Nimbolide (BioDeep_00000181677)

Main id: BioDeep_00000305938

 

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


Methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetic acid

化学式: C27H30O7 (466.199143)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=C2C(CC1C3=COC=C3)OC4C2(C(C5(C6C4OC(=O)C6(C=CC5=O)C)C)CC(=O)OC)C
InChI: InChI=1S/C27H30O7/c1-13-15(14-7-9-32-12-14)10-16-20(13)27(4)17(11-19(29)31-5)26(3)18(28)6-8-25(2)22(26)21(23(27)33-16)34-24(25)30/h6-9,12,15-17,21-23H,10-11H2,1-5H3

描述信息

Nimbolide is a triterpene derived from the leaves and flowers of neem (Azadirachta indica). Nimbolide induces apoptosis through inactivation of NF-κB. Nimbolide inhibits CDK4/CDK6 kinase activity. Nimbolide suppresses the NF-κB, Wnt, PI3K-Akt, MAPK and JAK-STAT signaling pathways[1].

同义名列表

4 个代谢物同义名

Methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetic acid; Methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadeca-7,13-dien-10-yl]acetate; methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate; Nimbolide



数据库引用编号

7 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)

4 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

  • Folashade O Katola, Olumayokun A Olajide. Nimbolide Targets Multiple Signalling Pathways to Reduce Neuroinflammation in BV-2 Microglia. Molecular neurobiology. 2023 Sep; 60(9):5450-5467. doi: 10.1007/s12035-023-03410-y. [PMID: 37314658]
  • Siddavaram Nagini, Manikandan Palrasu, Anupam Bishayee. Limonoids from neem (Azadirachta Indica A. Juss.) are potential anticancer drug candidates. Medicinal research reviews. 2023 Aug; ?(?):. doi: 10.1002/med.21988. [PMID: 37589457]
  • Jiang Huo, Yu Ding, Xinyuan Wei, Qi Chen, Bin Zhao. Antiosteoporosis and bone protective effect of nimbolide in steroid-induced osteoporosis rats. Journal of biochemical and molecular toxicology. 2022 Dec; 36(12):e23209. doi: 10.1002/jbt.23209. [PMID: 36086868]
  • Yifei Ma, Shan Xu, Juan Meng, Lu Li. Protective effect of nimbolide against streptozotocin induced gestational diabetes mellitus in rats via alteration of inflammatory reaction, oxidative stress, and gut microbiota. Environmental toxicology. 2022 Jun; 37(6):1382-1393. doi: 10.1002/tox.23491. [PMID: 35212444]
  • Amit Kumar Ram, Balasubramaniyan Vairappan, Bheemanathi Hanuman Srinivas. Nimbolide attenuates gut dysbiosis and prevents bacterial translocation by improving intestinal barrier integrity and ameliorating inflammation in hepatocellular carcinoma. Phytotherapy research : PTR. 2022 May; 36(5):2143-2160. doi: 10.1002/ptr.7434. [PMID: 35229912]
  • Pratibha Anchi, Biswajit Panda, Ravindra Bapu Mahajan, Chandraiah Godugu. Co-treatment of Nimbolide augmented the anti-arthritic effects of methotrexate while protecting against organ toxicities. Life sciences. 2022 Apr; 295(?):120372. doi: 10.1016/j.lfs.2022.120372. [PMID: 35143824]
  • Marina R Wylie, Ian H Windham, Faith C Blum, Hannah Wu, D Scott Merrell. In vitro antibacterial activity of nimbolide against Helicobacter pylori. Journal of ethnopharmacology. 2022 Mar; 285(?):114828. doi: 10.1016/j.jep.2021.114828. [PMID: 34763046]
  • Lin Zhang, Yujun Li, Daqing Sun, Feng Bai. Protective Effect of Nimbolide against High Fat Diet-induced Obesity in Rats via Nrf2/HO-1 Pathway. Journal of oleo science. 2022; 71(5):709-720. doi: 10.5650/jos.ess21389. [PMID: 35491096]
  • Perumal Elumalai, Devaraj Ezhilarasan, Subramanian Raghunandhakumar. Molecular Targets of Nimbolide for Anti-Cancer Therapy: An Updated Review. Journal of environmental pathology, toxicology and oncology : official organ of the International Society for Environmental Toxicology and Cancer. 2022; 41(2):69-88. doi: 10.1615/jenvironpatholtoxicoloncol.2021040263. [PMID: 35695653]
  • Venkatesh Pooladanda, Sowjanya Thatikonda, Omprakash Sunnapu, Shristy Tiwary, Praveen Kumar Vemula, M V N Kumar Talluri, Chandraiah Godugu. iRGD conjugated nimbolide liposomes protect against endotoxin induced acute respiratory distress syndrome. Nanomedicine : nanotechnology, biology, and medicine. 2021 04; 33(?):102351. doi: 10.1016/j.nano.2020.102351. [PMID: 33418136]
  • Sapana Bansod, Chandraiah Godugu. Nimbolide ameliorates pancreatic inflammation and apoptosis by modulating NF-κB/SIRT1 and apoptosis signaling in acute pancreatitis model. International immunopharmacology. 2021 Jan; 90(?):107246. doi: 10.1016/j.intimp.2020.107246. [PMID: 33310297]
  • Panawan Suttiarporn, Vachira Choommongkol. Microwave-Assisted Improved Extraction and Purification of Anticancer Nimbolide from Azadirachta indica (Neem) Leaves. Molecules (Basel, Switzerland). 2020 Jun; 25(12):. doi: 10.3390/molecules25122913. [PMID: 32599926]
  • Xin Cui, Ruijing Wang, Peimin Bian, Qingke Wu, Vidya Devanatha Desikan Seshadri, Lun Liu. Evaluation of antiarthritic activity of nimbolide against Freund's adjuvant induced arthritis in rats. Artificial cells, nanomedicine, and biotechnology. 2019 Dec; 47(1):3391-3398. doi: 10.1080/21691401.2019.1649269. [PMID: 31394949]
  • Zhifang Qiu, Kristina Andrijauskaite, Jay Morris, Michael J Wargovich. Disruption of Epigenetic Silencing in Human Colon Cancer Cells Lines Utilizing a Novel Supercritical CO2 Extract of Neem Leaf (Azadirachta indica). Anticancer research. 2019 Oct; 39(10):5473-5481. doi: 10.21873/anticanres.13740. [PMID: 31570441]
  • Shivaraju Annaldas, Mohd Aslam Saifi, Amit Khurana, Chandraiah Godugu. Nimbolide ameliorates unilateral ureteral obstruction-induced renal fibrosis by inhibition of TGF-β and EMT/Slug signalling. Molecular immunology. 2019 08; 112(?):247-255. doi: 10.1016/j.molimm.2019.06.003. [PMID: 31202101]
  • Snehalatha Diddi, Swarna Bale, Gauthami Pulivendala, Chandraiah Godugu. Nimbolide ameliorates fibrosis and inflammation in experimental murine model of bleomycin-induced scleroderma. Inflammopharmacology. 2019 Feb; 27(1):139-149. doi: 10.1007/s10787-018-0527-4. [PMID: 30218238]
  • Josephraj Sophia, Jaganathan Kowshik, Anju Dwivedi, Sujit K Bhutia, Bramanandam Manavathi, Rajakishore Mishra, Siddavaram Nagini. Nimbolide, a neem limonoid inhibits cytoprotective autophagy to activate apoptosis via modulation of the PI3K/Akt/GSK-3β signalling pathway in oral cancer. Cell death & disease. 2018 10; 9(11):1087. doi: 10.1038/s41419-018-1126-4. [PMID: 30352996]
  • Mandakini J Patel, Shreya Tripathy, Keya D Mukhopadhyay, Tamna Wangjam, April B Cabang, Jay Morris, Michael J Wargovich. A supercritical CO2 extract of neem leaf (A. indica) and its bioactive liminoid, nimbolide, suppresses colon cancer in preclinical models by modulating pro-inflammatory pathways. Molecular carcinogenesis. 2018 09; 57(9):1156-1165. doi: 10.1002/mc.22832. [PMID: 29697164]
  • Shandilya Mahamuni Baira, Amit Khurana, Jaganmohan Somagoni, R Srinivas, Chandraiah Godugu, M V N Kumar Talluri. First report on the pharmacokinetic profile of nimbolide, a novel anticancer agent in oral and intravenous administrated rats by LC/MS method. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Aug; 1092(?):191-198. doi: 10.1016/j.jchromb.2018.06.002. [PMID: 29908468]
  • Md Fahim Ahmad, Mohd Owais Ansari, Sana Jameel, Ab Latif Wani, Nuzhat Parveen, Hifzur R Siddique, G G H A Shadab. Protective role of nimbolide against chemotherapeutic drug hydroxyurea induced genetic and oxidative damage in an animal model. Environmental toxicology and pharmacology. 2018 Jun; 60(?):91-99. doi: 10.1016/j.etap.2018.04.006. [PMID: 29679812]
  • Ghedeir M Alshammari, Aristatile Balakrishnan, Thirunavukkarasu Chinnasamy. Nimbolide attenuate the lipid accumulation, oxidative stress and antioxidant in primary hepatocytes. Molecular biology reports. 2017 Dec; 44(6):463-474. doi: 10.1007/s11033-017-4132-1. [PMID: 29185131]
  • Subash Chandra Gupta, Sahdeo Prasad, Amit K Tyagi, Ajaikumar B Kunnumakkara, Bharat B Aggarwal. Neem (Azadirachta indica): An indian traditional panacea with modern molecular basis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2017 Oct; 34(?):14-20. doi: 10.1016/j.phymed.2017.07.001. [PMID: 28899496]
  • P Raja Singh, E Sugantha Priya, S Balakrishnan, R Arunkumar, G Sharmila, M Rajalakshmi, J Arunakaran. Nimbolide inhibits androgen independent prostate cancer cells survival and proliferation by modulating multiple pro-survival signaling pathways. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2016 Dec; 84(?):1623-1634. doi: 10.1016/j.biopha.2016.10.076. [PMID: 27889231]
  • Prodipta Sarkar, Saurabh Acharyya, Anirban Banerjee, Amarendra Patra, Karthika Thankamani, Hemanta Koley, Prasanta K Bag. Intracellular, biofilm-inhibitory and membrane-damaging activities of nimbolide isolated from Azadirachta indica A. Juss (Meliaceae) against meticillin-resistant Staphylococcus aureus. Journal of medical microbiology. 2016 Oct; 65(10):1205-1214. doi: 10.1099/jmm.0.000343. [PMID: 27553840]
  • Lingzhi Wang, Do Dang Khoa Phan, Jingwen Zhang, Pei-Shi Ong, Win Lwin Thuya, Ross Soo, Andrea Li-Ann Wong, Wei Peng Yong, Soo Chin Lee, Paul Chi-Lui Ho, Gautam Sethi, Boon Cher Goh. Anticancer properties of nimbolide and pharmacokinetic considerations to accelerate its development. Oncotarget. 2016 Jul; 7(28):44790-44802. doi: 10.18632/oncotarget.8316. [PMID: 27027349]
  • Chantana Chantana, Chavi Yenjai, Prasert Reubroycharoen, Pornthip Waiwut. Combination of Nimbolide and TNF-α-Increases Human Colon Adenocarcinoma Cell Death through JNK-mediated DR5 Up- regulation. Asian Pacific journal of cancer prevention : APJCP. 2016; 17(5):2637-41. doi: . [PMID: 27268643]
  • Yi-Hsien Hsieh, Chien-Hsing Lee, Hsiao-Yun Chen, Shu-Ching Hsieh, Chia-Liang Lin, Jen-Pi Tsai. Induction of cell cycle arrest, DNA damage, and apoptosis by nimbolide in human renal cell carcinoma cells. Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine. 2015 Sep; 36(10):7539-47. doi: 10.1007/s13277-015-3477-0. [PMID: 25916210]
  • Hisashi Kato-Noguchi, Md Abdus Salam, Osamu Ohno, Kiyotake Suenaga. Nimbolide B and nimbic acid B, phytotoxic substances in neem leaves with allelopathic activity. Molecules (Basel, Switzerland). 2014 May; 19(6):6929-40. doi: 10.3390/molecules19066929. [PMID: 24865604]
  • Swagata Karkare, Rishi Raj Chhipa, Jane Anderson, Xiaona Liu, Heather Henry, Anjelika Gasilina, Nicholas Nassar, Jayeeta Ghosh, Jason P Clark, Ashish Kumar, Giovanni M Pauletti, Pradip K Ghosh, Biplab Dasgupta. Direct inhibition of retinoblastoma phosphorylation by nimbolide causes cell-cycle arrest and suppresses glioblastoma growth. Clinical cancer research : an official journal of the American Association for Cancer Research. 2014 Jan; 20(1):199-212. doi: 10.1158/1078-0432.ccr-13-0762. [PMID: 24170547]
  • Subash C Gupta, Sahdeo Prasad, Dhanya R Sethumadhavan, Mangalam S Nair, Yin-Yuan Mo, Bharat B Aggarwal. Nimbolide, a limonoid triterpene, inhibits growth of human colorectal cancer xenografts by suppressing the proinflammatory microenvironment. Clinical cancer research : an official journal of the American Association for Cancer Research. 2013 Aug; 19(16):4465-76. doi: 10.1158/1078-0432.ccr-13-0080. [PMID: 23766363]
  • Suboj Babykutty, Priya P S, Nandini R J, M A Suresh Kumar, Mangalam S Nair, Priya Srinivas, Srinivas Gopala. Nimbolide retards tumor cell migration, invasion, and angiogenesis by downregulating MMP-2/9 expression via inhibiting ERK1/2 and reducing DNA-binding activity of NF-κB in colon cancer cells. Molecular carcinogenesis. 2012 Jun; 51(6):475-90. doi: 10.1002/mc.20812. [PMID: 21678498]
  • Subash C Gupta, Simone Reuter, Kanokkarn Phromnoi, Byoungduck Park, Padmanabhan S Hema, Mangalam Nair, Bharat B Aggarwal. Nimbolide sensitizes human colon cancer cells to TRAIL through reactive oxygen species- and ERK-dependent up-regulation of death receptors, p53, and Bax. The Journal of biological chemistry. 2011 Jan; 286(2):1134-46. doi: 10.1074/jbc.m110.191379. [PMID: 21078664]
  • Mercy Githua, Ahmed Hassanali, Joseph Keriko, Grace Murilla, Mary Ndungu, Gathu Nyagah. New antitrypanosomal tetranotriterpenoids from Azadirachta indica. African journal of traditional, complementary, and alternative medicines : AJTCAM. 2010 Apr; 7(3):207-13. doi: 10.4314/ajtcam.v7i3.54776. [PMID: 21461147]
  • Molay Kumar Roy, Masuko Kobori, Makiko Takenaka, Kazuhiko Nakahara, Hiroshi Shinmoto, Seiichiro Isobe, Tojiro Tsushida. Antiproliferative effect on human cancer cell lines after treatment with nimbolide extracted from an edible part of the neem tree (Azadirachta indica). Phytotherapy research : PTR. 2007 Mar; 21(3):245-50. doi: 10.1002/ptr.2058. [PMID: 17163581]
  • G Anitha, J Josepha Lourdu Raj, V Radha Krishnan, S Narasimhan, K Anand Solomon, S S Rajan. Semi-synthetic modification of nimbolide to 6-homodesacetylnimbin and 6-desacetylnimbin and their cytotoxic studies. Journal of Asian natural products research. 2007 Jan; 9(1):73-8. doi: 10.1080/10286020500383742. [PMID: 17365193]
  • B S Sastry, K Suresh Babu, T Hari Babu, S Chandrasekhar, P V Srinivas, A K Saxena, J Madhusudana Rao. Synthesis and biological activity of amide derivatives of nimbolide. Bioorganic & medicinal chemistry letters. 2006 Aug; 16(16):4391-4. doi: 10.1016/j.bmcl.2006.05.105. [PMID: 16793266]
  • Hathaitip Sritanaudomchai, Thanit Kusamran, Worapun Kuakulkiat, Nuntavan Bunyapraphatsara, Ankana Hiransalee, Anong Tepsuwan, Wannee R Kusamran. Quinone reductase inducers in Azadirachta indica A. Juss flowers, and their mechanisms of action. Asian Pacific journal of cancer prevention : APJCP. 2005 Jul; 6(3):263-9. doi: ". [PMID: 16235984]
  • K Anand Solomon, R Malathi, S S Rajan, G Anitha, J Josepha Lourdu Raj, S Narasimhan, G Suresh, Geetha Gopalakrishnan. The isomeric compounds nimbolide and isonimbolide. Acta crystallographica. Section C, Crystal structure communications. 2005 Feb; 61(Pt 2):o70-2. doi: 10.1107/s0108270104031385. [PMID: 15699572]
  • E Cohen, G B Quistad, J E Casida. Cytotoxicity of nimbolide, epoxyazadiradione and other limonoids from neem insecticide. Life sciences. 1996; 58(13):1075-81. doi: 10.1016/0024-3205(96)00061-6. [PMID: 8622560]
  • P G Kigodi, G Blaskó, Y Thebtaranonth, J M Pezzuto, G A Cordell. Spectroscopic and biological investigation of nimbolide and 28-deoxonimbolide from Azadirachta indica. Journal of natural products. 1989 Nov; 52(6):1246-51. doi: 10.1021/np50066a008. [PMID: 2614419]
  • T Glinsukon, R Somjaree, P Piyachaturawat, Y Thebtaranonth. Acute toxicity of nimbolide and nimbic acid in mice, rats and hamsters. Toxicology letters. 1986 Feb; 30(2):159-66. doi: 10.1016/0378-4274(86)90098-6. [PMID: 3754662]
  • S Rochanakij, Y Thebtaranonth, C Yenjai, Y Yuthavong. Nimbolide, a constituent of Azadirachta indica, inhibits Plasmodium falciparum in culture. The Southeast Asian journal of tropical medicine and public health. 1985 Mar; 16(1):66-72. doi: ". [PMID: 3895455]