Demethoxycurcumin (BioDeep_00000860097)

Main id: BioDeep_00000004132

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


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

化学式: C20H18O5 (338.1154178)
中文名称: 去甲氧基姜黄素
谱图信息: 最多检出来源 () 0%

Reviewed

Last reviewed on 2024-08-21.

Cite this Page

Demethoxycurcumin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/demethoxycurcumin (retrieved 2024-11-24) (BioDeep RN: BioDeep_00000860097). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: COC1=C(C=CC(=C1)C=CC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
InChI: InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+

描述信息

Demethoxycurcumin is the main active component of curcumin and has been shown to have anti-inflammatory and toxic effects on cancer cells.
Demethoxycurcumin is the main active component of curcumin and has been shown to have anti-inflammatory and toxic effects on cancer cells.

同义名列表

21 个代谢物同义名

1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-, (1E,6E)-; (1E,6E)-1-(4-HYDROXY-3-METHOXY-PHENYL)-7-(4-HYDROXYPHENYL)HEPTA-1,6-DIENE-3,5-DIONE; (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; 1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)- (VAN); 1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-; 1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; 1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione; Feruloyl-P-hydroxycinnnamoylmethane; 4-hydroxycinnamoyl(feroyl)methane; Demethoxycurcumin; AIDS-110025; 33171-16-3; AIDS110025; 22608-11-3; 24939-17-1; NSC687841; BHCFM; Curcumin II; Desmethoxycurcumin; Monodemethoxycurcumin



数据库引用编号

9 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)

63 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

  • Munirah F Aldayel. Enhancement of the Bioactive Compound Content and Antibacterial Activities in Curcuma Longa Using Zinc Oxide Nanoparticles. Molecules (Basel, Switzerland). 2023 Jun; 28(13):. doi: 10.3390/molecules28134935. [PMID: 37446597]
  • Jianmin Sang, Jinjin Chu, Xin Zhao, Hehua Quan, Zhongyao Ji, Shaowei Wang, Yunbing Tang, Zhiyan Hu, Huitao Li, Linxi Li, Ren-Shan Ge. Curcuminoids inhibit human and rat placental 3β-hydroxysteroid dehydrogenases: Structure-activity relationship and in silico docking analysis. Journal of ethnopharmacology. 2023 Apr; 305(?):116051. doi: 10.1016/j.jep.2022.116051. [PMID: 36572324]
  • Kiran Bharat Lokhande, Sarika Vishnu Pawar, Smriti Madkaiker, Ashish Shrivastava, Swamy K Venkateswara, Neelu Nawani, Minal Wani, Payel Ghosh, Ashutosh Singh. Screening of potential phytomolecules against MurG as drug target in nosocomial pathogen Pseudomonas aeruginosa: perceptions from computational campaign. Journal of biomolecular structure & dynamics. 2023 Mar; ?(?):1-14. doi: 10.1080/07391102.2023.2194005. [PMID: 36974974]
  • Yangyang Liao, Xinjie Zhang, Dongyi Cao, Fei Wang, Hulan Chen, Rui Li. Separation and identification of terpene-conjugated curcuminoids based on liquid chromatography-tandem mass spectrometry and their in vitro anti-inflammatory activities. Journal of separation science. 2023 Mar; ?(?):e2200789. doi: 10.1002/jssc.202200789. [PMID: 36892097]
  • 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]
  • Binjie Lu, Xiaolei Chen, Hua Chen, Qian Li, Hongwei Li, Yue Xu, Yuwei Li, Xiaofeng Shen, Rilei Jiang. Demethoxycurcumin mitigates inflammatory responses in lumbar disc herniation via MAPK and NF-κB pathways in vivo and in vitro. International immunopharmacology. 2022 Jul; 108(?):108914. doi: 10.1016/j.intimp.2022.108914. [PMID: 35729841]
  • Verónica Ibáñez Gaspar, Jasmin McCaul, Hilary Cassidy, Craig Slattery, Tara McMorrow. Effects of Curcumin Analogues DMC and EF24 in Combination with the Cytokine TRAIL against Kidney Cancer. Molecules (Basel, Switzerland). 2021 Oct; 26(20):. doi: 10.3390/molecules26206302. [PMID: 34684883]
  • Ahmed Alalaiwe, Jia-You Fang, Hsien-Ju Lee, Chun-Hui Chiu, Ching-Yun Hsu. The Demethoxy Derivatives of Curcumin Exhibit Greater Differentiation Suppression in 3T3-L1 Adipocytes Than Curcumin: A Mechanistic Study of Adipogenesis and Molecular Docking. Biomolecules. 2021 07; 11(7):. doi: 10.3390/biom11071025. [PMID: 34356649]
  • Thalita Alves Zanetti, Bruna Isabela Biazi, Giuliana Castello Coatti, Adrivanio Baranoski, Lilian Areal Marques, Amanda Cristina Corveloni, Mario Sergio Mantovani. Dimethoxycurcumin reduces proliferation and induces apoptosis in renal tumor cells more efficiently than demethoxycurcumin and curcumin. Chemico-biological interactions. 2021 Apr; 338(?):109410. doi: 10.1016/j.cbi.2021.109410. [PMID: 33582110]
  • Yi-Ming Chen, Wan-Chun Chiu, Yen-Shuo Chiu, Tong Li, Hsin-Ching Sung, Chien-Yu Hsiao. Supplementation of nano-bubble curcumin extract improves gut microbiota composition and exercise performance in mice. Food & function. 2020 Apr; 11(4):3574-3584. doi: 10.1039/c9fo02487e. [PMID: 32271330]
  • Jian-Liang Zhou, Jia-Yi Zheng, Xia-Qian Cheng, Gui-Zhong Xin, Shu-Ling Wang, Tian Xie. Chemical markers' knockout coupled with UHPLC-HRMS-based metabolomics reveals anti-cancer integration effects of the curcuminoids of turmeric (Curcuma longa L.) on lung cancer cell line. Journal of pharmaceutical and biomedical analysis. 2019 Oct; 175(?):112738. doi: 10.1016/j.jpba.2019.06.035. [PMID: 31362249]
  • Gabriel Manarin, Daniela Anderson, Jorgete Maria E Silva, Juliana da Silva Coppede, Persio Roxo-Junior, Ana Maria Soares Pereira, Fabio Carmona. Curcuma longa L. ameliorates asthma control in children and adolescents: A randomized, double-blind, controlled trial. Journal of ethnopharmacology. 2019 Jun; 238(?):111882. doi: 10.1016/j.jep.2019.111882. [PMID: 30991137]
  • 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]
  • Amrit Poudel, Jitendra Pandey, Hyeong-Kyu Lee. Geographical Discrimination in Curcuminoids Content of Turmeric Assessed by Rapid UPLC-DAD Validated Analytical Method. Molecules (Basel, Switzerland). 2019 May; 24(9):. doi: 10.3390/molecules24091805. [PMID: 31083285]
  • Jesmin Akter, Md Amzad Hossain, Kensaku Takara, Md Zahorul Islam, De-Xing Hou. Antioxidant activity of different species and varieties of turmeric (Curcuma spp): Isolation of active compounds. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2019 Jan; 215(?):9-17. doi: 10.1016/j.cbpc.2018.09.002. [PMID: 30266519]
  • 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]
  • Jagdish Mahale, Rajinder Singh, Lynne M Howells, Robert G Britton, Sameena M Khan, Karen Brown. Detection of Plasma Curcuminoids from Dietary Intake of Turmeric-Containing Food in Human Volunteers. Molecular nutrition & food research. 2018 08; 62(16):e1800267. doi: 10.1002/mnfr.201800267. [PMID: 29943914]
  • In-Cheng Chao, Chun-Ming Wang, Shao-Ping Li, Li-Gen Lin, Wen-Cai Ye, Qing-Wen Zhang. Simultaneous Quantification of Three Curcuminoids and Three Volatile Components of Curcuma longa Using Pressurized Liquid Extraction and High-Performance Liquid Chromatography. Molecules (Basel, Switzerland). 2018 06; 23(7):. doi: 10.3390/molecules23071568. [PMID: 29958431]
  • Wirginia Kukula-Koch, Aneta Grabarska, Jarogniew Łuszczki, Lidia Czernicka, Ewa Nowosadzka, Ewelina Gumbarewicz, Agata Jarząb, Gregoire Audo, Shakti Upadhyay, Kazimierz Głowniak, Andrzej Stepulak. Superior anticancer activity is demonstrated by total extract of Curcuma longa L. as opposed to individual curcuminoids separated by centrifugal partition chromatography. Phytotherapy research : PTR. 2018 May; 32(5):933-942. doi: 10.1002/ptr.6035. [PMID: 29368356]
  • 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]
  • Zeynep Kalaycıoğlu, Işıl Gazioğlu, F Bedia Erim. Comparison of antioxidant, anticholinesterase, and antidiabetic activities of three curcuminoids isolated from Curcuma longa L. Natural product research. 2017 Dec; 31(24):2914-2917. doi: 10.1080/14786419.2017.1299727. [PMID: 28287280]
  • Donald J Messner, Christine Surrago, Celia Fiordalisi, Wing Yin Chung, Kris V Kowdley. Isolation and characterization of iron chelators from turmeric (Curcuma longa): selective metal binding by curcuminoids. Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine. 2017 Oct; 30(5):699-708. doi: 10.1007/s10534-017-0038-6. [PMID: 28801864]
  • Annika Frank, Saleh Abu-Lafi, Azmi Adawi, Johannes S Schwed, Holger Stark, Anwar Rayan. From medicinal plant extracts to defined chemical compounds targeting the histamine H4 receptor: Curcuma longa in the treatment of inflammation. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2017 Oct; 66(10):923-929. doi: 10.1007/s00011-017-1075-x. [PMID: 28647836]
  • Long Chen, Lei Shi, Wenhua Wang, Youxin Zhou. ABCG2 downregulation in glioma stem cells enhances the therapeutic efficacy of demethoxycurcumin. Oncotarget. 2017 Jun; 8(26):43237-43247. doi: 10.18632/oncotarget.18018. [PMID: 28591733]
  • Supawadee Burapan, Mihyang Kim, Jaehong Han. Curcuminoid Demethylation as an Alternative Metabolism by Human Intestinal Microbiota. Journal of agricultural and food chemistry. 2017 Apr; 65(16):3305-3310. doi: 10.1021/acs.jafc.7b00943. [PMID: 28401758]
  • Muthu Ramkumar, Srinivasagam Rajasankar, Veerappan Venkatesh Gobi, Chinnasamy Dhanalakshmi, Thamilarasan Manivasagam, Arokiasamy Justin Thenmozhi, Musthafa Mohamed Essa, Ameer Kalandar, Ranganathan Chidambaram. Neuroprotective effect of Demethoxycurcumin, a natural derivative of Curcumin on rotenone induced neurotoxicity in SH-SY 5Y Neuroblastoma cells. BMC complementary and alternative medicine. 2017 Apr; 17(1):217. doi: 10.1186/s12906-017-1720-5. [PMID: 28420370]
  • Gary N Asher, Ying Xie, Ruin Moaddel, Mitesh Sanghvi, Katina S S Dossou, Angela D M Kashuba, Robert S Sandler, Roy L Hawke. Randomized Pharmacokinetic Crossover Study Comparing 2 Curcumin Preparations in Plasma and Rectal Tissue of Healthy Human Volunteers. Journal of clinical pharmacology. 2017 02; 57(2):185-193. doi: 10.1002/jcph.806. [PMID: 27503249]
  • Caiyun Wang, Xuan Chen, Shuang Hu, Xiaohong Bai. Development of a novel stirrerliquid/solid microextraction method for the separation and enrichment of trace levels of active compounds in traditional Chinese medicine. Journal of separation science. 2016 Nov; 39(22):4290-4298. doi: 10.1002/jssc.201600605. [PMID: 27659768]
  • Yonglu Wang, Liyao Wang, Xinyi Zhu, Dong Wang, Xueming Li. Choleretic Activity of Turmeric and its Active Ingredients. Journal of food science. 2016 Jul; 81(7):H1800-6. doi: 10.1111/1750-3841.13348. [PMID: 27228476]
  • Trong Tuan Dao, Pankaj Sehgal, Truong Thanh Tung, Jesper Vuust Møller, John Nielsen, Michael Palmgren, Søren Brøgger Christensen, Anja Thoe Fuglsang. Demethoxycurcumin Is A Potent Inhibitor of P-Type ATPases from Diverse Kingdoms of Life. PloS one. 2016; 11(9):e0163260. doi: 10.1371/journal.pone.0163260. [PMID: 27644036]
  • Pei-pei Zhou, Jin-feng Shan, Jian-lan Jiang. [Extraction Optimization of Rhizome of Curcuma longa by Response Surface Methodology and Support Vector Regression]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Dec; 38(12):2611-5. doi: ". [PMID: 27352545]
  • Y Panahi, M Ghanei, S Bashiri, A Hajihashemi, A Sahebkar. Short-term Curcuminoid Supplementation for Chronic Pulmonary Complications due to Sulfur Mustard Intoxication: Positive Results of a Randomized Double-blind Placebo-controlled Trial. Drug research. 2015 Nov; 65(11):567-73. doi: 10.1055/s-0034-1389986. [PMID: 25268878]
  • Hye-Lim Kwon, Myong-Soo Chung. Pilot-scale subcritical solvent extraction of curcuminoids from Curcuma long L. Food chemistry. 2015 Oct; 185(?):58-64. doi: 10.1016/j.foodchem.2015.03.114. [PMID: 25952841]
  • Odaine N Gordon, Paula B Luis, Rachel E Ashley, Neil Osheroff, Claus Schneider. Oxidative Transformation of Demethoxy- and Bisdemethoxycurcumin: Products, Mechanism of Formation, and Poisoning of Human Topoisomerase IIα. Chemical research in toxicology. 2015 May; 28(5):989-96. doi: 10.1021/acs.chemrestox.5b00009. [PMID: 25806475]
  • Wei Yang, Juan Fu, Miao Yu, Di Wang, Ying Rong, Ping Yao, Andreas K Nüssler, Hong Yan, Liegang Liu. Effects of three kinds of curcuminoids on anti-oxidative system and membrane deformation of human peripheral blood erythrocytes in high glucose levels. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2015; 35(2):789-802. doi: 10.1159/000369738. [PMID: 25634758]
  • Hong-Bin Chang, Bing-Huei Chen. Inhibition of lung cancer cells A549 and H460 by curcuminoid extracts and nanoemulsions prepared from Curcuma longa Linnaeus. International journal of nanomedicine. 2015; 10(?):5059-80. doi: 10.2147/ijn.s87225. [PMID: 26345201]
  • Kazuya Murata, Shinichi Matsumura, Yuri Yoshioka, Yoshihiro Ueno, Hideaki Matsuda. Screening of β-secretase and acetylcholinesterase inhibitors from plant resources. Journal of natural medicines. 2015 Jan; 69(1):123-9. doi: 10.1007/s11418-014-0859-3. [PMID: 25119528]
  • Jian-chun Luo, Xue-yuan Hu, Hong Wang, Yong-hong Zhang, Jing-qing Zhang. [Study on pharmacokinetics of demethoxycurcumin phospholipid complex in rats]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Nov; 37(11):2051-3. doi: NULL. [PMID: 26027131]
  • Kiyotaka Nakagawa, Jean-Marc Zingg, Sharon H Kim, Michael J Thomas, Gregory G Dolnikowski, Angelo Azzi, Teruo Miyazawa, Mohsen Meydani. Differential cellular uptake and metabolism of curcuminoids in monocytes/macrophages: regulatory effects on lipid accumulation. The British journal of nutrition. 2014 Jul; 112(1):8-14. doi: 10.1017/s0007114514000567. [PMID: 24725345]
  • Jueun Lee, Youngae Jung, Jeoung-Hwa Shin, Ho Kyoung Kim, Byeong Cheol Moon, Do Hyun Ryu, Geum-Sook Hwang. Secondary metabolite profiling of Curcuma species grown at different locations using GC/TOF and UPLC/Q-TOF MS. Molecules (Basel, Switzerland). 2014 Jul; 19(7):9535-51. doi: 10.3390/molecules19079535. [PMID: 25000465]
  • Qing-Miao Li, Wen-Yu Yang, Xue-Mei Tang, Mei Zhang, Xian-Jian Zhou, Guang-Ming Shu, Jun-Ning Zhao, Qing-Mao Fang. [Dynamic accumulation regulation of curcumin, demethoxycurcumin and bisdemethoxyeurcumin in three strains of curcuma longae rhizome]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Jun; 39(11):2000-4. doi: ". [PMID: 25272830]
  • 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]
  • Mayura Somchit, Chatchawan Changtam, Rungruedi Kimseng, Tanyarath Utaipan, Monthon Lertcanawanichakul, Apichart Suksamrarn, Warangkana Chunglok. Demethoxycurcumin from Curcuma longa rhizome suppresses iNOS induction in an in vitro inflamed human intestinal mucosa model. Asian Pacific journal of cancer prevention : APJCP. 2014; 15(4):1807-10. doi: 10.7314/apjcp.2014.15.4.1807. [PMID: 24641413]
  • Niyaz Ahmad, Sadiq Umar, Mohammad Ashafaq, Mohd Akhtar, Zeenat Iqbal, Mohd Samim, Farhan Jalees Ahmad. A comparative study of PNIPAM nanoparticles of curcumin, demethoxycurcumin, and bisdemethoxycurcumin and their effects on oxidative stress markers in experimental stroke. Protoplasma. 2013 Dec; 250(6):1327-38. doi: 10.1007/s00709-013-0516-9. [PMID: 23784381]
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  • 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]
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