Gentianine (BioDeep_00000000450)

 

Secondary id: BioDeep_00000859835

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


NICOTINIC ACID, 4-(2-HYDROXYETHYL)-5-VINYL-, .DELTA.-LACTONE

化学式: C10H9NO2 (175.0633)
中文名称: 秦艽甲素, 龙胆内酯, 龙胆碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 40.41%

分子结构信息

SMILES: C=CC1=C2CCOC(=O)C2=CN=C1
InChI: InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2

描述信息

Gentianine, also known as 4-(2-hydroxyethyl)-5-vinylnicotinate g-lactone, is a member of the class of compounds known as pyranopyridines. Pyranopyridines are polycyclic aromatic compounds containing a pyran ring fused to a pyridine ring. Gentianine is soluble (in water) and a strong basic compound (based on its pKa). Gentianine is a bitter tasting compound found in fenugreek, which makes gentianine a potential biomarker for the consumption of this food product.
Gentianine is a pyranopyridine, a lactone and a pyridine alkaloid.
Gentianine is a natural product found in Strychnos angolensis, Strychnos xantha, and other organisms with data available.
See also: Fenugreek seed (part of); Centaurium erythraea whole (part of).

同义名列表

28 个代谢物同义名

NICOTINIC ACID, 4-(2-HYDROXYETHYL)-5-VINYL-, .DELTA.-LACTONE; NICOTINIC ACID, 4-(2-HYDROXYETHYL)-5-VINYL-, delta-LACTONE; Nicotinic acid, 4-(2-hydroxyethyl)-5-vinyl-, gamma-lactone; 4-(2-hydroxyethyl)-5-vinylnicotinic acid gamma-lactone; 1H-Pyrano(3,4-c)pyridin-1-one, 5-ethenyl-3,4-dihydro-; 1H-Pyrano[3,4-c]pyridin-1-one, 5-ethenyl-3,4-dihydro-; 5-ethenyl-3,4-dihydro-1H-pyrano(3,4-c)pyridin-1-one; 1H-Pyrano(3,4-c)pyridin-1-one, 3,4-dihydro-5-vinyl-; 5-ethenyl-3,4-dihydro-1H-pyrano[3,4-c]pyridin-1-one; 4-(2-Hydroxyethyl)-5-vinylnicotinic acid γ-lactone; 4-(2-Hydroxyethyl)-5-vinylnicotinic acid g-lactone; 4-(2-Hydroxyethyl)-5-vinylnicotinate gamma-lactone; 5-vinyl-3,4-dihydro-1H-pyrano[3,4-c]pyridin-1-one; From Schultesia guianensis malme (Mata-Zombando); 5-ethenyl-3,4-dihydropyrano[3,4-c]pyridin-1-one; 4-(2-Hydroxyethyl)-5-vinylnicotinate g-lactone; 4-(2-Hydroxyethyl)-5-vinylnicotinate γ-lactone; 5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one; 5-VINYL-3,4-DIHYDROPYRANO(3,4-C)PYRIDIN-1-ONE; 4-27-00-02817 (Beilstein Handbook Reference); GENTIANINE [MI]; UNII-C2PD310UXB; gentiannine; Erythricine; C2PD310UXB; Gentianine; Gencianina; Gentianine



数据库引用编号

21 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)

71 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 11 AIMP2, FH, IL18, MAPK8, MAPK9, MYD88, NFKB1, NLRP3, NR3C1, STAT3, TLR4
Endosome membrane 2 MYD88, TLR4
Nucleus 9 AIMP2, FH, MAPK8, MAPK9, MYD88, NFKB1, NLRP3, NR3C1, STAT3
cytosol 11 AIMP2, FH, IL18, IL1B, MAPK8, MAPK9, MYD88, NFKB1, NLRP3, NR3C1, STAT3
centrosome 1 NR3C1
nucleoplasm 5 MAPK8, MAPK9, NFKB1, NR3C1, STAT3
RNA polymerase II transcription regulator complex 1 STAT3
Cell membrane 2 TLR4, TNF
Golgi apparatus membrane 1 NLRP3
Synapse 2 MAPK8, NR3C1
cell surface 4 ADIPOQ, MYD88, TLR4, TNF
Golgi membrane 1 NLRP3
lysosomal membrane 1 GAA
neuronal cell body 1 TNF
Cytoplasm, cytosol 4 AIMP2, IL18, IL1B, NLRP3
Lysosome 2 GAA, IL1B
plasma membrane 6 GAA, MAPK9, MYD88, STAT3, TLR4, TNF
Membrane 5 AIMP2, GAA, NLRP3, NR3C1, TLR4
axon 1 MAPK8
extracellular exosome 2 FH, GAA
Lysosome membrane 1 GAA
endoplasmic reticulum 2 ADIPOQ, NLRP3
extracellular space 6 ADIPOQ, IL10, IL18, IL1B, IL6, TNF
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 1 TLR4
Schaffer collateral - CA1 synapse 1 MAPK9
mitochondrion 5 FH, MAPK9, NFKB1, NLRP3, NR3C1
protein-containing complex 2 MYD88, NR3C1
intracellular membrane-bounded organelle 1 GAA
Single-pass type I membrane protein 1 TLR4
Secreted 7 ADIPOQ, GAA, IL10, IL18, IL1B, IL6, NLRP3
extracellular region 9 ADIPOQ, GAA, IL10, IL18, IL1B, IL6, NFKB1, NLRP3, TNF
mitochondrial matrix 2 FH, NR3C1
transcription regulator complex 2 NFKB1, STAT3
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 NR3C1
external side of plasma membrane 2 TLR4, TNF
Early endosome 1 TLR4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 1 TNF
Cytoplasm, cytoskeleton, spindle 1 NR3C1
spindle 1 NR3C1
collagen trimer 1 ADIPOQ
collagen-containing extracellular matrix 1 ADIPOQ
secretory granule 1 IL1B
nuclear speck 2 MAPK9, NR3C1
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 1 TLR4
chromatin 3 NFKB1, NR3C1, STAT3
phagocytic cup 2 TLR4, TNF
Chromosome 2 FH, NR3C1
site of double-strand break 1 FH
Endomembrane system 1 NLRP3
microtubule organizing center 1 NLRP3
Nucleus, nucleoplasm 1 NR3C1
tertiary granule membrane 1 GAA
lipopolysaccharide receptor complex 1 TLR4
secretory granule lumen 1 NFKB1
endoplasmic reticulum lumen 1 IL6
specific granule lumen 1 NFKB1
azurophil granule membrane 1 GAA
Secreted, extracellular exosome 1 IL1B
extrinsic component of cytoplasmic side of plasma membrane 1 MYD88
ficolin-1-rich granule membrane 1 GAA
basal dendrite 1 MAPK8
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
extrinsic component of plasma membrane 1 MYD88
[Isoform Alpha]: Cytoplasm 1 NR3C1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform Beta]: Nucleus 1 NR3C1
[Isoform Alpha-B]: Nucleus 1 NR3C1
interleukin-6 receptor complex 1 IL6
[Isoform Mitochondrial]: Mitochondrion 1 FH
[Isoform Cytoplasmic]: Cytoplasm, cytosol 1 FH
autolysosome lumen 1 GAA
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 1 NFKB1
NF-kappaB p50/p65 complex 1 NFKB1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yun-Xia Li, Lei Lv, Shao-Liang Li, Hai-Hua Qian. Gentianine alleviates dextran sulfate sodium-induced ulcerative colitis via inhibition of TLR4/NLRP3-mediated pyroptosis. International immunopharmacology. 2024 Jan; 126(?):111214. doi: 10.1016/j.intimp.2023.111214. [PMID: 37979455]
  • Na Wang, Yao Liu, Caixia Jia, Chengwen Gao, Ting Zheng, Mingxuan Wu, Qian Zhang, Xiangzhong Zhao, Zhiqiang Li, Jianxin Chen, Chuanhong Wu. Machine learning enables discovery of Gentianine targeting TLR4/NF-κB pathway to repair ischemic stroke injury. Pharmacological research. 2021 11; 173(?):105913. doi: 10.1016/j.phrs.2021.105913. [PMID: 34563661]
  • Rajani Kanta Mahapatra, Mahin Das. A computational approach to validate novel drug targets of gentianine from Swertiya chirayita in Plasmodium falciparum. Bio Systems. 2020 Oct; 196(?):104175. doi: 10.1016/j.biosystems.2020.104175. [PMID: 32593550]
  • Xiuhong Wu, Shuhan Tang, Yan Jin, Shanshan Wang, Xijun Wang, Masao Hattori, Hailong Zhang, Zhigang Wang. Determination of the metabolic profile of gentianine after oral administration to rats by high performance liquid chromatography/electrospray ionization-trap mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 May; 989(?):98-103. doi: 10.1016/j.jchromb.2015.01.007. [PMID: 25813903]
  • Hitesh Vaidya, Ramesh K Goyal, Sukhinder Kaur Cheema. Anti-diabetic activity of swertiamarin is due to an active metabolite, gentianine, that upregulates PPAR-γ gene expression in 3T3-L1 cells. Phytotherapy research : PTR. 2013 Apr; 27(4):624-7. doi: 10.1002/ptr.4763. [PMID: 22718571]
  • Shuang Li, Cheng-Wang Tian, Shuai Wu, Xiu-Wei Yang, Li-Li Wang, Tie-Jun Zhang. [Studies on metabolism of total terpene ketones from Swertia mussotii with human intestinal bacteria]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Dec; 37(24):3743-7. doi: . [PMID: 23627171]
  • Yosra Belaïd-Nouira, Hayfa Bakhta, Mohamed Bouaziz, Imen Flehi-Slim, Zohra Haouas, Hassen Ben Cheikh. Study of lipid profile and parieto-temporal lipid peroxidation in AlCl₃ mediated neurotoxicity. Modulatory effect of fenugreek seeds. Lipids in health and disease. 2012 Jan; 11(?):16. doi: 10.1186/1476-511x-11-16. [PMID: 22280491]
  • Zhi-Gang Wang, Xi-Jun Wang, Hui Sun, Li Chen, Chao-Mei Ma. Determination of novel nitrogen-containing metabolite after oral administration of swertiamarin to rats. Journal of Asian natural products research. 2012; 14(2):176-81. doi: 10.1080/10286020.2011.631132. [PMID: 22296159]
  • Yuelong Cao, Yinyu Shi, Yuxing Zheng, Meiyu Shi, Sing Kai Lo. Blood-nourishing and hard-softening capsule costs less in the management of osteoarthritic knee pain: a randomized controlled trial. Evidence-based complementary and alternative medicine : eCAM. 2005 Sep; 2(3):363-8. doi: 10.1093/ecam/neh104. [PMID: 16136214]
  • X F Yang, C Q Song. [Studies on the metabolism of gentiopicroside by rat intestinal flora]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2000 Nov; 25(11):673-6. doi: . [PMID: 12525070]
  • X H Wu, X Chen, S L Zhang, L Pang, C To, T T Wang, T C Hohman, J G Filep, J S Chan. Molecular mechanism(s) of insulin action on the expression of the angiotensinogen gene in kidney proximal tubular cells. Journal of the renin-angiotensin-aldosterone system : JRAAS. 2000 Jun; 1(2):166-74. doi: 10.3317/jraas.2000.021. [PMID: 11967809]
  • A Z Györy, D Lissner. Independence of ethacrynic acid-induced renal hydrogen ion excretion of sodium-volume depletion in man. Clinical science and molecular medicine. 1977 Aug; 53(2):125-32. doi: 10.1042/cs0530125. [PMID: 19190]