Imperialin (BioDeep_00000230203)

 

Secondary id: BioDeep_00000008332

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(3S,4aS,6aS,6bS,8aR,9S,9aS,12S,15aS,15bR,16aS,16bR)-3,9-dihydroxy-9,12,16b-trimethyldocosahydrobenzo[4,5]indeno[1,2-h]pyrido[1,2-b]isoquinolin-5(1H)-one

化学式: C27H43NO3 (429.3243)
中文名称: 西贝母碱, 西贝素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 84.39%

分子结构信息

SMILES: CC1CCC2C(C3CCC4C(C3CN2C1)CC5C4CC(=O)C6C5(CCC(C6)O)C)(C)O
InChI: InChI=1S/C27H43NO3/c1-15-4-7-25-27(3,31)21-6-5-17-18(20(21)14-28(25)13-15)11-22-19(17)12-24(30)23-10-16(29)8-9-26(22,23)2/h15-23,25,29,31H,4-14H2,1-3H3/t15-,16-,17+,18+,19-,20-,21+,22-,23+,25-,26+,27-/m0/s1

描述信息

Sipeimine is an alkaloid.
Imperialine is a natural product found in Fritillaria cirrhosa, Fritillaria thunbergii, and other organisms with data available.
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents > D014704 - Veratrum Alkaloids
Sipeimine is a natural product isolated from Fritillaria ussuriensis. IC50 value: Target: In vitro: Sipeimine can induce rejuvenation of a endophytic fungus; Sipeimine yield of the strain rejuvenated by adding 3\\% bulbus was effectively improved to 0.0563 mg/L and it is 21.9\\% higher than that of the initial strain [1]. In vivo:
Sipeimine is a natural product isolated from Fritillaria ussuriensis. IC50 value: Target: In vitro: Sipeimine can induce rejuvenation of a endophytic fungus; Sipeimine yield of the strain rejuvenated by adding 3\% bulbus was effectively improved to 0.0563 mg/L and it is 21.9\% higher than that of the initial strain [1]. In vivo:

同义名列表

20 个代谢物同义名

(3S,4aS,6aS,6bS,8aR,9S,9aS,12S,15aS,15bR,16aS,16bR)-3,9-dihydroxy-9,12,16b-trimethyldocosahydrobenzo[4,5]indeno[1,2-h]pyrido[1,2-b]isoquinolin-5(1H)-one; (1R,2S,6S,9S,10S,11R,14S,15S,18S,20S,23R,24S)-10,20-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-one; Cevan-6-one, 3,20-dihydroxy-, (3.beta.,5.alpha.,17.beta.)-; Cevan-6-one, 3,20-dihydroxy-, (3-beta,5-alpha,17-beta)-; peiminine hydrochloride, (3beta,5alpha,17beta)-isomer; peiminine nitrate salt, (3beta,5alpha,17beta)-isomer; (3-beta,5-alpha,17-beta)-3,20-Dihydroxycevan-6-one; 3beta,20beta-dihydroxy-6-one-5alpha-cevanine; peiminine, (3beta,5alpha,25alpha)-isomer; peiminine, (3beta,5alpha,17beta)-isomer; 3beta, 20-dihydroxy-5alpha-cevan-6-one; Imperialine ,(S); fritillarine; Imperialine; Kashmirine; zhebeinone; Imperialin; peiminine; sipeimine; Imperialine



数据库引用编号

19 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)

59 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。

亚细胞结构定位 关联基因列表


文献列表

  • Jiajin Xu, Zeyi Zhang, Hongtao Hu, Yaqin Yang, Chenghong Xiao, Luyi Xi, Jiahui Lu, Shasha Tian, Huajun Zhao. Synergistic antitumor effects of Peiminine and Doxorubicin on breast cancer through enhancing DNA damage via ZEB1. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2024 Apr; 173(?):116353. doi: 10.1016/j.biopha.2024.116353. [PMID: 38432128]
  • Maryam Ranjbar Bushehri, Nahid Babaei, Hadi Esmaeili Gouvarchin Ghaleh, Gholamreza Khamisipour, Gholamreza Farnoosh. Anti-inflammatory activity of peiminine in acetic acid-induced ulcerative colitis model. Inflammopharmacology. 2023 Oct; ?(?):. doi: 10.1007/s10787-023-01360-4. [PMID: 37855980]
  • Demei Huang, Zherui Shen, Sijing Zhao, Caixia Pei, Nan Jia, Yilan Wang, Yongcan Wu, Xiaomin Wang, Shihua Shi, Yacong He, Zhenxing Wang, Fei Wang. Sipeimine attenuates PM2.5-induced lung toxicity via suppression of NLRP3 inflammasome-mediated pyroptosis through activation of the PI3K/AKT pathway. Chemico-biological interactions. 2023 May; 376(?):110448. doi: 10.1016/j.cbi.2023.110448. [PMID: 36898572]
  • Chunyan Liu, Dong Zhen, Huanhuan Du, Guohua Gong, Yun Wu, Qianqian Ma, Zhe-Shan Quan. Synergistic anti-inflammatory effects of peimine, peiminine, and forsythoside a combination on LPS-induced acute lung injury by inhibition of the IL-17-NF-κB/MAPK pathway activation. Journal of ethnopharmacology. 2022 Sep; 295(?):115343. doi: 10.1016/j.jep.2022.115343. [PMID: 35533916]
  • Yilan Wang, Zherui Shen, Sijing Zhao, Demei Huang, Xiaomin Wang, Yongcan Wu, Caixia Pei, Shihua Shi, Nan Jia, Yacong He, Zhenxing Wang. Sipeimine ameliorates PM2.5-induced lung injury by inhibiting ferroptosis via the PI3K/Akt/Nrf2 pathway: A network pharmacology approach. Ecotoxicology and environmental safety. 2022 Jul; 239(?):113615. doi: 10.1016/j.ecoenv.2022.113615. [PMID: 35567927]
  • Yu-Hua Shi, Qin-Wei Huang, She-Min Zhu, Yue-Mei Zhou, Li-Jiang Zhang, Wen-Kang Huang, Jin-Jin Shao, Jian-Liang Zhou, Wen-Ting Zhang. Chemical profiling of Fritillariae thunbergii Miq prepared by different processing methods reveals two new quality markers: Zhebeininoside and imperialine-3-β-D-glucoside. Journal of ethnopharmacology. 2022 Jan; 283(?):114670. doi: 10.1016/j.jep.2021.114670. [PMID: 34653522]
  • Pankaj Kumar, Ashrita, Vishal Acharya, Ashish R Warghat. Comparative transcriptome analysis infers bulb derived in vitro cultures as a promising source for sipeimine biosynthesis in Fritillaria cirrhosa D. Don (Liliaceae, syn. Fritillaria roylei Hook.) - High value Himalayan medicinal herb. Phytochemistry. 2021 Mar; 183(?):112631. doi: 10.1016/j.phytochem.2020.112631. [PMID: 33370713]
  • Boxiang Du, Liang Cao, Kai Wang, Juanjuan Miu, Lei Yao, Zhihua Xu, Jie Song. Peiminine Attenuates Acute Lung Injury Induced by LPS Through Inhibiting Lipid Rafts Formation. Inflammation. 2020 Jun; 43(3):1110-1119. doi: 10.1007/s10753-020-01198-w. [PMID: 32152924]
  • Qing Lin, Mengke Qu, Hirak K Patra, Shanshan He, Luyao Wang, Xun Hu, Linyu Xiao, Yu Fu, Tao Gong, Qin He, Ling Zhang, Xun Sun, Zhirong Zhang. Mechanistic and therapeutic study of novel anti-tumor function of natural compound imperialine for treating non-small cell lung cancer. Journal of ethnopharmacology. 2020 Jan; 247(?):112283. doi: 10.1016/j.jep.2019.112283. [PMID: 31605736]
  • Simei Liu, Tiechui Yang, Tse Wai Ming, Tse Kathy Wai Gaun, Ting Zhou, Shu Wang, Bengui Ye. Isosteroid alkaloids with different chemical structures from Fritillariae cirrhosae bulbus alleviate LPS-induced inflammatory response in RAW 264.7 cells by MAPK signaling pathway. International immunopharmacology. 2020 Jan; 78(?):106047. doi: 10.1016/j.intimp.2019.106047. [PMID: 31816576]
  • Qiu-Yan Wang, Xin Dong, Juan Yang, Xiao-Ting Zhen, Li-Hong Ye, Chu Chu, Bin Wang, Yu-Han Hu, Hui Zheng, Jun Cao. Solid acids assisted matrix solid-phase dispersion microextraction of alkaloids by capillary electrophoresis coupled with quadrupole time-of-flight mass spectrometry. Journal of separation science. 2019 Dec; 42(23):3579-3588. doi: 10.1002/jssc.201900647. [PMID: 31617304]
  • Qing Lin, Mengke Qu, Bingjie Zhou, Hirak K Patra, Zihan Sun, Qiong Luo, Wenyu Yang, Yongcui Wu, Yu Zhang, Lin Li, Lang Deng, Leilei Wang, Tao Gong, Qin He, Ling Zhang, Xun Sun, Zhirong Zhang. Exosome-like nanoplatform modified with targeting ligand improves anti-cancer and anti-inflammation effects of imperialine. Journal of controlled release : official journal of the Controlled Release Society. 2019 10; 311-312(?):104-116. doi: 10.1016/j.jconrel.2019.08.037. [PMID: 31484040]
  • Zhibin Wang, Feng Cao, Yajun Chen, Zhenqiu Tang, Zhenyue Wang. Simultaneous Determination and Pharmacokinetics of Peimine and Peiminine in Beagle Dog Plasma by UPLC-MS/MS after the Oral Administration of Fritillariae ussuriensis Maxim and Fritillariae thunbergii Miq Powder. Molecules (Basel, Switzerland). 2018 06; 23(7):. doi: 10.3390/molecules23071573. [PMID: 29958456]
  • Jeong-Min Lim, Bina Lee, Ju-Hee Min, Eun-Young Kim, Jae-Hyun Kim, SooYeon Hong, Jwa-Jin Kim, Youngjoo Sohn, Hyuk-Sang Jung. Effect of peiminine on DNCB-induced atopic dermatitis by inhibiting inflammatory cytokine expression in vivo and in vitro. International immunopharmacology. 2018 Mar; 56(?):135-142. doi: 10.1016/j.intimp.2018.01.025. [PMID: 29414643]
  • Boxian Zhao, Chen Shen, Zhixing Zheng, Xiaoxiong Wang, Wenyang Zhao, Xin Chen, Fei Peng, Linmeng Xue, Mengting Shu, Xu Hou, Kaikai Wang, Chen Zhong, Jingxian Sun, Jinzhao Wan, Shiguang Zhao. Peiminine Inhibits Glioblastoma in Vitro and in Vivo Through Cell Cycle Arrest and Autophagic Flux Blocking. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2018; 51(4):1566-1583. doi: 10.1159/000495646. [PMID: 30497066]
  • Yu-Ming Liu, Ya-Dong Feng, Xi Lu, Jian-Bing Nie, Wei Li, Li-Ning Wang, Li-Jun Tian, Qing-Hua Liu. Isosteroidal alkaloids as potent dual-binding site inhibitors of both acetylcholinesterase and butyrylcholinesterase from the bulbs of Fritillaria walujewii. European journal of medicinal chemistry. 2017 Sep; 137(?):280-291. doi: 10.1016/j.ejmech.2017.06.007. [PMID: 28605675]
  • Juan He, Yong He, And Chu Zhang. Determination and Visualization of Peimine and Peiminine Content in Fritillaria thunbergii Bulbi Treated by Sulfur Fumigation Using Hyperspectral Imaging with Chemometrics. Molecules (Basel, Switzerland). 2017 Aug; 22(9):. doi: 10.3390/molecules22091402. [PMID: 28832506]
  • Jiachun Li, Dongpo Li, Youzhi Pan, Jun-Hua Hu, Wenzhe Huang, Zhen-Zhong Wang, Wei Xiao, Yu Wang. Simultaneous determination of ten bioactive constituents of Sanjie Zhentong Capsule in rat plasma by ultra-high-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. 2017 Jun; 1054(?):20-26. doi: 10.1016/j.jchromb.2017.03.001. [PMID: 28415020]
  • Yan Li, Abulimiti Yili, Jun Li, Aziz Muhamat, Haji Akber Aisa. New isosteroidal alkaloids with tracheal relaxant effect from the bulbs of Fritillaria pallidiflora Schrenk. Bioorganic & medicinal chemistry letters. 2016 Apr; 26(8):1983-7. doi: 10.1016/j.bmcl.2016.03.001. [PMID: 26965859]
  • Dongdong Wang, Qingdan Du, Houcong Li, Shu Wang. The Isosteroid Alkaloid Imperialine from Bulbs of Fritillaria cirrhosa Mitigates Pulmonary Functional and Structural Impairment and Suppresses Inflammatory Response in a COPD-Like Rat Model. Mediators of inflammation. 2016; 2016(?):4192483. doi: 10.1155/2016/4192483. [PMID: 27524867]
  • Qing Lin, Yu Fu, Jia Li, Mengke Qu, Li Deng, Tao Gong, Zhirong Zhang. A (polyvinyl caprolactam-polyvinyl acetate-polyethylene glycol graft copolymer)-dispersed sustained-release tablet for imperialine to simultaneously prolong the drug release and improve the oral bioavailability. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2015 Nov; 79(?):44-52. doi: 10.1016/j.ejps.2015.08.018. [PMID: 26349052]
  • Ke Wu, Chunfen Mo, Hengyi Xiao, Yun Jiang, Bengui Ye, Shu Wang. Imperialine and Verticinone from Bulbs of Fritillaria wabuensis Inhibit Pro-inflammatory Mediators in LPS-stimulated RAW 264.7 Macrophages. Planta medica. 2015 Jul; 81(10):821-9. doi: 10.1055/s-0035-1546170. [PMID: 26132855]
  • Qing Lin, Li-qin Ling, Ling Guo, Tao Gong, Xun Sun, Zhi-rong Zhang. Intestinal absorption characteristics of imperialine: in vitro and in situ assessments. Acta pharmacologica Sinica. 2015 Jul; 36(7):863-73. doi: 10.1038/aps.2015.27. [PMID: 26051111]
  • Qing Lyu, Fangfang Tou, Hong Su, Xiaoyong Wu, Xinyi Chen, Zhi Zheng. The natural product peiminine represses colorectal carcinoma tumor growth by inducing autophagic cell death. Biochemical and biophysical research communications. 2015 Jun; 462(1):38-45. doi: 10.1016/j.bbrc.2015.04.102. [PMID: 25935480]
  • Feng Pan, Kai Hou, Feng Gao, Bo Hu, Que Chen, Wei Wu. Peimisine and peiminine production by endophytic fungus Fusarium sp. isolated from Fritillaria unibracteata var. wabensis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Jul; 21(8-9):1104-9. doi: 10.1016/j.phymed.2014.04.010. [PMID: 24854573]
  • Zhi-Yu Guan, Li-Hua Zhang, Li-Hua Chen, Wei-Feng Zhu, Hong-Ning Liu. [Rat intestinal absorption trait of peimine and peiminine in Thunberg fritillary bulb extract]. Yao xue xue bao = Acta pharmaceutica Sinica. 2013 Dec; 48(12):1836-43. doi: ". [PMID: 24689243]
  • Qing Lin, Quan Zhang, Xu Song, Tao Gong, Xun Sun, Zhirong Zhang. Novel LC-MS/MS method for analyzing imperialine in rat plasma: development, validation, and application to pharmacokinetics. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Nov; 938(?):51-9. doi: 10.1016/j.jchromb.2013.08.033. [PMID: 24055750]
  • Hai Guo, Fuzhi Ji, Baorui Liu, Xiaofei Chen, Jingdong He, Jiening Gong. Peiminine ameliorates bleomycin-induced acute lung injury in rats. Molecular medicine reports. 2013 Apr; 7(4):1103-10. doi: 10.3892/mmr.2013.1312. [PMID: 23404624]
  • Li-hua Chen, Hui-min Zhang, Zhi-yu Guan, Wei-feng Zhu, Wen-jiao Yi, Yong-mei Guan, Sen Wang, Hong-ning Liu. Sex dependent pharmacokinetics, tissue distribution and excretion of peimine and peiminine in rats assessed by liquid chromatography-tandem mass spectrometry. Journal of ethnopharmacology. 2013 Jan; 145(1):77-84. doi: 10.1016/j.jep.2012.09.054. [PMID: 23123795]
  • Lihong Liu, Wenwei You, Liujuan Zheng, Feiyu Chen, Zhimin Jia. Determination of peimine and peiminine in Bulbus Fritillariae Thunbergii by capillary electrophoresis by indirect UV detection using N-(1-naphthyl)ethylenediamine dihydrochloride as probe. Electrophoresis. 2012 Jul; 33(14):2152-8. doi: 10.1002/elps.201200021. [PMID: 22821492]
  • Lihua Chen, Lili Liu, Weifeng Zhu, Huimin Zhang, Zhihong Yan, Hongning Liu. Comparative pharmacokinetic studies of peimine and peiminine in rat plasma by LC-MS-MS after oral administration of Fritillaria thunbergii Miq. and Fritillaria thunbergii Miq. - Glycyrrhiza uralensis Fisch. couple extract. Die Pharmazie. 2011 Sep; 66(9):684-9. doi: NULL. [PMID: 22026124]
  • Bao-zhong Duan, Lin-fang Huang, Shi-lin Chen. [Simultaneous determination of peimisine and sipeimine in Fritillaria walujewii regel and Fritillaria pallidiflora Schrenk by UPLC-ELSD]. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 Dec; 45(12):1541-4. doi: ". [PMID: 21351494]
  • Xiaodan Wu, Juanjuan Chen, Yuanjiang Pan. Simultaneous determination of peimine and peiminine in rat plasma by LC-ESI-MS employing solid-phase extraction. Biomedical chromatography : BMC. 2010 Aug; 24(8):902-7. doi: 10.1002/bmc.1384. [PMID: 20033892]
  • Li-hua Chen, Li-li Liu, Hong-ning Liu, Wei-feng Zhu, Wen-jiao Yi, Yi Zhao. [Simultaneous determination of peimine and peiminine in rat plasma by LC-MS/MS and its application in the pharmacokinetic study]. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 Jul; 45(7):891-4. doi: . [PMID: 20931788]
  • Hong Yin, Juan-Li Chen. Sipeimine-producing endophytic fungus isolated from Fritillaria ussuriensis. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Nov; 63(11-12):789-93. doi: 10.1515/znc-2008-11-1202. [PMID: 19227824]
  • Bao-Qin Lin, Hui Ji, Ping Li, Yan Jiang, Wei Fang. Selective antagonism activity of alkaloids from bulbs Fritillariae at muscarinic receptors: functional studies. European journal of pharmacology. 2006 Dec; 551(1-3):125-30. doi: 10.1016/j.ejphar.2006.08.066. [PMID: 17027747]
  • Ying Zhou, Hui Ji, Bao-Qin Lin, Yan Jiang, Ping Li. The effects of five alkaloids from Bulbus Fritillariae on the concentration of cAMP in HEK cells transfected with muscarinic M(2) receptor plasmid. The American journal of Chinese medicine. 2006; 34(5):901-10. doi: 10.1142/s0192415x06004375. [PMID: 17080553]
  • Guo-Xin Zhang, Juan Li, Peng Zhang, Han-Li Ruan, Yong-Hui Zhang, Hui-Fang Pi, Ji-Zhou Wu. [HPLC fingerprint of Fritillaria hupehensis]. Yao xue xue bao = Acta pharmaceutica Sinica. 2005 Sep; 40(9):850-3. doi: ". [PMID: 16342691]
  • Yan Xue, Hao-Liang Gu. [Determination of peimine and peiminine in Fritillaria thunbergii by HPLC-ELSD]. Yao xue xue bao = Acta pharmaceutica Sinica. 2005 Jun; 40(6):550-2. doi: . [PMID: 16144323]
  • Ping Li, Ling-Jie Zeng, Song-Lin Li, Ge Lin. The extraction of imperialine and imperialine-3 beta-glucoside from Fritillaria pallidiflora Schrenk and quantitative determination by HPLC-evaporative light scattering detection. Phytochemical analysis : PCA. 2002 May; 13(3):158-61. doi: 10.1002/pca.635. [PMID: 12099106]
  • H Zhen, Y Yang. [Experimental studies on the quality control of xiaoluo pills]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1996 Apr; 21(4):222-5, 255. doi: ". [PMID: 9208553]
  • D Xu, E Huang, C Li. [Alkaloid constituents of Fritillaria pallidiflora Schrenk]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1990 Sep; 15(9):551-2, 577. doi: ". [PMID: 2092715]
  • B C Qian, H J Xu. [Studies on the antitussive and sedative activities of peimine and peiminine]. Yao xue xue bao = Acta pharmaceutica Sinica. 1985 Apr; 20(4):306-8. doi: ". [PMID: 4072703]