Apigenin 7,4'-dimethyl ether (BioDeep_00000229903)

 

Secondary id: BioDeep_00000003833, BioDeep_00000269902, BioDeep_00000861998

human metabolite PANOMIX_OTCML-2023 Endogenous Chemicals and Drugs natural product


代谢物信息卡片


4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-

化学式: C17H14O5 (298.0841)
中文名称: 芹菜素二甲醚, 5-羟基-4’,7-二甲氧基黄酮,芹菜素二甲醚, 4,7-二甲氧基-5-羟基黄酮
谱图信息: 最多检出来源 Viridiplantae(plant) 13.46%

分子结构信息

SMILES: c1(cc(c2c(c1)oc(cc2=O)c1ccc(cc1)OC)O)OC
InChI: InChI=1S/C17H14O5/c1-20-11-5-3-10(4-6-11)15-9-14(19)17-13(18)7-12(21-2)8-16(17)22-15/h3-9,18H,1-2H3

描述信息

Apigenin 7,4-dimethyl ether, also known as apigenin dimethylether or 4,7-dimethylapigenin, belongs to the class of organic compounds known as 7-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, apigenin 7,4-dimethyl ether is considered to be a flavonoid lipid molecule. Apigenin 7,4-dimethyl ether is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, apigenin 7,4-dimethyl ether has been detected, but not quantified in, common sages and sweet basils. This could make apigenin 7,4-dimethyl ether a potential biomarker for the consumption of these foods. BioTransformer predicts that apigenin 7,4-dimethyl ether is a product of 4,5,7-trimethoxyflavone metabolism via an O-dealkylation reaction and catalyzed by CYP2C9 and CYP2C19 enzymes (PMID: 30612223).
4-methylgenkwanin, also known as apigenin dimethylether or 4,7-dimethylapigenin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 4-methylgenkwanin is considered to be a flavonoid lipid molecule. 4-methylgenkwanin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 4-methylgenkwanin can be found in common sage and sweet basil, which makes 4-methylgenkwanin a potential biomarker for the consumption of these food products.
Apigenin 7,4-dimethyl ether is a dimethoxyflavone that is the 7,4-dimethyl ether derivative of apigenin. It has a role as a plant metabolite. It is a dimethoxyflavone and a monohydroxyflavone. It is functionally related to an apigenin.
Apigenin 7,4-dimethyl ether is a natural product found in Teucrium polium, Calea jamaicensis, and other organisms with data available.
A dimethoxyflavone that is the 7,4-dimethyl ether derivative of apigenin.
The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C. zeyheri, and may serve as a potential source of lead compounds that can be developed as antifungal phytomedicines.And it also showed inhibition of the drug efflux pumps (with IC50 = 51.64 μg/ml). IC50:51.64 μg/ml(Candida albicans drug efflux pumps)[2] In vitro: The isolated 7,4'-Di-O-methylapigenin was further investigated for its inhibitory activity on ABC drug efflux pumps in C. albicans by monitoring an increase in ciprofloxacin, assessing the level of its accumulation, in response to reserpine. There was a higher accumulation of ciprofloxacin in Candida cells in the presence of 7,4'-Di-O-methylapigenin than with reserpine. The compound 7,4'-Di-O-methylapigenine demonstrated the activity in a dose-dependent manner with IC50 value of 51.64 μg/ml. These results support those obtained from synergism assays where by the underlying synergistic antifungal mechanisms could be due to blockage of ABC efflux pumps and increasing the susceptibility of Candida to miconazole.[2] In vivo: In searching for natural products as potential anti-inflammatory agents, 7,4'-Di-O-methylapigenin wasn't evaluated in vivo for its ability to inhibit acute inflammation.[1]
The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C. zeyheri, and may serve as a potential source of lead compounds that can be developed as antifungal phytomedicines.And it also showed inhibition of the drug efflux pumps (with IC50 = 51.64 μg/ml). IC50:51.64 μg/ml(Candida albicans drug efflux pumps)[2] In vitro: The isolated 7,4'-Di-O-methylapigenin was further investigated for its inhibitory activity on ABC drug efflux pumps in C. albicans by monitoring an increase in ciprofloxacin, assessing the level of its accumulation, in response to reserpine. There was a higher accumulation of ciprofloxacin in Candida cells in the presence of 7,4'-Di-O-methylapigenin than with reserpine. The compound 7,4'-Di-O-methylapigenine demonstrated the activity in a dose-dependent manner with IC50 value of 51.64 μg/ml. These results support those obtained from synergism assays where by the underlying synergistic antifungal mechanisms could be due to blockage of ABC efflux pumps and increasing the susceptibility of Candida to miconazole.[2] In vivo: In searching for natural products as potential anti-inflammatory agents, 7,4'-Di-O-methylapigenin wasn't evaluated in vivo for its ability to inhibit acute inflammation.[1]

同义名列表

53 个代谢物同义名

4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-; 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one; Apigenin 7,4-dimethyl ether pound>>Apigenin dimethylether; 5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one; 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-; 5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-4-benzopyrone; 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one; Flavone, 5-hydroxy-4,7-dimethoxy-; 5-Hydroxy-4,7-dimethoxy-flavone; 4,7-Dimethoxy-5-hydroxy flavone; 5-Hydroxy-4’,7-dimethoxyflavone; Flavone,5-hydroxy-4-7-dimethoxy; 5-Hydroxy-7,4’-dimethoxyflavone; 7,4-dimethoxy-5-hydroxyflavone; 4,7-dimethoxy-5-hydroxyflavone; 5-hydroxy-4,7-dimethoxyflavone; 5-hydroxy-7,4-dimethoxyflavone; 5-Hydroxy-7,4-dimethoxyflavone; 4,7-DIMETHOXY-5-HYDROXYFLAVONE; Apigenin 4’,7-dimethyl ether; Apigenin 7,4’-dimethyl ether; Apigenin-7,4’-dimethyl ether; Apigenin-7,4-dimethyl ether; Apigenin 4,7-dimethyl ether; apigenin-7,4-dimethyl ether; Apigenin 7,4-dimethyl ether; apigenin-7,4-dimethylether; Acacetin 7-o-methyl ether; Genkwanin 4’-methyl ether; 7,4’-Di-O-methylapigenin; Genkwanin 4-methyl ether; 4’,7-Di-O-methylapigenin; Acacetin 7-methyl ether; APIGENIN DIMETHYL ETHER; 4,7-DI-O-METHYLAPIGENIN; 7,4-Di-O-methylapigenin; 4’-Methoxytectochrysin; apigenin dimethylether; Apigenin, 7,4-dimethyl; 7,4’-Dimethylapigenin; 4’,7-Dimethylapigenin; 4-Methoxytectochrysin; 7,4-Dimethylapigenin; Flavone,7-dimethoxy-; 4,7-Dimethylapigenin; 7-O-Methylacacetin; 4-Methylgenkwanin; 7-METHYLACACETIN; UNII-LVC8MF8MWR; LVC8MF8MWR; 4',7-Dimethoxy-5-Hydroxyflavone; 7,4'-Di-O-methylapigenin; Apigenin 7,4'-dimethyl ether



数据库引用编号

20 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

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)

280 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 9 ANXA5, BRAF, CASP3, CASP7, MAPK1, MSMP, PIK3CA, TP53, TTC3
Peripheral membrane protein 1 ANXA5
Nucleus 6 BRAF, CASP3, CASP7, MAPK1, TP53, TTC3
cytosol 10 ANXA5, BRAF, CASP3, CASP7, LIPE, MAPK1, MAS1L, PIK3CA, TP53, TTC3
dendrite 1 MAOB
centrosome 2 MAPK1, TP53
nucleoplasm 6 CASP3, CASP7, MAPK1, MAS1L, TP53, TTC3
Cell membrane 3 BRAF, LIPE, MAS1L
Cytoplasmic side 1 MAOB
lamellipodium 1 PIK3CA
Multi-pass membrane protein 1 MAS1L
Synapse 1 MAPK1
glutamatergic synapse 2 BRAF, CASP3
Golgi apparatus 2 MAPK1, TTC3
Golgi membrane 1 INS
lysosomal membrane 1 GAA
neuronal cell body 2 CASP3, MAOB
postsynapse 1 BRAF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 CASP7, LIPE
Lysosome 1 GAA
Presynapse 1 BRAF
plasma membrane 6 BRAF, GAA, IFNLR1, MAPK1, MAS1L, PIK3CA
Membrane 7 ANXA5, GAA, IFNLR1, LIPE, MAS1L, TP53, TTC3
axon 1 CCK
caveola 2 LIPE, MAPK1
extracellular exosome 2 ANXA5, GAA
Lysosome membrane 1 GAA
endoplasmic reticulum 1 TP53
extracellular space 7 CASP7, CCK, IL10, IL17A, INS, MSMP, PNLIP
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 1 PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 4 BRAF, MAOB, MAPK1, TP53
protein-containing complex 1 TP53
intracellular membrane-bounded organelle 2 BRAF, GAA
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 IFNLR1
Secreted 8 CCK, GAA, IL10, IL17A, INS, MSMP, PNLIP, PRB1
extracellular region 9 ANXA5, CCK, GAA, IL10, IL17A, INS, MAPK1, PNLIP, PRB1
Mitochondrion outer membrane 1 MAOB
mitochondrial outer membrane 1 MAOB
Mitochondrion matrix 1 TP53
mitochondrial matrix 1 TP53
transcription regulator complex 1 TP53
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 MAPK1, TP53
external side of plasma membrane 2 ANXA5, IL17A
nucleolus 2 TP53, TTC3
Early endosome 1 MAPK1
Cell junction, focal adhesion 1 MAPK1
Cytoplasm, cytoskeleton 1 TP53
Cytoplasm, cytoskeleton, spindle 1 MAPK1
focal adhesion 2 ANXA5, MAPK1
spindle 1 MAPK1
Nucleus, PML body 1 TP53
PML body 1 TP53
collagen-containing extracellular matrix 1 ANXA5
Late endosome 1 MAPK1
Zymogen granule membrane 1 ANXA5
neuron projection 1 BRAF
chromatin 1 TP53
mitotic spindle 1 MAPK1
cytoskeleton 1 MAPK1
Secreted, extracellular space 1 CASP7
site of double-strand break 1 TP53
endosome lumen 1 INS
Lipid droplet 1 LIPE
Membrane, caveola 2 LIPE, MAPK1
tertiary granule membrane 1 GAA
cell body 1 BRAF
germ cell nucleus 1 TP53
replication fork 1 TP53
pseudopodium 1 MAPK1
ficolin-1-rich granule lumen 1 MAPK1
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 INS, MAPK1
nuclear matrix 1 TP53
transcription repressor complex 1 TP53
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
transport vesicle 1 INS
azurophil granule membrane 1 GAA
azurophil granule lumen 1 MAPK1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
mitochondrial envelope 1 MAOB
Single-pass type IV membrane protein 1 MAOB
vesicle membrane 1 ANXA5
[Isoform 1]: Nucleus 1 TP53
ficolin-1-rich granule membrane 1 GAA
death-inducing signaling complex 1 CASP3
endothelial microparticle 1 ANXA5
autolysosome lumen 1 GAA
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
interleukin-28 receptor complex 1 IFNLR1


文献列表

  • Noriyuki Natsume, Aki Yamano, Akio Watanabe, Takayuki Yonezawa, Je-Tae Woo, Tohru Yamakuni, Toshiaki Teruya. Effect of methoxyflavones contained in Kaempferia parviflora on CRE-mediated transcription in PC12D cells. Bioorganic & medicinal chemistry letters. 2020 12; 30(23):127606. doi: 10.1016/j.bmcl.2020.127606. [PMID: 33038547]
  • Rumbidzai Mangoyi, Jacob Midiwo, Stanley Mukanganyama. Isolation and characterization of an antifungal compound 5-hydroxy-7,4'-dimethoxyflavone from Combretum zeyheri. BMC complementary and alternative medicine. 2015 Nov; 15(?):405. doi: 10.1186/s12906-015-0934-7. [PMID: 26573005]
  • Qi-Shi-San Wu, Qing-Hu Wang, Yin-Tai Na. [Study on chemical constituents of Ixeris chinensis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2012 Dec; 35(12):1945-9. doi: . [PMID: 23705357]
  • Huixin Liu, Haibing Liao, Ke Yuan. [Chemical constituents contained in Aeschynanthus moningeriae]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Jul; 37(13):1963-7. doi: 10.4268/cjcmm20121321. [PMID: 23019879]
  • Jie Feng, Xiuwei Yang. [Constituents from the leaves of Aquilaria sinensis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Jan; 37(2):230-4. doi: . [PMID: 22737857]
  • Z Habibi, Z Cheraghi, S Ghasemi, M Yousefi. A new highly hydroxylated triterpene from Salvia atropatana Bunge. Natural product research. 2012; 26(20):1910-3. doi: 10.1080/14786419.2011.628668. [PMID: 22017660]
  • Somayyeh Gandomkar, Maryam Yousefi, Zohreh Habibi, Mohammad Ali As'habi. A new triterpene from Salvia xanthocheila Boiss. Natural product research. 2012; 26(7):648-53. doi: 10.1080/14786419.2010.541884. [PMID: 21848491]
  • Sandra Freitas, Silvia Costa, Camila Azevedo, Gerson Carvalho, Songeli Freire, Pedro Barbosa, Eudes Velozo, Robert Schaer, Marcienne Tardy, Roberto Meyer, Ivana Nascimento. Flavonoids inhibit angiogenic cytokine production by human glioma cells. Phytotherapy research : PTR. 2011 Jun; 25(6):916-21. doi: 10.1002/ptr.3338. [PMID: 21170924]
  • Xiaona Fan, Sheng Lin, Chenggen Zhu, Yang Liu, Jinfeng Hu, Xiaoguang Chen, Wenjie Wang, Naihong Chen, Jiangong Shi. [Aromatic constituents of Heteroplexis micocephal and their bioactivities]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Jan; 36(1):48-56. doi: . [PMID: 21473152]
  • Sayid Mahdi Mirghazanfari, Mansoor Keshavarz, Fatemeh Nabavizadeh, Nepton Soltani, Mohammad Kamalinejad. The effect of "Teucrium polium L." extracts on insulin release from in situ isolated perfused rat pancreas in a newly modified isolation method: the role of Ca2+ and K+ channels. Iranian biomedical journal. 2010 10; 14(4):178-85. doi: . [PMID: 21283261]
  • T Hari Babu, K Manjulatha, G Suresh Kumar, A Hymavathi, Ashok K Tiwari, Muraleedhar Purohit, J Madhusudana Rao, K Suresh Babu. Gastroprotective flavonoid constituents from Oroxylum indicum Vent. Bioorganic & medicinal chemistry letters. 2010 Jan; 20(1):117-20. doi: 10.1016/j.bmcl.2009.11.024. [PMID: 19948405]
  • R Ranga Rao, Ashok K Tiwari, P Prabhakar Reddy, K Suresh Babu, Amtul Z Ali, K Madhusudana, J Madhusudana Rao. New furanoflavanoids, intestinal alpha-glucosidase inhibitory and free-radical (DPPH) scavenging, activity from antihyperglycemic root extract of Derris indica (Lam.). Bioorganic & medicinal chemistry. 2009 Jul; 17(14):5170-5. doi: 10.1016/j.bmc.2009.05.051. [PMID: 19515570]
  • Hichem Henchiri, Bernard Bodo, Alexandre Deville, Lionel Dubost, Lazhar Zourgui, Aly Raies, Philippe Grellier, Lengo Mambu. Sesquiterpenoids from Teucrium ramosissimum. Phytochemistry. 2009 Jul; 70(11-12):1435-41. doi: 10.1016/j.phytochem.2009.08.012. [PMID: 19766274]
  • Ting Zhang, Daofeng Chen. Anticomplementary principles of a Chinese multiherb remedy for the treatment and prevention of SARS. Journal of ethnopharmacology. 2008 May; 117(2):351-61. doi: 10.1016/j.jep.2008.02.012. [PMID: 18400428]
  • Supinya Tewtrakul, Sanan Subhadhirasakul, Sopa Kummee. Anti-allergic activity of compounds from Kaempferia parviflora. Journal of ethnopharmacology. 2008 Feb; 116(1):191-3. doi: 10.1016/j.jep.2007.10.042. [PMID: 18077118]
  • William P Jones, Tatiana Lobo-Echeverri, Qiuwen Mi, Hee-Byung Chai, Djaja D Soejarto, Geoffrey A Cordell, Steven M Swanson, A Douglas Kinghorn. Cytotoxic constituents from the fruiting branches of Callicarpa americana collected in southern Florida. Journal of natural products. 2007 Mar; 70(3):372-7. doi: 10.1021/np060534z. [PMID: 17279798]
  • Zheng-wen Yu, Hai-yan Zhu, Xiao-sheng Yang, Qian-yun Sun, Xiao-jiang Hao. [Study on chemical constituents from Incarvillea arguta and their accelerating PC-12 cell differentiation]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Sep; 30(17):1335-8. doi: . [PMID: 16323541]
  • N D Martini, D R P Katerere, J N Eloff. Biological activity of five antibacterial flavonoids from Combretum erythrophyllum (Combretaceae). Journal of ethnopharmacology. 2004 Aug; 93(2-3):207-12. doi: 10.1016/j.jep.2004.02.030. [PMID: 15234754]
  • Ahmed H El-Ghorab, Khaled F El-Massry, Friedhelm Marx, Hoda M Fadel. Antioxidant activity of Egyptian Eucalyptus camaldulensis var. brevirostris leaf extracts. Die Nahrung. 2003 Feb; 47(1):41-5. doi: 10.1002/food.200390009. [PMID: 12653437]
  • C Weimann, U Goransson, U Pongprayoon-Claeson, P Claeson, L Bohlin, H Rimpler, M Heinrich. Spasmolytic effects of baccharis conferta and some of its constituents. The Journal of pharmacy and pharmacology. 2002 Jan; 54(1):99-104. doi: 10.1211/0022357021771797. [PMID: 11829135]
  • S B Chen, G Y Gao, H W Leung, H W Yeung, J S Yang, P G Xiao. Aquiledine and isoaquiledine, novel flavonoid alkaloids from Aquilegia ecalcarata. Journal of natural products. 2001 Jan; 64(1):85-7. doi: 10.1021/np000256i. [PMID: 11170673]
  • X D Ji, N Melman, K A Jacobson. Interactions of flavonoids and other phytochemicals with adenosine receptors. Journal of medicinal chemistry. 1996 Feb; 39(3):781-8. doi: 10.1021/jm950661k. [PMID: 8576921]
  • . . . . doi: . [PMID: 23184958]