Dehydrozingerone (BioDeep_00000011918)

 

Secondary id: BioDeep_00001868306

human metabolite Endogenous natural product


代谢物信息卡片


Methyl-3-methoxy-4-hydroxystyryl ketone, (e)-iosmer

化学式: C11H12O3 (192.0786)
中文名称: 脱氢姜酮, 脱氢姜黄素
谱图信息: 最多检出来源 Homo sapiens(not specific) 4.71%

分子结构信息

SMILES: CC(=O)/C=C/c1ccc(c(c1)OC)O
InChI: InChI=1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3+

描述信息

Dehydrozingerone is a flavouring ingredien
Flavouring ingredient

同义名列表

25 个代谢物同义名

Methyl-3-methoxy-4-hydroxystyryl ketone, (e)-iosmer; (3Z)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one; 3-BUTEN-2-ONE, 4-(4-HYDROXY-3-METHOXYPHENYL)-; 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one; Methyl-3-methoxy-4-hydroxy styryl ketone; Methyl-3-methoxy-4-hydroxystyryl ketone; 4-Hydroxy-3-methoxystyryl methyl ketone; 4-Hydroxy-3-methoxybenzylideneacetone; 3-Methoxy-4-hydroxybenzalacetone; 4-Hydroxy-3-methoxybenzalacetone; Vanillylidene acetone; Vanillylidenacetone; Vanillidene acetone; dehydro-[0]-Paradol; [0]-Dehydroparadol; Dehydrozingerone; Vanylidenacetone; Dehydrozingerol; Feruloylmethane; Vanillalacetone; FEMA 3738; MMHSK; MHSK; Dehydrozingerone; Dehydrozingerone



数据库引用编号

22 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)

16 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
Cytoplasm 12 ALB, ARG2, CAT, CDH1, CTNNB1, ELANE, MAPK14, MAPK8, MSMP, MTOR, PRKAA2, VEGFA
Peripheral membrane protein 1 MTOR
Endosome membrane 1 CD68
Endoplasmic reticulum membrane 1 MTOR
Nucleus 9 ALB, CDH1, CTNNB1, MAPK14, MAPK8, MPO, MTOR, PRKAA2, VEGFA
cytosol 10 ALB, CAT, CDH1, CTNNB1, ELANE, GSR, MAPK14, MAPK8, MTOR, PRKAA2
dendrite 2 MTOR, PRKAA2
phagocytic vesicle 2 ELANE, MTOR
trans-Golgi network 1 CDH1
centrosome 2 ALB, CTNNB1
nucleoplasm 7 CDH1, CTNNB1, MAPK14, MAPK8, MPO, MTOR, PRKAA2
Cell membrane 4 CDH1, CTNNB1, HTR3A, TNF
Cytoplasmic side 1 MTOR
Cleavage furrow 1 HTR3A
lamellipodium 2 CDH1, CTNNB1
Multi-pass membrane protein 1 HTR3A
Golgi apparatus membrane 1 MTOR
Synapse 3 CTNNB1, HTR3A, MAPK8
cell cortex 1 CTNNB1
cell junction 2 CDH1, CTNNB1
cell surface 3 ELANE, TNF, VEGFA
glutamatergic synapse 3 CDH1, CTNNB1, MAPK14
Golgi apparatus 4 ALB, CDH1, PRKAA2, VEGFA
Golgi membrane 2 INS, MTOR
lysosomal membrane 2 CD68, MTOR
neuronal cell body 2 PRKAA2, TNF
postsynapse 2 CDH1, HTR3A
presynaptic membrane 1 CTNNB1
Lysosome 3 CD68, MPO, MTOR
endosome 1 CDH1
plasma membrane 5 CD68, CDH1, CTNNB1, HTR3A, TNF
Membrane 8 CAT, CD68, CDH1, CTNNB1, HTR3A, MTOR, PRKAA2, VEGFA
axon 2 MAPK8, PRKAA2
basolateral plasma membrane 1 CTNNB1
extracellular exosome 7 ALB, CAT, CDH1, CTNNB1, ELANE, GSR, MPO
Lysosome membrane 2 CD68, MTOR
endoplasmic reticulum 2 ALB, VEGFA
extracellular space 9 ALB, CRP, ELANE, IL6, INS, MPO, MSMP, TNF, VEGFA
perinuclear region of cytoplasm 2 CDH1, CTNNB1
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 3 CDH1, CTNNB1, VEGFA
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
mitochondrion 4 ARG2, CAT, GSR, MAPK14
protein-containing complex 3 ALB, CAT, CTNNB1
intracellular membrane-bounded organelle 2 CAT, MPO
Microsome membrane 1 MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 2 CD68, CDH1
Secreted 6 ALB, CRP, IL6, INS, MSMP, VEGFA
extracellular region 11 ALB, CAT, CDH1, CRP, ELANE, IL6, INS, MAPK14, MPO, TNF, VEGFA
cytoplasmic side of plasma membrane 1 CDH1
Mitochondrion outer membrane 1 MTOR
mitochondrial outer membrane 1 MTOR
mitochondrial matrix 3 ARG2, CAT, GSR
anchoring junction 1 ALB
transcription regulator complex 1 CTNNB1
nuclear membrane 1 CDH1
external side of plasma membrane 2 GSR, TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
actin cytoskeleton 1 CDH1
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
Wnt signalosome 1 CTNNB1
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 2 CTNNB1, HTR3A
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 CTNNB1
focal adhesion 2 CAT, CTNNB1
Cell junction, adherens junction 2 CDH1, CTNNB1
flotillin complex 2 CDH1, CTNNB1
extracellular matrix 1 VEGFA
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 1 ELANE
secretory granule 3 ELANE, MPO, VEGFA
fascia adherens 1 CTNNB1
lateral plasma membrane 2 CDH1, CTNNB1
nuclear speck 2 MAPK14, PRKAA2
Postsynaptic cell membrane 1 HTR3A
neuron projection 1 HTR3A
ciliary basal body 1 ALB
Late endosome membrane 1 CD68
phagocytic cup 1 TNF
cell periphery 1 CTNNB1
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
centriole 1 ALB
Golgi apparatus, trans-Golgi network 1 CDH1
spindle pole 3 ALB, CTNNB1, MAPK14
blood microparticle 1 ALB
postsynaptic density, intracellular component 1 CTNNB1
serotonin-activated cation-selective channel complex 1 HTR3A
transmembrane transporter complex 1 HTR3A
microvillus membrane 1 CTNNB1
nuclear envelope 1 MTOR
Endomembrane system 2 CTNNB1, MTOR
endosome lumen 1 INS
cytoplasmic stress granule 1 PRKAA2
euchromatin 1 CTNNB1
azurophil granule 1 MPO
ficolin-1-rich granule lumen 2 CAT, MAPK14
secretory granule lumen 3 CAT, INS, MAPK14
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 ALB, IL6, INS
transcription repressor complex 1 ELANE
platelet alpha granule lumen 2 ALB, VEGFA
specific granule lumen 1 ELANE
transport vesicle 1 INS
azurophil granule membrane 1 CD68
beta-catenin-TCF complex 1 CTNNB1
azurophil granule lumen 2 ELANE, MPO
anaphase-promoting complex 1 CDH1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
presynaptic active zone cytoplasmic component 1 CTNNB1
phagocytic vesicle lumen 1 MPO
[Isoform 2]: Nucleus 1 CDH1
protein-DNA complex 1 CTNNB1
basal dendrite 1 MAPK8
apical junction complex 1 CDH1
nucleotide-activated protein kinase complex 1 PRKAA2
Cell junction, desmosome 1 CDH1
desmosome 1 CDH1
Cytoplasmic vesicle, phagosome 2 ELANE, MTOR
catenin complex 2 CDH1, CTNNB1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
beta-catenin-TCF7L2 complex 1 CTNNB1
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Saya Yamano, Yuka Tsukuda, Naoko Mizuhara, Yoshihiro Yamaguchi, Akira Ogita, Ken-Ichi Fujita. Dehydrozingerone enhances the fungicidal activity of glabridin against Saccharomyces cerevisiae and Candida albicans. Letters in applied microbiology. 2023 Apr; 76(4):. doi: 10.1093/lambio/ovad040. [PMID: 36990694]
  • Chunhong Liu, Yetian Li, Chaoling Wen, Zheng Yan, Opeyemi Joshua Olatunji, Zongsheng Yin. Dehydrozingerone Alleviates Hyperalgesia, Oxidative Stress and Inflammatory Factors in Complete Freund's Adjuvant-Induced Arthritic Rats. Drug design, development and therapy. 2022; 16(?):3015-3022. doi: 10.2147/dddt.s374827. [PMID: 36105319]
  • Satya Krishna Tirunavalli, Karthik Gourishetti, Rama Satya Sri Kotipalli, Madusudhana Kuncha, Muralidharan Kathirvel, Rajwinder Kaur, Mahesh Kumar Jerald, Ramakrishna Sistla, Sai Balaji Andugulapati. Dehydrozingerone ameliorates Lipopolysaccharide induced acute respiratory distress syndrome by inhibiting cytokine storm, oxidative stress via modulating the MAPK/NF-κB pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Nov; 92(?):153729. doi: 10.1016/j.phymed.2021.153729. [PMID: 34517257]
  • Pankaj Chibber, Chetan Kumar, Amarinder Singh, Syed Assim Haq, Irfan Ahmed, Anil Kumar, Surjeet Singh, Ram Vishwakarma, Gurdarshan Singh. Anti-inflammatory and analgesic potential of OA-DHZ; a novel semisynthetic derivative of dehydrozingerone. International immunopharmacology. 2020 Jun; 83(?):106469. doi: 10.1016/j.intimp.2020.106469. [PMID: 32251963]
  • Xiangmin Song, Xinyue Zhu, Ting Li, Cai Liang, Meng Zhang, Yu Shao, Jun Tao, Ranfeng Sun. Dehydrozingerone Inspired Discovery of Potential Broad-Spectrum Fungicidal Agents as Ergosterol Biosynthesis Inhibitors. Journal of agricultural and food chemistry. 2019 Oct; 67(41):11354-11363. doi: 10.1021/acs.jafc.9b04231. [PMID: 31532666]
  • Chetan Kumar, Reyaz Ur Rasool, Zainab Iqra, Yedukondalu Nalli, Prabhu Dutt, Naresh K Satti, Neha Sharma, Sumit G Gandhi, Anindya Goswami, Asif Ali. Alkyne-azide cycloaddition analogues of dehydrozingerone as potential anti-prostate cancer inhibitors via the PI3K/Akt/NF-kB pathway. MedChemComm. 2017 Nov; 8(11):2115-2124. doi: 10.1039/c7md00267j. [PMID: 30108729]
  • Marco A Obregón-Mendoza, María Mirian Estévez-Carmona, Simón Hernández-Ortega, Manuel Soriano-García, María Teresa Ramírez-Apan, Laura Orea, Hugo Pilotzi, Dino Gnecco, Julia Cassani, Raúl G Enríquez. Retro-Curcuminoids as Mimics of Dehydrozingerone and Curcumin: Synthesis, NMR, X-ray, and Cytotoxic Activity. Molecules (Basel, Switzerland). 2016 Dec; 22(1):. doi: 10.3390/molecules22010033. [PMID: 28036082]
  • Su Jin Kim, Hong Min Kim, Eun Soo Lee, Nami Kim, Jung Ok Lee, Hye Jeong Lee, Na Yeon Park, Joo Yeon Jo, Bo Young Ham, Si Hyun Han, Sun Hwa Park, Choon Hee Chung, Hyeon Soo Kim. Dehydrozingerone exerts beneficial metabolic effects in high-fat diet-induced obese mice via AMPK activation in skeletal muscle. Journal of cellular and molecular medicine. 2015 Mar; 19(3):620-9. doi: 10.1111/jcmm.12455. [PMID: 25582026]
  • Débora M Martinez, Angelita Barcellos, Angela M Casaril, Lucielli Savegnago, Eder J Lernardão. Antidepressant-like activity of dehydrozingerone: involvement of the serotonergic and noradrenergic systems. Pharmacology, biochemistry, and behavior. 2014 Dec; 127(?):111-7. doi: 10.1016/j.pbb.2014.10.010. [PMID: 25449795]
  • Vessela Kancheva, Adriana Slavova-Kazakova, Davide Fabbri, Maria Antonietta Dettori, Giovanna Delogu, Michał Janiak, Ryszard Amarowicz. Protective effects of equimolar mixtures of monomer and dimer of dehydrozingerone with α-tocopherol and/or ascorbyl palmitate during bulk lipid autoxidation. Food chemistry. 2014 Aug; 157(?):263-74. doi: 10.1016/j.foodchem.2014.02.036. [PMID: 24679780]
  • I Rahath Kubra, Pushpa S Murthy, L Jagan Mohan Rao. In vitro antifungal activity of dehydrozingerone and its fungitoxic properties. Journal of food science. 2013 Jan; 78(1):M64-9. doi: 10.1111/j.1750-3841.2012.03009.x. [PMID: 23278709]
  • Takao Koeduka, Bunta Watanabe, Shiro Suzuki, Jun Hiratake, Jun'ichi Mano, Kazufumi Yazaki. Characterization of raspberry ketone/zingerone synthase, catalyzing the alpha, beta-hydrogenation of phenylbutenones in raspberry fruits. Biochemical and biophysical research communications. 2011 Aug; 412(1):104-8. doi: 10.1016/j.bbrc.2011.07.052. [PMID: 21802408]
  • Wolfgang W Quitschke. Differential solubility of curcuminoids in serum and albumin solutions: implications for analytical and therapeutic applications. BMC biotechnology. 2008 Nov; 8(?):84. doi: 10.1186/1472-6750-8-84. [PMID: 18990234]
  • Li-yao Wang, Mian Zhang, Chao-feng Zhang, Zheng-tao Wang. Alkaloid and sesquiterpenes from the root tuber of Curcuma longa. Yao xue xue bao = Acta pharmaceutica Sinica. 2008 Jul; 43(7):724-7. doi: . [PMID: 18819476]
  • Desen Zheng, Geza Hrazdina. Molecular and biochemical characterization of benzalacetone synthase and chalcone synthase genes and their proteins from raspberry (Rubus idaeus L.). Archives of biochemistry and biophysics. 2008 Feb; 470(2):139-45. doi: 10.1016/j.abb.2007.11.013. [PMID: 18068110]
  • Chisako Yamagami, Miki Akamatsu, Noriko Motohashi, Shogo Hamada, Takao Tanahashi. Quantitative structure-activity relationship studies for antioxidant hydroxybenzalacetones by quantum chemical- and 3-D-QSAR(CoMFA) analyses. Bioorganic & medicinal chemistry letters. 2005 Jun; 15(11):2845-50. doi: 10.1016/j.bmcl.2005.03.087. [PMID: 15911266]
  • Ping-Chung Kuo, Amooru G Damu, Ching-Yuh Cherng, Jye-Fu Jeng, Che-Ming Teng, E-Jian Lee, Tian-Shung Wu. Isolation of a natural antioxidant, dehydrozingerone from Zingiber officinale and synthesis of its analogues for recognition of effective antioxidant and antityrosinase agents. Archives of pharmacal research. 2005 May; 28(5):518-28. doi: 10.1007/bf02977752. [PMID: 15974436]
  • M Rao, M M Kumar, M A Rao. In vitro and in vivo effects of phenolic antioxidants against cisplatin-induced nephrotoxicity. Journal of biochemistry. 1999 Feb; 125(2):383-90. doi: 10.1093/oxfordjournals.jbchem.a022298. [PMID: 9990138]
  • K I Priyadarsini, S N Guha, M N Rao. Physico-chemical properties and antioxidant activities of methoxy phenols. Free radical biology & medicine. 1998 Apr; 24(6):933-41. doi: 10.1016/s0891-5849(97)00382-1. [PMID: 9607603]
  • D V Rajakumar, M N Rao. Antioxidant properties of dehydrozingerone and curcumin in rat brain homogenates. Molecular and cellular biochemistry. 1994 Nov; 140(1):73-9. doi: 10.1007/bf00928368. [PMID: 7877600]
  • D V Rajakumar, M N Rao. Dehydrozingerone and its analogues as inhibitors of nonenzymatic lipid peroxidation. Die Pharmazie. 1994 Jul; 49(7):516-9. doi: ". [PMID: 8073062]
  • D V Rajakumar, M N Rao. Dehydrozingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers. Biochemical pharmacology. 1993 Dec; 46(11):2067-72. doi: 10.1016/0006-2952(93)90649-h. [PMID: 8267655]
  • G Elias, M N Rao. Inhibition of albumin denaturation and antiinflammatory activity of dehydrozingerone and its analogs. Indian journal of experimental biology. 1988 Jul; 26(7):540-2. doi: . [PMID: 3198157]
  • G B Singh, G D Leach, C K Atal. Antiinflammatory actions of methyl- and phenyl-3-methoxy-4-hydroxy styryl ketones. Arzneimittel-Forschung. 1987 Apr; 37(4):435-40. doi: . [PMID: 3496890]