Gardenin B (BioDeep_00000010424)

Main id: BioDeep_00000230807

 

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


5-Hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one

化学式: C19H18O7 (358.1052)
中文名称: 栀子黄素 B
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(c(c(c2c(c1OC)oc(cc2=O)c1ccc(cc1)OC)O)OC)OC
InChI: InChI=1S/C19H18O7/c1-22-11-7-5-10(6-8-11)13-9-12(20)14-15(21)17(23-2)19(25-4)18(24-3)16(14)26-13/h5-9,21H,1-4H3

描述信息

Gardenin b, also known as demethyltangeretin or 5-hydroxy-4,6,7,8-tetramethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, gardenin b is considered to be a flavonoid lipid molecule. Gardenin b is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Gardenin b can be found in mandarin orange (clementine, tangerine), peppermint, sweet basil, and winter savory, which makes gardenin b a potential biomarker for the consumption of these food products.
Gardenin B is a flavonoid isolated from Gardenia jasminoides. Gardenin B induces cell death in human leukemia cells involves multiple caspases[1].
Gardenin B is a flavonoid isolated from Gardenia jasminoides. Gardenin B induces cell death in human leukemia cells involves multiple caspases[1].

同义名列表

8 个代谢物同义名

5-Hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one; 5-Hydroxy-2-(4-methoxyphenyl)-6,7,8-trimethoxy-4H-1-benzopyran-4-one; 5-Hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one; 5-Hydroxy-4,6,7,8-tetramethoxyflavone; 5-demethyltangeretin; Demethyltangeretin; Gardenin B; Gardenin B



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

114 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 10 ANXA5, CASP2, CASP3, CCNB1, MCL1, MSMP, NQO1, PTGS2, SOD1, TNFSF11
Peripheral membrane protein 2 ANXA5, PTGS2
Endosome membrane 1 CTSD
Endoplasmic reticulum membrane 2 HMOX1, PTGS2
Nucleus 9 CASP2, CASP3, CCNB1, GABPA, HMOX1, MCL1, NQO1, PARP1, SOD1
cytosol 10 ANXA5, CASP2, CASP3, CCNB1, HMOX1, LIPE, MCL1, NQO1, PARP1, SOD1
dendrite 1 NQO1
nuclear body 1 PARP1
centrosome 1 CCNB1
nucleoplasm 7 CASP3, CCNB1, GABPA, HMOX1, MCL1, PARP1, SOD1
Cell membrane 3 LIPE, TNF, TNFSF11
Cytoplasmic side 1 HMOX1
Multi-pass membrane protein 1 CACNA1I
Synapse 1 NQO1
cell surface 1 TNF
glutamatergic synapse 1 CASP3
lysosomal membrane 1 CTSD
neuronal cell body 4 CASP3, NQO1, SOD1, TNF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 3 LIPE, NQO1, PARP1
Lysosome 1 CTSD
plasma membrane 3 CACNA1I, TNF, TNFSF11
Membrane 9 ANXA5, CACNA1I, CCNB1, HMOX1, LIPE, MCL1, NQO1, PARP1, TNFSF11
caveola 2 LIPE, PTGS2
extracellular exosome 3 ANXA5, CTSD, SOD1
endoplasmic reticulum 2 HMOX1, PTGS2
extracellular space 7 CTSD, HMOX1, MSMP, PNLIP, SOD1, TNF, TNFSF11
lysosomal lumen 1 CTSD
perinuclear region of cytoplasm 1 HMOX1
mitochondrion 3 MCL1, PARP1, SOD1
protein-containing complex 3 PARP1, PTGS2, SOD1
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
Secreted 4 MSMP, PNLIP, PRB1, TNFSF11
extracellular region 7 ANXA5, CTSD, PNLIP, PRB1, SOD1, TNF, TNFSF11
Single-pass membrane protein 1 MCL1
mitochondrial outer membrane 2 HMOX1, MCL1
mitochondrial matrix 2 CCNB1, SOD1
transcription regulator complex 1 PARP1
Bcl-2 family protein complex 1 MCL1
external side of plasma membrane 2 ANXA5, TNF
cytoplasmic vesicle 1 SOD1
nucleolus 2 CASP2, PARP1
axon cytoplasm 1 SOD1
recycling endosome 1 TNF
Single-pass type II membrane protein 2 TNF, TNFSF11
Membrane raft 2 CTSD, TNF
focal adhesion 1 ANXA5
Peroxisome 1 SOD1
mitochondrial intermembrane space 1 SOD1
collagen-containing extracellular matrix 2 ANXA5, CTSD
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
dendrite cytoplasm 1 SOD1
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
chromatin 2 GABPA, PARP1
phagocytic cup 1 TNF
Chromosome 1 PARP1
Nucleus, nucleolus 1 PARP1
spindle pole 1 CCNB1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
site of double-strand break 1 PARP1
nuclear envelope 1 PARP1
endosome lumen 1 CTSD
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
myosin complex 1 MCL1
Nucleus, nucleoplasm 1 MCL1
Melanosome 1 CTSD
ficolin-1-rich granule lumen 1 CTSD
endoplasmic reticulum lumen 1 PTGS2
voltage-gated calcium channel complex 1 CACNA1I
specific granule lumen 1 CTSD
tertiary granule lumen 1 CTSD
Single-pass type IV membrane protein 1 HMOX1
outer kinetochore 1 CCNB1
[Isoform 2]: Cytoplasm 1 TNFSF11
[Tumor necrosis factor ligand superfamily member 11, soluble form]: Secreted 1 TNFSF11
vesicle membrane 1 ANXA5
protein-DNA complex 1 PARP1
death-inducing signaling complex 1 CASP3
site of DNA damage 1 PARP1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cyclin B1-CDK1 complex 1 CCNB1
endothelial microparticle 1 ANXA5
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
endopeptidase complex 1 CASP2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Hui-Yun Tsai, Jia-Fang Yang, Yin-Bo Chen, Jia-Lin Guo, Shiming Li, Guor-Jien Wei, Chi-Tang Ho, Jue-Liang Hsu, Chi-I Chang, Yu-Shen Liang, Hsu-Sheng Yu, Yu-Kuo Chen. Acetylation Enhances the Anticancer Activity and Oral Bioavailability of 5-Demethyltangeretin. International journal of molecular sciences. 2022 Oct; 23(21):. doi: 10.3390/ijms232113284. [PMID: 36362072]
  • Ahmed A Al-Karmalawy, Mai M Farid, Ahmed Mostafa, Alia Y Ragheb, Sara H Mahmoud, Mahmoud Shehata, Noura M Abo Shama, Mohamed GabAllah, Gomaa Mostafa-Hedeab, Mona M Marzouk. Naturally Available Flavonoid Aglycones as Potential Antiviral Drug Candidates against SARS-CoV-2. Molecules (Basel, Switzerland). 2021 Oct; 26(21):. doi: 10.3390/molecules26216559. [PMID: 34770969]
  • Xin Huang, Junxiang Zhu, Li Wang, Huijuan Jing, Chaoyang Ma, Xingran Kou, Hongxin Wang. Inhibitory mechanisms and interaction of tangeretin, 5-demethyltangeretin, nobiletin, and 5-demethylnobiletin from citrus peels on pancreatic lipase: Kinetics, spectroscopies, and molecular dynamics simulation. International journal of biological macromolecules. 2020 Dec; 164(?):1927-1938. doi: 10.1016/j.ijbiomac.2020.07.305. [PMID: 32795575]
  • Ya-Chun Chou, Shiming Li, Chi-Tang Ho, Min-Hsiung Pan. Preparation and evaluation of self-microemulsifying delivery system containing 5-demethyltangeretin on inhibiting xenograft tumor growth in mice. International journal of pharmaceutics. 2020 Apr; 579(?):119134. doi: 10.1016/j.ijpharm.2020.119134. [PMID: 32057886]
  • Meiyan Wang, Dan Meng, Peng Zhang, Xiangxing Wang, Gang Du, Charles Brennan, Shiming Li, Chi-Tang Ho, Hui Zhao. Antioxidant Protection of Nobiletin, 5-Demethylnobiletin, Tangeretin, and 5-Demethyltangeretin from Citrus Peel in Saccharomyces cerevisiae. Journal of agricultural and food chemistry. 2018 Mar; 66(12):3155-3160. doi: 10.1021/acs.jafc.8b00509. [PMID: 29526093]
  • Hai-Fang Chen, Wu-Gang Zhang, Jin-Bin Yuan, Yan-Gang Li, Shi-Lin Yang, Wu-Liang Yang. Simultaneous quantification of polymethoxylated flavones and coumarins in Fructus aurantii and Fructus aurantii immaturus using HPLC-ESI-MS/MS. Journal of pharmaceutical and biomedical analysis. 2012 Feb; 59(?):90-5. doi: 10.1016/j.jpba.2011.10.013. [PMID: 22071443]
  • Marios A Menelaou, Hidelisa P Henandez, Francisco A Macías, Jeffrey D Weidenhamer, G Bruce Williamson, Frank R Fronczek, Helga D Fischer, Nikolaus H Fischer. Constituents of Calamintha ashei: effects on Florida sandhill species. Natural product communications. 2010 May; 5(5):685-94. doi: . [PMID: 20521531]
  • Ping Dong, Peiju Qiu, Yi Zhu, Shiming Li, Chi-Tang Ho, David Julian McClements, Hang Xiao. Simultaneous determination of four 5-hydroxy polymethoxyflavones by reversed-phase high performance liquid chromatography with electrochemical detection. Journal of chromatography. A. 2010 Jan; 1217(5):642-7. doi: 10.1016/j.chroma.2009.11.097. [PMID: 20022018]
  • Shiming Li, Min-Hsiung Pan, Ching-Shu Lai, Chih-Yu Lo, Slavik Dushenkov, Chi-Tang Ho. Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines. Bioorganic & medicinal chemistry. 2007 May; 15(10):3381-9. doi: 10.1016/j.bmc.2007.03.021. [PMID: 17391969]
  • M Morimoto, S Kumeda, K Komai. Insect antifeedant flavonoids from Gnaphalium affine D. Don. Journal of agricultural and food chemistry. 2000 May; 48(5):1888-91. doi: 10.1021/jf990282q. [PMID: 10820110]
  • D G Kingston, M M Rao, W V Zucker. Plant anticancer agents. IX. Constituents of Hyptis tomentosa. Journal of natural products. 1979 Sep; 42(5):496-9. doi: 10.1021/np50005a010. [PMID: 521819]