Chrysoeriol (BioDeep_00000000663)

 

Secondary id: BioDeep_00000398641

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


3 inverted exclamation mark -Methoxy-4 inverted exclamation mark ,5,7-trihydroxyflavone

化学式: C16H12O6 (300.0634)
中文名称: 金圣草(黄)素
谱图信息: 最多检出来源 Homo sapiens(feces) 41.73%

分子结构信息

SMILES: c1(cc(c2c(c1)oc(cc2=O)c1cc(c(cc1)O)OC)O)O
InChI: InChI=1S/C16H12O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-7,17-19H,1H3

描述信息

Chrysoeriol, also known as 3-O-methylluteolin, belongs to the class of organic compounds known as 3-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, chrysoeriol is considered to be a flavonoid lipid molecule. Chrysoeriol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Chrysoeriol is a bitter-tasting compound. Outside of the human body, chrysoeriol has been detected, but not quantified in, several different foods, such as wild celeries, ryes, hard wheat, alfalfa, and triticales. This could make chrysoeriol a potential biomarker for the consumption of these foods.
4,5,7-trihydroxy-3-methoxyflavone is the 3-O-methyl derivative of luteolin. It has a role as an antineoplastic agent, an antioxidant and a metabolite. It is a trihydroxyflavone and a monomethoxyflavone. It is functionally related to a luteolin. It is a conjugate acid of a 4,5-dihydroxy-3-methoxyflavon-7-olate(1-).
Chrysoeriol is a natural product found in Haplophyllum ramosissimum, Myoporum tenuifolium, and other organisms with data available.
See also: Acai (part of); Acai fruit pulp (part of).
Widespread flavone. Chrysoeriol is found in many foods, some of which are peanut, german camomile, tarragon, and alfalfa.
The 3-O-methyl derivative of luteolin.
Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1].
Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1].

同义名列表

34 个代谢物同义名

3 inverted exclamation mark -Methoxy-4 inverted exclamation mark ,5,7-trihydroxyflavone; 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one, 9CI; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-; 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one; 2-(5-methoxy,4-hydroxyphenyl)5,7-dihydroxy-benzpyran-4-one; 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyrone; 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one; Chryseriol;3-Methoxyapigenin;Luteolin 3-methyl ether; 2-(5-methoxy,7-dihydroxy-benzpyran-4-one; FLAVONE, 4,5,7-TRIHYDROXY-3-METHOXY-; 5,7,4’-Trihydroxy-3’-methoxyflavone; 3?-METHOXY-4?,5,7-TRIHYDROXYFLAVONE; 3’-Methoxy-4’,5,7-trihydroxyflavone; 4,5,7-Trihydroxy-3-methoxy-Flavone; 5,7,4-Trihydroxy-3-methoxyflavone; 4,5,7-trihydroxy-3-methoxyflavone; 3-Methoxy-4,5,7-trihydroxyflavone; SCZVLDHREVKTSH-UHFFFAOYSA-N; Luteolin 3’-methyl ether; Luteolin 3-methyl ether; 3’-O-Methylluteolin; 3’-Methoxyapigenin; 3-O-Methylluteolin; 3-Methoxyapigenin; 3-O-Methyluteolin; 8-chrysoeriol; Chrysoeriol; Chryseriol; Chrysoeril; Chrysoriol; Scoparol; CRESOROL; Chrysoeriol



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

225 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(225)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

640 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 15 AKT1, ANXA5, BCL2, CASP3, JAK2, MAPK14, MAPK3, MAPK8, MTOR, NFE2L2, NOS2, PIK3CA, PTGS2, STAT3, XDH
Peripheral membrane protein 4 ANXA5, JAK2, MTOR, PTGS2
Endoplasmic reticulum membrane 3 BCL2, MTOR, PTGS2
Mitochondrion membrane 1 ABCG2
Nucleus 12 AKT1, BCL2, CASP3, JAK2, JUND, MAPK14, MAPK3, MAPK8, MTOR, NFE2L2, NOS2, STAT3
cytosol 14 AKT1, ANXA5, BCL2, CASP3, JAK2, MAPK14, MAPK3, MAPK8, MTOR, NFE2L2, NOS2, PIK3CA, STAT3, XDH
dendrite 1 MTOR
mitochondrial membrane 1 ABCG2
phagocytic vesicle 1 MTOR
centrosome 1 NFE2L2
nucleoplasm 12 ABCG2, AKT1, CASP3, JAK2, JUND, MAPK14, MAPK3, MAPK8, MTOR, NFE2L2, NOS2, STAT3
RNA polymerase II transcription regulator complex 3 JUND, NFE2L2, STAT3
Cell membrane 3 ABCG2, AKT1, TNF
Cytoplasmic side 1 MTOR
lamellipodium 2 AKT1, PIK3CA
Multi-pass membrane protein 1 ABCG2
Golgi apparatus membrane 1 MTOR
Synapse 1 MAPK8
cell cortex 1 AKT1
cell surface 1 TNF
glutamatergic synapse 5 AKT1, CASP3, JAK2, MAPK14, MAPK3
Golgi apparatus 2 MAPK3, NFE2L2
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
neuronal cell body 2 CASP3, TNF
postsynapse 2 AKT1, JAK2
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 NFE2L2, NOS2
Lysosome 1 MTOR
plasma membrane 9 ABCG2, AKT1, JAK2, MAPK3, NFE2L2, NOS2, PIK3CA, STAT3, TNF
Membrane 6 ABCG2, AKT1, ANXA5, BCL2, JAK2, MTOR
apical plasma membrane 1 ABCG2
axon 2 CCK, MAPK8
caveola 3 JAK2, MAPK3, PTGS2
extracellular exosome 1 ANXA5
Lysosome membrane 1 MTOR
endoplasmic reticulum 2 BCL2, PTGS2
extracellular space 4 CCK, IL6, TNF, XDH
perinuclear region of cytoplasm 2 NOS2, PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 3 BCL2, MAPK14, MAPK3
protein-containing complex 3 AKT1, BCL2, PTGS2
Microsome membrane 2 MTOR, PTGS2
postsynaptic density 1 CASP3
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 2 CCK, IL6
extracellular region 5 ANXA5, CCK, IL6, MAPK14, TNF
cytoplasmic side of plasma membrane 1 JAK2
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, MTOR
transcription regulator complex 2 JUND, STAT3
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 ANXA5, TNF
microtubule cytoskeleton 1 AKT1
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
Early endosome 1 MAPK3
cell-cell junction 1 AKT1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
Apical cell membrane 1 ABCG2
Cytoplasm, perinuclear region 1 NOS2
Membrane raft 3 ABCG2, JAK2, TNF
pore complex 1 BCL2
Cell junction, focal adhesion 1 MAPK3
focal adhesion 3 ANXA5, JAK2, MAPK3
spindle 1 AKT1
Peroxisome 2 NOS2, XDH
sarcoplasmic reticulum 1 XDH
peroxisomal matrix 1 NOS2
Nucleus, PML body 1 MTOR
PML body 1 MTOR
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 1 ANXA5
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 1 MAPK3
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
ciliary basal body 1 AKT1
chromatin 3 JUND, NFE2L2, STAT3
mediator complex 1 NFE2L2
phagocytic cup 1 TNF
cytoskeleton 2 JAK2, MAPK3
brush border membrane 1 ABCG2
spindle pole 1 MAPK14
nuclear envelope 2 MAPK3, MTOR
Endomembrane system 2 JAK2, MTOR
endosome lumen 1 JAK2
Membrane, caveola 1 MAPK3
euchromatin 1 JAK2
myelin sheath 1 BCL2
pseudopodium 1 MAPK3
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
endoplasmic reticulum lumen 3 IL6, MAPK3, PTGS2
transcription repressor complex 1 JUND
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
vesicle membrane 1 ANXA5
extrinsic component of cytoplasmic side of plasma membrane 1 JAK2
protein-DNA complex 1 NFE2L2
external side of apical plasma membrane 1 ABCG2
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
Cytoplasmic vesicle, phagosome 1 MTOR
extrinsic component of plasma membrane 1 JAK2
granulocyte macrophage colony-stimulating factor receptor complex 1 JAK2
interleukin-12 receptor complex 1 JAK2
interleukin-23 receptor complex 1 JAK2
transcription factor AP-1 complex 1 JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cortical cytoskeleton 1 NOS2
interleukin-6 receptor complex 1 IL6
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Amit Gupta, Tapan Behl, Sukhbir Singh, Madhukar Garg, Ennus Tajuddin Tamboli, Sridevi Chigurupati, Shatha Ghazi Felemban, Ali Albarrati, Mohammed Albratty, Abdulkarim M Meraya. Quantification of Luteolin, Apigenin and Chrysoeriol in Tecoma stans by RP-HPLC Method. Journal of chromatographic science. 2023 Mar; ?(?):. doi: 10.1093/chromsci/bmad022. [PMID: 36951424]
  • Yu-Xi Liu, Ying-Jie Chen, Bo-Wen Xu, Xiu-Qiong Fu, Wen-Jun Ding, Sze-Man Amy Li, Xiao-Qi Wang, Jia-Ying Wu, Ying Wu, Xiaobing Dou, Bin Liu, Zhi-Ling Yu. Inhibition of STAT3 signaling contributes to the anti-melanoma effects of chrysoeriol. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Jan; 109(?):154572. doi: 10.1016/j.phymed.2022.154572. [PMID: 36610164]
  • Jia-Ying Wu, Ying-Jie Chen, Xiu-Qiong Fu, Jun-Kui Li, Ji-Yao Chou, Cheng-Le Yin, Jing-Xuan Bai, Ying Wu, Xiao-Qi Wang, Amy Sze-Man Li, Lut Yi Wong, Zhi-Ling Yu. Chrysoeriol suppresses hyperproliferation of rheumatoid arthritis fibroblast-like synoviocytes and inhibits JAK2/STAT3 signaling. BMC complementary medicine and therapies. 2022 Mar; 22(1):73. doi: 10.1186/s12906-022-03553-w. [PMID: 35296317]
  • Eun-Gyeong Kim, Sopheap Yun, Jae-Ryoung Park, Yoon-Hee Jang, Muhammad Farooq, Byoung-Ju Yun, Kyung-Min Kim. Bio-Efficacy of Chrysoeriol7, a Natural Chemical and Repellent, against Brown Planthopper in Rice. International journal of molecular sciences. 2022 Jan; 23(3):. doi: 10.3390/ijms23031540. [PMID: 35163461]
  • Luis Fernando Méndez-López, Pierluigi Caboni, Eder Arredondo-Espinoza, Juan J J Carrizales-Castillo, Isaías Balderas-Rentería, María Del Rayo Camacho-Corona. Bioassay-Guided Identification of the Antiproliferative Compounds of Cissus trifoliata and the Transcriptomic Effect of Resveratrol in Prostate Cancer Pc3 Cells. Molecules (Basel, Switzerland). 2021 Apr; 26(8):. doi: 10.3390/molecules26082200. [PMID: 33920405]
  • Jia-Ying Wu, Ying-Jie Chen, Lu Bai, Yu-Xi Liu, Xiu-Qiong Fu, Pei-Li Zhu, Jun-Kui Li, Ji-Yao Chou, Cheng-Le Yin, Ya-Ping Wang, Jing-Xuan Bai, Ying Wu, Zheng-Zhi Wu, Zhi-Ling Yu. Chrysoeriol ameliorates TPA-induced acute skin inflammation in mice and inhibits NF-κB and STAT3 pathways. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Mar; 68(?):153173. doi: 10.1016/j.phymed.2020.153173. [PMID: 31999977]
  • Jang Hoon Kim, Chang Hyun Jin. Inhibitory Activity of Flavonoids, Chrysoeriol and Luteolin-7-O-Glucopyranoside, on Soluble Epoxide Hydrolase from Capsicum chinense. Biomolecules. 2020 01; 10(2):. doi: 10.3390/biom10020180. [PMID: 31991570]
  • Tanapol Limboonreung, Patoomratana Tuchinda, Sukumal Chongthammakun. Chrysoeriol mediates mitochondrial protection via PI3K/Akt pathway in MPP+ treated SH-SY5Y cells. Neuroscience letters. 2020 01; 714(?):134545. doi: 10.1016/j.neulet.2019.134545. [PMID: 31622648]
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  • Aimin Wang, Rensai Li, Lei Ren, Xiali Gao, Yungang Zhang, Zhimin Ma, Daifu Ma, Yonghai Luo. A comparative metabolomics study of flavonoids in sweet potato with different flesh colors (Ipomoea batatas (L.) Lam). Food chemistry. 2018 Sep; 260(?):124-134. doi: 10.1016/j.foodchem.2018.03.125. [PMID: 29699652]
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  • Barbara Tóth, Erika Liktor-Busa, Norbert Kúsz, Ádám Szappanos, Attila Mándi, Tibor Kurtán, Edit Urbán, Judit Hohmann, Fang-Rong Chang, Andrea Vasas. Phenanthrenes from Juncus inflexus with Antimicrobial Activity against Methicillin-Resistant Staphylococcus aureus. Journal of natural products. 2016 11; 79(11):2814-2823. doi: 10.1021/acs.jnatprod.6b00581. [PMID: 27808510]
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  • Zhongjian Chen, Meng Chen, Hao Pan, Siyuan Sun, Liping Li, Su Zeng, Huidi Jiang. Role of catechol-O-methyltransferase in the disposition of luteolin in rats. Drug metabolism and disposition: the biological fate of chemicals. 2011 Apr; 39(4):667-74. doi: 10.1124/dmd.110.037333. [PMID: 21209248]
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