Piplartine (BioDeep_00000003874)
Main id: BioDeep_00000407589
human metabolite PANOMIX_OTCML-2023 Endogenous
代谢物信息卡片
化学式: C17H19NO5 (317.1263164)
中文名称: 荜茇酰胺
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O
InChI: InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+
描述信息
Piplartine is a member of cinnamamides and a dicarboximide.
Piperlongumine is a natural product found in Zanthoxylum gilletii, Macropiper, and other organisms with data available.
See also: Long Pepper (part of).
Piplartine is found in herbs and spices. Piplartine is an alkaloid from the roots of Piper longum (long pepper
Piperlongumine is a alkaloid[1], possesses ant-inflammatory, antibacterial, antiangiogenic, antioxidant, antitumor, and antidiabetic activities[2]. Piperlongumine induces ROS, and induces apoptosis in cancer cell lines[1]. Piperlongumine shows anti-cardiac fibrosis activity, suppresses myofibroblast transformation via suppression of the ERK1/2 signaling pathway. Piperlongumin could be used in the study of migrasome[2][3].
Piperlongumine is a alkaloid[1], possesses ant-inflammatory, antibacterial, antiangiogenic, antioxidant, antitumor, and antidiabetic activities[2]. Piperlongumine induces ROS, and induces apoptosis in cancer cell lines[1]. Piperlongumine shows anti-cardiac fibrosis activity, suppresses myofibroblast transformation via suppression of the ERK1/2 signaling pathway. Piperlongumin could be used in the study of migrasome[2][3].
Piperlongumine is a alkaloid[1], possesses ant-inflammatory, antibacterial, antiangiogenic, antioxidant, antitumor, and antidiabetic activities[2]. Piperlongumine induces ROS, and induces apoptosis in cancer cell lines[1]. Piperlongumine shows anti-cardiac fibrosis activity, suppresses myofibroblast transformation via suppression of the ERK1/2 signaling pathway. Piperlongumin could be used in the study of migrasome[2][3].
同义名列表
36 个代谢物同义名
2(1H)-Pyridinone, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-; 2(1H)-PYRIDINONE, 5,6-DIHYDRO-1-(1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2- PROPENYL)-, (E)-; 2(1H)-Pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-; 5,6-Dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-pyridinone; 5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-trans-2-propenyl]-2(1H)-pyridinone; Prop-2-en-1-one, 3-(3,4,5-trimethoxyphenyl)-1-(2,3-dihydropyridin-6(1H)-one-1-yl)-; 5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-2(1H)-pyridinone, 9CI; 1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-one; 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone #; 1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one; 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone; (E)-1-[3-(3,4,5-Trimethoxyphenyl)acryloyl]-5,6-dihydropyridin-2(1H)-one; 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one; (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one; 5,6-dihydro-1-[1-oxo-3-(3,4,5-triMethoxyphenyl)-allyl]-2(1H)-pyridinone; 1-[3-(3,4,5-Trimethoxy-phenyl)-acryloyl]-5,6-dihydro-1H-pyridin-2-one; 5,6-Dihydro-1-(3,4,5-trimethoxycinnamoyl)-2(1H)-pyridinone; N-(3,4,5-Trimethoxycinnamoyl)-D3-piperidin-2-one; Piperlongumine, >=97\\% (HPLC); Piperlongumine; Piplartine; PIPERLONGUMINE [INCI]; PIPERLONGUMINE [MI]; Prestwick3_000604; Prestwick2_000604; FERROUSFLUOBORATE; Piplartine;PPLGM; piperlonguminine; UNII-SGD66V4SVJ; Piperlongumine; BPBio1_000560; ACon1_001541; SGD66V4SVJ; Piplartine; A1-00162; PPLGM; 1-[1-oxo-3-(3,4,5-trimethoxyphenyl)prop-2-enyl]-2,3-dihydropyridin-6-one
数据库引用编号
22 个数据库交叉引用编号
- ChEBI: CHEBI:92424
- ChEBI: CHEBI:8241
- KEGG: C10166
- PubChem: 637858
- PubChem: 442653
- HMDB: HMDB0030341
- Metlin: METLIN68169
- ChEMBL: CHEMBL465843
- Wikipedia: Piperlongumine
- MeSH: piperlonguminine
- ChemIDplus: 0020069094
- KNApSAcK: C00002066
- foodb: FDB002004
- chemspider: 553441
- CAS: 20069-09-4
- medchemexpress: HY-N2329
- PMhub: MS000012863
- PubChem: 12352
- PDB-CCD: LQ4
- 3DMET: B03600
- NIKKAJI: J14.252B
- RefMet: Piplartine
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)
24 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 130372 - Macropiper:
- 130380 - Piper arborescens:
- 130380 - Piper arborescens: 10.1055/S-2005-864155
- 2231241 - Piper bantamense:
- 2231241 - Piper bantamense: 10.1055/S-2005-864155
- 398741 - Piper cenocladum:
- 405329 - Piper hongkongense: 10.1016/S0031-9422(96)00585-7
- 49511 - Piper longum:
- 49511 - Piper longum: 10.1016/0031-9422(88)80226-7
- 49511 - Piper longum L.: -
- 411948 - Piper macropiper:
- 411948 - Piper macropiper: 10.1055/S-2005-864155
- 13216 - Piper nigrum:
- 511550 - Piper puberulum: 10.1016/S0031-9422(96)00585-7
- 130414 - Piper retrofractum:
- 405319 - Piper sarmentosum: 10.1248/CPB.59.1178
- 405344 - Piper swartzianum:
- 405345 - Piper sylvaticum:
- 247704 - Piper tuberculatum:
- 247704 - Piper tuberculatum: -
- 16739 - Piperaceae: 10.1016/J.BCP.2015.03.014
- 33090 - Plants: -
- 1291627 - Zanthoxylum gilletii: 10.1007/BF01952540
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
- Shatakshi Mitra, Protha Biswas, Anupriya Bandyopadhyay, Vijaykumar Shivaji Gadekar, Abilash Valsala Gopalakrishnan, Manoj Kumar, Radha, Samapika Nandy. Piperlongumine: the amazing amide alkaloid from Piper in the treatment of breast cancer.
Naunyn-Schmiedeberg's archives of pharmacology.
2023 Nov; ?(?):. doi:
10.1007/s00210-023-02673-5
. [PMID: 37955690] - Indrajeet Singh, Richa Das, Ajay Kumar. Network pharmacology-based anti-colorectal cancer activity of piperlonguminine in the ethanolic root extract of Piper longum L.
Medical oncology (Northwood, London, England).
2023 Oct; 40(11):320. doi:
10.1007/s12032-023-02185-5
. [PMID: 37796360] - B Haridevamuthu, David Raj, D Kesavan, Subramani Muthuraman, Rajendran Saravana Kumar, Shahid Mahboob, Khalid Abdullah Al-Ghanim, Bader O Almutairi, Selvaraj Arokiyaraj, Pushparathinam Gopinath, Jesu Arockiaraj. Trihydroxy piperlongumine protects aluminium induced neurotoxicity in zebrafish: Behavioral and biochemical approach.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2023 Jun; 268(?):109600. doi:
10.1016/j.cbpc.2023.109600
. [PMID: 36889534] - Cui Shi, Kunhui Huang, John Soto, Renuka Sankaran, Vrinda Kalia, Onyekwere Onwumere, Michael Young, Linda Einbond, Stephen Redenti. Piperlongumine inhibits proliferation and oncogenic MYCN expression in chemoresistant metastatic retinoblastoma cells directly and through extracellular vesicles.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2023 May; 161(?):114554. doi:
10.1016/j.biopha.2023.114554
. [PMID: 36940616] - Lei Zhou, Kehan Wu, Yuxuan Gao, Ruizhi Qiao, Na Tang, Dianchao Dong, Xiao-Qiang Li, Qiuna Nong, Ding-Qiang Luo, Qianhan Xiao, Xin Fan, Qimei Duan, Wei Cao. Piperlonguminine attenuates renal fibrosis by inhibiting TRPC6.
Journal of ethnopharmacology.
2023 Apr; ?(?):116561. doi:
10.1016/j.jep.2023.116561
. [PMID: 37121453] - B Haridevamuthu, Boopathi Seenivasan, P Snega Priya, Subramani Muthuraman, Rajendran Saravana Kumar, K Manikanadan, Bader O Almutairi, Mikhlid H Almutairi, Selvaraj Arokiyaraj, Pushparathinam Gopinath, Jesu Arockiaraj. Hepatoprotective effect of dihydroxy piperlongumine in high cholesterol-induced non-alcoholic fatty liver disease zebrafish via antioxidant activity.
European journal of pharmacology.
2023 Feb; ?(?):175605. doi:
10.1016/j.ejphar.2023.175605
. [PMID: 36822456] - Xiaoyan He, Min Li, Zhi Ye, Xiaoling You, Jia Wang, Xin Xiao, Guofeng Zhu, Jun Wei, Yunhong Zha. Identification of Piperlongumine as Potent Inhibitor of Necroptosis.
Drug design, development and therapy.
2023; 17(?):1387-1394. doi:
10.2147/dddt.s397971
. [PMID: 37188283] - Lucia Jimenez, Andreia Silva, Giampaolo Calissi, Inês Grenho, Rita Monteiro, Victor Mayoral-Varo, Carmen Blanco-Aparicio, Joaquin Pastor, Victor Bustos, Franz Bracher, Diego Megías, Bibiana I Ferreira, Wolfgang Link. Screening Health-Promoting Compounds for Their Capacity to Induce the Activity of FOXO3.
The journals of gerontology. Series A, Biological sciences and medical sciences.
2022 08; 77(8):1485-1493. doi:
10.1093/gerona/glab265
. [PMID: 34508571] - Ashish Kumar, Manisha Naithani, Nitesh Kumar, Neha Singh, Shruti Agrawal, Ambika Sharma, Surabhi Thapliyal, Jagjit Singh, Shailendra Handu. Piperlongumine inhibits diethylnitrosamine induced hepatocellular carcinoma in rats.
Human & experimental toxicology.
2022 Jan; 41(?):9603271211073593. doi:
10.1177/09603271211073593
. [PMID: 35113675] - Zhenwen Xiao, Annamalai Vijayalakshmi. Protective effect of piperlongumine on inflammation and oxidative stress against ischemia-reperfusion injury in animal kidney.
Bratislavske lekarske listy.
2022; 123(12):878-884. doi:
10.4149/bll_2022_140
. [PMID: 36342874] - 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] - Minelly A da Silva, Harold H Fokoue, Saara N Fialho, Ana Paula de A Dos Santos, Norton R D L P Rossi, Aurileya de J Gouveia, Amália S Ferreira, Guilherme M Passarini, Ana F G Garay, Jorge J Alfonso, Andreimar M Soares, Fernando B Zanchi, Massuo J Kato, Carolina B G Teles, Christian C Kuehn. Antileishmanial activity evaluation of a natural amide and its synthetic analogs against Leishmania (V.) braziliensis: an integrated approach in vitro and in silico.
Parasitology research.
2021 Jun; 120(6):2199-2218. doi:
10.1007/s00436-021-07169-w
. [PMID: 33963899] - Ai-Ling Sun, Wen-Wen Mu, Yan-Mo Li, Ya-Lei Sun, Peng-Xiao Li, Ren-Min Liu, Jie Yang, Guo-Yun Liu. Piperlongumine Analogs Promote A549 Cell Apoptosis through Enhancing ROS Generation.
Molecules (Basel, Switzerland).
2021 May; 26(11):. doi:
10.3390/molecules26113243
. [PMID: 34071298] - Rui Xu, Jie Yang, Yun Qian, Huizi Deng, Zhihua Wang, Siyu Ma, Yawen Wei, Ning Yang, Qi Shen. Ferroptosis/pyroptosis dual-inductive combinational anti-cancer therapy achieved by transferrin decorated nanoMOF.
Nanoscale horizons.
2021 04; 6(4):348-356. doi:
10.1039/d0nh00674b
. [PMID: 33687417] - Xinhua Lu, Chenyang Xu, Zhexuan Xu, Chunya Lu, Rui Yang, Furui Zhang, Guojun Zhang. Piperlongumine inhibits the growth of non-small cell lung cancer cells via the miR-34b-3p/TGFBR1 pathway.
BMC complementary medicine and therapies.
2021 Jan; 21(1):15. doi:
10.1186/s12906-020-03123-y
. [PMID: 33413277] - 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] - Eleonora Turrini, Piero Sestili, Carmela Fimognari. Overview of the Anticancer Potential of the 'King of Spices' Piper nigrum and Its Main Constituent Piperine.
Toxins.
2020 11; 12(12):. doi:
10.3390/toxins12120747
. [PMID: 33256185] - Belem Yoval-Sánchez, Luis Francisco Calleja, María de la Luz Hernández-Esquivel, José Salud Rodríguez-Zavala. Piperlonguminine a new mitochondrial aldehyde dehydrogenase activator protects the heart from ischemia/reperfusion injury.
Biochimica et biophysica acta. General subjects.
2020 11; 1864(11):129684. doi:
10.1016/j.bbagen.2020.129684
. [PMID: 32679250] - Muhammad Torequl Islam, Jabed Hasan, H M Shadid Hossain Snigdha, Eunus S Ali, Javad Sharifi-Rad, Miquel Martorell, Mohammad S Mubarak. Chemical profile, traditional uses, and biological activities of Piper chaba Hunter: A review.
Journal of ethnopharmacology.
2020 Jul; 257(?):112853. doi:
10.1016/j.jep.2020.112853
. [PMID: 32283191] - Jinfeng Zhou, Zhengxiang Huang, Xiao Ni, Chen Lv. Piperlongumine induces apoptosis and G2/M phase arrest in human osteosarcoma cells by regulating ROS/PI3K/Akt pathway.
Toxicology in vitro : an international journal published in association with BIBRA.
2020 Jun; 65(?):104775. doi:
10.1016/j.tiv.2020.104775
. [PMID: 31987842] - Jie Liang, Jacqueline D Ziegler, Beate Jahraus, Christian Orlik, Renata Blatnik, Norbert Blank, Beate Niesler, Guido Wabnitz, Thomas Ruppert, Katrin Hübner, Emre Balta, Yvonne Samstag. Piperlongumine Acts as an Immunosuppressant by Exerting Prooxidative Effects in Human T Cells Resulting in Diminished TH17 but Enhanced Treg Differentiation.
Frontiers in immunology.
2020; 11(?):1172. doi:
10.3389/fimmu.2020.01172
. [PMID: 32595640] - 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] - Md Nazim Uddin Chy, Nishan Chakrabarty, Ajoy Roy, Arkajyoti Paul, Khadija Aktar Emu, Trishala Dutta, Emon Dutta, Irin Ferdous, Raju Das, Md Jahid Hasan, Syeda Mashnia Tasnim. Antibacterial, anthelmintic, and analgesic activities of Piper sylvaticum (Roxb.) leaves and in silico molecular docking and PASS prediction studies of its isolated compounds.
Journal of complementary & integrative medicine.
2019 Aug; 16(4):. doi:
10.1515/jcim-2018-0176
. [PMID: 31437123] - Zhenxing Liu, Zhichen Shi, Jieru Lin, Shuang Zhao, Min Hao, Junting Xu, Yuyin Li, Qing Zhao, Li Tao, Aipo Diao. Piperlongumine-induced nuclear translocation of the FOXO3A transcription factor triggers BIM-mediated apoptosis in cancer cells.
Biochemical pharmacology.
2019 05; 163(?):101-110. doi:
10.1016/j.bcp.2019.02.012
. [PMID: 30753811] - 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] - Jun Go, Tae-Shin Park, Geun-Hee Han, Hye-Yeon Park, Young-Kyoung Ryu, Yong-Hoon Kim, Jung Hwan Hwang, Dong-Hee Choi, Jung-Ran Noh, Dae Youn Hwang, Sanghee Kim, Won Keun Oh, Chul-Ho Lee, Kyoung-Shim Kim. Piperlongumine decreases cognitive impairment and improves hippocampal function in aged mice.
International journal of molecular medicine.
2018 Oct; 42(4):1875-1884. doi:
10.3892/ijmm.2018.3782
. [PMID: 30066827] - Ammad Ahmad Farooqi, Rukset Attar, Ilhan Yaylim, Muhammad Zahid Qureshi, Milica Todorovska, Gökçe Şeker Karatoprak, Saeideh Najafi, Uteuliyev Yerzhan Sabitaliyevich, Tokmurziyeva Gulnara Zhenisovna, Damião Pergentino De Sousa, Xiukun Lin. Piperlongumine as anticancer agent: The story so far about killing many birds with one stone.
Cellular and molecular biology (Noisy-le-Grand, France).
2018 Aug; 64(11):102-107. doi:
10.14715/cmb/2018.64.11.19
. [PMID: 30213297] - Kamil Piska, Agnieszka Gunia-Krzyżak, Paulina Koczurkiewicz, Katarzyna Wójcik-Pszczoła, Elżbieta Pękala. Piperlongumine (piplartine) as a lead compound for anticancer agents - Synthesis and properties of analogues: A mini-review.
European journal of medicinal chemistry.
2018 Aug; 156(?):13-20. doi:
10.1016/j.ejmech.2018.06.057
. [PMID: 30006159] - Yuri Campelo, Alicia Ombredane, Andreanne G Vasconcelos, Lucas Albuquerque, Daniel C Moreira, Alexandra Plácido, Jefferson Rocha, Harold Hilarion Fokoue, Lydia Yamaguchi, Ana Mafud, Yvonne P Mascarenhas, Cristina Delerue-Matos, Tatiana Borges, Graziella A Joanitti, Daniel Arcanjo, Massuo J Kato, Selma A S Kuckelhaus, Marcos P N Silva, Josué de Moraes, José Roberto S A Leite. Structure⁻Activity Relationship of Piplartine and Synthetic Analogues against Schistosoma mansoni and Cytotoxicity to Mammalian Cells.
International journal of molecular sciences.
2018 06; 19(6):. doi:
10.3390/ijms19061802
. [PMID: 29921756] - Flávio Rogério da Nóbrega, Ozlem Ozdemir, Sheila Cristina S Nascimento Sousa, Joice Nascimento Barboza, Hasan Turkez, Damião Pergentino de Sousa. Piplartine Analogues and Cytotoxic Evaluation against Glioblastoma.
Molecules (Basel, Switzerland).
2018 Jun; 23(6):. doi:
10.3390/molecules23061382
. [PMID: 29890617] - Gabriela Alves Licursi Vieira, Marco Túlio Alves da Silva, Luis Octávio Regasini, Fernando Cotinguiba, Helen Julie Laure, José César Rosa, Maysa Furlan, Regina Maria Barretto Cicarelli. Trypanosoma cruzi: analysis of two different strains after piplartine treatment.
The Brazilian journal of infectious diseases : an official publication of the Brazilian Society of Infectious Diseases.
2018 May; 22(3):208-218. doi:
10.1016/j.bjid.2018.02.009
. [PMID: 29879424] - Yuki Yamaguchi, Takashi Kasukabe, Shunichi Kumakura. Piperlongumine rapidly induces the death of human pancreatic cancer cells mainly through the induction of ferroptosis.
International journal of oncology.
2018 Mar; 52(3):1011-1022. doi:
10.3892/ijo.2018.4259
. [PMID: 29393418] - 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] - Jia Liu, Weijin Liu, Yongquan Lu, Hao Tian, Chunli Duan, Lingling Lu, Ge Gao, Xia Wu, Xiaomin Wang, Hui Yang. Piperlongumine restores the balance of autophagy and apoptosis by increasing BCL2 phosphorylation in rotenone-induced Parkinson disease models.
Autophagy.
2018; 14(5):845-861. doi:
10.1080/15548627.2017.1390636
. [PMID: 29433359] - Jin Sil Seok, Chang Hee Jeong, Michael C Petriello, Han Geuk Seo, Hyunjin Yoo, Kwonho Hong, Sung Gu Han. Piperlongumine decreases cell proliferation and the expression of cell cycle-associated proteins by inhibiting Akt pathway in human lung cancer cells.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2018 Jan; 111(?):9-18. doi:
10.1016/j.fct.2017.10.058
. [PMID: 29109039] - Jana Wiemann, Julia Karasch, Anne Loesche, Lucie Heller, Wolfgang Brandt, René Csuk. Piperlongumine B and analogs are promising and selective inhibitors for acetylcholinesterase.
European journal of medicinal chemistry.
2017 Oct; 139(?):222-231. doi:
10.1016/j.ejmech.2017.07.081
. [PMID: 28802122] - 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] - Wayne Harshbarger, Sudershan Gondi, Scott B Ficarro, John Hunter, Durga Udayakumar, Deepak Gurbani, William D Singer, Yan Liu, Lianbo Li, Jarrod A Marto, Kenneth D Westover. Structural and Biochemical Analyses Reveal the Mechanism of Glutathione S-Transferase Pi 1 Inhibition by the Anti-cancer Compound Piperlongumine.
The Journal of biological chemistry.
2017 Jan; 292(1):112-120. doi:
10.1074/jbc.m116.750299
. [PMID: 27872191] - Li-Chen Han, Paul A Stanley, Paul J Wood, Pallavi Sharma, Anchala I Kuruppu, Tracey D Bradshaw, John E Moses. Horner-Wadsworth-Emmons approach to piperlongumine analogues with potent anti-cancer activity.
Organic & biomolecular chemistry.
2016 Aug; 14(31):7585-93. doi:
10.1039/c6ob01160h
. [PMID: 27443386] - Youjun Xiao, Maohua Shi, Qian Qiu, Mingcheng Huang, Shan Zeng, Yaoyao Zou, Zhongping Zhan, Liuqin Liang, Xiuyan Yang, Hanshi Xu. Piperlongumine Suppresses Dendritic Cell Maturation by Reducing Production of Reactive Oxygen Species and Has Therapeutic Potential for Rheumatoid Arthritis.
Journal of immunology (Baltimore, Md. : 1950).
2016 06; 196(12):4925-34. doi:
10.4049/jimmunol.1501281
. [PMID: 27183580] - Harsharan Dhillon, Sujan Mamidi, Phillip McClean, Katie M Reindl. Transcriptome Analysis of Piperlongumine-Treated Human Pancreatic Cancer Cells Reveals Involvement of Oxidative Stress and Endoplasmic Reticulum Stress Pathways.
Journal of medicinal food.
2016 Jun; 19(6):578-85. doi:
10.1089/jmf.2015.0152
. [PMID: 27119744] - Hao Wang, Jia Liu, Ge Gao, Xia Wu, Xiaomin Wang, Hui Yang. Protection effect of piperine and piperlonguminine from Piper longum L. alkaloids against rotenone-induced neuronal injury.
Brain research.
2016 05; 1639(?):214-27. doi:
10.1016/j.brainres.2015.07.029
. [PMID: 26232071] - 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] - Hengjie Yuan, Katie L Houck, Ye Tian, Uddalak Bharadwaj, Ken Hull, Zhou Zhou, Mingzhao Zhu, Mingzhao Zhou, Xiaoping Wu, David J Tweardy, Daniel Romo, Xiaoyun Fu, Yanjun Zhang, Jianning Zhang, Jing-fei Dong. Piperlongumine Blocks JAK2-STAT3 to Inhibit Collagen-Induced Platelet Reactivity Independent of Reactive Oxygen Species.
PloS one.
2015; 10(12):e0143964. doi:
10.1371/journal.pone.0143964
. [PMID: 26645674] - Daniel P Bezerra, Paulo Michel P Ferreira, Camila Maria L Machado, Nayara C de Aquino, Edilberto R Silveira, Roger Chammas, Claudia Pessoa. Antitumour efficacy of Piper tuberculatum and piplartine based on the hollow fiber assay.
Planta medica.
2015 Jan; 81(1):15-9. doi:
10.1055/s-0034-1383363
. [PMID: 25519832] - Tae Hyong Kim, Jieun Song, Sung-Hak Kim, Arav Krishnavadan Parikh, Xiaokui Mo, Kamalakannan Palanichamy, Balveen Kaur, Jianhua Yu, Sung Ok Yoon, Ichiro Nakano, Chang-Hyuk Kwon. Piperlongumine treatment inactivates peroxiredoxin 4, exacerbates endoplasmic reticulum stress, and preferentially kills high-grade glioma cells.
Neuro-oncology.
2014 Oct; 16(10):1354-64. doi:
10.1093/neuonc/nou088
. [PMID: 24879047] - Hanns Möhler, Rolf W Pfirrmann, Karl Frei. Redox-directed cancer therapeutics: Taurolidine and Piperlongumine as broadly effective antineoplastic agents (review).
International journal of oncology.
2014 Oct; 45(4):1329-36. doi:
10.3892/ijo.2014.2566
. [PMID: 25175943] - Seong-Su Han, Sangwoo Han, Natalie L Kamberos. Piperlongumine inhibits the proliferation and survival of B-cell acute lymphoblastic leukemia cell lines irrespective of glucocorticoid resistance.
Biochemical and biophysical research communications.
2014 Sep; 452(3):669-75. doi:
10.1016/j.bbrc.2014.08.131
. [PMID: 25193702] - 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] - Sae-Kwang Ku, Jeong Ah Kim, Jong-Sup Bae. Piperlonguminine downregulates endothelial protein C receptor shedding in vitro and in vivo.
Inflammation.
2014 Apr; 37(2):435-42. doi:
10.1007/s10753-013-9756-2
. [PMID: 24127121] - Marise Maleck, Bruna Ferreira, Jacenir Mallet, Anthony Guimarães, Massuo Kato. Cytotoxicity of piperamides towards Aedes aegypti (Diptera: Culicidae).
Journal of medical entomology.
2014 Mar; 51(2):458-63. doi:
10.1603/me13069
. [PMID: 24724297] - 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] - Serge Ginzburg, Konstantin V Golovine, Petr B Makhov, Robert G Uzzo, Alexander Kutikov, Vladimir M Kolenko. Piperlongumine inhibits NF-κB activity and attenuates aggressive growth characteristics of prostate cancer cells.
The Prostate.
2014 Feb; 74(2):177-86. doi:
10.1002/pros.22739
. [PMID: 24151226] - Narisu Bao, Sarangowa Ochir, Zhaorigetu Sun, Gereltu Borjihan, Takashi Yamagishi. Occurrence of piperidine alkaloids in Piper species collected in different areas.
Journal of natural medicines.
2014 Jan; 68(1):211-4. doi:
10.1007/s11418-013-0773-0
. [PMID: 23625168] - Hai-peng Lei, Xian-qiang Chen, Chun-feng Qiao, Yang Liu, Jing Zhao. [Chemical constituents from twigs of Piper hancei].
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2014 Jan; 37(1):69-71. doi:
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- Jian-Xin Yao, Zhi-Feng Yao, Zhan-Feng Li, Yong-Biao Liu. Radio-sensitization by Piper longumine of human breast adenoma MDA-MB-231 cells in vitro.
Asian Pacific journal of cancer prevention : APJCP.
2014; 15(7):3211-7. doi:
10.7314/apjcp.2014.15.7.3211
. [PMID: 24815473] - 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] - Y Wang, J-W Wang, X Xiao, Y Shan, B Xue, G Jiang, Q He, J Chen, H-G Xu, R-X Zhao, K D Werle, R Cui, J Liang, Y-L Li, Z-X Xu. Piperlongumine induces autophagy by targeting p38 signaling.
Cell death & disease.
2013 Oct; 4(?):e824. doi:
10.1038/cddis.2013.358
. [PMID: 24091667] - 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] - Lígia Moura Burci, Isabela Tiemy Pereira, Luisa Mota da Silva, Rosely Valéria Rodrigues, Valdir Alves Facundo, Júlio Sanches Linhares Teixeira Militão, Adair Roberto Soares Santos, Maria Consuelo Andrade Marques, Cristiane Hatsuko Baggio, Maria Fernanda de Paula Werner. Antiulcer and gastric antisecretory effects of dichloromethane fraction and piplartine obtained from fruits of Piper tuberculatum Jacq. in rats.
Journal of ethnopharmacology.
2013 Jun; 148(1):165-74. doi:
10.1016/j.jep.2013.04.006
. [PMID: 23588092] - 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] - Malin Jarvius, Mårten Fryknäs, Pädraig D'Arcy, Chao Sun, Linda Rickardson, Joachim Gullbo, Caroline Haglund, Peter Nygren, Stig Linder, Rolf Larsson. Piperlongumine induces inhibition of the ubiquitin-proteasome system in cancer cells.
Biochemical and biophysical research communications.
2013 Feb; 431(2):117-23. doi:
10.1016/j.bbrc.2013.01.017
. [PMID: 23318177] - Seong-Su Han, Dong-Ju Son, Hwakyung Yun, Natalie L Kamberos, Siegfried Janz. Piperlongumine inhibits proliferation and survival of Burkitt lymphoma in vitro.
Leukemia research.
2013 Feb; 37(2):146-54. doi:
10.1016/j.leukres.2012.11.009
. [PMID: 23237561] - Ludmila Nakamura Rapado, Alessandro de Sá Pinheiro, Priscila Orechio de Moraes Victor Lopes, Harold Hilarion Fokoue, Marcus Tullius Scotti, Joaquim Vogt Marques, Fernanda Pires Ohlweiler, Sueli Ivone Borrely, Carlos Alberto de Bragança Pereira, Massuo Jorge Kato, Eliana Nakano, Lydia Fumiko Yamaguchi. Schistosomiasis control using piplartine against Biomphalaria glabrata at different developmental stages.
PLoS neglected tropical diseases.
2013; 7(6):e2251. doi:
10.1371/journal.pntd.0002251
. [PMID: 23755312] - Vidadala Ramasubba Rao, Puppala Muthenna, Gundeti Shankaraiah, Chandrasekhar Akileshwari, Kothapalli Hari Babu, Ganji Suresh, Katragadda Suresh Babu, Rotte Sateesh Chandra Kumar, Kothakonda Rajendra Prasad, Potharaju Ashok Yadav, J Mark Petrash, Geereddy Bhanuprakash Reddy, Janaswamy Madhusudana Rao. Synthesis and biological evaluation of new piplartine analogues as potent aldose reductase inhibitors (ARIs).
European journal of medicinal chemistry.
2012 Nov; 57(?):344-61. doi:
10.1016/j.ejmech.2012.09.014
. [PMID: 23124161] - L Bao, G Borjihan. Hypolipidemic effects of piperlonguminine in HepG2 cells and in Wistar rats.
Die Pharmazie.
2012 Oct; 67(10):858-61. doi:
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. [PMID: 23136721] - Josué de Moraes, Carlos Nascimento, Lydia F Yamaguchi, Massuo J Kato, Eliana Nakano. Schistosoma mansoni: in vitro schistosomicidal activity and tegumental alterations induced by piplartine on schistosomula.
Experimental parasitology.
2012 Oct; 132(2):222-7. doi:
10.1016/j.exppara.2012.07.004
. [PMID: 22796749] - 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] - Josué de Moraes, Carlos Nascimento, Priscilla O M V Lopes, Eliana Nakano, Lydia F Yamaguchi, Massuo J Kato, Toshie Kawano. Schistosoma mansoni: In vitro schistosomicidal activity of piplartine.
Experimental parasitology.
2011 Feb; 127(2):357-64. doi:
10.1016/j.exppara.2010.08.021
. [PMID: 20832410] - D Jyothi, P Vanathi, P Mangala Gowri, V Rama Subba Rao, J Madhusudana Rao, A S Sreedhar. Diferuloylmethane augments the cytotoxic effects of piplartine isolated from Piper chaba.
Toxicology in vitro : an international journal published in association with BIBRA.
2009 Sep; 23(6):1085-91. doi:
10.1016/j.tiv.2009.05.023
. [PMID: 19501152] - Juvenia B Fontenele, L Kalyne A M Leal, Edilberto R Silveira, F Helder Felix, Cícero F Bezerra Felipe, Glauce S B Viana. Antiplatelet effects of piplartine, an alkamide isolated from Piper tuberculatum: possible involvement of cyclooxygenase blockade and antioxidant activity.
The Journal of pharmacy and pharmacology.
2009 Apr; 61(4):511-5. doi:
10.1211/jpp/61.04.0014
. [PMID: 19298699] - 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] - 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] - F Cícero Bezerra Felipe, Jucélio Trajano Sousa Filho, Louise Emanuele de Oliveira Souza, Jefferson Alexandre Silveira, Daniel Esdras de Andrade Uchoa, Edilberto Rocha Silveira, Otília Deusdênia Loiola Pessoa, Glauce S de Barros Viana. Piplartine, an amide alkaloid from Piper tuberculatum, presents anxiolytic and antidepressant effects in mice.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2007 Sep; 14(9):605-12. doi:
10.1016/j.phymed.2006.12.015
. [PMID: 17399971] - Wen Xia, Ji-Ping Zeng, Lian-Bi Chen, An-Li Jiang, Lan Xiang, Jun Xu, Xing Cui, En-Ji Han. Inhibition of beta-amyloid precursor protein gene in SK-N-SH cells by piperlonguminine/dihydropiperlonguminine components separated from Chinese herbal medicine Futokadsura stem.
The Chinese journal of physiology.
2007 Aug; 50(4):157-63. doi:
"
. [PMID: 17982913] - Masaya Iwashita, Masaki Saito, Yasunaga Yamaguchi, Ryoji Takagaki, Norimichi Nakahata. Inhibitory effect of ethanol extract of Piper longum L. on rabbit platelet aggregation through antagonizing thromboxane A2 receptor.
Biological & pharmaceutical bulletin.
2007 Jul; 30(7):1221-5. doi:
10.1248/bpb.30.1221
. [PMID: 17603157] - D P Bezerra, F O Castro, A P N N Alves, C Pessoa, M O Moraes, E R Silveira, M A S Lima, F J M Elmiro, L V Costa-Lotufo. In vivo growth-inhibition of Sarcoma 180 by piplartine and piperine, two alkaloid amides from Piper.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas.
2006 Jun; 39(6):801-7. doi:
10.1590/s0100-879x2006000600014
. [PMID: 16751987] - Kyeong-Soo Kim, Jeong Ah Kim, Seung-Yong Eom, Seung Ho Lee, Kyung Rak Min, Youngsoo Kim. Inhibitory effect of piperlonguminine on melanin production in melanoma B16 cell line by downregulation of tyrosinase expression.
Pigment cell research.
2006 Feb; 19(1):90-8. doi:
10.1111/j.1600-0749.2005.00281.x
. [PMID: 16420250] - Kyung Rak Min, Kyeong-Soo Kim, Jai Seup Ro, Seung Ho Lee, Jeong Ah Kim, Jong Keun Son, Youngsoo Kim. Piperlonguminine from Piper longum with inhibitory effects on alpha-melanocyte-stimulating hormone-induced melanogenesis in melanoma B16 cells.
Planta medica.
2004 Dec; 70(12):1115-8. doi:
10.1055/s-2004-835836
. [PMID: 15643542] - Hosana M Debonsi Navickiene, Vanderlan da S Bolzani, Massuo J Kato, Ana Maria S Pereira, Bianca Waléria Bertoni, Suzelei Castro França, Maysa Furlan. Quantitative determination of anti-fungal and insecticide amides in adult plants, plantlets and callus from Piper tuberculatum by reverse-phase high-performance liquid chromatography.
Phytochemical analysis : PCA.
2003 Sep; 14(5):281-4. doi:
10.1002/pca.716
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