emissive silica nanorods for the sustained release and ameliorated anticancer efficacy of a Ru(arene) complex bearing piperlongumine natural product. Dalton transactions (Cambridge, England : 2003). 2024 Jan; 53(4):1616-1629. doi: 10.1039/d3dt02940a. [PMID: 38165714]
  • Ping Xu, Juan Xiao, Shuixia Chi. Piperlongumine attenuates oxidative stress, inflammatory, and apoptosis through modulating the GLUT-2/4 and AKT signaling pathway in streptozotocin-induced diabetic rats. Journal of biochemical and molecular toxicology. 2021 Jun; 35(6):1-12. doi: 10.1002/jbt.22763. [PMID: 33724628]
  • C Ye, J Ye, H Wu, F Zhang, Y Liu. Evidence of TWIST1 and transforming growth factor-B1 aberrant expressions as novel therapeutic targets in modulating the severity of osteoarthritis with focus on biologic agents. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society. 2020 Dec; 71(6):. doi: 10.26402/jpp.2020.6.06. [PMID: 33727429]
  • Chun Lu, Bing Zhang, Tingting Xu, Wenxin Zhang, Bin Bai, Zhongxiang Xiao, Liqin Wu, Guang Liang, Yali Zhang, Yuanrong Dai. Piperlongumine reduces ovalbumin‑induced asthma and airway inflammation by regulating nuclear factor‑κB activation. International journal of molecular medicine. 2019 Nov; 44(5):1855-1865. doi: 10.3892/ijmm.2019.4322. [PMID: 31485644]
  • Ana Paula Ribeiro Povinelli, Gabriel Zazeri, Marcelo de Freitas Lima, Marinônio Lopes Cornélio. Details of the cooperative binding of piperlongumine with rat serum albumin obtained by spectroscopic and computational analyses. Scientific reports. 2019 10; 9(1):15667. doi: 10.1038/s41598-019-52187-5. [PMID: 31666676]
  • Sandeep Kumar, Navneet Agnihotri. Piperlongumine, a piper alkaloid targets Ras/PI3K/Akt/mTOR signaling axis to inhibit tumor cell growth and proliferation in DMH/DSS induced experimental colon cancer. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Jan; 109(?):1462-1477. doi: 10.1016/j.biopha.2018.10.182. [PMID: 30551398]
  • Yu Liu, Qian-Yu Li, Yu-Ping Wang, Yi-Ming Liu, Bin Liu, Mei-Mei Liu, Bing-Mi Liu. Spectroscopic investigation of the anticancer alkaloid piperlongumine binding to human serum albumin from the viewpoint of drug delivery. Luminescence : the journal of biological and chemical luminescence. 2018 Mar; 33(2):305-311. doi: 10.1002/bio.3414. [PMID: 29044986]
  • Keshav Karki, Erik Hedrick, Ravi Kasiappan, Un-Ho Jin, Stephen Safe. Piperlongumine Induces Reactive Oxygen Species (ROS)-Dependent Downregulation of Specificity Protein Transcription Factors. Cancer prevention research (Philadelphia, Pa.). 2017 Aug; 10(8):467-477. doi: 10.1158/1940-6207.capr-17-0053. [PMID: 28673967]
  • Jian Sun, Ping Xu, Xueping Du, Qinggang Zhang, Yuchang Zhu. Piperlongumine attenuates collagen-induced arthritis via expansion of myeloid-derived suppressor cells and inhibition of the activation of fibroblast-like synoviocytes. Molecular medicine reports. 2015 Apr; 11(4):2689-94. doi: 10.3892/mmr.2014.3001. [PMID: 25435301]
  • Lan Yao, Hai-ping Chen, Qing Ma. Piperlongumine alleviates lupus nephritis in MRL-Fas(lpr) mice by regulating the frequency of Th17 and regulatory T cells. Immunology letters. 2014 Sep; 161(1):76-80. doi: 10.1016/j.imlet.2014.05.001. [PMID: 24837470]
  • P Makhov, K Golovine, E Teper, A Kutikov, R Mehrazin, A Corcoran, A Tulin, R G Uzzo, V M Kolenko. Piperlongumine promotes autophagy via inhibition of Akt/mTOR signalling and mediates cancer cell death. British journal of cancer. 2014 Feb; 110(4):899-907. doi: 10.1038/bjc.2013.810. [PMID: 24434432]
  • Itadaki Yamaguchi, Hisashi Matsuda, Hailong Zhang, Makoto Hamao, Chihiro Yamashita, Yuichiro Kogami, Haruka Kon'I, Megumi Murata, Seikou Nakamura, Masayuki Yoshikawa. Adipogenic effects of piperlonguminine in 3T3-L1 cells and plasma concentrations of several amide constituents from Piper chaba extracts after treatment of mice. Journal of natural medicines. 2014 Jan; 68(1):74-82. doi: 10.1007/s11418-013-0770-3. [PMID: 23584920]
  • Erdenebaatar Sarnaizul, Gereltu Borjihan, Huricha Baigude, Aona, Menghe, Narisu, Zhaorigetu. LC analysis and pharmacokinetic study of synthetic piperlonguminine in rat plasma after oral administration. Biomedical chromatography : BMC. 2013 Jul; 27(7):821-4. doi: 10.1002/bmc.2879. [PMID: 23519637]
  • Zhi-Yong Jiang, Wen-Feng Liu, Xue-Mei Zhang, Jie Luo, Yun-Bao Ma, Ji-Jun Chen. Anti-HBV active constituents from Piper longum. Bioorganic & medicinal chemistry letters. 2013 Apr; 23(7):2123-7. doi: 10.1016/j.bmcl.2013.01.118. [PMID: 23434420]
  • Phercyles Veiga-Santos, Vânia Cristina Desoti, Nathielle Miranda, Tânia Ueda-Nakamura, Benedito Prado Dias-Filho, Sueli Oliveira Silva, Diogenes Aparício Garcia Cortez, João Carlos Palazzo de Mello, Celso Vataru Nakamura. The natural compounds piperovatine and piperlonguminine induce autophagic cell death on Trypanosoma cruzi. Acta tropica. 2013 Mar; 125(3):349-56. doi: 10.1016/j.actatropica.2012.11.014. [PMID: 23228524]
  • L Bao, G Borjihan. Hypolipidemic effects of piperlonguminine in HepG2 cells and in Wistar rats. Die Pharmazie. 2012 Oct; 67(10):858-61. doi: NULL. [PMID: 23136721]
  • Junhui Liu, Ying Bi, Rong Luo, Xia Wu. Simultaneous UFLC-ESI-MS/MS determination of piperine and piperlonguminine in rat plasma after oral administration of alkaloids from Piper longum L.: application to pharmacokinetic studies in rats. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Oct; 879(27):2885-90. doi: 10.1016/j.jchromb.2011.08.018. [PMID: 21903488]
  • Janine Zaugg, Igor Baburin, Barbara Strommer, Hyun-Jung Kim, Steffen Hering, Matthias Hamburger. HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site. Journal of natural products. 2010 Feb; 73(2):185-91. doi: 10.1021/np900656g. [PMID: 20085307]
  • Daniel P Bezerra, Cláudia Pessoa, Manoel Odorico de Moraes, Nylane M N de Alencar, Rodney O Mesquita, Michael W Lima, Ana Paula N N Alves, Otília Deusdênia L Pessoa, João Henrique Chaves, Edilberto R Silveira, Letícia V Costa-Lotufo. In vivo growth inhibition of sarcoma 180 by piperlonguminine, an alkaloid amide from the Piper species. Journal of applied toxicology : JAT. 2008 Jul; 28(5):599-607. doi: 10.1002/jat.1311. [PMID: 17975786]
  • Hisashi Matsuda, Kiyofumi Ninomiya, Toshio Morikawa, Daisuke Yasuda, Itadaki Yamaguchi, Masayuki Yoshikawa. Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes. Bioorganic & medicinal chemistry letters. 2008 Mar; 18(6):2038-42. doi: 10.1016/j.bmcl.2008.01.101. [PMID: 18289853]
  • Chun-Jie Ma, Gereltu Borjihan, Hurilebagen, Tegexi, Surina. [Antiatherogenic effect of piperlonguminine on experimental atherosclerosis in rabbits]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Feb; 33(4):436-40, 469. doi: NULL. [PMID: 18533506]
  • Joaquim V Marques, Rodrigo O Saga Kitamura, João Henrique G Lago, Maria Claudia M Young, Elsie F Guimarães, Massuo J Kato. Antifungal amides from Piper scutifolium and Piper hoffmanseggianum. Journal of natural products. 2007 Dec; 70(12):2036-9. doi: 10.1021/np070347g. [PMID: 18031016]
  • T S Paskhina, G A Iarovaia, A L Laufer, O M Gulikova, S S Trapeznikova, N A Morozova, O V Makarova, I B Tikhomirov, V F Sysoev, E S Mach. [The content and activity of basic components of kinin system in blood serum of patients with rheumatism]. Voprosy meditsinskoi khimii. 1970 Mar; 16(2):152-61. doi: NULL. [PMID: 5311053]