Daphnoretin (BioDeep_00000000512)

human metabolite PANOMIX_OTCML-2023 blood metabolite

代谢物信息卡片

7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-7-yl)oxy]-2H-chromen-2-one

化学式: C19H12O7 (352.05830019999996)
中文名称: 西瑞香素
谱图信息: 最多检出来源 () 0%

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

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

5 个代谢物同义名

7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-7-yl)oxy]-2H-chromen-2-one; 7-hydroxy-6-methoxy-3,7-dicoumaryl ether; Daphnoretin; Dephnoretin; Thymelol

数据库引用编号

16 个数据库交叉引用编号

ChEBI: CHEBI:4324
KEGG: C09216
PubChem: 5281406
HMDB: HMDB0250858
Metlin: METLIN67525
ChEMBL: CHEMBL508494
Wikipedia: Daphnoretin
KNApSAcK: C00002463
chemspider: 4444756
CAS: 2034-69-7
PMhub: MS000010170
PubChem: 11407
3DMET: B02774
NIKKAJI: J419.756I
RefMet: Daphnoretin
medchemexpress: HY-N0699

分类词条

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)

77 个相关的物种来源信息

142738 Stellera chamaejasme:
5691 Trypanosoma brucei: 10.1128/AAC.00044-13
53861 Securigera varia:
181251 Securigera elegans:
4222 Carthamus tinctorius: 10.1023/B:CONC.0000025456.09089.84
57577 Trifolium pratense: 10.1016/J.CLPT.2004.08.023
2753872 Daphne acutiloba: 10.1016/S0031-9422(98)00181-2
66680 Daphne mezereum:
885948 Daphne tangutica:
118892 Coronilla scorpioides:
347984 Coronilla viminalis: 10.1076/PHBI.34.2.114.13188
390707 Coronilla vaginalis:
142181 Edgeworthia chrysantha:
1477590 Daphne genkwa:
329675 Daphne odora: 10.1248/CPB.34.595
2715869 Daphne papyracea: 10.1248/CPB.34.595
224034 Daphne gnidium:
546994 Daphne bholua: 10.1016/S0367-326X(99)00010-6
202097 Scapholeberis mucronata: 10.1016/S0367-326X(99)00010-6
2783874 Daphne mucronata: 10.1016/S0367-326X(99)00010-6
637481 Artemisia keiskeana: 10.1021/NP010103A
714517 Wikstroemia indica:
266085 Ruta montana:
2516486 Enkleia malaccensis: 10.1021/NP50048A051
142184 Enkleia siamensis: 10.1021/NP50048A051
452763 Boenninghausenia albiflora:
699060 Dirca occidentalis: 10.1002/JPS.2600721112
155104 Diarthron vesiculosum: 10.1021/NP50037A018
452791 Ruta corsica: 10.1016/J.FITOTE.2003.12.014
1872696 Wikstroemia retusa: 10.1055/S-2006-961557
69845 Thymelaea hirsuta: 10.1002/(SICI)1099-1573(199806)12:4<282::AID-PTR225>3.0.CO;2-X
1902363 Peddiea fischeri: 10.1021/NP50026A020
2203444 Edgeworthia gardneri:
2807248 Linostoma pauciflorum: 10.1016/J.PHYTOL.2011.08.009
390704 Coronilla repanda: 10.1055/S-0028-1099842
2885539 Wikstroemia uva-ursi: 10.1002/JPS.2600680545
37565 Ruta graveolens: 10.1055/S-0028-1099923
142738 Stellera chamaejasme:
5691 Trypanosoma brucei: 10.1128/AAC.00044-13
53861 Securigera varia:
181251 Securigera elegans:
4222 Carthamus tinctorius: 10.1023/B:CONC.0000025456.09089.84
57577 Trifolium pratense: 10.1016/J.CLPT.2004.08.023
2753872 Daphne acutiloba: 10.1016/S0031-9422(98)00181-2
66680 Daphne mezereum:
885948 Daphne tangutica:
118892 Coronilla scorpioides:
347984 Coronilla viminalis: 10.1076/PHBI.34.2.114.13188
390707 Coronilla vaginalis:
142181 Edgeworthia chrysantha:
1477590 Daphne genkwa:
329675 Daphne odora: 10.1248/CPB.34.595
2715869 Daphne papyracea: 10.1248/CPB.34.595
224034 Daphne gnidium:
546994 Daphne bholua: 10.1016/S0367-326X(99)00010-6
202097 Scapholeberis mucronata: 10.1016/S0367-326X(99)00010-6
2783874 Daphne mucronata: 10.1016/S0367-326X(99)00010-6
637481 Artemisia keiskeana: 10.1021/NP010103A
714517 Wikstroemia indica:
266085 Ruta montana:
2516486 Enkleia malaccensis: 10.1021/NP50048A051
142184 Enkleia siamensis: 10.1021/NP50048A051
452763 Boenninghausenia albiflora:
699060 Dirca occidentalis: 10.1002/JPS.2600721112
155104 Diarthron vesiculosum: 10.1021/NP50037A018
452791 Ruta corsica: 10.1016/J.FITOTE.2003.12.014
1872696 Wikstroemia retusa: 10.1055/S-2006-961557
69845 Thymelaea hirsuta: 10.1002/(SICI)1099-1573(199806)12:4<282::AID-PTR225>3.0.CO;2-X
1902363 Peddiea fischeri: 10.1021/NP50026A020
2203444 Edgeworthia gardneri:
2807248 Linostoma pauciflorum: 10.1016/J.PHYTOL.2011.08.009
390704 Coronilla repanda: 10.1055/S-0028-1099842
2885539 Wikstroemia uva-ursi: 10.1002/JPS.2600680545
37565 Ruta graveolens: 10.1055/S-0028-1099923
9606 Homo sapiens: -
329675 Daphne odora: -
33090 Plants: -

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

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]