Fagomine (BioDeep_00000007906)

 

Secondary id: BioDeep_00000863413

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


3,4-Piperidinediol, 2-(hydroxymethyl)-, (2R,3R,4R)-

化学式: C6H13NO3 (147.0895)
中文名称: (2R,3R,4R)-2-羟甲基哌啶-3,4-二醇, 桑叶生物碱, 桑多酚, 荞麦碱
谱图信息: 最多检出来源 Homo sapiens(otcml) 6.21%

分子结构信息

SMILES: C1CNC(C(C1O)O)CO
InChI: InChI=1S/C6H13NO3/c8-3-4-6(10)5(9)1-2-7-4/h4-10H,1-3H2

描述信息

Fagomine is an alkaloid found in the seeds of Castanospermum australe (commonly known as the Black Bean or the Moreton Bay Chestnut) (PMID: 25583438). Castanospermum australe is a large evergreen tree of the legume family native to the east coast of Australia in Queensland and New South Wales, and to the Pacific islands of Vanuatu, New Caledonia, and the island of New Britain (Papua New Guinea). The seeds are poisonous, but become edible when carefully prepared by roasting, cutting up into small pieces, leaching with running water for several days, and pounding into flour (Wikipedia).
Fagomine is a member of piperidines.
Fagomine is a natural product found in Lycium chinense, Angylocalyx pynaertii, and other organisms with data available.
Alkaloid from buckwheat seeds (Fagopyrum esculentum). Fagomine is found in common buckwheat and cereals and cereal products.
Fagomine is a mild glycosidase inhibitor. The Ki of the iminosugar Fagomine is 4.8 μM, 39 μM, and 70 μM for Amyloglucosidase (A.niger), β-Glucosidase (bovine), and Isomaltase (yeast), respectively.
Fagomine is a mild glycosidase inhibitor. The Ki of the iminosugar Fagomine is 4.8 μM, 39 μM, and 70 μM for Amyloglucosidase (A.niger), β-Glucosidase (bovine), and Isomaltase (yeast), respectively.

同义名列表

20 个代谢物同义名

3,4-Piperidinediol, 2-(hydroxymethyl)-, (2R,3R,4R)-; (2R,3R,4R)-2-(Hydroxymethyl)-3,4-piperidinediol; (2r,3r,4r)-2-(hydroxymethyl)piperidine-3,4-diol; 2-(Hydroxymethyl)-(2R,3R,4R)-3,4-Piperidinediol; (2R,3R,4R)-2-Hydroxymethyl-piperidine-3,4-diol; (2r,3r,4r)-2-hydroxymethylpiperidine-3,4-diol; D-arabino-Hexitol, 1,2,5-trideoxy-1,5-imino-; 1,5-imino-1,2,5-trideoxy-D-arabino-hexitol; 1,2,5-Trideoxy-1,5-imino-D-arabino-hexitol; YZNNBIPIQWYLDM-HSUXUTPPSA-N; UNII-1M10C1P4SM; FAGOMINE, (+)-; FAGOMINE, (D)-; (D)-fagomine; 1M10C1P4SM; D-Fagomine; Fagomine; FAG; 2-hydroxymethylpiperidine-3,4-diol; Fagomine



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

61 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 5 MAPK14, MAPK8, PRKAA2, PYGB, SIRT1
Peripheral membrane protein 2 CYP1B1, GBA1
Endoplasmic reticulum membrane 1 CYP1B1
Nucleus 5 MAPK14, MAPK8, PPARGC1A, PRKAA2, SIRT1
cytosol 7 GPT, LEP, MAPK14, MAPK8, PPARGC1A, PRKAA2, SIRT1
dendrite 2 ADORA1, PRKAA2
trans-Golgi network 1 GBA1
nucleoplasm 5 MAPK14, MAPK8, PPARGC1A, PRKAA2, SIRT1
Cell membrane 3 ADORA1, TNF, TREH
Multi-pass membrane protein 1 ADORA1
Synapse 2 ADORA1, MAPK8
cell surface 2 ADIPOQ, TNF
glutamatergic synapse 2 GHRL, MAPK14
Golgi apparatus 2 GBA1, PRKAA2
Golgi membrane 1 INS
lysosomal membrane 2 GAA, GBA1
neuronal cell body 3 ADORA1, PRKAA2, TNF
postsynapse 1 GHRL
presynaptic membrane 1 ADORA1
Lysosome 2 GAA, GBA1
plasma membrane 5 ADORA1, GAA, GCG, TNF, TREH
presynaptic active zone 1 ADORA1
terminal bouton 1 ADORA1
Membrane 6 CYP1B1, GAA, LGALS3BP, PRKAA2, PYGB, TREH
axon 3 GHRL, MAPK8, PRKAA2
basolateral plasma membrane 1 ADORA1
extracellular exosome 6 GAA, GBA1, GPT, LGALS3BP, PYGB, TREH
Lysosome membrane 2 GAA, GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 2 ADIPOQ, GBA1
extracellular space 8 ADIPOQ, GCG, GHRL, IL6, INS, LEP, LGALS3BP, TNF
lysosomal lumen 2 GAA, GBA1
Schaffer collateral - CA1 synapse 1 GHRL
mitochondrion 3 CYP1B1, MAPK14, SIRT1
intracellular membrane-bounded organelle 2 CYP1B1, GAA
Microsome membrane 1 CYP1B1
chromatin silencing complex 1 SIRT1
Secreted 8 ADIPOQ, GAA, GCG, GHRL, IL6, INS, LEP, LGALS3BP
extracellular region 11 ADIPOQ, GAA, GCG, GHRL, IL6, INS, LEP, LGALS3BP, MAPK14, PYGB, TNF
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 1 LGALS3BP
dendritic spine 1 ADORA1
neuronal dense core vesicle lumen 1 GHRL
nucleolus 1 SIRT1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 ADORA1
heterochromatin 1 SIRT1
Membrane raft 1 TNF
axolemma 1 ADORA1
collagen trimer 1 ADIPOQ
Nucleus, PML body 2 PPARGC1A, SIRT1
PML body 2 PPARGC1A, SIRT1
collagen-containing extracellular matrix 2 ADIPOQ, LGALS3BP
nuclear speck 2 MAPK14, PRKAA2
nuclear inner membrane 1 SIRT1
chromatin 2 PPARGC1A, SIRT1
phagocytic cup 1 TNF
spindle pole 1 MAPK14
blood microparticle 1 LGALS3BP
Lipid-anchor, GPI-anchor 1 TREH
fibrillar center 1 SIRT1
nuclear envelope 1 SIRT1
endosome lumen 1 INS
tertiary granule membrane 1 GAA
cytoplasmic stress granule 1 PRKAA2
euchromatin 1 SIRT1
side of membrane 1 TREH
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 4 GCG, GHRL, INS, MAPK14
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 GCG, GHRL, IL6, INS
transport vesicle 1 INS
azurophil granule membrane 1 GAA
azurophil granule lumen 1 PYGB
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
calyx of Held 1 ADORA1
[Isoform 1]: Nucleus 1 PPARGC1A
ficolin-1-rich granule membrane 1 GAA
basal dendrite 1 MAPK8
eNoSc complex 1 SIRT1
rDNA heterochromatin 1 SIRT1
nucleotide-activated protein kinase complex 1 PRKAA2
[Glucagon-like peptide 1]: Secreted 1 GCG
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
platelet dense granule lumen 1 LGALS3BP
interleukin-6 receptor complex 1 IL6
asymmetric synapse 1 ADORA1
autolysosome lumen 1 GAA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[SirtT1 75 kDa fragment]: Cytoplasm 1 SIRT1
[Isoform B4]: Nucleus 1 PPARGC1A
[Isoform B4-8a]: Cytoplasm 1 PPARGC1A
[Isoform B5]: Nucleus 1 PPARGC1A
[Isoform 9]: Nucleus 1 PPARGC1A


文献列表

  • Isabella Supardi Parida, Soo Takasu, Kiyotaka Nakagawa. A comprehensive review on the production, pharmacokinetics and health benefits of mulberry leaf iminosugars: Main focus on 1-deoxynojirimycin, d-fagomine, and 2-O-ɑ-d-galactopyranosyl-DNJ. Critical reviews in food science and nutrition. 2021 Oct; ?(?):1-29. doi: 10.1080/10408398.2021.1989660. [PMID: 34658276]
  • Sara Ramos-Romero, Mercè Hereu, Lidia Atienza, Susana Amézqueta, Josefina Casas, Silvia Muñoz, Isabel Medina, Bernat Miralles-Pérez, Marta Romeu, Josep L Torres. The Buckwheat Iminosugar d-Fagomine Attenuates Sucrose-Induced Steatosis and Hypertension in Rats. Molecular nutrition & food research. 2020 01; 64(1):e1900564. doi: 10.1002/mnfr.201900564. [PMID: 31657510]
  • Mercè Hereu, Sara Ramos-Romero, Cristina Busquets, Lidia Atienza, Susana Amézqueta, Bernat Miralles-Pérez, Maria Rosa Nogués, Lucía Méndez, Isabel Medina, Josep Lluís Torres. Effects of combined D-fagomine and omega-3 PUFAs on gut microbiota subpopulations and diabetes risk factors in rats fed a high-fat diet. Scientific reports. 2019 11; 9(1):16628. doi: 10.1038/s41598-019-52678-5. [PMID: 31719544]
  • Mercè Hereu, Sara Ramos-Romero, Roser Marín-Valls, Susana Amézqueta, Bernat Miralles-Pérez, Marta Romeu, Lucía Méndez, Isabel Medina, Josep Lluís Torres. Combined Buckwheat d-Fagomine and Fish Omega-3 PUFAs Stabilize the Populations of Gut Prevotella and Bacteroides While Reducing Weight Gain in Rats. Nutrients. 2019 Oct; 11(11):. doi: 10.3390/nu11112606. [PMID: 31683529]
  • Liwen Zhang, Yongliang Bai, Shulan Su, Zhen Ouyang, Li Liu, Gang Pan, Dawei Qian, Jinao Duan. Metabolism, transformation and dynamic changes of alkaloids in silkworm during feeding mulberry leaves. Natural product research. 2019 Apr; 33(8):1182-1190. doi: 10.1080/14786419.2018.1465422. [PMID: 29862842]
  • Sara Ramos-Romero, Mercè Hereu, Lidia Atienza, Josefina Casas, Núria Taltavull, Marta Romeu, Susana Amézqueta, Gabriel Dasilva, Isabel Medina, Josep L Torres. Functional Effects of the Buckwheat Iminosugar d-Fagomine on Rats with Diet-Induced Prediabetes. Molecular nutrition & food research. 2018 08; 62(16):e1800373. doi: 10.1002/mnfr.201800373. [PMID: 29979820]
  • Weili Han, Xiangxiang Chen, Huimin Yu, Lingyun Chen, Mei Shen. Seasonal variations of iminosugars in mulberry leaves detected by hydrophilic interaction chromatography coupled with tandem mass spectrometry. Food chemistry. 2018 Jun; 251(?):110-114. doi: 10.1016/j.foodchem.2018.01.058. [PMID: 29426416]
  • Susana Amézqueta, Sara Ramos-Romero, Carolina Martínez-Guimet, Albert Moreno, Mercè Hereu, Josep Lluís Torres. Fate of d-Fagomine after Oral Administration to Rats. Journal of agricultural and food chemistry. 2017 Jun; 65(22):4414-4420. doi: 10.1021/acs.jafc.7b01026. [PMID: 28489364]
  • Eunice Molinar-Toribio, Jara Pérez-Jiménez, Sara Ramos-Romero, Livia Gómez, Núria Taltavull, Maria Rosa Nogués, Alberto Adeva, Olga Jáuregui, Jesús Joglar, Pere Clapés, Josep Lluís Torres. D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats. Food & function. 2015 Aug; 6(8):2614-9. doi: 10.1039/c5fo00591d. [PMID: 26130374]
  • Shuang Yang, Baolian Wang, Xuejun Xia, Xue Li, Renyun Wang, Li Sheng, Dan Li, Yuling Liu, Yan Li. Simultaneous quantification of three active alkaloids from a traditional Chinese medicine Ramulus Mori (Sangzhi) in rat plasma using liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2015 May; 109(?):177-83. doi: 10.1016/j.jpba.2015.02.019. [PMID: 25778928]
  • Fu-xiang Jiang, Qiao-zhen Liu, Dan Zhao, Cui-ting Luo, Cui-ping Guo, Wen-cai Ye, Cheng Luo, Heru Chen. A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition. European journal of medicinal chemistry. 2014 Apr; 77(?):211-22. doi: 10.1016/j.ejmech.2014.03.004. [PMID: 24642564]
  • Sara Ramos-Romero, Eunice Molinar-Toribio, Livia Gómez, Jara Pérez-Jiménez, Marta Casado, Pere Clapés, Benjamín Piña, Josep Lluís Torres. Effect of (D)-fagomine on excreted Enterobacteria and weight gain in rats fed a high-fat high-sucrose diet. Obesity (Silver Spring, Md.). 2014 Apr; 22(4):976-9. doi: 10.1002/oby.20640. [PMID: 24124117]
  • Livia Gómez, Eunice Molinar-Toribio, María Ángeles Calvo-Torras, Carles Adelantado, M Emília Juan, Joana M Planas, Xavier Cañas, Carles Lozano, Sergio Pumarola, Pere Clapés, Josep Lluís Torres. D-Fagomine lowers postprandial blood glucose and modulates bacterial adhesion. The British journal of nutrition. 2012 Jun; 107(12):1739-46. doi: 10.1017/s0007114511005009. [PMID: 22017795]
  • Susana Amézqueta, Esther Galán, Elisabet Fuguet, Montserrat Carrascal, Joaquín Abián, Josep Lluís Torres. Determination of D-fagomine in buckwheat and mulberry by cation exchange HPLC/ESI-Q-MS. Analytical and bioanalytical chemistry. 2012 Feb; 402(5):1953-60. doi: 10.1007/s00216-011-5639-2. [PMID: 22207282]
  • Bin Liu. [Study on chemical constituents of Peganum multisectum]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Nov; 34(11):1719-21. doi: . [PMID: 22506396]
  • Kiyotaka Nakagawa, Kenta Ogawa, Ohki Higuchi, Toshiyuki Kimura, Teruo Miyazawa, Masatoshi Hori. Determination of iminosugars in mulberry leaves and silkworms using hydrophilic interaction chromatography-tandem mass spectrometry. Analytical biochemistry. 2010 Sep; 404(2):217-22. doi: 10.1016/j.ab.2010.05.007. [PMID: 20470744]
  • Anna Golisz, Mami Sugano, Yoshiharu Fujii. Microarray expression profiling of Arabidopsis thaliana L. in response to allelochemicals identified in buckwheat. Journal of experimental botany. 2008; 59(11):3099-109. doi: 10.1093/jxb/ern168. [PMID: 18603616]
  • Guang-xiong Zhou, Jie-wu Ruan, Mei-yan Huang, Wen-cai Ye, Ye-wei He. [Alkaloid constituents from silkworm dropping of Bombyx mori]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Nov; 30(11):1384-5. doi: ". [PMID: 18323202]
  • Wei-li Han, Li Liu, Xiao-qi Zhang, Wen-cai Ye, Yi-le Pan, Xin-sheng Yao. [Chemical constituents from leaves of Morus multicaulis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Apr; 32(8):695-8. doi: . [PMID: 17608222]
  • H Nojima, I Kimura, F J Chen, Y Sugihara, M Haruno, A Kato, N Asano. Antihyperglycemic effects of N-containing sugars from Xanthocercis zambesiaca, Morus bombycis, Aglaonema treubii, and Castanospermum australe in streptozotocin-diabetic mice. Journal of natural products. 1998 Mar; 61(3):397-400. doi: 10.1021/np970277l. [PMID: 9544568]
  • N Asano, K Oseki, H Kizu, K Matsui. Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases. Journal of medicinal chemistry. 1994 Oct; 37(22):3701-6. doi: 10.1021/jm00048a006. [PMID: 7966130]
  • G W Fleet, A Karpas, R A Dwek, L E Fellows, A S Tyms, S Petursson, S K Namgoong, N G Ramsden, P W Smith, J C Son. Inhibition of HIV replication by amino-sugar derivatives. FEBS letters. 1988 Sep; 237(1-2):128-32. doi: 10.1016/0014-5793(88)80185-6. [PMID: 3169233]