Chrysoeriol (BioDeep_00000000663)

 

Secondary id: BioDeep_00000398641

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


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

化学式: C16H12O6 (300.06338519999997)
中文名称: 金圣草(黄)素
谱图信息: 最多检出来源 Homo sapiens(feces) 0.24%

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

33 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



数据库引用编号

23 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)

194 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

  • 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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  • Mohamed A Farag, Heba Handoussa, Mostafa I Fekry, Ludger A Wessjohann. Metabolite profiling in 18 Saudi date palm fruit cultivars and their antioxidant potential via UPLC-qTOF-MS and multivariate data analyses. Food & function. 2016 Feb; 7(2):1077-86. doi: 10.1039/c5fo01570g. [PMID: 26781334]
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  • Pui Ying Lam, Hongjia Liu, Clive Lo. Completion of Tricin Biosynthesis Pathway in Rice: Cytochrome P450 75B4 Is a Unique Chrysoeriol 5'-Hydroxylase. Plant physiology. 2015 Aug; 168(4):1527-36. doi: 10.1104/pp.15.00566. [PMID: 26082402]
  • Chi-Chih Chang, Sheau Ling Ho, Shoei-Sheng Lee. Acylated glucosylflavones as α-glucosidase inhibitors from Tinospora crispa leaf. Bioorganic & medicinal chemistry. 2015 Jul; 23(13):3388-96. doi: 10.1016/j.bmc.2015.04.053. [PMID: 25999202]
  • Yearam Jung, Soon Young Shin, Yeonjoong Yong, Hyeryoung Jung, Seunghyun Ahn, Young Han Lee, Yoongho Lim. Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships. Chemical biology & drug design. 2015 May; 85(5):574-85. doi: 10.1111/cbdd.12445. [PMID: 25298094]
  • Atsuyoshi Nishina, Motohiko Ukiya, Makoto Fukatsu, Mamoru Koketsu, Masayuki Ninomiya, Daisuke Sato, Junpei Yamamoto, Kazuo Kobayashi-Hattori, Takeshi Okubo, Hideyo Tokuoka, Hirokazu Kimura. Effects of Various 5,7-Dihydroxyflavone Analogs on Adipogenesis in 3T3-L1 Cells. Biological & pharmaceutical bulletin. 2015; 38(11):1794-800. doi: 10.1248/bpb.b15-00489. [PMID: 26521830]
  • Hua-Qing Liu, Tian-Lin Wang. [Chemical constituents from flower of Lonicera fragrantissima]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Aug; 37(8):1383-5. doi: . [PMID: 25726645]
  • Daniela Ribeiro, Marisa Freitas, Sara M Tomé, Artur M S Silva, Graça Porto, Eurico J Cabrita, M Manuel B Marques, Eduarda Fernandes. Inhibition of LOX by flavonoids: a structure-activity relationship study. European journal of medicinal chemistry. 2014 Jan; 72(?):137-45. doi: 10.1016/j.ejmech.2013.11.030. [PMID: 24368208]
  • Ki-Suk Kim, Dong Jin Lim, Hea Jung Yang, Eun-Kyeong Choi, Min Hee Shin, Kwang Seok Ahn, Sang Hoon Jung, Jae Young Um, Hee-Jae Jung, Jun Hee Lee, Seok-Geun Lee, Sung-Ki Jung, Hyeung-Jin Jang. The multi-targeted effects of Chrysanthemum herb extract against Escherichia coli O157:H7. Phytotherapy research : PTR. 2013 Sep; 27(9):1398-406. doi: 10.1002/ptr.4859. [PMID: 23255247]
  • Jin Hwan Lee, Ki Hun Park, Myoung-Hee Lee, Hyun-Tae Kim, Woo Duck Seo, Jun Young Kim, In-Youl Baek, Dae Sik Jang, Tae Joung Ha. Identification, characterisation, and quantification of phenolic compounds in the antioxidant activity-containing fraction from the seeds of Korean perilla (Perilla frutescens) cultivars. Food chemistry. 2013 Jan; 136(2):843-52. doi: 10.1016/j.foodchem.2012.08.057. [PMID: 23122135]
  • Ibrahim Demirtas, Ramazan Erenler, Mahfuz Elmastas, Ahmet Goktasoglu. Studies on the antioxidant potential of flavones of Allium vineale isolated from its water-soluble fraction. Food chemistry. 2013 Jan; 136(1):34-40. doi: 10.1016/j.foodchem.2012.07.086. [PMID: 23017389]
  • Ayumi Uehara, Tsukasa Iwashina. Flavonoids from the Japanese monotypic genus, Nipponanthemum. Natural product communications. 2012 Aug; 7(8):1005-6. doi: . [PMID: 22978216]
  • Xiao-Ye Sun, Hong-Hua Wu, Ai-Zhen Fu, Peng Zhang. [Chemical constituents of Trichosanthes kirilowii Maxim]. Yao xue xue bao = Acta pharmaceutica Sinica. 2012 Jul; 47(7):922-5. doi: . [PMID: 22993858]
  • Sumi Wijaya, Khoo Teng Jin, Ting Kang Nee, Christophe Wiart. In vitro 5-LOX inhibitory and antioxidant activities of extracts and compounds from the aerial parts of Lopholaena coriifolia (Sond.) E. Phillips & C.A. Sm. Journal of complementary & integrative medicine. 2012 Jun; 9(?):Article 11. doi: 10.1515/1553-3840.1615. [PMID: 22728459]
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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]
  • Federico Ferreres, Angel Gil-Izquierdo, Juliana Vinholes, Clara Grosso, Patrícia Valentão, Paula B Andrade. Approach to the study of C-glycosyl flavones acylated with aliphatic and aromatic acids from Spergularia rubra by high-performance liquid chromatography-photodiode array detection/electrospray ionization multi-stage mass spectrometry. Rapid communications in mass spectrometry : RCM. 2011 Mar; 25(6):700-12. doi: 10.1002/rcm.4910. [PMID: 21337631]
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  • Atef A El-Hela, Hussein A Al-Amier, Taghreed A Ibrahim. Comparative study of the flavonoids of some Verbena species cultivated in Egypt by using high-performance liquid chromatography coupled with ultraviolet spectroscopy and atmospheric pressure chemical ionization mass spectrometry. Journal of chromatography. A. 2010 Oct; 1217(41):6388-93. doi: 10.1016/j.chroma.2010.08.025. [PMID: 20817165]
  • Young Ho Kim, Young Soon Lee, Eun Mi Choi. Chrysoeriol isolated from Eurya cilliata leaves protects MC3T3-E1 cells against hydrogen peroxide-induced inhibition of osteoblastic differentiation. Journal of applied toxicology : JAT. 2010 Oct; 30(7):666-73. doi: 10.1002/jat.1539. [PMID: 20981859]
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