Danthron (BioDeep_00000406552)

 

Secondary id: BioDeep_00000002382, BioDeep_00000864926

natural product PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


1,8-dihydroxyanthraquinone

化学式: C14H8O4 (240.0422568)
中文名称: 1,8-二羟基蒽醌
谱图信息: 最多检出来源 Viridiplantae(plant) 1.49%

分子结构信息

SMILES: C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=CC=C3O
InChI: InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H

描述信息

A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AB - Contact laxatives
D005765 - Gastrointestinal Agents > D002400 - Cathartics
D009676 - Noxae > D009153 - Mutagens
Danthron is a natural product extracted from the traditional Chinese medicine Salvia miltiorrhiza Bunge. Danthron functions in regulating glucose and lipid metabolism by activating AMPK.
Danthron is a natural product extracted from the traditional Chinese medicine Salvia miltiorrhiza Bunge. Danthron functions in regulating glucose and lipid metabolism by activating AMPK.
Danthron is a natural product extracted from the traditional Chinese medicine Salvia miltiorrhiza Bunge. Danthron functions in regulating glucose and lipid metabolism by activating AMPK.

同义名列表

5 个代谢物同义名

1,8-dihydroxyanthraquinone; Danthron; Dantron; Chrysazin; Danthron



数据库引用编号

36 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)

46 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

  • Razieh Amini, Shadi Moradi, Rezvan Najafi, Mehrdokht Mazdeh, Amir Taherkhani. BACE1 Inhibition Utilizing Organic Compounds Holds Promise as a Potential Treatment for Alzheimer's and Parkinson's Diseases. Oxidative medicine and cellular longevity. 2024; 2024(?):6654606. doi: 10.1155/2024/6654606. [PMID: 38425997]
  • Chuanrui Ma, Zhongyan Wang, Ronglin Xia, Lingling Wei, Chao Zhang, Jing Zhang, Linna Zhao, Han Wu, Lin Kang, Shu Yang. Danthron ameliorates obesity and MAFLD through activating the interplay between PPARα/RXRα heterodimer and adiponectin receptor 2. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 May; 137(?):111344. doi: 10.1016/j.biopha.2021.111344. [PMID: 33581653]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Xiujin Shi, Yi Zhang, Baidi Lin, Yang Zhou, Wei Suo, Juanjuan Wei, Lin Zhang, Jie Lin, Fucheng Xiao, Limin Zhao, Yang Lin. Danthron attenuates experimental atherosclerosis by targeting foam cell formation. Experimental physiology. 2021 03; 106(3):653-662. doi: 10.1113/ep089021. [PMID: 33450102]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Sameer Shakeel Ansari, Rizwan Hasan Khan, Saeeda Naqvi. Probing the intermolecular interactions into serum albumin and anthraquinone systems: a spectroscopic and docking approach. Journal of biomolecular structure & dynamics. 2018 Oct; 36(13):3362-3375. doi: 10.1080/07391102.2017.1388284. [PMID: 28974158]
  • C Anisha, P Sachidanandan, E K Radhakrishnan. Endophytic Paraconiothyrium sp. from Zingiber officinale Rosc. Displays Broad-Spectrum Antimicrobial Activity by Production of Danthron. Current microbiology. 2018 Mar; 75(3):343-352. doi: 10.1007/s00284-017-1387-7. [PMID: 29101453]
  • Aditya Arvindekar, Tanaji More, Pavan V Payghan, Kirti Laddha, Nanda Ghoshal, Akalpita Arvindekar. Evaluation of anti-diabetic and alpha glucosidase inhibitory action of anthraquinones from Rheum emodi. Food & function. 2015 Aug; 6(8):2693-700. doi: 10.1039/c5fo00519a. [PMID: 26145710]
  • Rong Zhou, Ling Wang, Xing Xu, Jing Chen, Li-hong Hu, Li-li Chen, Xu Shen. Danthron activates AMP-activated protein kinase and regulates lipid and glucose metabolism in vitro. Acta pharmacologica Sinica. 2013 Aug; 34(8):1061-9. doi: 10.1038/aps.2013.39. [PMID: 23770982]
  • . Toxicology study of senna (CAS No. 8013-11-4) in C57BL/6NTAC Mice and toxicology and carcinogenesis study of senna in genetically modified C3B6.129F1/Tac-Trp53tm1Brd haploinsufficient mice (Feed Studies). National Toxicology Program genetically modified model report. 2012 Apr; ?(15):1-114. doi: . [PMID: 23001288]
  • Pius S Fasinu, Patrick J Bouic, Bernd Rosenkranz. An overview of the evidence and mechanisms of herb-drug interactions. Frontiers in pharmacology. 2012; 3(?):69. doi: 10.3389/fphar.2012.00069. [PMID: 22557968]
  • Samuel Takashi Saito, Danielle da Silva Trentin, Alexandre José Macedo, Cristina Pungartnik, Grace Gosmann, Jaqueline de Deos Silveira, Temenouga Nikolova Guecheva, João Antonio Pêgas Henriques, Martin Brendel. Bioguided Fractionation Shows Cassia alata Extract to Inhibit Staphylococcus epidermidis and Pseudomonas aeruginosa Growth and Biofilm Formation. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):867103. doi: 10.1155/2012/867103. [PMID: 22548121]
  • Jie Tian, Xuan Chen, Xiaohong Bai. Comparison of dispersive liquid-liquid microextraction based on organic solvent and ionic liquid combined with high-performance liquid chromatography for the analysis of emodin and its metabolites in urine samples. Journal of separation science. 2012 Jan; 35(1):145-52. doi: 10.1002/jssc.201100729. [PMID: 22144110]
  • Wenshuo Zhang, Robert M Sargis, Paul A Volden, Christopher M Carmean, Xiao J Sun, Matthew J Brady. PCB 126 and other dioxin-like PCBs specifically suppress hepatic PEPCK expression via the aryl hydrocarbon receptor. PloS one. 2012; 7(5):e37103. doi: 10.1371/journal.pone.0037103. [PMID: 22615911]
  • Hong Yang, Li-na Xu, Cheng-yan He, Xin Liu, Rou-yu Fang, Tong-hui Ma. CFTR chloride channel as a molecular target of anthraquinone compounds in herbal laxatives. Acta pharmacologica Sinica. 2011 Jun; 32(6):834-9. doi: 10.1038/aps.2011.46. [PMID: 21602836]
  • Maher Kammoun, Sonia Miladi, Yassine Ben Ali, Mohamed Damak, Youssef Gargouri, Sofiane Bezzine. In vitro study of the PLA2 inhibition and antioxidant activities of Aloe vera leaf skin extracts. Lipids in health and disease. 2011 Feb; 10(?):30. doi: 10.1186/1476-511x-10-30. [PMID: 21310091]
  • Weijun Kong, Xinhua Xia, Jiabo Wang, Canping Zhou, Fang Fang, Xiaoyan Xing, Cheng Jin, Yanling Zhao, Qingce Zang, Xiaohe Xiao. Solid-phase extraction and ultra high-performance liquid chromatography tandem mass spectrometry analysis of the gastrointestinal absorption of emodin in different digestive segments of rats. Journal of separation science. 2011 Feb; 34(3):260-7. doi: 10.1002/jssc.201000757. [PMID: 21268248]
  • Haitao Zhang, Rong Zhou, Li Li, Jing Chen, Lili Chen, Chenjing Li, Hong Ding, Liang Yu, Lihong Hu, Hualiang Jiang, Xu Shen. Danthron functions as a retinoic X receptor antagonist by stabilizing tetramers of the receptor. The Journal of biological chemistry. 2011 Jan; 286(3):1868-75. doi: 10.1074/jbc.m110.166215. [PMID: 21084305]
  • Fabrice Nesslany, Sophie Simar-Meintières, Hervé Ficheux, Daniel Marzin. Aloe-emodin-induced DNA fragmentation in the mouse in vivo comet assay. Mutation research. 2009 Aug; 678(1):13-9. doi: 10.1016/j.mrgentox.2009.06.004. [PMID: 19559101]
  • Itsuko Fukuda, Atsushi Kaneko, Shin Nishiumi, Masaya Kawase, Rika Nishikiori, Nobuhide Fujitake, Hitoshi Ashida. Structure-activity relationships of anthraquinones on the suppression of DNA-binding activity of the aryl hydrocarbon receptor induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Journal of bioscience and bioengineering. 2009 Mar; 107(3):296-300. doi: 10.1016/j.jbiosc.2008.10.008. [PMID: 19269596]
  • Evandro L Duarte, Tiago R Oliveira, Daiane S Alves, Vicente Micol, M Teresa Lamy. On the interaction of the anthraquinone barbaloin with negatively charged DMPG bilayers. Langmuir : the ACS journal of surfaces and colloids. 2008 Apr; 24(8):4041-9. doi: 10.1021/la703896w. [PMID: 18318556]
  • Wen-Fu Tang, Qin Yu, Mei-Hua Wan, Feng Qin, Yong-Gang Wang, Guang-Yuan Chen, Mao-Zhi Liang, Xi Huang. Simultaneous determination and pharmacokinetic studies of aloe emodin and chrysophanol in rats after oral administration of Da-Cheng-Qi decoction by high-performance liquid chromatography. Biomedical chromatography : BMC. 2007 Jul; 21(7):701-7. doi: 10.1002/bmc.808. [PMID: 17370297]
  • Rosa E Moo-Puc, Gonzalo J Mena-Rejon, Leovigildo Quijano, Roberto Cedillo-Rivera. Antiprotozoal activity of Senna racemosa. Journal of ethnopharmacology. 2007 Jun; 112(2):415-6. doi: 10.1016/j.jep.2007.03.028. [PMID: 17481835]
  • Dongming Yan, Yueming Ma. Simultaneous quantification of five anthraquinones in rat plasma by high-performance liquid chromatography with fluorescence detection. Biomedical chromatography : BMC. 2007 May; 21(5):502-7. doi: 10.1002/bmc.784. [PMID: 17294506]
  • Leena Laitinen, Elina Takala, Heikki Vuorela, Pia Vuorela, Ann Marie Kaukonen, Martti Marvola. Anthranoid laxatives influence the absorption of poorly permeable drugs in human intestinal cell culture model (Caco-2). European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2007 Apr; 66(1):135-45. doi: 10.1016/j.ejpb.2006.09.006. [PMID: 17098405]
  • Katarzyna Skupińska, Monika Zylm, Irena Misiewicz, Teresa Kasprzycka-Guttman. Interaction of anthracene and its oxidative derivatives with human serum albumin. Acta biochimica Polonica. 2006; 53(1):101-12. doi: . [PMID: 16404478]
  • Bo-Kyung Sung, Moo-Key Kim, Wang-Hyu Lee, Dong-Heon Lee, Hoi-Seon Lee. Growth responses of Cassia obtusifolia toward human intestinal bacteria. Fitoterapia. 2004 Jul; 75(5):505-9. doi: 10.1016/j.fitote.2004.03.012. [PMID: 15261390]
  • Yong-Soo Kwon, Jae-Young Koh, Dong-Keun Song, Hyoung-Chun Kim, Myung-Sang Kwon, Yeon-Sik Choi, Myung-Bok Wie. Danthron inhibits the neurotoxicity induced by various compounds causing oxidative damages including beta-amyloid (25-35) in primary cortical cultures. Biological & pharmaceutical bulletin. 2004 May; 27(5):723-6. doi: 10.1248/bpb.27.723. [PMID: 15133254]
  • L D Kong, Christopher H K Cheng, R X Tan. Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. Journal of ethnopharmacology. 2004 Apr; 91(2-3):351-5. doi: 10.1016/j.jep.2004.01.013. [PMID: 15120460]
  • S Gupta, T Chaudhuri, P Seth, D K Ganguly, A K Giri. Antimutagenic effects of black tea (World Blend) and its two active polyphenols theaflavins and thearubigins in Salmonella assays. Phytotherapy research : PTR. 2002 Nov; 16(7):655-61. doi: 10.1002/ptr.1038. [PMID: 12410547]
  • Ausra Nemeikaite-Ceniene, Egle Sergediene, Henrikas Nivinskas, Narimantas Cenas. Cytotoxicity of natural hydroxyanthraquinones: role of oxidative stress. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2002 Sep; 57(9-10):822-7. doi: 10.1515/znc-2002-9-1012. [PMID: 12440719]
  • H Matsuda, H Shimoda, T Morikawa, M Yoshikawa. Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity. Bioorganic & medicinal chemistry letters. 2001 Jul; 11(14):1839-42. doi: 10.1016/s0960-894x(01)00318-3. [PMID: 11459643]
  • S J Semple, S M Pyke, G D Reynolds, R L Flower. In vitro antiviral activity of the anthraquinone chrysophanic acid against poliovirus. Antiviral research. 2001 Mar; 49(3):169-78. doi: 10.1016/s0166-3542(01)00125-5. [PMID: 11428243]
  • K Kågedal, D Bironaite, K Ollinger. Anthraquinone cytotoxicity and apoptosis in primary cultures of rat hepatocytes. Free radical research. 1999 Nov; 31(5):419-28. doi: 10.1080/10715769900300981. [PMID: 10547186]
  • S O Mueller, M Schmitt, W Dekant, H Stopper, J Schlatter, P Schreier, W K Lutz. Occurrence of emodin, chrysophanol and physcion in vegetables, herbs and liquors. Genotoxicity and anti-genotoxicity of the anthraquinones and of the whole plants. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1999 May; 37(5):481-91. doi: 10.1016/s0278-6915(99)00027-7. [PMID: 10456676]
  • S O Müeller, W K Lutz, H Stopper. Factors affecting the genotoxic potency ranking of natural anthraquinones in mammalian cell culture systems. Mutation research. 1998 May; 414(1-3):125-9. doi: 10.1016/s1383-5718(98)00047-3. [PMID: 9630566]
  • A Nishikawa, Y Kase, T Hayakawa, T Yanagisawa, J Kanno, Y Hayashi. Enhancement of cell proliferation and prostaglandin biosynthesis by 1,8-dihydroxyanthraquinone in the rat large intestine. Carcinogenesis. 1997 Jun; 18(6):1259-63. doi: 10.1093/carcin/18.6.1259. [PMID: 9214611]
  • S O Müller, I Eckert, W K Lutz, H Stopper. Genotoxicity of the laxative drug components emodin, aloe-emodin and danthron in mammalian cells: topoisomerase II mediated?. Mutation research. 1996 Dec; 371(3-4):165-73. doi: 10.1016/s0165-1218(96)90105-6. [PMID: 9008718]
  • W Lang. Pharmacokinetic-metabolic studies with 14C-aloe emodin after oral administration to male and female rats. Pharmacology. 1993 Oct; 47 Suppl 1(?):110-9. doi: 10.1159/000139849. [PMID: 8234417]
  • G Krumbiegel, H U Schulz. Rhein and aloe-emodin kinetics from senna laxatives in man. Pharmacology. 1993 Oct; 47 Suppl 1(?):120-4. doi: 10.1159/000139850. [PMID: 8234418]
  • R B Sund, T Junker, K E Malterud. A note on the complex metabolism of danthron infused into the rat. Pharmacology. 1993 Oct; 47 Suppl 1(?):134-7. doi: 10.1159/000139852. [PMID: 8234420]
  • E Leng-Peschlow, K P Odenthal, W Voderholzer, S Müller-Lissner. Chronic sennoside treatment does not cause habituation and secondary hyperaldosteronism in rats. Pharmacology. 1993 Oct; 47 Suppl 1(?):162-71. doi: 10.1159/000139856. [PMID: 8234425]
  • S L Perkins, J F Livesey. A rapid high-performance thin-layer chromatographic urine screen for laxative abuse. Clinical biochemistry. 1993 Jun; 26(3):179-81. doi: 10.1016/0009-9120(93)90023-y. [PMID: 8330386]
  • H S Yun-Choi, J H Kim, M Takido. Potential inhibitors of platelet aggregation from plant sources, V. Anthraquinones from seeds of Cassia obtusifolia and related compounds. Journal of natural products. 1990 May; 53(3):630-3. doi: 10.1021/np50069a014. [PMID: 2213033]
  • P Sjöberg, U Hedelin, T Kronevi, A Lydén-Sokolowski, G Magnusson, G Montin, I M Olofsson, N G Lindquist. Pigmentation of kidneys and lymph nodes of mesocolon in rats fed diets containing the laxative danthron. Toxicology letters. 1988 Dec; 44(3):299-306. doi: 10.1016/0378-4274(88)90169-5. [PMID: 3217945]
  • R B Sund, S O Elvegård. Anthraquinone laxatives: metabolism and transport of danthron and rhein in the rat small and large intestine in vitro. Pharmacology. 1988; 36 Suppl 1(?):144-51. doi: 10.1159/000138434. [PMID: 3368513]
  • R B Sund. Studies on laxatives: biliary and urinary excretion in rats given danthron by intravenous infusion or gastric intubation. Pharmacology & toxicology. 1987 Aug; 61(2):130-7. doi: 10.1111/j.1600-0773.1987.tb01790.x. [PMID: 3671328]
  • J Morton. The detection of laxative abuse. Annals of clinical biochemistry. 1987 Jan; 24 ( Pt 1)(?):107-8. doi: 10.1177/000456328702400116. [PMID: 3827173]
  • J P Moreau, S Moreau, S Skinner. Comparative physiological disposition of some anthraquinone glycosides and aglycones. Biopharmaceutics & drug disposition. 1985 Jul; 6(3):325-34. doi: 10.1002/bdd.2510060307. [PMID: 4041558]
  • F A de Wolff, E J de Haas, M Verweij. A screening method for establishing laxative abuse. Clinical chemistry. 1981 Jun; 27(6):914-7. doi: . [PMID: 6894566]
  • C Eugène, C Patriarche, A Bergue, J Quevauvilliers. [Tienilic acid as a likely cause of "auto immune" active hepatitis (author's transl)]. La Nouvelle presse medicale. 1980 Jun; 9(27):1885-7. doi: . [PMID: 6157146]
  • L Giuliani, G Carmignani, E Belgrano, P Puppo. Transcatheter arterial embolization in urological tumors: the use of isobutyl-2-cyanoacrylate. The Journal of urology. 1979 May; 121(5):630-4. doi: 10.1016/s0022-5347(17)56913-x. [PMID: 439260]
  • M F KOSSOVER, M E BECKHAM, S A THREEFOOT. INFLUENCE OF AN ORAL PERISTALTIC STIMULANT, DANTHRON, ON THE PHENOLSULPHONPHTHALEIN EXCRETION TEST. The American journal of the medical sciences. 1964 Jun; 247(?):694-9. doi: 10.1097/00000441-196406000-00010. [PMID: 14169817]