Xanthotoxol (BioDeep_00000000359)

 

Secondary id: BioDeep_00000861007

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2-Propenoic acid, 3-(6,7-dihydroxy-5-benzofuranyl)-, .delta.-lactone

化学式: C11H6O4 (202.0266076)
中文名称: 花椒毒酚, 花椒毒醇
谱图信息: 最多检出来源 Homo sapiens(blood) 0.16%

分子结构信息

SMILES: c12c(c(c3c(c1)ccc(=O)o3)O)occ2
InChI: InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H

描述信息

Isolated from Aegle marmelos (bael fruit), Angelica archangelica (angelica) and the seeds of Pastinaca sativa (parsnip). Xanthotoxol is found in many foods, some of which are fats and oils, green vegetables, herbs and spices, and fig.
Xanthotoxol is found in fats and oils. Xanthotoxol is isolated from Aegle marmelos (bael fruit), Angelica archangelica (angelica) and the seeds of Pastinaca sativa (parsnip
Xanthotoxol is an 8-hydroxyfurocoumarin.
Xanthotoxol is a natural product found in Citrus canaliculata, Prangos tschimganica, and other organisms with data available.
D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins
Xanthotoxol (8-Hydroxypsoralen) is a biologically active linear furocoumarin, shows strong pharmacological activities as anti-inflammatory, antioxidant, 5-HT antagonistic, and neuroprotective effects.
Xanthotoxol (8-Hydroxypsoralen) It is a kind of fragrant bean substance, and it is a CYP450 inhibitor. Xanthotoxol has anti-inflammatory, anti-inflammatory, and 5-HT antagonistic and protective effects. Xanthotoxol inhibited CYP3A4 sum CYP1A2 IC50s separation 7.43 μM sum 27.82 μM. Xanthotoxol can pass through MAPK and NF-κB, inhibiting inflammation[1][2][3][4].
Xanthotoxol (8-Hydroxypsoralen) is a biologically active linear furocoumarin, shows strong pharmacological activities as anti-inflammatory, antioxidant, 5-HT antagonistic, and neuroprotective effects.

同义名列表

38 个代谢物同义名

2-Propenoic acid, 3-(6,7-dihydroxy-5-benzofuranyl)-, .delta.-lactone; InChI=1/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13; 6-(3,4-Dichlorophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole; 2-Propenoic acid,7-dihydroxy-5-benzofuranyl)-, .delta.-lactone; 5-Benzofuranacrylic acid, 6,7-dihydroxy-, .delta.-lactone; 5-Benzofuranacrylic acid, 6,7-dihydroxy-, gamma-lactone; 6,7-Dihydroxy-5-benzofuranacrylic acid gamma-lactone; 9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one, 9CI; 7H-Furo(3,2-g)(1)benzopyran-7-one, 9-hydroxy-; 7H-Furo[3,2-g][1]benzopyran-7-one, 9-hydroxy-; 5-19-06-00014 (Beilstein Handbook Reference); 7H-Furo[3,2-g][1]benzopyran-7-one,9-hydroxy-; 9-Hydroxy-7H-furo(3,2-g)(1)benzopyran-7-one; 9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one; 9-Hydroxy-7H-furo[3,2-g]chromen-7-one #; 9-hydroxy-2H-furo[3,2-g]chromen-2-one; 9-Hydroxy-7H-furo[3,2-g]chromen-7-one; 9-hydroxy-furo[3,2-g]chromen-7-one; 9-hydroxyfuro[3,2-g]chromen-7-one; 8-hydroxyfuranocoumarins; an 8-hydroxyfurocoumarin; 8-Hydroxyfuranocoumarin; Xanthotol; Xanthotoxol; 8-hydroxyfurocoumarins; 8-hydroxyfurocoumarin; 7H-Furo[3, 9-hydroxy-; Psoralen, 8-hydroxy-; 8-Hydroxyanthotoxol; 8-hydroxy-psoralen; 8-Hydroxypsoralene; Xanthotoxol (6CI); 8-hydroxypsoralen; UNII-8RL486L8A5; Xanthotoxol; 8RL486L8A5; Xanthoxol; XANTHOTOL; Demethylmethoxsalen



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(0)

PlantCyc(0)

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)

63 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

  • Xinyi Gao, Yayue Yang, Jianyu Zhu, Yuxin Zhang, Chenghao Wang, Zhifei Wang, Wenli Mi, Lixia Du. Xanthotoxol relieves itch in mice via suppressing spinal GRP/GRPR signaling. European journal of pharmacology. 2023 Oct; ?(?):176147. doi: 10.1016/j.ejphar.2023.176147. [PMID: 37871763]
  • L Zhu, S Sun, W Wu, Y Zhang, C Lin, L Ji. Xanthotoxol alleviates secondary brain injury after intracerebral hemorrhage by inhibiting microglia-mediated neuroinflammation and oxidative stress. Neuro-Chirurgie. 2023 Mar; 69(3):101426. doi: 10.1016/j.neuchi.2023.101426. [PMID: 36921390]
  • Xian Lin, Jingfeng Liu, Yujiao Zou, Cheng Tao, Jian Chen. Xanthotoxol suppresses non-small cell lung cancer progression and might improve patients' prognosis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Oct; 105(?):154364. doi: 10.1016/j.phymed.2022.154364. [PMID: 35932608]
  • Baimei Shi, Jianghong Liu, Qian Zhang, Shixiang Wang, Pu Jia, Liujiao Bian, Xiaohui Zheng. Effect of co-administration of Acori Tatarinowii Rhizoma volatile oil on pharmacokinetic fate of xanthotoxol, oxypeucedanin hydrate, and byakangelicin from Angelicae Dahuricae Radix in rat. Journal of separation science. 2020 Jun; 43(12):2349-2362. doi: 10.1002/jssc.201901250. [PMID: 32222035]
  • Guiyuan He, Johanna Troberg, Xia Lv, Yang-Liu Xia, Liang-Liang Zhu, Jing Ning, Guang-Bo Ge, Moshe Finel, Ling Yang. Identification and characterization of human UDP-glucuronosyltransferases responsible for xanthotoxol glucuronidation. Xenobiotica; the fate of foreign compounds in biological systems. 2018 Feb; 48(2):109-116. doi: 10.1080/00498254.2017.1283719. [PMID: 28689454]
  • Lien Ngo, Phuong Tran, Seong-Ho Ham, Jung-Hee Cho, Hea-Young Cho, Yong-Bok Lee. Simultaneous determination of imperatorin and its metabolite xanthotoxol in rat plasma and urine by LC-MS/MS and its application to pharmacokinetic studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Feb; 1044-1045(?):30-38. doi: 10.1016/j.jchromb.2016.12.037. [PMID: 28064067]
  • Vamshi K Manda, Bharathi Avula, Amar G Chittiboyina, Ikhlas A Khan, Larry A Walker, Shabana I Khan. Inhibition of CYP3A4 and CYP1A2 by Aegle marmelos and its constituents. Xenobiotica; the fate of foreign compounds in biological systems. 2016; 46(2):117-25. doi: 10.3109/00498254.2015.1053006. [PMID: 26247834]
  • Juan Zhang, Min Zhang, Shan Fu, Tao Li, Shuang Wang, Minmin Zhao, Weijing Ding, Chunying Wang, Qiao Wang. Simultaneous determination of imperatorin and its metabolite xanthotoxol in rat plasma by using HPLC-ESI-MS coupled with hollow fiber liquid phase microextraction. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jan; 945-946(?):185-92. doi: 10.1016/j.jchromb.2013.11.050. [PMID: 24342512]
  • Stavros E Bariamis, Marilena Marin, Constantinos M Athanassopoulos, Christos Kontogiorgis, Zinovia Tsimali, Dionissios Papaioannou, Giovanni Sindona, Giovanni Romeo, Konstantinos Avgoustakis, Dimitra Hadjipavlou-Litina. Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives. European journal of medicinal chemistry. 2013 Feb; 60(?):155-69. doi: 10.1016/j.ejmech.2012.11.043. [PMID: 23291118]
  • Zhao Chen, Jiajing Wang, Danxia Chen, Guorong Fan, Yutian Wu. Sodium desoxycholate-assisted capillary electrochromatography with methacrylate ester-based monolithic column on fast separation and determination of coumarin analogs in Angelica dahurica extract. Electrophoresis. 2012 Sep; 33(18):2884-91. doi: 10.1002/elps.201200120. [PMID: 22930555]
  • Aihong Zhao, Xiuwei Yang, Xinbao Yang, Jianxun Liu, Qiuling Wang, Wenquan Wang. [A new natural product from root of Angelica dahurica cv. Qibaizhi]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Aug; 37(16):2400-7. doi: . [PMID: 23234138]
  • Amani S Awaad, Nabilah A Al-Jaber, Gamal A Soliman, Mounerah R Al-Outhman, Mohamed E Zain, John E Moses, Reham M El-Meligy. New biological activities of Casimiroa edulis leaf extract and isolated compounds. Phytotherapy research : PTR. 2012 Mar; 26(3):452-7. doi: 10.1002/ptr.3690. [PMID: 22173732]
  • Man Liu, Xiaowei Shi, Wei Yang, Songchen Liu, Na Wang, Rui Shi, Shi Qiao, Qiao Wang, Yongli Wang. Quantitative analysis of nine coumarins in rat urine and bile after oral administration of Radix Glehniae extract by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. Biomedical chromatography : BMC. 2011 Jul; 25(7):783-93. doi: 10.1002/bmc.1517. [PMID: 20878664]
  • Eunjin Shin, Chul Lee, Sang Hyun Sung, Young Choong Kim, Bang Yeon Hwang, Mi Kyeong Lee. Antifibrotic activity of coumarins from Cnidium monnieri fruits in HSC-T6 hepatic stellate cells. Journal of natural medicines. 2011 Apr; 65(2):370-4. doi: 10.1007/s11418-010-0485-7. [PMID: 21082271]
  • Winnie Lai Ting Kan, Bin Ma, Ge Lin. Sulfur fumigation processing of traditional chinese medicinal herbs: beneficial or detrimental?. Frontiers in pharmacology. 2011; 2(?):84. doi: 10.3389/fphar.2011.00084. [PMID: 22207851]
  • Bang-Le Zhang, Cheng-Qi Fan, Lei Dong, Fang-Dao Wang, Jian-Min Yue. Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure-activity relationship study. European journal of medicinal chemistry. 2010 Nov; 45(11):5258-64. doi: 10.1016/j.ejmech.2010.08.045. [PMID: 20832915]
  • Ying Xie, Weiquan Zhao, Tingting Zhou, Guorong Fan, Yutian Wu. An efficient strategy based on MAE, HPLC-DAD-ESI-MS/MS and 2D-prep-HPLC-DAD for the rapid extraction, separation, identification and purification of five active coumarin components from Radix Angelicae Dahuricae. Phytochemical analysis : PCA. 2010 Sep; 21(5):473-82. doi: 10.1002/pca.1222. [PMID: 20931624]
  • Guo-Qang Liu, Jing Dong, Hong Wang, Yuki Hashi, Shi-Zhong Chen. Differentiation of four pairs of furocoumarin isomers by electrospray ionization tandem mass spectrometry. European journal of mass spectrometry (Chichester, England). 2010; 16(2):215-20. doi: 10.1255/ejms.1070. [PMID: 20212330]
  • K Nagendra Prasad, Lye Yee Chew, Hock Eng Khoo, Kin Weng Kong, Azrina Azlan, Amin Ismail. Antioxidant capacities of peel, pulp, and seed fractions of Canarium odontophyllum Miq. fruit. Journal of biomedicine & biotechnology. 2010; 2010(?):. doi: 10.1155/2010/871379. [PMID: 20936182]
  • Toshifumi Hirata, Misato Fujii, Kazuhiro Akita, Noriyuki Yanaka, Kaori Ogawa, Masanori Kuroyanagi, Daiki Hongo. Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer. Bioorganic & medicinal chemistry. 2009 Jan; 17(1):25-8. doi: 10.1016/j.bmc.2008.11.039. [PMID: 19054677]
  • Ya Zhao, Zhong Yuan. [A new coumarin glycoside from Glehnia littoralis]. Yao xue xue bao = Acta pharmaceutica Sinica. 2007 Oct; 42(10):1070-3. doi: . [PMID: 18229615]
  • Ying Xie, Yi Chen, Mei Lin, Jun Wen, Guorong Fan, Yutian Wu. High-performance liquid chromatographic method for the determination and pharmacokinetic study of oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma. Journal of pharmaceutical and biomedical analysis. 2007 May; 44(1):166-72. doi: 10.1016/j.jpba.2007.02.002. [PMID: 17344014]
  • Yi Chen, Guorong Fan, Bin Chen, Ying Xie, Huiling Wu, Yutian Wu, Chao Yan, Jianmin Wang. Separation and quantitative analysis of coumarin compounds from Angelica dahurica (Fisch. ex Hoffm) Benth. et Hook. f by pressurized capillary electrochromatography. Journal of pharmaceutical and biomedical analysis. 2006 Apr; 41(1):105-16. doi: 10.1016/j.jpba.2005.10.033. [PMID: 16318908]
  • Yuan-yan Luu, Li Li, Cun Zhang, Yong-qing Xiao. [Studies on chemical constituents in roots of Heracleum rapula]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Apr; 31(8):667-8. doi: . [PMID: 16830827]
  • S Cui, X Liu, X Yang, D Liu, Y Xiao, K Bada, M Taniguchi. [Chemical composition of Pleurospermym rivulorum (Diels)]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1995 Dec; 20(12):743-4, 763. doi: ". [PMID: 8703339]
  • Y Q Xiao, Y F Sun, X H Liu. [Chemical constituents of Notopterygium incisum Ting]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1994 Jul; 19(7):421-2, 447. doi: ". [PMID: 7802950]
  • . . . . doi: . [PMID: 15009205]