Rottlerin (BioDeep_00000002501)

   

PANOMIX_OTCML-2023


代谢物信息卡片


(2E) -1- [ 6- [ (3-Acetyl-2,4,6-trihydroxy-5-methylphenyl) methyl ] -5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl ] -3-phenyl-2-propene-1-one

化学式: C30H28O8 (516.1784088)
中文名称: 粗糠柴毒素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 24.49%

分子结构信息

SMILES: c(C(C)=O)(c(O)1)c(O)c(Cc(c(O)3)c(O)c(C(=O)C=Cc(c4)cccc4)c(c32)OC(C)(C)C=C2)c(O)c1C
InChI: InChI=1S/C30H28O8/c1-15-24(33)19(27(36)22(16(2)31)25(15)34)14-20-26(35)18-12-13-30(3,4)38-29(18)23(28(20)37)21(32)11-10-17-8-6-5-7-9-17/h5-13,33-37H,14H2,1-4H3/b11-10+

描述信息

Rottlerin is a chromenol that is 2,2-dimethyl-2H-chromene substituted by hydroxy groups at positions 5 and 7, a 3-acetyl-2,4,6-trihydroxy-5-methylbenzyl group at position 6 and a (1E)-3-oxo-1-phenylprop-1-en-3-yl group at position 8. A potassium channel opener, it is isolated from Mallotus philippensis. It has a role as an antineoplastic agent, an apoptosis inducer, a metabolite, a K-ATP channel agonist, an antihypertensive agent and an anti-allergic agent. It is an enone, a chromenol, a benzenetriol, a methyl ketone and an aromatic ketone.
Rottlerin is a natural product found in Mallotus philippensis with data available.
A chromenol that is 2,2-dimethyl-2H-chromene substituted by hydroxy groups at positions 5 and 7, a 3-acetyl-2,4,6-trihydroxy-5-methylbenzyl group at position 6 and a (1E)-3-oxo-1-phenylprop-1-en-3-yl group at position 8. A potassium channel opener, it is isolated from Mallotus philippensis.
D004791 - Enzyme Inhibitors
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.546
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.549
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.548
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.550
Rottlerin, a natural product purified from Mallotus Philippinensis, is a specific PKC inhibitor, with IC50 values for PKCδ of 3-6 μM, PKCα,β,γ of 30-42 μM, PKCε,η,ζ of 80-100 μM. Rottlerin acts as a direct mitochondrial uncoupler, and stimulates autophagy by targeting a signaling cascade upstream of mTORC1. Rottlerin induces apoptosis via caspase 3 activation[1][2][3]. Rottlerin inhibits HIV-1 integration and Rabies virus (RABV) infection[4][5].
Rottlerin, a natural product purified from Mallotus Philippinensis, is a specific PKC inhibitor, with IC50 values for PKCδ of 3-6 μM, PKCα,β,γ of 30-42 μM, PKCε,η,ζ of 80-100 μM. Rottlerin acts as a direct mitochondrial uncoupler, and stimulates autophagy by targeting a signaling cascade upstream of mTORC1. Rottlerin induces apoptosis via caspase 3 activation[1][2][3]. Rottlerin inhibits HIV-1 integration and Rabies virus (RABV) infection[4][5].

同义名列表

33 个代谢物同义名

(E)-1-(6-((3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl)-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl)-3-phenyl-2-propen-1-one; (E)-1-[6-[(3-Acetyl-2,4,6-trihydroxy-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one; (E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methyl-phenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-chromen-8-yl]-3-phenyl-prop-2-en-1-one; 1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one; (E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one; (2E)-1-[6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-phenylprop-2-en-1-one; (2E)-1-(6-(3-ACETYL-2,4,6-TRIHYDROXY-5-METHYLBENZYL)-5,7-DIHYDROXY-2,2-DIMETHYL-2H-CHROMEN-8-YL)-3-PHENYLPROP-2-EN-1-ONE; 1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one; (E)-1-(6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-phenylprop-2-en-1-one; 1-(6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-phenylprop-2-en-1-one; Acetophenone, 3-((8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl)-2,4,6-trihydroxy-5-methyl-; 1-[6-(3-Acetyl-2,4,6-trihydroxy-5-methyl-benzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-phenyl-propenone; 3-((8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl)-2,4,6-trihydroxy-5-methyl-acetophenone; 3-[(8-Cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl]-2,4,6-trihydroxy-5-methylacetophenone; 5,7-dihydroxy-2,2-dimethyl-6-(2,4,6-trihydroxy-3-methyl-5-acetylbenzyl)-8-cinnamoyl-1,2-chromene; 5-18-05-00695 (Beilstein Handbook Reference); Rottlerin - CAS 82-08-6; BiomolKI2_000064; BCBcMAP01_000019; UNII-E29LP3ZMUH; ROTTLERIN [MI]; Lopac0_001052; Tox21_501052; IDI1_002135; mallotoxin; E29LP3ZMUH; Rottlerin; BMK1-F10; Kamalin; (2E) -1- [ 6- [ (3-Acetyl-2,4,6-trihydroxy-5-methylphenyl) methyl ] -5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl ] -3-phenyl-2-propene-1-one; Mallotoxin; NSC 56346; NSC 94525; NSC 56346; NSC 94525



数据库引用编号

25 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

  • Samuel Cota Teixeira, Marina Paschoalino, Guilherme de Souza, Alessandra Monteiro Rosini, Joed Pires de Lima Junior, Luana Carvalho Luz, Aryani Felixa Fajardo Martínez, Rosiane Nascimento Alves, Marcos Paulo Oliveira Almeida, Jaqueline Lopes Damasceno, Marcelo José Barbosa Silva, Francesca Ietta, Bellisa Freitas Barbosa, Eloisa Amália Vieira Ferro, Carlos Henrique Gomes Martins. Rottlerin impairs early and late steps of Toxoplasma gondii infection in human trophoblast cells and villous explants. Chemico-biological interactions. 2023 Sep; ?(?):110716. doi: 10.1016/j.cbi.2023.110716. [PMID: 37722575]
  • Eun-Joo Shin, Ji Hoon Jeong, Bao-Trong Nguyen, Naveen Sharma, Cuong Ngoc Kim Tran, Seung-Yeol Nah, Yi Lee, Jae Kyung Byun, Sung Kwon Ko, Hyoung-Chun Kim. Ginsenoside Re attenuates 8-OH-DPAT-induced serotonergic behaviors in mice via interactive modulation between PKCδ gene and Nrf2. Drug and chemical toxicology. 2023 Mar; 46(2):281-296. doi: 10.1080/01480545.2021.2022689. [PMID: 35707918]
  • Eun-Joo Shin, Ji Hoon Jeong, Bao-Trong Nguyen, Naveen Sharma, Seung-Yeol Nah, Yoon Hee Chung, Yi Lee, Jae Kyung Byun, Toshitaka Nabeshima, Sung Kwon Ko, Hyoung-Chun Kim. Ginsenoside Re Protects against Serotonergic Behaviors Evoked by 2,5-Dimethoxy-4-iodo-amphetamine in Mice via Inhibition of PKCδ-Mediated Mitochondrial Dysfunction. International journal of molecular sciences. 2021 Jul; 22(13):. doi: 10.3390/ijms22137219. [PMID: 34281274]
  • Tsong-Hai Lee, Jiun-Liang Chen, Pei-Shan Liu, Ming-Ming Tsai, Su-Jane Wang, Hsi-Lung Hsieh. Rottlerin, a natural polyphenol compound, inhibits upregulation of matrix metalloproteinase-9 and brain astrocytic migration by reducing PKC-δ-dependent ROS signal. Journal of neuroinflammation. 2020 Jun; 17(1):177. doi: 10.1186/s12974-020-01859-5. [PMID: 32505192]
  • Sarot Cheenpracha, Stephen G Pyne, Brian O Patrick, Raymond J Andersen, Wisanu Maneerat, Surat Laphookhieo. Mallopenins A-E, Antibacterial Phenolic Derivatives from the Fruits of Mallotus philippensis. Journal of natural products. 2019 08; 82(8):2174-2180. doi: 10.1021/acs.jnatprod.9b00182. [PMID: 31318550]
  • Ji Hye Yang, Moon-Hee Choi, Chang-Su Na, Sam Seok Cho, Jae Hoon Kim, Sae Kwang Ku, Il Je Cho, Hyun-Jae Shin, Sung Hwan Ki. Bamboo Stems (Phyllostachys nigra variety henosis) Containing Polyphenol Mixtures Activate Nrf2 and Attenuate Phenylhydrazine-Induced Oxidative Stress and Liver Injury. Nutrients. 2019 Jan; 11(1):. doi: 10.3390/nu11010114. [PMID: 30626086]
  • Angele M De Silva, Rían W Manville, Geoffrey W Abbott. Deconstruction of an African folk medicine uncovers a novel molecular strategy for therapeutic potassium channel activation. Science advances. 2018 11; 4(11):eaav0824. doi: 10.1126/sciadv.aav0824. [PMID: 30443601]
  • Hao Wang, Weisha Liu, Meng Sun, Dubo Chen, Lingbing Zeng, Liqun Lu, Jing Xie. Inhibitor analysis revealed that clathrin-mediated endocytosis is involed in cellular entry of type III grass carp reovirus. Virology journal. 2018 05; 15(1):92. doi: 10.1186/s12985-018-0993-8. [PMID: 29793525]
  • Lixia Wang, Yingying Hou, Xuyuan Yin, Jingna Su, Zhe Zhao, Xiantao Ye, Xiuxia Zhou, Li Zhou, Zhiwei Wang. Rottlerin inhibits cell growth and invasion via down-regulation of Cdc20 in glioma cells. Oncotarget. 2016 Oct; 7(43):69770-69782. doi: 10.18632/oncotarget.11974. [PMID: 27626499]
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  • Eun-Joo Shin, Yunsung Nam, Thu-Hien Thi Tu, Yong Kwang Lim, Myung-Bok Wie, Dae-Joong Kim, Ji Hoon Jeong, Hyoung-Chun Kim. Protein kinase Cδ mediates trimethyltin-induced neurotoxicity in mice in vivo via inhibition of glutathione defense mechanism. Archives of toxicology. 2016 Apr; 90(4):937-53. doi: 10.1007/s00204-015-1516-7. [PMID: 25895139]
  • Veronika Matschke, Ilaria Piccini, Janina Schubert, Eva Wrobel, Florian Lang, Johann Matschke, Elsie Amedonu, Sven G Meuth, Timo Strünker, Nathalie Strutz-Seebohm, Boris Greber, Jürgen Scherkenbeck, Guiscard Seebohm. The Natural Plant Product Rottlerin Activates Kv7.1/KCNE1 Channels. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2016; 40(6):1549-1558. doi: 10.1159/000453205. [PMID: 27997884]
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  • Katka Szilagyi, Alexander B Meijer, Annette E Neele, Paul Verkuijlen, Michael Leitges, Sandrine Dabernat, Elisabeth Förster-Waldl, Kaan Boztug, Alexandre Belot, Taco W Kuijpers, Georg Kraal, Menno P J de Winther, Timo K van den Berg. PKCδ is dispensible for oxLDL uptake and foam cell formation by human and murine macrophages. Cardiovascular research. 2014 Dec; 104(3):467-76. doi: 10.1093/cvr/cvu213. [PMID: 25253077]
  • Rajiv Lochan Tiwari, Vishal Singh, Ankita Singh, Minakshi Rana, Anupam Verma, Nikhil Kothari, Monica Kohli, Jaishri Bogra, Madhu Dikshit, Manoj Kumar Barthwal. PKCδ-IRAK1 axis regulates oxidized LDL-induced IL-1β production in monocytes. Journal of lipid research. 2014 07; 55(7):1226-44. doi: 10.1194/jlr.m045658. [PMID: 24792928]
  • Wenyan Lu, Cuihong Lin, Yonghe Li. Rottlerin induces Wnt co-receptor LRP6 degradation and suppresses both Wnt/β-catenin and mTORC1 signaling in prostate and breast cancer cells. Cellular signalling. 2014 Jun; 26(6):1303-9. doi: 10.1016/j.cellsig.2014.02.018. [PMID: 24607787]
  • Dhruv Kumar, Sharmila Shankar, Rakesh K Srivastava. Rottlerin induces autophagy and apoptosis in prostate cancer stem cells via PI3K/Akt/mTOR signaling pathway. Cancer letters. 2014 Feb; 343(2):179-89. doi: 10.1016/j.canlet.2013.10.003. [PMID: 24125861]
  • Qian Chen, Wenqiang Zhang, Hao Ran, Lizhao Feng, Hao Yan, Xinyi Mu, Yingying Han, Wei Liu, Guoliang Xia, Chao Wang. PKCδ and θ possibly mediate FSH-induced mouse oocyte maturation via NOX-ROS-TACE cascade signaling pathway. PloS one. 2014; 9(10):e111423. doi: 10.1371/journal.pone.0111423. [PMID: 25350560]
  • Panai Song, Shikun Yang, Li Xiao, Xiaoxuan Xu, Chengyuan Tang, Yuyan Yang, Mingming Ma, Jiefu Zhu, Fuyou Liu, Lin Sun. PKCδ promotes high glucose induced renal tubular oxidative damage via regulating activation and translocation of p66Shc. Oxidative medicine and cellular longevity. 2014; 2014(?):746531. doi: 10.1155/2014/746531. [PMID: 25371776]
  • Mayank Gangwar, Manish Kumar Gautam, Amit Kumar Sharma, Yamini B Tripathi, R K Goel, Gopal Nath. Antioxidant capacity and radical scavenging effect of polyphenol rich Mallotus philippenensis fruit extract on human erythrocytes: an in vitro study. TheScientificWorldJournal. 2014; 2014(?):279451. doi: 10.1155/2014/279451. [PMID: 25525615]
  • Dhruv Kumar, Sharmila Shankar, Rakesh K Srivastava. Rottlerin-induced autophagy leads to the apoptosis in breast cancer stem cells: molecular mechanisms. Molecular cancer. 2013 Dec; 12(1):171. doi: 10.1186/1476-4598-12-171. [PMID: 24359639]
  • Nari Yun, Sun-Mee Lee. Activation of protein kinase C delta reduces hepatocellular damage in ischemic preconditioned rat liver. The Journal of surgical research. 2013 Dec; 185(2):869-76. doi: 10.1016/j.jss.2013.07.005. [PMID: 23932656]
  • Shreyans K Jain, Anup S Pathania, Samdarshi Meena, Rajni Sharma, Ashok Sharma, Baljinder Singh, Bishan D Gupta, Shashi Bhushan, Sandip B Bharate, Ram A Vishwakarma. Semisynthesis of mallotus B from rottlerin: evaluation of cytotoxicity and apoptosis-inducing activity. Journal of natural products. 2013 Sep; 76(9):1724-30. doi: 10.1021/np400433g. [PMID: 24041234]
  • Tze Khee Chan, David S W Ng, Chang Cheng, Shou Ping Guan, Hock Meng Koh, W S Fred Wong. Anti-allergic actions of rottlerin from Mallotus philippinensis in experimental mast cell-mediated anaphylactic models. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Jul; 20(10):853-60. doi: 10.1016/j.phymed.2013.03.012. [PMID: 23632085]
  • Jose Raul Gonzalez-Garcia, Zoltan Machaty, F Anthony Lai, Karl Swann. The dynamics of PKC-induced phosphorylation triggered by Ca2+ oscillations in mouse eggs. Journal of cellular physiology. 2013 Jan; 228(1):110-9. doi: 10.1002/jcp.24110. [PMID: 22566126]
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  • Se Won Park, Christopher M Schonhoff, Cynthia R L Webster, M Sawkat Anwer. Protein kinase Cδ differentially regulates cAMP-dependent translocation of NTCP and MRP2 to the plasma membrane. American journal of physiology. Gastrointestinal and liver physiology. 2012 Sep; 303(5):G657-65. doi: 10.1152/ajpgi.00529.2011. [PMID: 22744337]
  • Emanuela Maioli, Claudia Torricelli, Giuseppe Valacchi. Rottlerin and curcumin: a comparative analysis. Annals of the New York Academy of Sciences. 2012 Jul; 1259(?):65-76. doi: 10.1111/j.1749-6632.2012.06514.x. [PMID: 22758638]
  • Y C Muñoz, G I Gomez, M Moreno, C L Solis, L E Valladares, V Velarde. Dehydroepiandrosterone prevents the aggregation of platelets obtained from postmenopausal women with type 2 diabetes mellitus through the activation of the PKC/eNOS/NO pathway. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2012 Jul; 44(8):625-31. doi: 10.1055/s-0032-1309056. [PMID: 22517552]
  • Eun-Joo Shin, Chu Xuan Duong, Xuan-Khanh Thi Nguyen, Zhengyi Li, Guoying Bing, Jae-Hyung Bach, Dae Hun Park, Keiichi Nakayama, Syed F Ali, Anumantha G Kanthasamy, Jean Lud Cadet, Toshitaka Nabeshima, Hyoung-Chun Kim. Role of oxidative stress in methamphetamine-induced dopaminergic toxicity mediated by protein kinase Cδ. Behavioural brain research. 2012 Jun; 232(1):98-113. doi: 10.1016/j.bbr.2012.04.001. [PMID: 22512859]
  • Yadong Gao, Jinjing Zou, Shuang Geng, Junwen Zheng, Jiong Yang. Role of protein kinase C in the activation of store-operated Ca(2+) entry in airway smooth muscle cells. Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban. 2012 Jun; 32(3):303-310. doi: 10.1007/s11596-012-0053-3. [PMID: 22684549]
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  • Young Soon Lee, Eun Mi Choi. Effect of pollen from Typha angustata on hydrogen peroxide induced toxicity in osteoblastic MC3T3-E1 cells. Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology. 2012 Feb; 41(2):171-7. doi: 10.1111/j.1600-0714.2011.01077.x. [PMID: 21958211]
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  • Yoshimasa Komatsuzaki, Yusuke Hatanaka, Gen Murakami, Hideo Mukai, Yasushi Hojo, Minoru Saito, Tetsuya Kimoto, Suguru Kawato. Corticosterone induces rapid spinogenesis via synaptic glucocorticoid receptors and kinase networks in hippocampus. PloS one. 2012; 7(4):e34124. doi: 10.1371/journal.pone.0034124. [PMID: 22509272]
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  • Mario Schelhaas, Bhavin Shah, Michael Holzer, Peter Blattmann, Lena Kühling, Patricia M Day, John T Schiller, Ari Helenius. Entry of human papillomavirus type 16 by actin-dependent, clathrin- and lipid raft-independent endocytosis. PLoS pathogens. 2012; 8(4):e1002657. doi: 10.1371/journal.ppat.1002657. [PMID: 22536154]
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  • Lionel Tcatchoff, Sofia Andersson, Audrun Utskarpen, Tove Irene Klokk, Sigrid S Skånland, Sascha Pust, Volker Gerke, Kirsten Sandvig. Annexin A1 and A2: roles in retrograde trafficking of Shiga toxin. PloS one. 2012; 7(7):e40429. doi: 10.1371/journal.pone.0040429. [PMID: 22792315]
  • Lei Lei, Zhongyu Li, Guangming Zhong. Rottlerin-mediated inhibition of Chlamydia trachomatis growth and uptake of sphingolipids is independent of p38-regulated/activated protein kinase (PRAK). PloS one. 2012; 7(9):e44733. doi: 10.1371/journal.pone.0044733. [PMID: 22970301]
  • Eun Jung Park, Taeg Kyu Kwon. Rottlerin enhances IL-1β-induced COX-2 expression through sustained p38 MAPK activation in MDA-MB-231 human breast cancer cells. Experimental & molecular medicine. 2011 Dec; 43(12):669-75. doi: 10.3858/emm.2011.43.12.077. [PMID: 21971413]
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