dictamine (BioDeep_00000017301)

 

Secondary id: BioDeep_00000003758, BioDeep_00000861612

human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs Cytotoxicity


代谢物信息卡片


4-27-00-02030 (Beilstein Handbook Reference)

化学式: C12H9NO2 (199.0633254)
中文名称: 白藓碱, 白鲜碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.31%

分子结构信息

SMILES: COC1=C2C(OC=C2)=NC3=CC=CC=C13
InChI: InChI=1S/C12H9NO2/c1-14-11-8-4-2-3-5-10(8)13-12-9(11)6-7-15-12/h2-7H,1H3

描述信息

Dictamnine is an oxacycle, an organonitrogen heterocyclic compound, an organic heterotricyclic compound and an alkaloid antibiotic.
Dictamnine is a natural product found in Haplophyllum bucharicum, Haplophyllum cappadocicum, and other organisms with data available.
A furoquinoline alkaloid, dictamnine, is very common within the family Rutaceae. It is the main alkaloid in the roots of Dictamnus albus and responsible for the mutagenicity of the drug derived from crude extracts. Dictamnine was also reported to be a phototoxic and photomutagenic compound. It participates in the severe skin phototoxicity of the plant.
Dictamnine (Dictamine) exhibits cytotoxicity to human cervical and colon cancer cells and also has antibacterial and antifungal activities.
Dictamnine (Dictamine) exhibits cytotoxicity to human cervical and colon cancer cells and also has antibacterial and antifungal activities.

同义名列表

27 个代谢物同义名

4-27-00-02030 (Beilstein Handbook Reference); Furo(2,3-b)quinoline, 4-methoxy-; Furo[2,3-b]quinoline, 4-methoxy-; 4-Methoxyfuro[2,3-b]quinoline #; 4-Methoxy-furo[2,3-b]quinoline; 4-methoxyfuro(2,3-b)quinoline; 4-Methoxyfuro[2,3-b]quinoline; Dictamnine;Dectamine; Spectrum3_000101; Spectrum2_000349; Spectrum5_000086; Spectrum4_001383; DICTAMNINE [MI]; Dictamnine,(S); Oprea1_134081; DivK1c_006140; Oprea1_294767; KBio2_003645; KBio2_006213; KBio3_000802; KBio2_001077; KBio1_001084; Dictamnine; Diktaminin; dictamine; Dectamine; C12H9NO2



数据库引用编号

15 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)

72 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

  • Yihan Huang, Chenrui Zhao, Guodong Zheng, Yujuan Yuan, Ling Gong, Rui Liu, Jingang An. Dictamnine Ameliorates DNFB-Induced Atopic Dermatitis Like Skin Lesions in Mice by Inhibiting M1 Macrophage Polarization and Promoting Autophagy. Biological & pharmaceutical bulletin. 2024 Jan; 47(1):175-186. doi: 10.1248/bpb.b23-00436. [PMID: 38092386]
  • Xiaojin Chang, Guangyao Li, Bufan Yang, Dongju Lin. Protection of schisantherin A against dictamnine-induced hepatotoxicity: Pharmacokinetic insights. Journal of applied toxicology : JAT. 2023 Oct; ?(?):. doi: 10.1002/jat.4557. [PMID: 37873635]
  • Minxuan Yuan, Xiaogui Liang, Duantao Cao, Hongliang Wu, Suling Xiao, Hui Liang, Hang Li, Yingjin Huang, Hongyi Wei, Wenwen Peng, Xiaoxiang Fu. Dictamnine suppresses the development of pear ring rot induced by Botryosphaeria dothidea infection by disrupting the chitin biosynthesis. Pesticide biochemistry and physiology. 2023 Sep; 195(?):105534. doi: 10.1016/j.pestbp.2023.105534. [PMID: 37666587]
  • Can Tu, Zhao-Juan Guo, Bing-Qian Jiang, Qian-Jun Kang, Ting Wang. [Difference in liver injury induced by dictamnine between males and females: based on untargeted metabolomics]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 Jun; 48(12):3317-3326. doi: 10.19540/j.cnki.cjcmm.20230119.401. [PMID: 37382016]
  • Niuniu Yang, Haifeng Shao, Jialin Deng, Yan Yang, Zongxiang Tang, Guanyi Wu, Yanqing Liu. Dictamnine ameliorates chronic itch in DNFB-induced atopic dermatitis mice via inhibiting MrgprA3. Biochemical pharmacology. 2023 02; 208(?):115368. doi: 10.1016/j.bcp.2022.115368. [PMID: 36493846]
  • Wenbo Yang, Peng Liu, Ying Chen, Qingyu Lv, Zhongtian Wang, Wenhua Huang, Hua Jiang, Yuling Zheng, Yongqiang Jiang, Liping Sun. Dictamnine Inhibits the Adhesion to and Invasion of Uropathogenic Escherichia Coli (UPEC) to Urothelial Cells. Molecules (Basel, Switzerland). 2022 Jan; 27(1):. doi: 10.3390/molecules27010272. [PMID: 35011504]
  • Qiyan Lin, Huida Guan, Chao Ma, Liangni Chen, Lanlan Cao, Hanze Liu, Xuemei Cheng, Changhong Wang. Biotransformation patterns of dictamnine in vitro/in vivo and its relative molecular mechanism of dictamnine-induced acute liver injury in mice. Environmental toxicology and pharmacology. 2021 Jul; 85(?):103628. doi: 10.1016/j.etap.2021.103628. [PMID: 33652109]
  • Rui Liu, Shiling Hu, Yuanyuan Ding, Jue Wang, Yuejin Wang, Jiapan Gao, Langchong He. Dictamnine is an effective anti-anaphylactoid compound acting via the MrgX2 receptor located on mast cells. Phytotherapy research : PTR. 2021 Jun; 35(6):3181-3193. doi: 10.1002/ptr.7007. [PMID: 33893660]
  • Chin-Yu Lin, Yun-Ting Hsieh, Long Yi Chan, Ting-Ya Yang, Tomoji Maeda, Tsong-Min Chang, Huey-Chun Huang. Dictamnine delivered by PLGA nanocarriers ameliorated inflammation in an oxazolone-induced dermatitis mouse model. Journal of controlled release : official journal of the Controlled Release Society. 2021 01; 329(?):731-742. doi: 10.1016/j.jconrel.2020.10.007. [PMID: 33031879]
  • Zhuo-Qing Li, Ling-Li Wang, Jing Zhou, Xian Zheng, Yan Jiang, Ping Li, Hui-Jun Li. Integration of transcriptomics and metabolomics profiling reveals the metabolic pathways affected in dictamnine-induced hepatotoxicity in mice. Journal of proteomics. 2020 02; 213(?):103603. doi: 10.1016/j.jprot.2019.103603. [PMID: 31812602]
  • Fuguo Shi, Hong Pan, Baodong Cui, Yi Li, Linyan Huang, Yuanfu Lu. Dictamnine-induced hepatotoxicity in mice: the role of metabolic activation of furan. Toxicology and applied pharmacology. 2019 02; 364(?):68-76. doi: 10.1016/j.taap.2018.12.012. [PMID: 30578885]
  • Jing Ying Wang, Zhe Wang, Ming Yue Li, Zhihong Zhang, Chunliu Mi, Hong Xiang Zuo, Yue Xing, Yan-Ling Wu, Li-Hua Lian, Guang Hua Xu, Lian Xun Piao, Juan Ma, Xuejun Jin. Dictamnine promotes apoptosis and inhibits epithelial-mesenchymal transition, migration, invasion and proliferation by downregulating the HIF-1α and Slug signaling pathways. Chemico-biological interactions. 2018 Dec; 296(?):134-144. doi: 10.1016/j.cbi.2018.09.014. [PMID: 30266538]
  • Qiongyin Fan, Baosheng Zhao, Chunguo Wang, Jingxuan Zhang, Jinying Wu, Ting Wang, Anlong Xu. Subchronic Toxicity Studies of Cortex Dictamni Extracts in Mice and Its Potential Hepatotoxicity Mechanisms in Vitro. Molecules (Basel, Switzerland). 2018 Sep; 23(10):. doi: 10.3390/molecules23102486. [PMID: 30274140]
  • Yi-Ran Wang, Yong-Hui Li, Tao Guo, Hai-Long Li, Yin-Feng Tan, Zhong Zhang, Xu-Guang Zhang, Shi-Ying Mai, Jun-Qing Zhang. Measurement of pharmacokinetics and tissue distribution of three bioactive constituents from Zanthoxylum armatum DC in rat plasma and tissues through UFLC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Jun; 1087-1088(?):80-89. doi: 10.1016/j.jchromb.2018.04.032. [PMID: 29723699]
  • Pinning Feng, Xinrong Hu, Xiaoliang Wu, Jun Dong, Xiuyu Cai. Characterization of an epoxide-derived metabolite of dictamnine using high-performance liquid chromatography with hybrid linear trap quadrupole orbitrap mass spectrometry. Journal of separation science. 2016 Dec; 39(24):4858-4865. doi: 10.1002/jssc.201600980. [PMID: 27790853]
  • Pei Wang, Yunli Zhao, Yingdong Zhu, Jianbo Sun, Aaron Yerke, Shengmin Sang, Zhiguo Yu. Metabolism of dictamnine in liver microsomes from mouse, rat, dog, monkey, and human. Journal of pharmaceutical and biomedical analysis. 2016 Feb; 119(?):166-74. doi: 10.1016/j.jpba.2015.11.016. [PMID: 26683990]
  • Taijun Yin, Guanyi Yang, Yong Ma, Beibei Xu, Ming Hu, Ming You, Song Gao. Developing an activity and absorption-based quality control platform for Chinese traditional medicine: Application to Zeng-Sheng-Ping(Antitumor B). Journal of ethnopharmacology. 2015 Aug; 172(?):195-201. doi: 10.1016/j.jep.2015.06.019. [PMID: 26099633]
  • Jian-Bo Sun, Wei Qu, Fu-Qin Guan, Lin-Zhen Li, Jing-Yu Liang. A new quinoline alkaloid from the roots of Dictamnus angustifolius. Chinese journal of natural medicines. 2014 Mar; 12(3):222-4. doi: 10.1016/s1875-5364(14)60037-6. [PMID: 24702810]
  • Pei Wang, Jianbo Sun, Jingyao Xu, Qin Yan, Enze Gao, Wei Qu, Yunli Zhao, Zhiguo Yu. Pharmacokinetics, tissue distribution and excretion study of dictamnine, a major bioactive component from the root bark of Dictamnus dasycarpus Turcz. (Rutaceae). Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Dec; 942-943(?):1-8. doi: 10.1016/j.jchromb.2013.10.025. [PMID: 24200865]
  • Pei Wang, Jianbo Sun, Enze Gao, Yunli Zhao, Wei Qu, Zhiguo Yu. Simultaneous determination of limonin, dictamnine, obacunone and fraxinellone in rat plasma by a validated UHPLC-MS/MS and its application to a pharmacokinetic study after oral administration of Cortex Dictamni extract. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Jun; 928(?):44-51. doi: 10.1016/j.jchromb.2013.03.018. [PMID: 23611843]
  • Xinzhou Yang, Yunjiang Feng, Sandra Duffy, Vicky M Avery, David Camp, Ronald J Quinn, Rohan A Davis. A new quinoline epoxide from the Australian plant Drummondita calida. Planta medica. 2011 Sep; 77(14):1644-7. doi: 10.1055/s-0030-1270963. [PMID: 21472648]
  • Can Xiao, Yuan Yuan, Yang-zhou Ding, Tie-fei Jin, Gang Pei. [Study on the alkaloids from the stem of Zanthoxylum dissitum]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Apr; 34(4):551-3. doi: . [PMID: 21809541]
  • Carlos Andres Coy Barrera, Ericsson David Coy Barrera, Diana Susana Granados Falla, Gabriela Delgado Murcia, Luis Enrique Cuca Suarez. seco-limonoids and quinoline alkaloids from Raputia heptaphylla and their antileishmanial activity. Chemical & pharmaceutical bulletin. 2011; 59(7):855-9. doi: 10.1248/cpb.59.855. [PMID: 21720036]
  • Sen Wang, Shuiping Ou, Yongmei Guan, Dezhi Wu, Lihua Chen, Weifeng Zhu. [Dermatopharmacokinetic studies of liangfu cream in mice skin]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Sep; 35(17):2254-7. doi: 10.4268/cjcmm20101707. [PMID: 21137331]
  • Xiaojuan Yang, Yanfang Liu, Zhong Bao, Yong Jiang, Pengfei Tu. [Simultaneous determination of three active compounds in root barks of Dictamnus dasycarpus by RP-HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Jan; 35(2):187-90. doi: . [PMID: 20394291]
  • Sen Wang, Weifeng Zhu, Shuiping Ou, Yongmeii Guan, Lihua Chen, Ming Yang. [Effects of penetration enhancers on in vitro percutaneous absorption and amount retained in skin of paeonol, dictamnine, fraxinellone and glycyrrhetinic acid in Liangfu cream]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Jul; 34(14):1778-82. doi: . [PMID: 19894505]
  • Vanessa Gisele Pasqualotto Severino, Cristiane de Melo Cazal, Moacir Rossi Forim, Maria Fátima das Graças Fernandes da Silva, Edson Rodrigues-Filho, João Batista Fernandes, Paulo Cezar Vieira. Isolation of secondary metabolites from Hortia oreadica (Rutaceae) leaves through high-speed counter-current chromatography. Journal of chromatography. A. 2009 May; 1216(19):4275-81. doi: 10.1016/j.chroma.2009.02.009. [PMID: 19249788]
  • Na Guo, Lu Yu, Rizeng Meng, Junwen Fan, Dacheng Wang, Guang Sun, Xuming Deng. Global gene expression profile of Saccharomyces cerevisiae induced by dictamnine. Yeast (Chichester, England). 2008 Sep; 25(9):631-41. doi: 10.1002/yea.1614. [PMID: 18727144]
  • Guohong Yang, Daofeng Chen. Alkaloids from the roots of Zanthoxylum nitidum and their antiviral and antifungal effects. Chemistry & biodiversity. 2008 Sep; 5(9):1718-22. doi: 10.1002/cbdv.200890160. [PMID: 18816524]
  • Hung-Yi Huang, Tsutomu Ishikawa, Chien-Fang Peng, Ian-Lih Tsai, Ih-Sheng Chen. Constituents of the root wood of Zanthoxylum wutaiense with antitubercular activity. Journal of natural products. 2008 Jul; 71(7):1146-51. doi: 10.1021/np700719e. [PMID: 18564877]
  • A Orlita, M Sidwa-Gorycka, E Malinski, M Czerwicka, J Kumirska, M Golebiowski, E Lojkowska, P Stepnowski. Effective biotic elicitation of Ruta graveolens L. shoot cultures by lysates from Pectobacterium atrosepticum and Bacillus sp. Biotechnology letters. 2008 Mar; 30(3):541-5. doi: 10.1007/s10529-007-9559-3. [PMID: 17968510]
  • Jih-Jung Chen, Tzu-Ying Wang, Tsong-Long Hwang. Neolignans, a coumarinolignan, lignan derivatives, and a chromene: anti-inflammatory constituents from Zanthoxylum avicennae. Journal of natural products. 2008 Feb; 71(2):212-7. doi: 10.1021/np070594k. [PMID: 18211005]
  • Aleksandra Orlita, Matylda Sidwa-Gorycka, Jolanta Kumirska, Edmund Maliński, Ewa M Siedlecka, Jerzy Gajdus, Ewa Lojkowska, Piotr Stepnowski. Identification of Ruta graveolens L. metabolites accumulated in the presence of abiotic elicitors. Biotechnology progress. 2008 Jan; 24(1):128-33. doi: 10.1021/bp070261d. [PMID: 18052337]
  • Christoph M Schempp, Birgit Simon-Haarhaus, Richard Krieger, Jan C Simon. Solar simulator-induced phototoxicity of the furoquinoline alkaloid dictamnine compared to 8-methoxypsoralen and 5-methoxypsoralen. Planta medica. 2006 Aug; 72(10):941-3. doi: 10.1055/s-2006-947166. [PMID: 16972199]
  • Y Jiang, S P Li, H T Chang, Y T Wang, P F Tu. Pressurized liquid extraction followed by high-performance liquid chromatography for determination of seven active compounds in Cortex Dictamni. Journal of chromatography. A. 2006 Mar; 1108(2):268-72. doi: 10.1016/j.chroma.2006.01.077. [PMID: 16458903]
  • Cheng-fang Du, Xin-xin Yang, Peng-fei Tu. [Studies on chemical constituents in bark of dictamnus dasycarpus]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Nov; 30(21):1663-6. doi: . [PMID: 16400943]
  • H Sağlam, T Gözler, B Gözler. A new prenylated arylnaphthalene lignan from Haplophyllum myrtifolium. Fitoterapia. 2003 Sep; 74(6):564-9. doi: 10.1016/s0367-326x(03)00147-3. [PMID: 12946719]
  • Milijaona Randrianarivelojosia, Valérie T Rasidimanana, Harison Rabarison, Peter K Cheplogoi, Michel Ratsimbason, Dulcie A Mulholland, Philippe Mauclère. Plants traditionally prescribed to treat tazo (malaria) in the eastern region of Madagascar. Malaria journal. 2003 Jul; 2(?):25. doi: 10.1186/1475-2875-2-25. [PMID: 12921540]
  • Mary W Muriithi, W-R Abraham, Jonathan Addae-Kyereme, Ian Scowen, Simon L Croft, Peter M Gitu, Howard Kendrick, E N M Njagi, Colin W Wright. Isolation and in vitro antiplasmodial activities of alkaloids from Teclea trichocarpa: in vivo antimalarial activity and X-ray crystal structure of normelicopicine. Journal of natural products. 2002 Jul; 65(7):956-9. doi: 10.1021/np0106182. [PMID: 12141852]
  • Zhi Long Liu, Yuan Jian Xu, Jien Wu, Swee Hock Goh, Shuit Hung Ho. Feeding deterrents from Dictamnus dasycarpus Turcz against two stored-product insects. Journal of agricultural and food chemistry. 2002 Mar; 50(6):1447-50. doi: 10.1021/jf010838l. [PMID: 11879018]
  • C Ito, M Itoigawa, T Otsuka, H Tokuda, H Nishino, H Furukawa. Constituents of Boronia pinnata. Journal of natural products. 2000 Oct; 63(10):1344-8. doi: 10.1021/np0000318. [PMID: 11076549]
  • C M Schempp, M Sonntag, E Schöpf, J C Simon. [Dermatitis bullosa striata pratensis caused by Dictamnus albus L. (burning bush)]. Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete. 1996 Sep; 47(9):708-10. doi: 10.1007/s001050050494. [PMID: 8999028]
  • O Schimmer, I Kühne. Mutagenic compounds in an extract from Rutae Herba (Ruta graveolens L.). II. UV-A mediated mutagenicity in the green alga Chlamydomonas reinhardtii by furoquinoline alkaloids and furocoumarins present in a commercial tincture from Rutae Herba. Mutation research. 1990 Jan; 243(1):57-62. doi: 10.1016/0165-7992(90)90123-2. [PMID: 2300085]
  • J B Hudson. Plant photosensitizers with antiviral properties. Antiviral research. 1989 Sep; 12(2):55-74. doi: 10.1016/0166-3542(89)90070-3. [PMID: 2688551]
  • M Mizuta, H Kanamori. Mutagenic activities of dictamnine and gamma-fagarine from dictamni radicis cortex (Rutaceae). Mutation research. 1985 Dec; 144(4):221-5. doi: 10.1016/0165-7992(85)90054-5. [PMID: 4069140]