Narciclasine (BioDeep_00000000724)

   

PANOMIX_OTCML-2023


代谢物信息卡片


(1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S-(2-alpha,3-beta,4-beta,4a-beta))-

化学式: C14H13NO7 (307.0691988)
中文名称: 水仙环素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 3.64%

分子结构信息

SMILES: C1OC2=C(O1)C(=C3C(=C2)C4=CC(C(C(C4NC3=O)O)O)O)O
InChI: InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1

描述信息

Narciclasine is a member of phenanthridines. It has a role as a metabolite.
Narciclasine is a natural product found in Lycoris sanguinea, Lycoris squamigera, and other organisms with data available.
A natural product found in Narcissus pseudonarcissus.
Narciclasine is a plant growth modulator. Narciclasine modulates the Rho/Rho kinase/LIM kinase/cofilin signaling pathway, greatly increasing GTPase RhoA activity as well as inducing actin stress fiber formation in a RhoA-dependent manner.

同义名列表

18 个代谢物同义名

(1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S-(2-alpha,3-beta,4-beta,4a-beta))-; [1,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, [2S-(2.alpha.,3.beta.,4.beta.,4a.beta.)]-; [1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S,3R,4S,4aR)-; [1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S,3R,4S,4aR); (2S,3R,4S,4aR)-3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one; (2S,3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one; (2s,3r,4s,4ar)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro[1,3]dioxolo[4,5-j]phenanthridin-6(2h)-one; (2S,3R,4S,4aR)-2,3,4,7-Tetrahydroxy-3,4,4a,5-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one; 3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one; Narciclasine, >=98\\% (HPLC); Lycoricidinol; Lycoricidin-A; Lycorcidinol; Nacriclasine; Narciclasina; Narciclasine; NCI60_002146; 3KF



数据库引用编号

17 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)

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

  • Xinhao Chen, Hua Li. Bruceine D and Narclasine inhibit the proliferation of breast cancer cells and the prediction of potential drug targets. PloS one. 2024; 19(1):e0297203. doi: 10.1371/journal.pone.0297203. [PMID: 38215156]
  • Siwei Qiao, Jingyuan Yao, Qizhi Wang, Linwei Li, Bi Wang, Xu Feng, Zhong Wang, Min Yin, Yu Chen, Shu Xu. Anti-fungal effects of amaryllidaceous alkaloids from bulbs of Lycoris spp. against Magnaporthe oryzae. Pest management science. 2023 Feb; ?(?):. doi: 10.1002/ps.7420. [PMID: 36810871]
  • Christine J Kempthorne, Suresh Borra, Manoj Kumar, Chanti Babu Dokuburra, David K Liscombe, James McNulty. Identification of haemanthamine as a phytotoxic alkaloid in Narcissus pseudonarcissus L. (Daffodil) emerging buds. Natural product research. 2023 Feb; ?(?):1-7. doi: 10.1080/14786419.2023.2174536. [PMID: 36744673]
  • Yuanyuan Tian, Jiao Wang, Xiaori Qin, Shibing Li, Cheng Lan, Xiaoning Sun. Narciclasine ameliorated T cell mediated acute liver injury through activating AMPK pathway. Cellular immunology. 2022 12; 382(?):104631. doi: 10.1016/j.cellimm.2022.104631. [PMID: 36272268]
  • Veronique Mathieu, Breana Laguera, Marco Masi, Sara Adriana Dulanto, Tanner W Bingham, Lucas W Hernandez, David Sarlah, Antonio Evidente, Denis L J Lafontaine, Alexander Kornienko, Michelle A Lane. Amaryllidaceae Alkaloids Decrease the Proliferation, Invasion, and Secretion of Clinically Relevant Cytokines by Cultured Human Colon Cancer Cells. Biomolecules. 2022 09; 12(9):. doi: 10.3390/biom12091267. [PMID: 36139106]
  • Yi Kong, Jian Jiang, Yuqiong Huang, Xin Liu, Zilin Jin, Li Li, Fen Wei, Xinxin Liu, Jie Yin, Yonghui Zhang, Qingyi Tong, Hongxiang Chen. Narciclasine inhibits phospholipase A2 and regulates phospholipid metabolism to ameliorate psoriasis-like dermatitis. Frontiers in immunology. 2022; 13(?):1094375. doi: 10.3389/fimmu.2022.1094375. [PMID: 36700214]
  • Rong Tang, Liu Jia, Yunlong Li, Junbo Zheng, Pingping Qi. Narciclasine attenuates sepsis-induced myocardial injury by modulating autophagy. Aging. 2021 05; 13(11):15151-15163. doi: 10.18632/aging.203078. [PMID: 34035183]
  • Jerald J Nair, Johannes van Staden. Insight to the antifungal properties of Amaryllidaceae constituents. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Jul; 73(?):152753. doi: 10.1016/j.phymed.2018.11.013. [PMID: 30773353]
  • Deepali Katoch, Dharmesh Kumar, Yogendra S Padwad, Bikram Singh, Upendra Sharma. Pseudolycorine N-oxide, a new N-oxide from Narcissus tazetta. Natural product research. 2020 Jul; 34(14):2051-2058. doi: 10.1080/14786419.2019.1574785. [PMID: 30784301]
  • Ramakrishnan Gopalakrishnan, Hittu Matta, Sunju Choi, Preet M Chaudhary. Narciclasine, an isocarbostyril alkaloid, has preferential activity against primary effusion lymphoma. Scientific reports. 2020 03; 10(1):5712. doi: 10.1038/s41598-020-62690-9. [PMID: 32235878]
  • Manoj Kumar Kingsley, Ballambattu Vishnu Bhat, Bhawana Ashok Badhe, Benet Bosco Dhas, Subhash Chandra Parija. Narciclasine improves outcome in sepsis among neonatal rats via inhibition of calprotectin and alleviating inflammatory responses. Scientific reports. 2020 02; 10(1):2947. doi: 10.1038/s41598-020-59716-7. [PMID: 32076015]
  • Deepali Katoch, Dharmesh Kumar, Yogendra S Padwad, Bikram Singh, Upendra Sharma. Narciclasine-4-O-β-D-xylopyranoside, a new narciclasine glycoside from Zephyranthes minuta. Natural product research. 2020 Jan; 34(2):233-240. doi: 10.1080/14786419.2018.1527836. [PMID: 30636443]
  • Deepali Katoch, Upendra Sharma. Simultaneous quantification and identification of Amaryllidaceae alkaloids in Narcissus tazetta by ultra performance liquid chromatography-diode array detector-electrospray ionisation tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2019 Oct; 175(?):112750. doi: 10.1016/j.jpba.2019.06.047. [PMID: 31330284]
  • Jacqueline Bräutigam, Iris Bischoff, Christoph Schürmann, Giulia Buchmann, Jeremy Epah, Simone Fuchs, Elke Heiss, Ralf P Brandes, Robert Fürst. Narciclasine inhibits angiogenic processes by activation of Rho kinase and by downregulation of the VEGF receptor 2. Journal of molecular and cellular cardiology. 2019 10; 135(?):97-108. doi: 10.1016/j.yjmcc.2019.08.001. [PMID: 31381906]
  • Lucie Rárová, Bhekumthetho Ncube, Johannes Van Staden, Robert Fürst, Miroslav Strnad, Jiri Gruz. Identification of Narciclasine as an in Vitro Anti-Inflammatory Component of Cyrtanthus contractus by Correlation-Based Metabolomics. Journal of natural products. 2019 05; 82(5):1372-1376. doi: 10.1021/acs.jnatprod.8b00973. [PMID: 30933514]
  • Chun-Yan Shen, Xi-Lin Xu, Lin-Jiang Yang, Jian-Guo Jiang. Identification of narciclasine from Lycoris radiata (L'Her.) Herb. and its inhibitory effect on LPS-induced inflammatory responses in macrophages. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 Mar; 125(?):605-613. doi: 10.1016/j.fct.2019.02.003. [PMID: 30738987]
  • Chuan Cao, Wei Huang, Nan Zhang, Fengbo Wu, Ting Xu, Xiaoli Pan, Cheng Peng, Bo Han. Narciclasine induces autophagy-dependent apoptosis in triple-negative breast cancer cells by regulating the AMPK-ULK1 axis. Cell proliferation. 2018 Dec; 51(6):e12518. doi: 10.1111/cpr.12518. [PMID: 30152053]
  • Xiaoyun Wang, Fengbo Wu, Guoyou Li, Nan Zhang, Xiangrong Song, Yu Zheng, Changyang Gong, Bo Han, Gu He. Lipid-modified cell-penetrating peptide-based self-assembly micelles for co-delivery of narciclasine and siULK1 in hepatocellular carcinoma therapy. Acta biomaterialia. 2018 07; 74(?):414-429. doi: 10.1016/j.actbio.2018.05.030. [PMID: 29787814]
  • Suresh Borra, Ringaile Lapinskaite, Christine Kempthorne, David Liscombe, James McNulty, Tomas Hudlicky. Isolation, Synthesis, and Semisynthesis of Amaryllidaceae Constituents from Narcissus and Galanthus sp.: De Novo Total Synthesis of 2- epi-Narciclasine. Journal of natural products. 2018 06; 81(6):1451-1459. doi: 10.1021/acs.jnatprod.8b00218. [PMID: 29787267]
  • Jerald J Nair, Anke Wilhelm, Susanna L Bonnet, Johannes van Staden. Antibacterial constituents of the plant family Amaryllidaceae. Bioorganic & medicinal chemistry letters. 2017 11; 27(22):4943-4951. doi: 10.1016/j.bmcl.2017.09.052. [PMID: 29033234]
  • Xiaoning Cao, Fei Ma, Tingting Xu, Junjie Wang, Sichen Liu, Gaihong Li, Qian Su, Zhijun Qiao, XiaoFan Na. Transcriptomic analysis reveals key early events of narciclasine signaling in Arabidopsis root apex. Plant cell reports. 2016 Nov; 35(11):2381-2401. doi: 10.1007/s00299-016-2042-7. [PMID: 27562382]
  • Yanfeng Hu, Xiaofan Na, Jiaolong Li, Lijing Yang, Jia You, Xiaolei Liang, Jianfeng Wang, Liang Peng, Yurong Bi. Narciclasine, a potential allelochemical, affects subcellular trafficking of auxin transporter proteins and actin cytoskeleton dynamics in Arabidopsis roots. Planta. 2015 Dec; 242(6):1349-60. doi: 10.1007/s00425-015-2373-6. [PMID: 26232920]
  • Simone Fuchs, Louise T Hsieh, Werner Saarberg, Clemens A J Erdelmeier, Thomas A Wichelhaus, Liliana Schaefer, Egon Koch, Robert Fürst. Haemanthus coccineus extract and its main bioactive component narciclasine display profound anti-inflammatory activities in vitro and in vivo. Journal of cellular and molecular medicine. 2015 May; 19(5):1021-32. doi: 10.1111/jcmm.12493. [PMID: 25754537]
  • Yanfeng Hu, Jiaolong Li, Lijing Yang, Wenbin Nan, Xiaoping Cao, Yurong Bi. Inhibition of root growth by narciclasine is caused by DNA damage-induced cell cycle arrest in lettuce seedlings. Protoplasma. 2014 Sep; 251(5):1113-24. doi: 10.1007/s00709-014-0619-y. [PMID: 24482192]
  • Dinar S C Wahyuni, Frank van der Kooy, Peter G L Klinkhamer, Rob Verpoorte, Kirsten Leiss. The use of bio-guided fractionation to explore the use of leftover biomass in Dutch flower bulb production as allelochemicals against weeds. Molecules (Basel, Switzerland). 2013 Apr; 18(4):4510-25. doi: 10.3390/molecules18044510. [PMID: 23595089]
  • Andrea Lubbe, Henk Gude, Robert Verpoorte, Young Hae Choi. Seasonal accumulation of major alkaloids in organs of pharmaceutical crop Narcissus Carlton. Phytochemistry. 2013 Apr; 88(?):43-53. doi: 10.1016/j.phytochem.2012.12.008. [PMID: 23318143]
  • Deepali Katoch, Shiv Kumar, Neeraj Kumar, Bikram Singh. Simultaneous quantification of Amaryllidaceae alkaloids from Zephyranthes grandiflora by UPLC-DAD/ESI-MS/MS. Journal of pharmaceutical and biomedical analysis. 2012 Dec; 71(?):187-92. doi: 10.1016/j.jpba.2012.08.001. [PMID: 22939505]
  • Jerald J Nair, Lucie Rárová, Miroslav Strnad, Jaume Bastida, Johannes van Staden. Apoptosis-inducing effects of distichamine and narciprimine, rare alkaloids of the plant family Amaryllidaceae. Bioorganic & medicinal chemistry letters. 2012 Oct; 22(19):6195-9. doi: 10.1016/j.bmcl.2012.08.005. [PMID: 22921081]
  • Yanfeng Hu, Lijing Yang, Xiaofan Na, Jia You, Wei Hu, Xiaolei Liang, Jie Liu, Lina Mao, Xiaoming Wang, Huahua Wang, Yurong Bi. Narciclasine inhibits the responses of Arabidopsis roots to auxin. Planta. 2012 Aug; 236(2):597-612. doi: 10.1007/s00425-012-1632-z. [PMID: 22476291]
  • Hongxia Lu, Qi Wan, Huahua Wang, Xiaofan Na, Xiaomin Wang, Yurong Bi. Oxidative stress and mitochondrial dysfunctions are early events in narciclasine-induced programmed cell death in tobacco Bright Yellow-2 cells. Physiologia plantarum. 2012 Jan; 144(1):48-58. doi: 10.1111/j.1399-3054.2011.01521.x. [PMID: 21916896]
  • Xiaofan Na, Yanfeng Hu, Kun Yue, Hongxia Lu, Pengfei Jia, Huahua Wang, Xiaomin Wang, Yurong Bi. Concentration-dependent effects of narciclasine on cell cycle progression in Arabidopsis root tips. BMC plant biology. 2011 Dec; 11(?):184. doi: 10.1186/1471-2229-11-184. [PMID: 22204558]
  • You-Yi Zhao, Yong-Qi Liang, Yu Chen, Hao Sun, Ming Wang, Xu Feng. [Study on chemical constituents of the bulbs of Lycoris longituba]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Sep; 34(9):1366-8. doi: ". [PMID: 22260001]
  • Xiaofan Na, Yanfeng Hu, Kun Yue, Hongxia Lu, Pengfei Jia, Huahua Wang, Xiaomin Wang, Yurong Bi. Narciclasine modulates polar auxin transport in Arabidopsis roots. Journal of plant physiology. 2011 Jul; 168(11):1149-56. doi: 10.1016/j.jplph.2011.01.025. [PMID: 21511360]
  • Gwendoline Van Goietsenoven, Jenna Hutton, Jean-Paul Becker, Benjamin Lallemand, Francis Robert, Florence Lefranc, Christine Pirker, Guy Vandenbussche, Pierre Van Antwerpen, Antonio Evidente, Walter Berger, Martine Prévost, Jerry Pelletier, Robert Kiss, Terri Goss Kinzy, Alexander Kornienko, Véronique Mathieu. Targeting of eEF1A with Amaryllidaceae isocarbostyrils as a strategy to combat melanomas. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2010 Nov; 24(11):4575-84. doi: 10.1096/fj.10-162263. [PMID: 20643906]
  • Florence Lefranc, Sébastien Sauvage, Gwendoline Van Goietsenoven, Véronique Mégalizzi, Delphine Lamoral-Theys, Olivier Debeir, Sabine Spiegl-Kreinecker, Walter Berger, Véronique Mathieu, Christine Decaestecker, Robert Kiss. Narciclasine, a plant growth modulator, activates Rho and stress fibers in glioblastoma cells. Molecular cancer therapeutics. 2009 Jul; 8(7):1739-50. doi: 10.1158/1535-7163.mct-08-0932. [PMID: 19531573]
  • George R Pettit, Sylvie Ducki, Stephen A Eastham, Noeleen Melody. Antineoplastic agents. 454. Synthesis of the strong cancer cell growth inhibitors trans-dihydronarciclasine and 7-deoxy-trans-dihydronarciclasine (1a). Journal of natural products. 2009 Jul; 72(7):1279-82. doi: 10.1021/np9001948. [PMID: 19522518]
  • Laurent Ingrassia, Florence Lefranc, Janique Dewelle, Laurent Pottier, Véronique Mathieu, Sabine Spiegl-Kreinecker, Sébastien Sauvage, Mohamed El Yazidi, Mischaël Dehoux, Walter Berger, Eric Van Quaquebeke, Robert Kiss. Structure-activity relationship analysis of novel derivatives of narciclasine (an Amaryllidaceae isocarbostyril derivative) as potential anticancer agents. Journal of medicinal chemistry. 2009 Feb; 52(4):1100-14. doi: 10.1021/jm8013585. [PMID: 19199649]
  • Xueliang Fang, Lei Shao, Hui Zhang, Shaomeng Wang. CHMIS-C: a comprehensive herbal medicine information system for cancer. Journal of medicinal chemistry. 2005 Mar; 48(5):1481-8. doi: 10.1021/jm049838d. [PMID: 15743190]
  • Wouter G van Doorn, Andrea Sinz, Monic M Tomassen. Daffodil flowers delay senescence in cut Iris flowers. Phytochemistry. 2004 Mar; 65(5):571-7. doi: 10.1016/j.phytochem.2003.12.008. [PMID: 15003420]
  • Yurong Bi, Jinkui Guo, Lixin Zhang, Yumshing Wong. Changes in some enzymes of microbodies and plastid development in excised radish cotyledons: effect of narciclasine. Journal of plant physiology. 2003 Sep; 160(9):1041-9. doi: 10.1078/0176-1617-00911. [PMID: 14593805]
  • F M Veronese, G Ceriotti, F Baccichetti, F Carlassare, F Moschini, P Caliceti, O Schiavon, M Carenza, S Lora. In vitro and in vivo behaviour of narciclasine released from matrices based on poly (2-hydroxyethyl methacrylate). Farmaco (Societa chimica italiana : 1989). 1991 Sep; 46(9):1061-70. doi: . [PMID: 1807291]
  • I Svagrová, K Stulík, V Pacáková, P Caliceti, F M Veronese. Determination of narciclasine in serum by reversed-phase high-performance liquid chromatography: comparison of amperometric, ultraviolet photometric and fluorescence detection. Journal of chromatography. 1991 Jan; 563(1):95-102. doi: 10.1016/0378-4347(91)80280-p. [PMID: 2061398]