Bisdemethoxycurcumin (BioDeep_00000267521)

Main id: BioDeep_00000017290

 

PANOMIX_OTCML-2023 Antitumor activity natural product


代谢物信息卡片


1,7-bis(4-hydroxyphenyl)-1,6-Heptadiene-3,5-dione(E,E)

化学式: C19H16O4 (308.1049)
中文名称: 双去甲氧基姜黄素, 双去氧基姜黄素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=CC=C1/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O
InChI: InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+

描述信息

(E,E)-Bisdemethoxycurcumin ((E,E)-Curcumin III) is a curcumin derivative with anti-inflammatory and anticancer activities.
(E,E)-Bisdemethoxycurcumin ((E,E)-Curcumin III) is a curcumin derivative with anti-inflammatory and anticancer activities.
Bisdemethoxycucurmin (Curcumin III), a curcuminoid, has antioxidant and antiinflammatory activities[1][2].
Bisdemethoxycucurmin (Curcumin III), a curcuminoid, has antioxidant and antiinflammatory activities[1][2].

同义名列表

14 个代谢物同义名

1,7-bis(4-hydroxyphenyl)-1,6-Heptadiene-3,5-dione(E,E); 1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione; Bis(4-hydroxycinnamoyl)methane; Bis(p-hydroxycinnamoyl)methane; Bis-demethoxycurcumin; Bisdemethoxycurcumin; 1,9-Bis(4-hydroxyphenyl)-2,7-nonadiene-4,6-dione; (E,E)-Curcumin III; (E,E)-Didemethoxycurcumin; (E,E)-Bisdemethoxycurcumin; Curcumin III; Didemethoxycurcumin; Bisdemethoxycucurmin; Bisdemethoxycurcumin



数据库引用编号

21 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)

80 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。

亚细胞结构定位 关联基因列表


文献列表

  • Juan Antonio Giménez-Bastida, María Ángeles Ávila-Gálvez, Miguel Carmena-Bargueño, Horacio Pérez-Sánchez, Juan Carlos Espín, Antonio González-Sarrías. Physiologically relevant curcuminoids inhibit angiogenesis via VEGFR2 in human aortic endothelial cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2022 Aug; 166(?):113254. doi: 10.1016/j.fct.2022.113254. [PMID: 35752269]
  • Xiaoqin Ding, Yan Chen, Lina Zhou, Ruoyun Wu, Tunyu Jian, Han Lyu, Yan Liu, Jian Chen. Bisdemethoxycurcumin Attenuated Renal Injury via Activation of Keap1/Nrf2 Pathway in High-Fat Diet-Fed Mice. International journal of molecular sciences. 2022 Jul; 23(13):. doi: 10.3390/ijms23137395. [PMID: 35806399]
  • Jin-Xing Wei, Yi Luo, Yan Xu, Jian-Hui Xiao. Osteoinductive activity of bisdemethoxycurcumin and its synergistic protective effect with human amniotic mesenchymal stem cells against ovariectomy-induced osteoporosis mouse model. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Feb; 146(?):112605. doi: 10.1016/j.biopha.2021.112605. [PMID: 35062070]
  • Natalia Miklášová, Peter Herich, Juan Carlos Dávila-Becerril, Joaquín Barroso-Flores, Eva Fischer-Fodor, Jindra Valentová, Janka Leskovská, Jozef Kožíšek, Peter Takáč, Ján Mojžiš. Evaluation of Antiproliferative Palladium(II) Complexes of Synthetic Bisdemethoxycurcumin towards In Vitro Cytotoxicity and Molecular Docking on DNA Sequence. Molecules (Basel, Switzerland). 2021 Jul; 26(14):. doi: 10.3390/molecules26144369. [PMID: 34299644]
  • Lahcen Tamegart, Abdellatif Abbaoui, Abdelaati El Khiat, Moulay Mustapha Bouyatas, Halima Gamrani. Lead (Pb) exposure induces physiological alterations in the serotoninergic and vasopressin systems causing anxiogenic-like behavior in Meriones shawi: Assessment of BDMC as a neuroprotective compound for Pb-neurotoxicity and kidney damages. Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS). 2021 May; 65(?):126722. doi: 10.1016/j.jtemb.2021.126722. [PMID: 33524682]
  • Sudha Ramkumar, H V Thulasiram, Ameeta RaviKumar. Improvement in serum amylase and glucose levels in diabetic rats on oral administration of bisdemethoxycurcumin from Curcuma longa and limonoids from Azadirachta indica. Journal of food biochemistry. 2021 04; 45(4):e13674. doi: 10.1111/jfbc.13674. [PMID: 33634871]
  • Jian Liu, Qilong Wang, Emmanuel Omari-Siaw, Michael Adu-Frimpong, Jing Liu, Ximing Xu, Jiangnan Yu. Enhanced oral bioavailability of Bisdemethoxycurcumin-loaded self-microemulsifying drug delivery system: Formulation design, in vitro and in vivo evaluation. International journal of pharmaceutics. 2020 Nov; 590(?):119887. doi: 10.1016/j.ijpharm.2020.119887. [PMID: 32950666]
  • Fuquan Jin, Xueqin Chen, Hao Yan, Zhifei Xu, Bo Yang, Peihua Luo, Qiaojun He. Bisdemethoxycurcumin attenuates cisplatin-induced renal injury through anti-apoptosis, anti-oxidant and anti-inflammatory. European journal of pharmacology. 2020 May; 874(?):173026. doi: 10.1016/j.ejphar.2020.173026. [PMID: 32088177]
  • Gina Córdoba-David, Aroa Duro-Castano, Regiane Cardoso Castelo-Branco, Cristian González-Guerrero, Pablo Cannata, Ana B Sanz, María J Vicent, Alberto Ortiz, Adrián M Ramos. Effective Nephroprotection Against Acute Kidney Injury with a Star-Shaped Polyglutamate-Curcuminoid Conjugate. Scientific reports. 2020 02; 10(1):2056. doi: 10.1038/s41598-020-58974-9. [PMID: 32029842]
  • Mayuko Itaya, Taiki Miyazawa, Jean-Marc Zingg, Takahiro Eitsuka, Angelo Azzi, Mohsen Meydani, Teruo Miyazawa, Kiyotaka Nakagawa. The differential cellular uptake of curcuminoids in vitro depends dominantly on albumin interaction. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Jun; 59(?):152902. doi: 10.1016/j.phymed.2019.152902. [PMID: 30981184]
  • Fuquan Jin, Ying Jin, Jiangxia Du, Liyu Jiang, Ying Zhang, Ziying Zhao, Bo Yang, Peihua Luo, Qiaojun He. Bisdemethoxycurcumin protects against renal fibrosis via activation of fibroblast apoptosis. European journal of pharmacology. 2019 Mar; 847(?):26-31. doi: 10.1016/j.ejphar.2019.01.012. [PMID: 30660576]
  • Meng Fu, Shuilian Fu, Saihong Ni, Danni Wang, Tie Hong. Inhibitory effects of bisdemethoxycurcumin on mast cell-mediated allergic diseases. International immunopharmacology. 2018 Dec; 65(?):182-189. doi: 10.1016/j.intimp.2018.10.005. [PMID: 30316076]
  • Chengxin Wu, Wei Wang, Feifei Quan, Pengfei Chen, Jiali Qian, Lei Zhou, Qiaosheng Pu. Sensitive analysis of curcuminoids via micellar electrokinetic chromatography with laser-induced native fluorescence detection and mixed micelles-induced fluorescence synergism. Journal of chromatography. A. 2018 Aug; 1564(?):207-213. doi: 10.1016/j.chroma.2018.06.012. [PMID: 29891402]
  • Martin Purpura, Ryan P Lowery, Jacob M Wilson, Haider Mannan, Gerald Münch, Valentina Razmovski-Naumovski. Analysis of different innovative formulations of curcumin for improved relative oral bioavailability in human subjects. European journal of nutrition. 2018 Apr; 57(3):929-938. doi: 10.1007/s00394-016-1376-9. [PMID: 28204880]
  • Guo-Yun Liu, Yong-Zheng Sun, Na Zhou, Xiu-Mei Du, Jie Yang, Shang-Jing Guo. 3,3'-OH curcumin causes apoptosis in HepG2 cells through ROS-mediated pathway. European journal of medicinal chemistry. 2016 Apr; 112(?):157-163. doi: 10.1016/j.ejmech.2016.02.019. [PMID: 26894841]
  • Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Francesca Condello, Agnese Petrini, Rosario Scopelliti, Tina Riedel, Paul J Dyson. Organometallic rhodium(III) and iridium(III) cyclopentadienyl complexes with curcumin and bisdemethoxycurcumin co-ligands. Dalton transactions (Cambridge, England : 2003). 2015 Dec; 44(47):20523-31. doi: 10.1039/c5dt03037d. [PMID: 26548708]
  • Arul Prakash Francis, Selvam Ganapathy, Venkata Rajsekhar Palla, Prakhya Balakrishna Murthy, Thiyagarajan Devasena. Future of nano bisdemethoxy curcumin analog: guaranteeing safer intravenous delivery. Environmental toxicology and pharmacology. 2015 Jan; 39(1):467-74. doi: 10.1016/j.etap.2014.12.018. [PMID: 25596481]
  • Christina Schiborr, Alexa Kocher, Dariush Behnam, Josef Jandasek, Simone Toelstede, Jan Frank. The oral bioavailability of curcumin from micronized powder and liquid micelles is significantly increased in healthy humans and differs between sexes. Molecular nutrition & food research. 2014 Mar; 58(3):516-27. doi: 10.1002/mnfr.201300724. [PMID: 24402825]
  • Hiroki Sato, Victor Tuan Giam Chuang, Keishi Yamasaki, Noriyuki Yamaotsu, Hiroshi Watanabe, Kohei Nagumo, Makoto Anraku, Daisuke Kadowaki, Yu Ishima, Shuichi Hirono, Masaki Otagiri, Toru Maruyama. Differential effects of methoxy group on the interaction of curcuminoids with two major ligand binding sites of human serum albumin. PloS one. 2014; 9(2):e87919. doi: 10.1371/journal.pone.0087919. [PMID: 24498401]
  • Mei-Chun Kou, Shu-Yuan Chiou, Ching-Yi Weng, Lisu Wang, Chi-Tang Ho, Ming-Jiuan Wu. Curcuminoids distinctly exhibit antioxidant activities and regulate expression of scavenger receptors and heme oxygenase-1. Molecular nutrition & food research. 2013 Sep; 57(9):1598-610. doi: 10.1002/mnfr.201200227. [PMID: 23386263]
  • Kun Wang, Feng Qiu. Curcuminoid metabolism and its contribution to the pharmacological effects. Current drug metabolism. 2013 Sep; 14(7):791-806. doi: 10.2174/13892002113149990102. [PMID: 23937173]
  • Yanyu Xiao, Xi Chen, Liu Yang, Xieting Zhu, Lang Zou, Fanfei Meng, Qineng Ping. Preparation and oral bioavailability study of curcuminoid-loaded microemulsion. Journal of agricultural and food chemistry. 2013 Apr; 61(15):3654-60. doi: 10.1021/jf400002x. [PMID: 23451842]
  • Jun Li, Yue Liu, Jun-Qi Wei, Kun Wang, Li-Xia Chen, Xin-Sheng Yao, Feng Qiu. Isolation and identification of phase 1 metabolites of curcuminoids in rats. Planta medica. 2012 Aug; 78(12):1351-6. doi: 10.1055/s-0032-1314990. [PMID: 22753036]
  • Wanwarang Wongcharoen, Sasivimon Jai-Aue, Arintaya Phrommintikul, Weerachai Nawarawong, Surin Woragidpoonpol, Thitipong Tepsuwan, Apichard Sukonthasarn, Nattayaporn Apaijai, Nipon Chattipakorn. Effects of curcuminoids on frequency of acute myocardial infarction after coronary artery bypass grafting. The American journal of cardiology. 2012 Jul; 110(1):40-4. doi: 10.1016/j.amjcard.2012.02.043. [PMID: 22481014]
  • Rui Li, Xue Qiao, Qingyan Li, Rong He, Min Ye, Cheng Xiang, Xionghao Lin, Dean Guo. Metabolic and pharmacokinetic studies of curcumin, demethoxycurcumin and bisdemethoxycurcumin in mice tumor after intragastric administration of nanoparticle formulations by liquid chromatography coupled with tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Sep; 879(26):2751-8. doi: 10.1016/j.jchromb.2011.07.042. [PMID: 21856253]
  • John Cuomo, Giovanni Appendino, Adam S Dern, Erik Schneider, Toni P McKinnon, Mark J Brown, Stefano Togni, Brian M Dixon. Comparative absorption of a standardized curcuminoid mixture and its lecithin formulation. Journal of natural products. 2011 Apr; 74(4):664-9. doi: 10.1021/np1007262. [PMID: 21413691]
  • Chatchawan Changtam, Poonpilas Hongmanee, Apichart Suksamrarn. Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. European journal of medicinal chemistry. 2010 Oct; 45(10):4446-57. doi: 10.1016/j.ejmech.2010.07.003. [PMID: 20691508]
  • Yunbao Liu, Muraleedharan G Nair. An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds. Journal of natural products. 2010 Jul; 73(7):1193-5. doi: 10.1021/np1000945. [PMID: 20565070]
  • Chatchawan Changtam, Harry P de Koning, Hasan Ibrahim, M Sohail Sajid, Matthew K Gould, Apichart Suksamrarn. Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species. European journal of medicinal chemistry. 2010 Mar; 45(3):941-56. doi: 10.1016/j.ejmech.2009.11.035. [PMID: 20004045]
  • R Douglas Shytle, Paula C Bickford, Kavon Rezai-zadeh, L Hou, Jin Zeng, Jun Tan, Paul R Sanberg, Cyndy D Sanberg, Bill Roschek, Ryan C Fink, Randall S Alberte. Optimized turmeric extracts have potent anti-amyloidogenic effects. Current Alzheimer research. 2009 Dec; 6(6):564-71. doi: 10.2174/156720509790147115. [PMID: 19715544]
  • S Mahattanadul, T Nakamura, P Panichayupakaranant, N Phdoongsombut, K Tungsinmunkong, P Bouking. Comparative antiulcer effect of bisdemethoxycurcumin and curcumin in a gastric ulcer model system. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2009 Apr; 16(4):342-51. doi: 10.1016/j.phymed.2008.12.005. [PMID: 19188055]
  • Songyot Anuchapreeda, Singkome Tima, Chadarat Duangrat, Pornngarm Limtrakul. Effect of pure curcumin, demethoxycurcumin, and bisdemethoxycurcumin on WT1 gene expression in leukemic cell lines. Cancer chemotherapy and pharmacology. 2008 Sep; 62(4):585-94. doi: 10.1007/s00280-007-0642-1. [PMID: 18034345]
  • Hyun-Ock Pae, Sun-Oh Jeong, Hak Sung Kim, Seong Heak Kim, Yung Sun Song, Sung-kwun Kim, Kyu-Yun Chai, Hun-Taeg Chung. Dimethoxycurcumin, a synthetic curcumin analogue with higher metabolic stability, inhibits NO production, inducible NO synthase expression and NF-kappaB activation in RAW264.7 macrophages activated with LPS. Molecular nutrition & food research. 2008 Sep; 52(9):1082-91. doi: 10.1002/mnfr.200700333. [PMID: 18481332]
  • Marlène Backleh-Sohrt, Perihan Ekici, Guenter Leupold, Harun Parlar. Efficiency of foam fractionation for the enrichment of nonpolar compounds from aqueous extracts of plant materials. Journal of natural products. 2005 Sep; 68(9):1386-9. doi: 10.1021/np049743e. [PMID: 16180819]
  • Narasimhanaidu Kamalakkannan, Rajagopalan Rukkumani, Penumathsa Suresh Varma, Periyasamy Viswanathan, Kallikat Narayanan Rajasekharan, Venugopal Padmanabhan Menon. Comparative effects of curcumin and an analogue of curcumin in carbon tetrachloride-induced hepatotoxicity in rats. Basic & clinical pharmacology & toxicology. 2005 Jul; 97(1):15-21. doi: 10.1111/j.1742-7843.2005.pto_97103.x. [PMID: 15943754]
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  • Lisa A May, Elena Tourkina, Stanley R Hoffman, Thomas A Dix. Detection and quantitation of curcumin in mouse lung cell cultures by matrix-assisted laser desorption ionization time of flight mass spectrometry. Analytical biochemistry. 2005 Feb; 337(1):62-9. doi: 10.1016/j.ab.2004.10.037. [PMID: 15649376]
  • Pornngarm Limtrakul, Songyot Anuchapreeda, Duang Buddhasukh. Modulation of human multidrug-resistance MDR-1 gene by natural curcuminoids. BMC cancer. 2004 Apr; 4(?):13. doi: 10.1186/1471-2407-4-13. [PMID: 15090070]
  • Anusuya Srivivasan, Venugopal P Menon, Viswanathan Periaswamy, K N Rajasekaran. Protection of pancreatic beta-cell by the potential antioxidant bis-o-hydroxycinnamoyl methane, analogue of natural curcuminoid in experimental diabetes. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2003 Sep; 6(3):327-33. doi: NULL. [PMID: 14738713]
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