Liensinine (BioDeep_00000618767)

Main id: BioDeep_00000024838

 

PANOMIX_OTCML-2023


代谢物信息卡片


Phenol, 4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-2-((1,2,3,4-tetrahydro-1-((4-hydroxyphenyl)methyl)-6-methoxy-2-methyl-7-isoquinolinyl)oxy)-, (R-(R*,R*))-

化学式: C37H42N2O6 (610.3042712000001)
中文名称: 莲心碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)OC4=C(C=CC(=C4)CC5C6=CC(=C(C=C6CCN5C)OC)OC)O)OC
InChI: InChI=1S/C37H42N2O6/c1-38-14-13-26-20-35(43-4)37(22-29(26)30(38)16-23-6-9-27(40)10-7-23)45-33-18-24(8-11-32(33)41)17-31-28-21-36(44-5)34(42-3)19-25(28)12-15-39(31)2/h6-11,18-22,30-31,40-41H,12-17H2,1-5H3

描述信息

Liensinine is an autophagy/mitophagy inhibitor. Liensinine, a major isoquinoline alkaloid, extracted from the seed embryo of Nelumbo nucifera Gaertn, has a wide range of biological activities, including anti-arrhythmias, anti-hypertension, anti-pulmonary fibrosis, relaxation on vascular smooth muscle, etc[1].
Liensinine is an autophagy/mitophagy inhibitor. Liensinine, a major isoquinoline alkaloid, extracted from the seed embryo of Nelumbo nucifera Gaertn, has a wide range of biological activities, including anti-arrhythmias, anti-hypertension, anti-pulmonary fibrosis, relaxation on vascular smooth muscle, etc[1].

同义名列表

9 个代谢物同义名

Phenol, 4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-2-((1,2,3,4-tetrahydro-1-((4-hydroxyphenyl)methyl)-6-methoxy-2-methyl-7-isoquinolinyl)oxy)-, (R-(R*,R*))-; Phenol, 4-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]-2-[[(1R)-1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinyl]oxy]-; 4-[[(1R)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2-[[(1R)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl]oxy]phenol; 4-[[(1R)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2-[[(1R)-1-(4-hydroxybenzyl)-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl]oxy]phenol; AIDS-226949; Liensinine; AIDS226949; 2586-96-1; 4-[(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-({1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)phenol



数据库引用编号

6 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)

3 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

  • Zhiqiang Feng, Shuai Zhang, Qiurong Han, Tianhao Chu, Huaqing Wang, Li Yu, Weihua Zhang, Jun Liu, Weizheng Liang, Jun Xue, Xueliang Wu, Chunze Zhang, Yijia Wang. Liensinine sensitizes colorectal cancer cells to oxaliplatin by targeting HIF-1α to inhibit autophagy. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Jul; 129(?):155647. doi: 10.1016/j.phymed.2024.155647. [PMID: 38703660]
  • Biao Ma, Sai Shi, Wei Guo, Hailin Zhang, Zhen Zhao, Hailong An. Liensinine, a Novel and Food-Derived Compound, Exerts Potent Antihepatoma Efficacy via Inhibiting the Kv10.1 Channel. Journal of agricultural and food chemistry. 2024 Mar; 72(9):4689-4702. doi: 10.1021/acs.jafc.3c06142. [PMID: 38382537]
  • Peizhi Jia, Daxin Chen, Ying Zhu, Meiling Wang, Jianwei Zeng, Ling Zhang, Qiaoyan Cai, Dawei Lian, Chunyu Zhao, Yaoyao Xu, Jianfeng Chu, Shan Lin, Jun Peng, Wei Lin. Liensinine improves AngII-induced vascular remodeling via MAPK/TGF-β1/Smad2/3 signaling. Journal of ethnopharmacology. 2023 Dec; 317(?):116768. doi: 10.1016/j.jep.2023.116768. [PMID: 37308031]
  • Fang Shen, Celiang Wu, Xiaomei Zhong, En Ma, Jun Peng, Weidong Zhu, Da Wo, Dan-Ni Ren. Liensinine prevents ischemic injury following myocardial infarction via inhibition of Wnt/β‑catenin signaling activation. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Jun; 162(?):114675. doi: 10.1016/j.biopha.2023.114675. [PMID: 37044026]
  • Liping Liang, Shiwei Ye, Ruilai Jiang, Xiao Zhou, Junjie Zhou, Shuiyun Meng. Liensinine alleviates high fat diet (HFD)-induced non-alcoholic fatty liver disease (NAFLD) through suppressing oxidative stress and inflammation via regulating TAK1/AMPK signaling. International immunopharmacology. 2022 Mar; 104(?):108306. doi: 10.1016/j.intimp.2021.108306. [PMID: 34999396]
  • Yang Yang, Peng Yang, Cong Huang, Yuming Wu, Zhe Zhou, Xuejun Wang, Shengqi Wang. Inhibitory effect on SARS-CoV-2 infection of neferine by blocking Ca2+ -dependent membrane fusion. Journal of medical virology. 2021 10; 93(10):5825-5832. doi: 10.1002/jmv.27117. [PMID: 34061377]
  • Guang-Ming Yang, Jie Sun, Yang Pan, Jun-Li Zhang, Min Xiao, Min-Sheng Zhu. Isolation and identification of a tribenzylisoquinoline alkaloid from Nelumbo nucifera Gaertn, a novel potential smooth muscle relaxant. Fitoterapia. 2018 Jan; 124(?):58-65. doi: 10.1016/j.fitote.2017.10.020. [PMID: 29108933]
  • W-K Lee, S Probst, M P Santoyo-Sánchez, W Al-Hamdani, I Diebels, J-K von Sivers, E Kerek, E J Prenner, F Thévenod. Initial autophagic protection switches to disruption of autophagic flux by lysosomal instability during cadmium stress accrual in renal NRK-52E cells. Archives of toxicology. 2017 Oct; 91(10):3225-3245. doi: 10.1007/s00204-017-1942-9. [PMID: 28321485]
  • Yangyang Yu, Shennan Sun, Shifeng Wang, Qiao Zhang, Ming Li, Feng Lan, Shiyou Li, Chunsheng Liu. Liensinine- and Neferine-Induced Cardiotoxicity in Primary Neonatal Rat Cardiomyocytes and Human-Induced Pluripotent Stem Cell-Derived Cardiomyocytes. International journal of molecular sciences. 2016 Jan; 17(2):. doi: 10.3390/ijms17020186. [PMID: 26840304]
  • Yumi Sugimoto, Katsumi Nishimura, Atsuko Itoh, Takao Tanahashi, Hiroshi Nakajima, Hideo Oshiro, Shujian Sun, Takahiro Toda, Jun Yamada. Serotonergic mechanisms are involved in antidepressant-like effects of bisbenzylisoquinolines liensinine and its analogs isolated from the embryo of Nelumbo nucifera Gaertner seeds in mice. The Journal of pharmacy and pharmacology. 2015 Dec; 67(12):1716-22. doi: 10.1111/jphp.12473. [PMID: 26246025]
  • Song-Feng Lv, Xiang-hong Wang, Hong-wei Li, Xiao-lei Zhang, Bo Wang. Quantification of liensinine in rat plasma using ultra-performance liquid chromatography tandem mass spectrometry and its application to a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Jun; 992(?):43-6. doi: 10.1016/j.jchromb.2015.04.023. [PMID: 25939097]
  • Li-Sheng Peng, Xiao-Yan Jiang, Zhong-Xin Li, Tie-Gang Yi, Bin Huang, Hui-Lin Li, Zhen Zeng, Yu Liu, Song-Ling Peng, Jin-Song He, Li He, Li-Ping Peng. A simple U-HPLC-MS/MS method for the determination of liensinine and isoliensinine in rat plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Jun; 991(?):29-33. doi: 10.1016/j.jchromb.2015.03.027. [PMID: 25910234]
  • Guoxin Hu, Ren-ai Xu, Yao-yao Dong, Yi-yan Wang, Wen-wen Yao, Zhi-chuan Chen, Dongxin Chen, Tiao Bu, Ren-shan Ge. Simultaneous determination of liensinine, isoliensinine and neferine in rat plasma by UPLC-MS/MS and application of the technique to pharmacokinetic studies. Journal of ethnopharmacology. 2015 Apr; 163(?):94-8. doi: 10.1016/j.jep.2015.01.020. [PMID: 25636663]
  • Qi Shen, Minjuan Zuo, Li Ma, Ye Tian, Lu Wang, Huidi Jiang, Quan Zhou, Hui Zhou, Lushan Yu, Su Zeng. Demethylation of neferine in human liver microsomes and formation of quinone methide metabolites mediated by CYP3A4 accentuates its cytotoxicity. Chemico-biological interactions. 2014 Dec; 224(?):89-99. doi: 10.1016/j.cbi.2014.10.014. [PMID: 25451576]
  • Lushan Yu, Qi Shen, Quan Zhou, Huidi Jiang, Huichang Bi, Min Huang, Hui Zhou, Su Zeng. In vitro characterization of ABC transporters involved in the absorption and distribution of liensinine and its analogs. Journal of ethnopharmacology. 2013 Nov; 150(2):485-91. doi: 10.1016/j.jep.2013.08.061. [PMID: 24036064]
  • Yong Xie, Yi Zhang, Long-Tao Zhang, Shao-Xiao Zeng, Ze-Bin Guo, Bao-Dong Zheng. Protective effects of alkaloid compounds from Nelumbinis Plumula on tert-butyl hydroperoxide-induced oxidative stress. Molecules (Basel, Switzerland). 2013 Aug; 18(9):10285-300. doi: 10.3390/molecules180910285. [PMID: 24064445]
  • Ying Huang, Libo Zhao, Yun Bai, Ping Liu, Jialing Wang, Jizhou Xiang. Simultaneous determination of liensinine, isoliensinine and neferine from seed embryo of Nelumbo nucifera Gaertn. in rat plasma by a rapid HPLC method and its application to a pharmacokinetic study. Arzneimittel-Forschung. 2011; 61(6):347-52. doi: 10.1055/s-0031-1296209. [PMID: 21827045]
  • Shao Liu, Bin Wang, Xin-Zhong Li, Long-feng Qi, Yi-Zeng Liang. Preparative separation and purification of liensinine, isoliensinine and neferine from seed embryo of Nelumbo nucifera GAERTN using high-speed counter-current chromatography. Journal of separation science. 2009 Jul; 32(14):2476-81. doi: 10.1002/jssc.200800766. [PMID: 19557808]
  • Yi Chen, Guorong Fan, Huiling Wu, Yutian Wu, Annabel Mitchell. Separation, identification and rapid determination of liensine, isoliensinine and neferine from embryo of the seed of Nelumbo nucifera Gaertn. by liquid chromatography coupled to diode array detector and tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2007 Jan; 43(1):99-104. doi: 10.1016/j.jpba.2006.06.016. [PMID: 16846715]
  • Jun-Hua Xiao, Jia-Hua Zhang, Hong-Lei Chen, Xiu-Ling Feng, Jia-Ling Wang. Inhibitory effects of isoliensinine on bleomycin-induced pulmonary fibrosis in mice. Planta medica. 2005 Mar; 71(3):225-30. doi: 10.1055/s-2005-837821. [PMID: 15770542]
  • Yoshiki Kashiwada, Akihiro Aoshima, Yasumasa Ikeshiro, Yuh-Pan Chen, Hiroshi Furukawa, Masataka Itoigawa, Toshihiro Fujioka, Kunihide Mihashi, L Mark Cosentino, Susan L Morris-Natschke, Kuo-Hsiung Lee. Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids. Bioorganic & medicinal chemistry. 2005 Jan; 13(2):443-8. doi: 10.1016/j.bmc.2004.10.020. [PMID: 15598565]
  • X Zhang, W Wen, X Hu, S Luo, H Cai. [Determination of liensinine in plasma by high performance liquid chromatography]. Se pu = Chinese journal of chromatography. 1997 Jul; 15(4):347-8. doi: NULL. [PMID: 15739474]
  • X Hu, X Zhang, H Cai, S Lou, W Yin. [Pharmacokinetics of liensinine in rabbits]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1992 Oct; 17(10):622-4, inside back cover. doi: NULL. [PMID: 1294182]