4',5,7-Trimethoxyflavone (BioDeep_00000017602)

 

Secondary id: BioDeep_00000600171

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


4H-1-Benzenopyran-4-one, 5,7-dimethoxy-2-(4-methoxyphenyl)-

化学式: C18H16O5 (312.0997686)
中文名称: 4,5,7-三甲氧基黄酮, 4',5,7-三甲氧基黄酮, 5,7,4-三甲氧基黄酮
谱图信息: 最多检出来源 Astragalus membranaceus(otcml) 29.41%

分子结构信息

SMILES: c1(cc(c2c(c1)oc(cc2=O)c1ccc(cc1)OC)OC)OC
InChI: InChI=1S/C18H16O5/c1-20-12-6-4-11(5-7-12)15-10-14(19)18-16(22-3)8-13(21-2)9-17(18)23-15/h4-10H,1-3H3

描述信息

4,5,7-Trimethoxyflavone, also known as trimethylapigenin, 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, 4,5,7-trimethoxyflavone is considered to be a flavonoid lipid molecule. 4,5,7-Trimethoxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4,5,7-trimethoxyflavone has been detected, but not quantified in, a few different foods, such as citrus, mandarin orange (clementine, tangerine), and sweet oranges. This could make 4,5,7-trimethoxyflavone a potential biomarker for the consumption of these foods.
4,5,7-Trimethoxyflavone is an ether and a member of flavonoids.
4,5,7-Trimethoxyflavone is a natural product found in Tanacetum vulgare, Citrus medica, and other organisms with data available.
See also: Tangerine peel (part of).
Occurs in the peel of Citrus reticulata (mandarin). 4,5,7-Trimethylapigenin is found in sweet orange and citrus.
5,7,4'-Trimethoxyflavone is isolated from Kaempferia parviflora (KP) that is a famous medicinal plant from Thailand. 5,7,4'-Trimethoxyflavone induces apoptosis, as evidenced by increments of sub-G1 phase, DNA fragmentation, annexin-V/PI staining, the Bax/Bcl-xL ratio, proteolytic activation of caspase-3, and degradation of poly (ADP-ribose) polymerase (PARP) protein.5,7,4'-Trimethoxyflavone is significantly effective at inhibiting proliferation of SNU-16 human gastric cancer cells in a concentration dependent manner[1].
5,7,4'-Trimethoxyflavone is isolated from Kaempferia parviflora (KP) that is a famous medicinal plant from Thailand. 5,7,4'-Trimethoxyflavone induces apoptosis, as evidenced by increments of sub-G1 phase, DNA fragmentation, annexin-V/PI staining, the Bax/Bcl-xL ratio, proteolytic activation of caspase-3, and degradation of poly (ADP-ribose) polymerase (PARP) protein.5,7,4'-Trimethoxyflavone is significantly effective at inhibiting proliferation of SNU-16 human gastric cancer cells in a concentration dependent manner[1].

同义名列表

44 个代谢物同义名

4H-1-Benzenopyran-4-one, 5,7-dimethoxy-2-(4-methoxyphenyl)-; 5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-1-benzenopyran-4-one; 4H-1-Benzopyran-4-one, 5,7-dimethoxy-2-(4-methoxyphenyl)-; 5,7-Dimethoxy-4-oxo-2-(4-methoxyphenyl)-4H-1-benzopyran; 5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-1-Benzopyran-4-one; 5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one #; 5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one; 5,7-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one; 5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one; 5,7-Dimethoxy-2-(4-methoxyphenyl)chromone; 6-Hydroxy-4,5,7-trimethoxyflavone; Apigenin 5,7,4-trimethyl ether; 5,7,4’-Tri-O-methylapigenin; 5,?7,?4-?Trimethoxyflavone; Flavone, 4,5,7-trimethoxy-; 5,7,4-Tri-O-methylapigenin; Apigenin, trimethyl ether; 5, 7, 4-Trimethoxyflavone; 5,7,4’-Trimethoxyapigenin; 4,5,7-trimethoxy-flavone; 4,5,7-trimethyl-apigenin; 5,7,4;-TRIMETHOXYFLAVONE; 5,7,4’-Trimethoxyflavone; 4’,5,7-Trimethoxyflavone; 5,7,4-Trimethoxyapigenin; Apigenin trimethyl ether; 4,5,7-Trimethylapigenin; 5,7,4-Trimethoxyflavone; 5,7,4-trimethylapigenin; 4,5,7-trimethoxyflavone; 5,7,4-rimethoxyflavone; 457-Trimethoxyflavone; Tri-O-methylapigenin; Trimethylapigenin; Trimethylapogamin; Spectrum3_001138; Spectrum5_001684; Spectrum4_001985; Spectrum2_000471; UNII-F50JU8E74U; Oprea1_073610; KBio3_002135; F50JU8E74U; 5,?7,?4'-?Trimethoxyflavone



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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43 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

  • Akida Alishir, Jae Sik Yu, Minji Park, Jin-Chul Kim, Changhyun Pang, Jung Kyu Kim, Tae Su Jang, Won Hee Jung, Ki Hyun Kim. Ulmusakidian, a new coumarin glycoside and antifungal phenolic compounds from the root bark of Ulmus davidiana var. japonica. Bioorganic & medicinal chemistry letters. 2021 03; 36(?):127828. doi: 10.1016/j.bmcl.2021.127828. [PMID: 33508466]
  • 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]
  • 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]
  • Catheleeya Mekjaruskul, Michael Jay, Bungorn Sripanidkulchai. Pharmacokinetics, bioavailability, tissue distribution, excretion, and metabolite identification of methoxyflavones in Kaempferia parviflora extract in rats. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2342-53. doi: 10.1124/dmd.112.047142. [PMID: 22961680]
  • Pattara Sawasdee, Chalisa Sabphon, Duangporn Sitthiwongwanit, Udom Kokpol. Anticholinesterase activity of 7-methoxyflavones isolated from Kaempferia parviflora. Phytotherapy research : PTR. 2009 Dec; 23(12):1792-4. doi: 10.1002/ptr.2858. [PMID: 19548291]
  • Chavi Yenjai, Khanchara Prasanphen, Supawadee Daodee, Varima Wongpanich, Prasat Kittakoop. Bioactive flavonoids from Kaempferia parviflora. Fitoterapia. 2004 Jan; 75(1):89-92. doi: 10.1016/j.fitote.2003.08.017. [PMID: 14693228]
  • I M Lyckander, K E Malterud. Lipophilic flavonoids from Orthosiphon spicatus prevent oxidative inactivation of 15-lipoxygenase. Prostaglandins, leukotrienes, and essential fatty acids. 1996 Apr; 54(4):239-46. doi: 10.1016/s0952-3278(96)90054-x. [PMID: 8804120]