Melibiose (BioDeep_00000003232)

Main id: BioDeep_00000015333

Secondary id: BioDeep_00001868471

natural product human metabolite PANOMIX_OTCML-2023 BioNovoGene_Lab2019


代谢物信息卡片


(2S,3R,4S,5S,6R)-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol

化学式: C12H22O11 (342.1162)
中文名称: 聚葡萄糖, 异麦芽糖, 蜜二糖, 异麦芽糖(麦芽糖)
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(C1C(C(C(C(O1)OCC2C(C(C(C(O2)O)O)O)O)O)O)O)O
InChI: InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9

描述信息

Melibiose (CAS: 585-99-9) is a disaccharide consisting of one galactose and one glucose moiety in an alpha (1-6) glycosidic linkage. This sugar is produced and metabolized only by enteric and lactic acid bacteria and other microbes, such as Dickeya dadantii, Escherichia, Leuconostoc, and Saccharomyces (PMID: 19734309, 28453942). It is not an endogenous metabolite but may be obtained from the consumption of partially fermented molasses, brown sugar, or honey. Antibodies to melibiose will appear in individuals affected by Chagas disease (Trypanosoma cruzi infection). Melibiose is not metabolized by humans but can be broken down by gut microflora, such as E. coli. In fact, E. coli is able to utilize melibiose as a sole source of carbon. Melibiose is first imported by the melibiose permease, MelB and then converted into β-D-glucose and β-D-galactose by the α-galactosidase encoded by melA. Because of its poor digestibility, melibiose (along with rhamnose) can be used together for noninvasive intestinal mucosa barrier testing. This test can be used to assess malabsorption or impairment of intestinal permeability. Recent studies with dietary melibiose have shown that it can strongly affect the Th cell responses to an ingested antigen. It has been suggested that melibiose could be used to enhance the induction of oral tolerance (PMID: 17986780).
Isomaltose is composed of two glucose units and suitable as a non-cariogenic sucrose replacement and is favorable in products for diabetics and prediabetic dispositions.
Isomaltose is composed of two glucose units and suitable as a non-cariogenic sucrose replacement and is favorable in products for diabetics and prediabetic dispositions.

同义名列表

20 个代谢物同义名

(2S,3R,4S,5S,6R)-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol; 6-O-alpha-D-Galactopyranosyl-alpha-D-glucopyranose; 6-O-Α-D-galactopyranosyl-α-D-glucopyranose; 6-O-alpha-D-Galactopyranosyl-D-glucose; 6-O-Α-D-galactopyranosyl-D-glucose; alpha-D-Melibiose; alpha-Melibiose; D-(+)-Melibiose; Α-D-melibiose; Polydextrose; Α-melibiose; D-Melibiose; ISOMALTOSE; Melibiose; Brachiose; Melibiose; 6-O-α-D-Glucopyranosyl-D-glucose; D-Isomaltose; Isomaltose; Isomaltose



数据库引用编号

33 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(7)

BioCyc(0)

PlantCyc(1)

代谢反应

42 个相关的代谢反应过程信息。

Reactome(39)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(3)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

17 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 4 CAT, GLA, ODC1, SLC9A1
Peripheral membrane protein 1 GBA1
Endoplasmic reticulum membrane 1 GLA
cytosol 4 AGXT, CAT, MB, ODC1
trans-Golgi network 1 GBA1
nucleoplasm 3 ATP2B1, CD2, SLC9A1
Cell membrane 4 ATP2B1, CD2, SLC9A1, TREH
lamellipodium 1 SLC9A1
Multi-pass membrane protein 2 ATP2B1, SLC9A1
Synapse 1 ATP2B1
cell surface 2 CD2, SLC9A1
glutamatergic synapse 1 ATP2B1
Golgi apparatus 4 CD2, GBA1, GLA, SI
lysosomal membrane 2 GAA, GBA1
mitochondrial inner membrane 1 GATM
presynaptic membrane 1 ATP2B1
Lysosome 3 GAA, GBA1, GLA
plasma membrane 7 ATP2B1, CD2, GAA, LCT, SI, SLC9A1, TREH
synaptic vesicle membrane 1 ATP2B1
Membrane 7 ATP2B1, CAT, GAA, GLA, SI, SLC9A1, TREH
apical plasma membrane 2 SI, SLC9A1
basolateral plasma membrane 2 ATP2B1, SLC9A1
brush border 1 SI
extracellular exosome 12 AMY2A, ATP2B1, CAT, GAA, GATM, GBA1, GLA, LYZ, MB, SI, SLC9A1, TREH
Lysosome membrane 2 GAA, GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 1 GBA1
extracellular space 4 AMY2A, CSF3, LYZ, TG
lysosomal lumen 4 CSF3, GAA, GBA1, GLA
perinuclear region of cytoplasm 1 SLC9A1
intercalated disc 1 SLC9A1
mitochondrion 3 CAT, GATM, SLC9A1
protein-containing complex 2 CAT, CD2
intracellular membrane-bounded organelle 4 AGXT, ATP2B1, CAT, GAA
Single-pass type I membrane protein 2 CD2, LCT
Secreted 3 CSF3, GAA, TG
extracellular region 9 AMY2A, CAT, CD2, CSF3, ELN, GAA, GLA, LYZ, TG
cytoplasmic side of plasma membrane 1 CD2
mitochondrial matrix 1 CAT
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
external side of plasma membrane 1 CD2
Secreted, extracellular space, extracellular matrix 1 ELN
T-tubule 1 SLC9A1
sarcoplasm 1 MB
cell-cell junction 1 CD2
Apical cell membrane 1 LCT
Mitochondrion inner membrane 1 GATM
Membrane raft 1 SLC9A1
focal adhesion 2 CAT, SLC9A1
extracellular matrix 1 ELN
Peroxisome 2 AGXT, CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 2 AGXT, CAT
peroxisomal membrane 1 CAT
mitochondrial intermembrane space 1 GATM
collagen-containing extracellular matrix 1 ELN
lateral plasma membrane 1 ATP2B1
cell projection 1 ATP2B1
Basolateral cell membrane 2 ATP2B1, SLC9A1
Lipid-anchor, GPI-anchor 1 TREH
tertiary granule membrane 1 GAA
Presynaptic cell membrane 1 ATP2B1
side of membrane 1 TREH
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
specific granule lumen 1 LYZ
tertiary granule lumen 1 LYZ
azurophil granule membrane 1 GAA
azurophil granule lumen 2 GLA, LYZ
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GLA
immunological synapse 1 ATP2B1
endoplasmic reticulum-Golgi intermediate compartment 1 GLA
ficolin-1-rich granule membrane 1 GAA
external side of apical plasma membrane 1 LCT
elastic fiber 1 ELN
endocytic vesicle lumen 1 CSF3
Cytoplasm, sarcoplasm 1 MB
catalase complex 1 CAT
autolysosome lumen 1 GAA
photoreceptor ribbon synapse 1 ATP2B1
cation-transporting ATPase complex 1 SLC9A1


文献列表

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  • Lianyu Zhou, Lu Jiao, Jiasheng Ju, Xuelan Ma. Effect of Sodium Selenite on the Metabolite Profile of Epichloë sp. Mycelia from Festuca sinensis in Solid Culture. Biological trace element research. 2022 Nov; 200(11):4865-4879. doi: 10.1007/s12011-021-03054-w. [PMID: 34973128]
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  • Huimin Jia, Junjie Tao, Wenqi Zhong, Xudong Jiao, Shuangshuang Chen, Mengting Wu, Zhongshan Gao, Chunhui Huang. Nutritional Component Analyses in Different Varieties of Actinidia eriantha Kiwifruit by Transcriptomic and Metabolomic Approaches. International journal of molecular sciences. 2022 Sep; 23(18):. doi: 10.3390/ijms231810217. [PMID: 36142128]
  • Misato Ota, Toshiaki Makino. History and the immunostimulatory effects of heat-processed licorice root products with or without honey. Journal of ethnopharmacology. 2022 Jun; 292(?):115108. doi: 10.1016/j.jep.2022.115108. [PMID: 35189279]
  • Eri Kokubo, Shunsuke Morita, Hirotaka Nagashima, Kazutaka Oshio, Hiroshi Iwamoto, Kazuhiro Miyaji. Blood Glucose Response of a Low-Carbohydrate Oral Nutritional Supplement with Isomaltulose and Soluble Dietary Fiber in Individuals with Prediabetes: A Randomized, Single-Blind Crossover Trial. Nutrients. 2022 Jun; 14(12):. doi: 10.3390/nu14122386. [PMID: 35745116]
  • Tatsuro Amano, Daichi Watanabe, Junto Otsuka, Yumi Okamoto, Shota Takada, Naoto Fujii, Glen P Kenny, Yasuaki Enoki, Daisuke Maejima. Comparison of hydration efficacy of carbohydrate-electrolytes beverages consisting of isomaltulose and sucrose in healthy young adults: A randomized crossover trial. Physiology & behavior. 2022 05; 249(?):113770. doi: 10.1016/j.physbeh.2022.113770. [PMID: 35247444]
  • Kinga Gostomska-Pampuch, Andrzej Gamian, Karol Rawicz-Pruszyński, Katarzyna Gęca, Joanna Tkaczuk-Włach, Ilona Jonik, Kinga Ożga, Magdalena Staniszewska. Proteins in human body fluids contain in vivo antigen analog of the melibiose-derived glycation product: MAGE. Scientific reports. 2022 05; 12(1):7520. doi: 10.1038/s41598-022-11638-2. [PMID: 35525899]
  • Ryota Kobayashi, Miki Sakazaki, Yukie Nagai, Kenji Asaki, Takeo Hashiguchi, Hideyuki Negoro. Effects of Different Types of Carbohydrates on Arterial Stiffness: A Comparison of Isomaltulose and Sucrose. Nutrients. 2021 Dec; 13(12):. doi: 10.3390/nu13124493. [PMID: 34960045]
  • Tatsuro Amano, Shingo Katayama, Yumi Okamoto, Junto Otsuka, Naoto Fujii, Glen P Kenny, Takeshi Nishiyasu, Yasuaki Enoki, Daisuke Maejima. Comparisons of isomaltulose, sucrose, and mixture of glucose and fructose ingestions on postexercise hydration state in young men. European journal of nutrition. 2021 Dec; 60(8):4519-4529. doi: 10.1007/s00394-021-02614-z. [PMID: 34129073]
  • Junto Otsuka, Yumi Okamoto, Naoto Fujii, Yasuaki Enoki, Daisuke Maejima, Takeshi Nishiyasu, Tatsuro Amano. Effects of Isomaltulose Ingestion on Thermoregulatory Responses during Exercise in a Hot Environment. International journal of environmental research and public health. 2021 05; 18(11):. doi: 10.3390/ijerph18115760. [PMID: 34072006]
  • Magdalena Staniszewska, Agnieszka Bronowicka-Szydełko, Kinga Gostomska-Pampuch, Jerzy Szkudlarek, Arkadiusz Bartyś, Tadeusz Bieg, Elżbieta Gamian, Agata Kochman, Bolesław Picur, Jadwiga Pietkiewicz, Piotr Kuropka, Wiesław Szeja, Jerzy Wiśniewski, Piotr Ziółkowski, Andrzej Gamian. The melibiose-derived glycation product mimics a unique epitope present in human and animal tissues. Scientific reports. 2021 02; 11(1):2940. doi: 10.1038/s41598-021-82585-7. [PMID: 33536563]
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  • Tatsuro Amano, Yuki Sugiyama, Junya Okumura, Naoto Fujii, Glen P Kenny, Takeshi Nishiyasu, Yoshimitsu Inoue, Narihiko Kondo, Katsumi Sasagawa, Yasuaki Enoki, Daisuke Maejima. Effects of isomaltulose ingestion on postexercise hydration state and heat loss responses in young men. Experimental physiology. 2019 10; 104(10):1494-1504. doi: 10.1113/ep087843. [PMID: 31400765]
  • Kambiz Morabbi Heravi, Hildegard Watzlawick, Josef Altenbuchner. The melREDCA Operon Encodes a Utilization System for the Raffinose Family of Oligosaccharides in Bacillus subtilis. Journal of bacteriology. 2019 08; 201(15):. doi: 10.1128/jb.00109-19. [PMID: 31138628]
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  • Zhi-Peng Wang, Qin-Qing Wang, Song Liu, Xiao-Fang Liu, Xin-Jun Yu, Yun-Lin Jiang. Efficient Conversion of Cane Molasses Towards High-Purity Isomaltulose and Cellular Lipid Using an Engineered Yarrowia lipolytica Strain in Fed-Batch Fermentation. Molecules (Basel, Switzerland). 2019 Mar; 24(7):. doi: 10.3390/molecules24071228. [PMID: 30925836]
  • Dahyun Hwang, Hye-Ryung Park, Sue Jung Lee, Han Wool Kim, Jae Hwan Kim, Kwang-Soon Shin. Oral administration of palatinose vs sucrose improves hyperglycemia in normal C57BL/6J mice. Nutrition research (New York, N.Y.). 2018 11; 59(?):44-52. doi: 10.1016/j.nutres.2018.06.010. [PMID: 30442232]
  • Fiona E Kendall, Olivia Marchand, Jillian J Haszard, Bernard J Venn. The Comparative Effect on Satiety and Subsequent Energy Intake of Ingesting Sucrose or Isomaltulose Sweetened Trifle: A Randomized Crossover Trial. Nutrients. 2018 Oct; 10(10):. doi: 10.3390/nu10101504. [PMID: 30326587]
  • Parameswaran Hariharan, Elena Tikhonova, João Medeiros-Silva, Aike Jeucken, Mikhail V Bogdanov, William Dowhan, Jos F Brouwers, Markus Weingarth, Lan Guan. Structural and functional characterization of protein-lipid interactions of the Salmonella typhimurium melibiose transporter MelB. BMC biology. 2018 08; 16(1):85. doi: 10.1186/s12915-018-0553-0. [PMID: 30075778]
  • Takumi Kawaguchi, Dan Nakano, Tetsuharu Oriishi, Takuji Torimura. Effects of isomaltulose on insulin resistance and metabolites in patients with non‑alcoholic fatty liver disease: A metabolomic analysis. Molecular medicine reports. 2018 Aug; 18(2):2033-2042. doi: 10.3892/mmr.2018.9223. [PMID: 29956790]
  • Kaarel Adamberg, Signe Adamberg, Karin Ernits, Anneli Larionova, Tiia Voor, Madis Jaagura, Triinu Visnapuu, Tiina Alamäe. Composition and metabolism of fecal microbiota from normal and overweight children are differentially affected by melibiose, raffinose and raffinose-derived fructans. Anaerobe. 2018 Aug; 52(?):100-110. doi: 10.1016/j.anaerobe.2018.06.009. [PMID: 29935270]
  • Emma J Stevenson, Anthony Watson, Stephan Theis, Anja Holz, Liam D Harper, Mark Russell. A comparison of isomaltulose versus maltodextrin ingestion during soccer-specific exercise. European journal of applied physiology. 2017 Nov; 117(11):2321-2333. doi: 10.1007/s00421-017-3719-5. [PMID: 28929343]
  • Passakorn Suraphad, Phim On Suklaew, Sathaporn Ngamukote, Sirichai Adisakwattana, Kittana Mäkynen. The Effect of Isomaltulose Together with Green Tea on Glycemic Response and Antioxidant Capacity: A Single-Blind, Crossover Study in Healthy Subjects. Nutrients. 2017 May; 9(5):. doi: 10.3390/nu9050464. [PMID: 28481230]
  • Seiya Tanaka, Aki Shinoki, Hiroshi Hara. Melibiose, a Nondigestible Disaccharide, Promotes Absorption of Quercetin Glycosides in Rat Small Intestine. Journal of agricultural and food chemistry. 2016 Dec; 64(49):9335-9341. doi: 10.1021/acs.jafc.6b03714. [PMID: 27794607]
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