quinolizidine (BioDeep_00001878012)

   


代谢物信息卡片


quinolizidine

化学式: C9H17N (139.1360922)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CCN2CCCCC2C1
InChI: InChI=1S/C9H17N/c1-3-7-10-8-4-2-6-9(10)5-1/h9H,1-8H2

描述信息

同义名列表

1 个代谢物同义名

quinolizidine



数据库引用编号

4 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)

0 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

  • Zhan-Xing Hu, Ji Zhang, Tong Zhang, Cai-Yan Tian, Qiao An, Ping Yi, Chun-Mao Yuan, Zhong-Kai Zhang, Li-Hua Zhao, Xiao-Jiang Hao. Aloperine-Type Alkaloids with Antiviral and Antifungal Activities from the Seeds of Sophora alopecuroides L. Journal of agricultural and food chemistry. 2024 Apr; 72(14):8225-8236. doi: 10.1021/acs.jafc.4c00992. [PMID: 38557068]
  • Wenbing Zhi, Shengnan Jiang, Zongren Xu, Yuye An, Jing Chen, Ye Li, Yang Liu, Hong Zhang. Oxysophocarpine inhibits airway inflammation and mucus hypersecretion through JNK/AP-1 pathway in vivo and in vitro. Fitoterapia. 2022 Oct; 162(?):105278. doi: 10.1016/j.fitote.2022.105278. [PMID: 35970410]
  • Jawameer R Hama, Daniel Bernardo Garcia Jorgensen, Efstathios Diamantopoulos, Thomas D Bucheli, Hans Chr Bruun Hansen, Bjarne W Strobel. Indole and quinolizidine alkaloids from blue lupin leach to agricultural drainage water. The Science of the total environment. 2022 Aug; 834(?):155283. doi: 10.1016/j.scitotenv.2022.155283. [PMID: 35439507]
  • Zhan-Xing Hu, Peng Zhang, Ji-Bin Zou, Qiao An, Ping Yi, Chun-Mao Yuan, Zhong-Kai Zhang, Li-Hua Zhao, Xiao-Jiang Hao. Quinolizidine Alkaloids with Antitomato Spotted Wilt Virus and Insecticidal Activities from the Seeds of Thermopsis lanceolata R. Br. Journal of agricultural and food chemistry. 2022 Jul; 70(29):9214-9226. doi: 10.1021/acs.jafc.2c02546. [PMID: 35849433]
  • Davide Mancinotti, Karen Michiko Frick, Fernando Geu-Flores. Biosynthesis of quinolizidine alkaloids in lupins: mechanistic considerations and prospects for pathway elucidation. Natural product reports. 2022 07; 39(7):1423-1437. doi: 10.1039/d1np00069a. [PMID: 35302146]
  • Luis Díaz, Willy Cely-Veloza, Ericsson Coy-Barrera. Identification of Anti-Proliferative Compounds from Genista monspessulana Seeds through Covariate-Based Integration of Chemical Fingerprints and Bioactivity Datasets. Molecules (Basel, Switzerland). 2022 Jun; 27(13):. doi: 10.3390/molecules27133996. [PMID: 35807242]
  • Shaza H Aly, Ahmed M Elissawy, Ahmed E Allam, Shaimaa M Farag, Omayma A Eldahshan, Mohamed A Elshanawany, Abdel Nasser B Singab. New quinolizidine alkaloid and insecticidal activity of Sophora secundiflora and Sophora tomentosa against Culex pipiens (Diptera: Culicidae). Natural product research. 2022 Jun; 36(11):2722-2734. doi: 10.1080/14786419.2021.1919108. [PMID: 33974474]
  • Freddy A Bernal, Ericsson Coy-Barrera. Composition and Antifungal Activity of the Alkaloidal Fraction of Lupinus mirabilis Leaves: A Biochemometrics-Based Exploration. Molecules (Basel, Switzerland). 2022 Apr; 27(9):. doi: 10.3390/molecules27092832. [PMID: 35566183]
  • Jian-Chun Li, Zhi-Jun Zhang, Dan Liu, Ming-Yan Jiang, Rong-Tao Li, Hong-Mei Li. Quinolizidine alkaloids from the roots of Sophora flavescens. Natural product research. 2022 Apr; 36(7):1781-1788. doi: 10.1080/14786419.2020.1817011. [PMID: 32924588]
  • Wenxi He, Haifeng Zhou, Xiaoyu He. Aloperine protects beta-cells against streptozocin-induced injury to attenuate diabetes by targeting NOS1. European journal of pharmacology. 2022 Feb; 916(?):174721. doi: 10.1016/j.ejphar.2021.174721. [PMID: 34954231]
  • Willy Cely-Veloza, Diego Quiroga, Ericsson Coy-Barrera. Quinolizidine-Based Variations and Antifungal Activity of Eight Lupinus Species Grown under Greenhouse Conditions. Molecules (Basel, Switzerland). 2022 Jan; 27(1):. doi: 10.3390/molecules27010305. [PMID: 35011535]
  • Isabelle Pouny, Christophe Long, Muriel Batut, Yannick Aussagues, Naubron Jean Valère, Gaston Achoundong, Bruno David, Catherine Lavaud, Georges Massiot. Quinolizidine Alkaloids from Cylicomorpha solmsii. Journal of natural products. 2021 04; 84(4):1198-1202. doi: 10.1021/acs.jnatprod.0c01261. [PMID: 33606529]
  • Katarzyna Czepiel, Paweł Krajewski, Paulina Wilczura, Patrycja Bielecka, Wojciech Święcicki, Magdalena Kroc. Expression Profiles of Alkaloid-Related Genes across the Organs of Narrow-Leafed Lupin (Lupinus angustifolius L.) and in Response to Anthracnose Infection. International journal of molecular sciences. 2021 Mar; 22(5):. doi: 10.3390/ijms22052676. [PMID: 33800929]
  • Jibin Zou, Lihua Zhao, Ping Yi, Qiao An, Longxiang He, Yanan Li, Huayong Lou, Chunmao Yuan, Wei Gu, Liejun Huang, Zhanxing Hu, Xiaojiang Hao. Quinolizidine Alkaloids with Antiviral and Insecticidal Activities from the Seeds of Sophora tonkinensis Gagnep. Journal of agricultural and food chemistry. 2020 Dec; 68(50):15015-15026. doi: 10.1021/acs.jafc.0c06032. [PMID: 33285067]
  • Weiwei Li, Yanshu Li, Yi Zhao, Lina Ren. The protective effects of aloperine against ox-LDL-induced endothelial dysfunction and inflammation in HUVECs. Artificial cells, nanomedicine, and biotechnology. 2020 Dec; 48(1):107-115. doi: 10.1080/21691401.2019.1699816. [PMID: 31852304]
  • Luis Alberto Aguilar-Acosta, Sergio O Serna-Saldivar, José Rodríguez-Rodríguez, Anayansi Escalante-Aburto, Cristina Chuck-Hernández. Effect of Ultrasound Application on Protein Yield and Fate of Alkaloids during Lupin Alkaline Extraction Process. Biomolecules. 2020 02; 10(2):. doi: 10.3390/biom10020292. [PMID: 32069921]
  • Mingning Qiu, Jie Liu, Yongxia Su, Jianjun Liu, Chenchen Wu, Baoyu Zhao. Aloperine Induces Apoptosis by a Reactive Oxygen Species Activation Mechanism in Human Ovarian Cancer Cells. Protein and peptide letters. 2020; 27(9):860-869. doi: 10.2174/0929866527666200320094313. [PMID: 32196436]
  • Xiaobo Huang, Hui Xu. Advances on the Bioactivities, Total Synthesis, Structural Modification, and Structure-Activity Relationships of Cytisine Derivatives. Mini reviews in medicinal chemistry. 2020; 20(5):369-395. doi: 10.2174/1389557519666191104121821. [PMID: 31686638]
  • Sarvinoz I Rustamova, Nargiza A Tsiferova, Ozoda J Khamidova, Ranokhon Sh Kurbannazarova, Petr G Merzlyak, Zainab A Khushbaktova, Vladimir N Syrov, Erkin Kh Botirov, Kamila A Eshbakova, Ravshan Z Sabirov. Effect of plant flavonoids on the volume regulation of rat thymocytes under hypoosmotic stress. Pharmacological reports : PR. 2019 Dec; 71(6):1079-1087. doi: 10.1016/j.pharep.2019.05.023. [PMID: 31629088]
  • Li-Jun He, Jun-Shan Liu, Ding Luo, Yuan-Ru Zheng, Yu-Bo Zhang, Guo-Cai Wang, Yao-Lan Li. Quinolizidine alkaloids from Sophora tonkinensis and their anti-inflammatory activities. Fitoterapia. 2019 Nov; 139(?):104391. doi: 10.1016/j.fitote.2019.104391. [PMID: 31682871]
  • Jun-Shan Liu, Chu-Ying Huo, Hui-Hui Cao, Chun-Lin Fan, Jian-Yang Hu, Li-Juan Deng, Zi-Bin Lu, Hua-Yi Yang, Lin-Zhong Yu, Zhi-Xian Mo, Zhi-Ling Yu. Aloperine induces apoptosis and G2/M cell cycle arrest in hepatocellular carcinoma cells through the PI3K/Akt signaling pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Aug; 61(?):152843. doi: 10.1016/j.phymed.2019.152843. [PMID: 31039533]
  • Zhi Chang, Peng Zhang, Min Zhang, Feng Jun, Zhiqiang Hu, Jiamei Yang, Yuhua Wu, Ru Zhou. Aloperine suppresses human pulmonary vascular smooth muscle cell proliferation via inhibiting inflammatory response. The Chinese journal of physiology. 2019 Jul; 62(4):157-165. doi: 10.4103/cjp.cjp_27_19. [PMID: 31535631]
  • Karen M Frick, Rhonda C Foley, Kadambot H M Siddique, Karam B Singh, Lars G Kamphuis. The role of jasmonate signalling in quinolizidine alkaloid biosynthesis, wounding and aphid predation response in narrow-leafed lupin. Functional plant biology : FPB. 2019 04; 46(5):443-454. doi: 10.1071/fp18278. [PMID: 30940332]
  • Magdalena Kroc, Grzegorz Koczyk, Katarzyna A Kamel, Katarzyna Czepiel, Olga Fedorowicz-Strońska, Paweł Krajewski, Joanna Kosińska, Jan Podkowiński, Paulina Wilczura, Wojciech Święcicki. Transcriptome-derived investigation of biosynthesis of quinolizidine alkaloids in narrow-leafed lupin (Lupinus angustifolius L.) highlights candidate genes linked to iucundus locus. Scientific reports. 2019 02; 9(1):2231. doi: 10.1038/s41598-018-37701-5. [PMID: 30783128]
  • Michael Wink. Quinolizidine and Pyrrolizidine Alkaloid Chemical Ecology - a Mini-Review on Their Similarities and Differences. Journal of chemical ecology. 2019 Feb; 45(2):109-115. doi: 10.1007/s10886-018-1005-6. [PMID: 30079442]
  • Hanqing Wang, Changbo Xia, Li Chen, Jianjun Zhao, Weiwei Tao, Xia Zhang, Jianhuan Wang, Xiaojuan Gao, Jingjiao Yong, Jin-Ao Duan. Phytochemical Information and Biological Activities of Quinolizidine Alkaloids in Sophora: A Comprehensive Review. Current drug targets. 2019; 20(15):1572-1586. doi: 10.2174/1389450120666190618125816. [PMID: 31215388]
  • Jing Zhao, Ge Zhang, Min Li, Qinghua Luo, Yu Leng, Xu Liu. Neuro-protective effects of aloperine in an Alzheimer's disease cellular model. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Dec; 108(?):137-143. doi: 10.1016/j.biopha.2018.09.008. [PMID: 30218858]
  • Hanqing Wang, Dong Xiao, Wei Li, Xia Zhang, Xiaojuan Gao, Jingjiao Yong, Jianjun Zhao, Kazuo Koike. A simple and fast quantitative analysis of quinolizidine alkaloids and their biosynthetic precursor, lysine, in Sophora alopecuroides by hydrophilic interaction chromatography coupled with triple-quadrupole tandem mass spectroscopy. Phytochemical analysis : PCA. 2018 Sep; 29(5):500-506. doi: 10.1002/pca.2757. [PMID: 29573297]
  • Karen M Frick, Rhonda C Foley, Lars G Kamphuis, Kadambot H M Siddique, Gagan Garg, Karam B Singh. Characterization of the genetic factors affecting quinolizidine alkaloid biosynthesis and its response to abiotic stress in narrow-leafed lupin (Lupinus angustifolius L.). Plant, cell & environment. 2018 09; 41(9):2155-2168. doi: 10.1111/pce.13172. [PMID: 29473655]
  • Benedict T Green, Stephen T Lee, Kevin D Welch, Daniel Cook. Anagyrine desensitization of peripheral nicotinic acetylcholine receptors. A potential biomarker of quinolizidine alkaloid teratogenesis in cattle. Research in veterinary science. 2017 Dec; 115(?):195-200. doi: 10.1016/j.rvsc.2017.04.019. [PMID: 28494312]
  • Ting Yang, Istvan Nagy, Davide Mancinotti, Sophie Lisa Otterbach, Trine Bundgaard Andersen, Mohammed Saddik Motawia, Torben Asp, Fernando Geu-Flores. Transcript profiling of a bitter variety of narrow-leafed lupin to discover alkaloid biosynthetic genes. Journal of experimental botany. 2017 Nov; 68(20):5527-5537. doi: 10.1093/jxb/erx362. [PMID: 29155974]
  • Fan Wu, Wanxia Yao, Jiamei Yang, Min Zhang, Yanping Xu, Yinju Hao, Lin Yan, Yang Niu, Tao Sun, Jianqiang Yu, Ru Zhou. Protective effects of aloperin on monocroline-induced pulmonary hypertension via regulation of Rho A/Rho kinsase pathway in rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Nov; 95(?):1161-1168. doi: 10.1016/j.biopha.2017.08.126. [PMID: 28926926]
  • Somnuk Bunsupa, Mami Yamazaki, Kazuki Saito. Lysine-derived Alkaloids: Overview and Update on Biosynthesis and Medicinal Applications with Emphasis on Quinolizidine Alkaloids. Mini reviews in medicinal chemistry. 2017; 17(12):1002-1012. doi: 10.2174/1389557516666160506151213. [PMID: 27151143]
  • Sumira Jan, Azra N Kamili, Javid A Parray, Yashbir S Bedi, Parvaiz Ahmad. Microclimatic variation in UV perception and related disparity in tropane and quinolizidine alkaloid composition of Atropa acuminata, Lupinus polyphyllus and Hyoscyamus niger. Journal of photochemistry and photobiology. B, Biology. 2016 Aug; 161(?):230-5. doi: 10.1016/j.jphotobiol.2016.04.028. [PMID: 27285814]
  • Yan Zhang, Wen-Zhong Hu, Xiao-Zhong Chen, Yu-Bo Peng, Li-Yan Song, Yu-Sheng Shi. [Bioactive quinolizidine alkaloids from Sophora tonkinensis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2016 Jun; 41(12):2261-2266. doi: 10.4268/cjcmm20161215. [PMID: 28901070]
  • Joseph P Michael. Simple Indolizidine and Quinolizidine Alkaloids. The Alkaloids. Chemistry and biology. 2016; 75(?):1-498. doi: 10.1016/bs.alkal.2014.12.001. [PMID: 26777309]
  • He Wang, Shu Yang, Hong Zhou, Mingna Sun, Lingran Du, Minyan Wei, Meixia Luo, Jingzhu Huang, Hongzhu Deng, Yinghong Feng, Jun Huang, Yi Zhou. Aloperine executes antitumor effects against multiple myeloma through dual apoptotic mechanisms. Journal of hematology & oncology. 2015 Mar; 8(?):26. doi: 10.1186/s13045-015-0120-x. [PMID: 25886453]
  • M R Silva, C M Alvarez, P M García, M A Ruiz. Assessing the genotoxicities of sparteine and compounds isolated from Lupinus mexicanus and L. montanus seeds by using comet assay. Genetics and molecular research : GMR. 2014 Dec; 13(4):10510-7. doi: 10.4238/2014.december.12.12. [PMID: 25511034]
  • Li Zhang, Yanxin Zheng, Hongzhu Deng, Lei Liang, Juan Peng. Aloperine induces G2/M phase cell cycle arrest and apoptosis in HCT116 human colon cancer cells. International journal of molecular medicine. 2014 Jun; 33(6):1613-20. doi: 10.3892/ijmm.2014.1718. [PMID: 24682388]
  • Sook Yee Liew, Chung Yeng Looi, Mohammadjavad Paydar, Foo Kit Cheah, Kok Hoong Leong, Won Fen Wong, Mohd Rais Mustafa, Marc Litaudon, Khalijah Awang. Subditine, a new monoterpenoid indole alkaloid from bark of Nauclea subdita (Korth.) Steud. induces apoptosis in human prostate cancer cells. PloS one. 2014; 9(2):e87286. doi: 10.1371/journal.pone.0087286. [PMID: 24551054]
  • Juan A Araya, Alejandra E Ramírez, Daniela Figueroa-Aroca, Gastón J Sotes, Claudia Pérez, Jose Becerra, Francisco Saez-Orellana, Leonardo Guzmán, Luis G Aguayo, Jorge Fuentealba. Modulation of neuronal nicotinic receptor by quinolizidine alkaloids causes neuroprotection on a cellular Alzheimer model. Journal of Alzheimer's disease : JAD. 2014; 42(1):143-55. doi: 10.3233/jad-132045. [PMID: 24825567]
  • Benedict T Green, Stephen T Lee, Kevin D Welch, Kip E Panter. Plant alkaloids that cause developmental defects through the disruption of cholinergic neurotransmission. Birth defects research. Part C, Embryo today : reviews. 2013 Dec; 99(4):235-46. doi: 10.1002/bdrc.21049. [PMID: 24339035]
  • Benjamin Hornoy, Anne Atlan, Michèle Tarayre, Sébastien Dugravot, Michael Wink. Alkaloid concentration of the invasive plant species Ulex europaeus in relation to geographic origin and herbivory. Die Naturwissenschaften. 2012 Nov; 99(11):883-92. doi: 10.1007/s00114-012-0970-9. [PMID: 23007201]
  • Anna Basile, Maria Pascale, Silvia Franceschelli, Erika Nieddu, Marco T Mazzei, Paola Fossa, Maria Caterina Turco, Mauro Mazzei. Matrine modulates HSC70 levels and rescues ΔF508-CFTR. Journal of cellular physiology. 2012 Sep; 227(9):3317-23. doi: 10.1002/jcp.24028. [PMID: 22170045]
  • Erick Korir, Joyce J Kiplimo, Neil R Crouch, Nivan Moodley, Neil A Koorbanally. Quinolizidine alkaloids from Sophora velutina subsp. zimbabweensis (Fabaceae: Sophoreae). Natural product communications. 2012 Aug; 7(8):999-1003. doi: . [PMID: 22978215]
  • Hanqing Wang, Sheng Guo, Dawei Qian, Yefei Qian, Jin-ao Duan. Comparative analysis of quinolizidine alkaloids from different parts of Sophora alopecuroides seeds by UPLC-MS/MS. Journal of pharmaceutical and biomedical analysis. 2012 Aug; 67-68(?):16-21. doi: 10.1016/j.jpba.2012.04.024. [PMID: 22613581]
  • Daniel Cook, Stephen T Lee, James A Pfister, Clint A Stonecipher, Kevin D Welch, Benedict T Green, Kip E Panter. Alkaloid Profiling as an Approach to Differentiate Lupinus garfieldensis, Lupinus sabinianus and Lupinus sericeus. Phytochemical analysis : PCA. 2012 May; 23(3):278-84. doi: 10.1002/pca.1355. [PMID: 21953740]
  • Somnuk Bunsupa, Kae Katayama, Emi Ikeura, Akira Oikawa, Kiminori Toyooka, Kazuki Saito, Mami Yamazaki. Lysine decarboxylase catalyzes the first step of quinolizidine alkaloid biosynthesis and coevolved with alkaloid production in leguminosae. The Plant cell. 2012 Mar; 24(3):1202-16. doi: 10.1105/tpc.112.095885. [PMID: 22415272]
  • Jia-Ming Yang, Siu-Po Ip, Yanfang Xian, Ming Zhao, Zhi-Xiu Lin, John Hok Keung Yeung, Raphael Chiu Yeung Chan, Shui-Shan Lee, Chun-Tao Che. Impact of the herbal medicine Sophora flavescens on the oral pharmacokinetics of indinavir in rats: the involvement of CYP3A and P-glycoprotein. PloS one. 2012; 7(2):e31312. doi: 10.1371/journal.pone.0031312. [PMID: 22359586]
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  • Markus Ganzera, Anja Krüger, Michael Wink. Determination of quinolizidine alkaloids in different Lupinus species by NACE using UV and MS detection. Journal of pharmaceutical and biomedical analysis. 2010 Dec; 53(5):1231-5. doi: 10.1016/j.jpba.2010.05.030. [PMID: 20580181]
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