Aloperine (BioDeep_00000008296)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


rel-(6R,6aR,13R,13aS)-2,3,4,6,6a,7,8,9,10,12,13,13a-Dodecahydro-1H-6,13-methanodipyrido[1,2-a:3,2-e]azocine

化学式: C15H24N2 (232.1939)
中文名称: 苦豆碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 90.58%

分子结构信息

SMILES: C1=C2CCCNC2C2CC1C1CCCCN1C2
InChI: InChI=1S/C15H24N2/c1-2-7-17-10-13-9-12(14(17)5-1)8-11-4-3-6-16-15(11)13/h8,12-16H,1-7,9-10H2

描述信息

Aloperine is a natural product found in Thinicola incana, Sophora alopecuroides, and other organisms with data available.
Aloperine is an alkaloid in sophora plants such as Sophora alopecuroides L, which has shown anti-cancer, anti-inflammatory and anti-virus properties[1]. Aloperine is widely used to treat patients with allergic contact dermatitis eczema and other skin inflammation in China[2]. Aloperine induces apoptosis and autophagy in HL-60 cells[1].
Aloperine is an alkaloid in sophora plants such as Sophora alopecuroides L, which has shown anti-cancer, anti-inflammatory and anti-virus properties[1]. Aloperine is widely used to treat patients with allergic contact dermatitis eczema and other skin inflammation in China[2]. Aloperine induces apoptosis and autophagy in HL-60 cells[1].

同义名列表

17 个代谢物同义名

(6R,6aR,13S,13aS)-1,3,4,6,6a,7,8,9,10,12,13,13a-dodecahydro-2H-6,13-methanodipyrido[1,2-a:3,2-e]azocine; Aloperine; rel-(6R,6aR,13R,13aS)-2,3,4,6,6a,7,8,9,10,12,13,13a-Dodecahydro-1H-6,13-methanodipyrido[1,2-a:3,2-e]azocine; (6R,6aR,13R,13aS)-2,3,4,6,6a,7,8,9,10,12,13,13a-dodecahydro-1H-6,13-methanodipyrido[1,2-a:3,2-e]azocine; (6r,6ar,13r,13as)-1,3,4,6,6a,7,8,9,10,12,13,13a-dodecahydro-2h-6,13-methanodipyrido[1,2-a:3,2-e]azocine; 1,3,4,6,6a,7,8,9,10,12,13,13a-Dodecahydro-2H-6,13-methanodipyrido[1,2-a:3,2-e]azocine; (1R,2S,9R,10R)-3,15-DIAZATETRACYCLO[7.7.1.0(2),?.0(1)?,(1)?]HEPTADEC-7-ENE; (1R,2S,9R,10R)-3,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadec-7-ene; (1R,2S,9R,10R)-3,15-diazatetracyclo[7.7.1.0?,?.0??,??]heptadec-7-ene; (1R,2S,9R,10R)-3,15-diazatetracyclo[7.7.1.02,7.010,15]heptadec-7-ene; Ormosanine, 16,17-didehydro-9-de-2-piperidinyl-, (7-alpha,9-alpha)-; (7-alpha,9-alpha)-9-De-2-piperidinyl-16,17-didehydro-ormosanine; 6-epi-aloperine; Aloperine, 96\\%; Alop1 compound; CID 3772951; Aloperine



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)

20 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
Cytoplasm 10 AKT1, BCL2, CASP9, CAT, CCNB1, MAPK8, MTOR, PIK3CA, PTGS2, STAT3
Peripheral membrane protein 3 CTSB, MTOR, PTGS2
Endoplasmic reticulum membrane 4 BCL2, HMOX1, MTOR, PTGS2
Nucleus 10 AKT1, BCL2, CASP9, CCNB1, GABPA, HMOX1, MAPK8, MTOR, PARP1, STAT3
cytosol 11 AKT1, BCL2, CASP9, CAT, CCNB1, HMOX1, MAPK8, MTOR, PARP1, PIK3CA, STAT3
dendrite 1 MTOR
nuclear body 1 PARP1
phagocytic vesicle 1 MTOR
centrosome 1 CCNB1
nucleoplasm 8 AKT1, CCNB1, GABPA, HMOX1, MAPK8, MTOR, PARP1, STAT3
RNA polymerase II transcription regulator complex 1 STAT3
Cell membrane 2 AKT1, TNF
Cytoplasmic side 2 HMOX1, MTOR
lamellipodium 2 AKT1, PIK3CA
Golgi apparatus membrane 1 MTOR
Synapse 1 MAPK8
cell cortex 1 AKT1
cell surface 1 TNF
glutamatergic synapse 1 AKT1
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
neuronal cell body 1 TNF
postsynapse 1 AKT1
Cytoplasm, cytosol 1 PARP1
Lysosome 2 CTSB, MTOR
plasma membrane 4 AKT1, PIK3CA, STAT3, TNF
Membrane 7 AKT1, BCL2, CAT, CCNB1, HMOX1, MTOR, PARP1
apical plasma membrane 1 CTSB
axon 2 CCK, MAPK8
caveola 1 PTGS2
extracellular exosome 2 CAT, CTSB
Lysosome membrane 1 MTOR
endoplasmic reticulum 3 BCL2, HMOX1, PTGS2
extracellular space 6 CCK, CTSB, CXCL8, HMOX1, IL6, TNF
perinuclear region of cytoplasm 3 CTSB, HMOX1, PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 4 BCL2, CASP9, CAT, PARP1
protein-containing complex 6 AKT1, BCL2, CASP9, CAT, PARP1, PTGS2
intracellular membrane-bounded organelle 1 CAT
Microsome membrane 2 MTOR, PTGS2
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 3 CCK, CXCL8, IL6
extracellular region 6 CAT, CCK, CTSB, CXCL8, IL6, TNF
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 3 BCL2, HMOX1, MTOR
mitochondrial matrix 2 CAT, CCNB1
Extracellular side 1 CTSB
transcription regulator complex 2 PARP1, STAT3
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 CTSB, TNF
microtubule cytoskeleton 1 AKT1
nucleolus 1 PARP1
cell-cell junction 1 AKT1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
Apical cell membrane 1 CTSB
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 CAT
spindle 1 AKT1
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 MTOR
PML body 1 MTOR
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 1 CTSB
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
ciliary basal body 1 AKT1
chromatin 3 GABPA, PARP1, STAT3
phagocytic cup 1 TNF
Chromosome 1 PARP1
Secreted, extracellular space 1 CTSB
Nucleus, nucleolus 1 PARP1
spindle pole 1 CCNB1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
site of double-strand break 1 PARP1
nuclear envelope 2 MTOR, PARP1
Endomembrane system 1 MTOR
Melanosome 1 CTSB
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 2 CAT, CTSB
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 2 IL6, PTGS2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
Single-pass type IV membrane protein 1 HMOX1
apoptosome 1 CASP9
outer kinetochore 1 CCNB1
protein-DNA complex 1 PARP1
basal dendrite 1 MAPK8
Cytoplasmic vesicle, phagosome 1 MTOR
site of DNA damage 1 PARP1
peptidase inhibitor complex 1 CTSB
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
cyclin B1-CDK1 complex 1 CCNB1
endolysosome lumen 1 CTSB
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
BAD-BCL-2 complex 1 BCL2
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
caspase complex 1 CASP9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
  • Zhaoyang Hu, Jiaxue Li, Quanhua Liu, Rían W Manville, Geoffrey W Abbott. The plant-derived alkaloid aloperine prevents ischemia/reperfusion injury-induced sudden cardiac death. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2023 Jul; 37(7):e22999. doi: 10.1096/fj.202300253r. [PMID: 37249366]
  • Peiwen Zhou, Zizhao Lao, Haishan Long, Pan Pan, Feng Liao, Wenjiang Zheng, Zonghui Li, Jianfeng Dai, Helu Liu, Yong Jiang, Xiaohong Liu, Wenbiao Wang, Jianguo Wu, Geng Li. The in vitro and in vivo antiviral effects of aloperine against Zika virus infection. Journal of medical virology. 2023 07; 95(7):e28913. doi: 10.1002/jmv.28913. [PMID: 37409639]
  • 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]
  • Kun Wang, Jia-Jing Wu, Xin-Zhang, Qing-Xuan Zeng, Na Zhang, Wei-Jin Huang, Sheng Tang, Yan-Xiang Wang, Wei-Jia Kong, You-Chun Wang, Ying-Hong Li, Dan-Qing Song. Discovery and evolution of 12N-substituted aloperine derivatives as anti-SARS-CoV-2 agents through targeting late entry stage. Bioorganic chemistry. 2021 10; 115(?):105196. doi: 10.1016/j.bioorg.2021.105196. [PMID: 34333425]
  • 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]
  • Mingning Qiu, Jie Liu, Ping Feng, Yongxia Su, Rong Guo, Fangyun Shi, Shuai Wang, Baoyu Zhao. Cytochrome P450s regulates aloperine-induced pathological changes in mouse liver and kidney. Research in veterinary science. 2020 Oct; 132(?):97-100. doi: 10.1016/j.rvsc.2020.06.005. [PMID: 32544634]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • Xiao-Ying Yuan, Hui-Min Ma, Rui-Zhi Li, Rui-Yan Wang, Wei Liu, Jian-You Guo. Topical application of aloperine improves 2,4-dinitrofluorobenzene-induced atopic dermatitis-like skin lesions in NC/Nga mice. European journal of pharmacology. 2011 May; 658(2-3):263-9. doi: 10.1016/j.ejphar.2011.02.013. [PMID: 21371468]
  • Ze Lin, Chang-Fa Huang, Xiao-Shan Liu, Jikai Jiang. In vitro anti-tumour activities of quinolizidine alkaloids derived from Sophora flavescens Ait. Basic & clinical pharmacology & toxicology. 2011 May; 108(5):304-9. doi: 10.1111/j.1742-7843.2010.00653.x. [PMID: 21159130]
  • Xiao-Ying Yuan, Wei Liu, Ping Zhang, Rui-Yan Wang, Jian-You Guo. Effects and mechanisms of aloperine on 2, 4-dinitrofluorobenzene-induced allergic contact dermatitis in BALB/c mice. European journal of pharmacology. 2010 Mar; 629(1-3):147-52. doi: 10.1016/j.ejphar.2009.12.007. [PMID: 20006963]
  • Bin Liu, Ren-Bing Shi. [Constituents in the alkaloid fraction of Kushen decoction]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Apr; 31(7):557-60. doi: . [PMID: 16780157]
  • C C Zhou, H B Gao, X B Sun, H B Shi, W Liu, H N Yuan, Z X Wang. [Anti-inflammatory and anti-allergic action of aloperine]. Zhongguo yao li xue bao = Acta pharmacologica Sinica. 1989 Jul; 10(4):360-5. doi: . [PMID: 2533795]