Daphnoretin (BioDeep_00000284752)

Main id: BioDeep_00000017361

Secondary id: BioDeep_00000000512, BioDeep_00000869093

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


Daphnoretin

化学式: C19H12O7 (352.0583)
中文名称: 西瑞香素
谱图信息: 最多检出来源 Mus musculus(blood) 11.8%

分子结构信息

SMILES: COC1=C(C=C2C(=C1)C=C(C(=O)O2)OC3=CC4=C(C=C3)C=CC(=O)O4)O
InChI: InChI=1S/C19H12O7/c1-23-16-6-11-7-17(19(22)26-15(11)9-13(16)20)24-12-4-2-10-3-5-18(21)25-14(10)8-12/h2-9,20H,1H3

描述信息

relative retention time with respect to 9-anthracene Carboxylic Acid is 1.010
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.011
Daphnoretin (Dephnoretin), isolated from Wikstroemia indica, possesses antiviral activity[1]. Daphnoretin likes PMA, may direct activation of protein kinase C which in turn activated NADPH oxidase and elicited respiratory burst[2].
Daphnoretin (Dephnoretin), isolated from Wikstroemia indica, possesses antiviral activity[1]. Daphnoretin likes PMA, may direct activation of protein kinase C which in turn activated NADPH oxidase and elicited respiratory burst[2].

同义名列表

4 个代谢物同义名

Daphnoretin; Dephnoretin; Thymelol; Daphnoretin



数据库引用编号

24 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)

150 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 13 AIMP2, BCL2, CASP12, CASP3, CASP9, CDK2, MAPK3, NLRP3, NR1D1, PIK3CA, PTGS2, STAT3, STAT5A
Peripheral membrane protein 1 PTGS2
Endoplasmic reticulum membrane 3 ATF6, BCL2, PTGS2
Nucleus 12 AIMP2, ATF6, BCL2, CASP3, CASP9, CDK2, ITGB3, MAPK3, NLRP3, NR1D1, STAT3, STAT5A
cytosol 12 AIMP2, ATF6, BCL2, CASP3, CASP9, CDK2, MAPK3, NLRP3, PIK3CA, PRKCQ, STAT3, STAT5A
dendrite 1 NR1D1
nuclear body 1 NR1D1
centrosome 1 CDK2
nucleoplasm 8 ATF6, CASP3, CDK2, ITGB3, MAPK3, NR1D1, STAT3, STAT5A
RNA polymerase II transcription regulator complex 3 ATF6, STAT3, STAT5A
Cell membrane 2 ITGB3, TNF
lamellipodium 1 PIK3CA
ruffle membrane 1 ITGB3
Golgi apparatus membrane 2 ATF6, NLRP3
Synapse 1 ITGB3
cell surface 3 ITGA2B, ITGB3, TNF
glutamatergic synapse 3 CASP3, ITGB3, MAPK3
Golgi apparatus 2 ATF6, MAPK3
Golgi membrane 2 ATF6, NLRP3
neuronal cell body 2 CASP3, TNF
Cytoplasm, cytosol 2 AIMP2, NLRP3
endosome 1 CDK2
plasma membrane 7 ITGA2B, ITGB3, MAPK3, PIK3CA, PRKCQ, STAT3, TNF
Membrane 6 AIMP2, ATF6, BCL2, ITGA2B, ITGB3, NLRP3
apical plasma membrane 1 ITGB3
caveola 2 MAPK3, PTGS2
extracellular exosome 2 ITGA2B, ITGB3
endoplasmic reticulum 5 ATF6, BCL2, CASP12, NLRP3, PTGS2
extracellular space 2 IL10, TNF
perinuclear region of cytoplasm 1 PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 4 BCL2, CASP9, MAPK3, NLRP3
protein-containing complex 4 BCL2, CASP9, ITGB3, PTGS2
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 ITGA2B, ITGB3
Secreted 2 IL10, NLRP3
extracellular region 3 IL10, NLRP3, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
transcription regulator complex 2 CDK2, STAT3
centriolar satellite 1 PRKCQ
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 CDK2
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 3 ITGA2B, ITGB3, TNF
dendritic spine 1 NR1D1
Early endosome 1 MAPK3
cell-cell junction 1 ITGB3
recycling endosome 1 TNF
Single-pass type II membrane protein 2 ATF6, TNF
postsynaptic membrane 1 ITGB3
Membrane raft 1 TNF
pore complex 1 BCL2
Cell junction, focal adhesion 2 ITGB3, MAPK3
focal adhesion 3 ITGA2B, ITGB3, MAPK3
Cell projection, dendritic spine 1 NR1D1
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Postsynaptic cell membrane 1 ITGB3
Late endosome 1 MAPK3
receptor complex 1 ITGB3
neuron projection 1 PTGS2
chromatin 4 ATF6, NR1D1, STAT3, STAT5A
phagocytic cup 1 TNF
cytoskeleton 1 MAPK3
chromosome, telomeric region 1 CDK2
blood microparticle 1 ITGA2B
microvillus membrane 1 ITGB3
nuclear envelope 3 ATF6, CDK2, MAPK3
Endomembrane system 1 NLRP3
Membrane, caveola 1 MAPK3
microtubule organizing center 1 NLRP3
Cell projection, dendrite 1 NR1D1
Melanosome 1 ITGB3
myelin sheath 1 BCL2
pseudopodium 1 MAPK3
filopodium membrane 1 ITGB3
endoplasmic reticulum lumen 2 MAPK3, PTGS2
male germ cell nucleus 1 CDK2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
apoptosome 1 CASP9
Cajal body 1 CDK2
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
condensed chromosome 1 CDK2
Nucleus, Cajal body 1 CDK2
platelet alpha granule membrane 2 ITGA2B, ITGB3
X chromosome 1 CDK2
Y chromosome 1 CDK2
integrin complex 2 ITGA2B, ITGB3
cyclin-dependent protein kinase holoenzyme complex 1 CDK2
lamellipodium membrane 1 ITGB3
cyclin E1-CDK2 complex 1 CDK2
cyclin E2-CDK2 complex 1 CDK2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
alphav-beta3 integrin-vitronectin complex 1 ITGB3
alphav-beta3 integrin-IGF-1-IGF1R complex 1 ITGB3
Cell projection, lamellipodium membrane 1 ITGB3
alpha9-beta1 integrin-ADAM8 complex 1 ITGB3
alphav-beta3 integrin-HMGB1 complex 1 ITGB3
alphav-beta3 integrin-PKCalpha complex 1 ITGB3
glycinergic synapse 1 ITGB3
integrin alphaIIb-beta3 complex 2 ITGA2B, ITGB3
integrin alphav-beta3 complex 1 ITGB3
BAD-BCL-2 complex 1 BCL2
[Processed cyclic AMP-dependent transcription factor ATF-6 alpha]: Nucleus 1 ATF6
cyclin A2-CDK2 complex 1 CDK2
cyclin A1-CDK2 complex 1 CDK2
NLRP1 inflammasome complex 1 CASP12
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
caspase complex 1 CASP9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Sandra Liliana Porras-Dávila, Alejandro Zamilpa, Enrique Jiménez-Ferrer, Antonio Jiménez-Aparicio, Mayra Alejandra Santillán-Urquiza, Fernanda Díaz-Patricio, Maribel Herrera-Ruiz. Anti-inflammatory and Neuroprotective effects of standardized fractions in herniarin and daphnoretin from Distictis buccinatoria. Chemistry & biodiversity. 2023 Mar; ?(?):e202200969. doi: 10.1002/cbdv.202200969. [PMID: 36973180]
  • Yu-Chuen Huang, Chun-Ping Huang, Chin-Ping Lin, Kai-Chien Yang, Yu-Jie Lei, Hao-Pei Wang, Yueh-Hsiung Kuo, Yu-Jen Chen. Naturally Occurring Bicoumarin Compound Daphnoretin Inhibits Growth and Induces Megakaryocytic Differentiation in Human Chronic Myeloid Leukemia Cells. Cells. 2022 10; 11(20):. doi: 10.3390/cells11203252. [PMID: 36291120]
  • Yuanhao Liang, Liang Xu, Hongtian Yang, Wenli Xu, Ruixue Hu, Xiaoying Fan, Yufeng Liu. Analysis on the interaction and binding properties of daphnoretin and human serum albumin in the presence of cisplatin: multi-spectroscopic methods and docking simulation. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2021 Apr; 159(?):105723. doi: 10.1016/j.ejps.2021.105723. [PMID: 33482316]
  • Hoda Fathy. Polyphenolics from Gymnocarpos decandrus Forssk roots and their biological activities. Natural product research. 2021 Mar; 35(5):858-862. doi: 10.1080/14786419.2019.1607336. [PMID: 31081700]
  • Guo Feng, Yun-Long Chen, Wei Li, Lai-Lai Li, Zeng-Guang Wu, Zi-Jun Wu, Yue Hai, Si-Chao Zhang, Chuan-Qi Zheng, Chang-Xiao Liu, Xin He. Exploring the Q-marker of "sweat soaking method" processed radix Wikstroemia indica: Based on the "effect-toxicity-chemicals" study. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Jun; 45(?):49-58. doi: 10.1016/j.phymed.2018.03.063. [PMID: 29691116]
  • Chien-An Chen, Chien-Kuo Liu, Ming-Ling Hsu, Chih-Wen Chi, Chun-Chuan Ko, Jian-Syun Chen, Cheng-Ta Lai, Hen-Hong Chang, Tzung-Yan Lee, Yuen-Liang Lai, Yu-Jen Chen. Daphnoretin modulates differentiation and maturation of human dendritic cells through down-regulation of c-Jun N-terminal kinase. International immunopharmacology. 2017 Oct; 51(?):25-30. doi: 10.1016/j.intimp.2017.07.021. [PMID: 28772243]
  • Labib Noman, Feyza Oke-Altuntas, Amar Zellagui, Ayse Sahin Yaglioglu, Ibrahim Demirtas, Susana M Cardoso, Salah Akkal, Noureddine Gherraf, Salah Rhouati. A novel benzimidazole and other constituents with antiproliferative and antioxidant properties from Thymelaea microphylla Coss. et Dur. Natural product research. 2017 Sep; 31(17):2032-2041. doi: 10.1080/14786419.2016.1274888. [PMID: 28105861]
  • Yi-Yi-Li-Ge-Qi Hu, Sa-Li Cao, Long-Fei Lin, Jing Fu, Xiao-Xu Dong, Chun-Jing Yang, Miao Zhang, Jian Ni. [Simultaneous determination of daphnetin, daphnoretin, daphneticin in rat plasma by LC-MS/MS and its application in pharmacokinetic study]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 May; 42(10):1964-1970. doi: 10.19540/j.cnki.cjcmm.20170307.003. [PMID: 29090558]
  • Hong Yan, Ting Ouyang, Qiong-Liang Yang, Biao Xiang, Xin-Hua Xia. [Tissue distribution of galactosyl daphnoretin liposomes in rats]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2016 Sep; 41(18):3457-3462. doi: 10.4268/cjcmm20161823. [PMID: 28925132]
  • Lan Wei, Xiaobo Wang, Shanxue Mu, Lixin Sun, Zhiguo Yu. Ultra high performance liquid chromatography with electrospray ionization tandem mass spectrometry coupled with hierarchical cluster analysis to evaluate Wikstroemia indica (L.) C. A. Mey. from different geographical regions. Journal of separation science. 2015 Jun; 38(12):2093-100. doi: 10.1002/jssc.201401398. [PMID: 25866087]
  • Xing-Nuo Li, Sheng-Qiang Tong, Dong-Ping Cheng, Qing-Yong Li, Ji-Zhong Yan. Coumarins from Edgeworthia chrysantha. Molecules (Basel, Switzerland). 2014 Feb; 19(2):2042-8. doi: 10.3390/molecules19022042. [PMID: 24531219]
  • Oue-artorn Rajachan, Somdej Kanokmedhakul, Phitak Nasomjai, Kwanjai Kanokmedhakul. Chemical constituents and biological activities from roots of Enkleia siamensis. Natural product research. 2014; 28(4):268-70. doi: 10.1080/14786419.2013.838241. [PMID: 24047498]
  • L Zheng, W W Yang, J Y Guo, Y R Jia, L X Sun. Stability of daphnoretin in vitro. Die Pharmazie. 2012 Apr; 67(4):277-82. doi: NULL. [PMID: 22570931]
  • Jian-Ke Wang, Wei Li, Jian-Min Guo, Chang Lin, Xiao-Lan Zhao, Yan Liu, Yan Yang. [Study on quality standards of decoction pieces of Indian stringbush root with sweat]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Dec; 34(12):1848-50. doi: ". [PMID: 22500418]
  • Victor M Navarro-García, Gabriela Rojas, Margarita Avilés, Macrina Fuentes, Gerardo Zepeda. In vitro antifungal activity of coumarin extracted from Loeselia mexicana Brand. Mycoses. 2011 Sep; 54(5):e569-71. doi: 10.1111/j.1439-0507.2010.01993.x. [PMID: 21605187]
  • Jinjuan Zhang, Ying Xiong, Wei Li, Guilin Zhang, Jianke Wang, Chang Lin, Yan Liu. [Comparison of acute toxicity of extract of unprocessed indian atringbush root and its two different processed products]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 May; 36(9):1172-4. doi: . [PMID: 21842643]
  • Wing-Shan Ho, Jun-Yi Xue, Samuel S M Sun, Vincent E C Ooi, Yao-Lan Li. Antiviral activity of daphnoretin isolated from Wikstroemia indica. Phytotherapy research : PTR. 2010 May; 24(5):657-61. doi: 10.1002/ptr.2935. [PMID: 19610034]
  • Cai-Fang Wang, Rao-Rao Li, Lan-Lan Huang, Li-Qun Zhong, Si-Tong Yuan. [Studies on chemical constituents of Daphne genkwa]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Apr; 32(4):508-11. doi: . [PMID: 19645232]
  • Wei Zhang, Wei-Dong Zhang, Chuan Zhang, Run-Hui Liu, Ting-Zhao Li, Peng Fu, Lei Shan. Antitumor activities of extracts and compounds from the roots of Daphne tangutica Maxim. Phytotherapy research : PTR. 2007 Nov; 21(11):1113-5. doi: 10.1002/ptr.2227. [PMID: 17628482]
  • Tian-Zhu Zhang, Chun-Yan Wei, Guo-Hai Xu, Se-Won Park. 7-Hydroxy-6-methoxy-3-[(2-oxo-2H-1-benzopyran-7-yl)oxy]-2H-1-benzopyran-2-one. Acta crystallographica. Section C, Crystal structure communications. 2006 Feb; 62(Pt 2):o86-8. doi: 10.1107/s0108270106000874. [PMID: 16456294]
  • Lie-Chwen Lin, Kuo-Yi Yang, Yen-Fei Chen, Shau-Chun Wang, Tung-Hu Tsai. Measurement of daphnoretin in plasma of freely moving rat by liquid chromatography. Journal of chromatography. A. 2005 May; 1073(1-2):285-9. doi: 10.1016/j.chroma.2004.09.041. [PMID: 15909531]
  • Wei Zhang, Wei-dong Zhang, Ting-zhao Li, Chuan Zhang, Run-hui Liu, Yun Zhou, Juan Su. [Studies on the chemical constituents in roots of Daphne odora var. atrocaulis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Apr; 30(7):513-5. doi: . [PMID: 16011095]
  • N Suh, L Luyengi, H H Fong, A D Kinghorn, J M Pezzuto. Discovery of natural product chemopreventive agents utilizing HL-60 cell differentiation as a model. Anticancer research. 1995 Mar; 15(2):233-9. doi: . [PMID: 7762989]
  • F N Ko, Y L Chang, Y H Kuo, Y L Lin, C M Teng. Daphnoretin, a new protein kinase C activator isolated from Wikstroemia indica C.A. Mey. The Biochemical journal. 1993 Oct; 295 ( Pt 1)(?):321-7. doi: 10.1042/bj2950321. [PMID: 8216237]
  • T Konishi, S Wada, S Kiyosawa. [Constituents of the leaves of Daphne pseudo-mezereum]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1993 Sep; 113(9):670-5. doi: 10.1248/yakushi1947.113.9_670. [PMID: 8229666]
  • C Y Duh, C H Phoebe, J M Pezzuto, A D Kinghorn, N R Farnsworth. Plant anticancer agents, XLII. Cytotoxic constituents from Wikstroemia elliptica. Journal of natural products. 1986 Jul; 49(4):706-9. doi: 10.1021/np50046a031. [PMID: 3783168]
  • S S Handa, A D Kinghorn, G A Cordell, N R Farnsworth. Plant anticancer agents. XXVI. Constituents of Peddiea fischeri. Journal of natural products. 1983 Mar; 46(2):248-50. doi: 10.1021/np50026a020. [PMID: 6875580]