MiMeDB: Showing metabocard for Melibiose (MMDBc0000014)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:24:48 UTC

Update Date

2024-04-30 19:30:51 UTC

Metabolite ID

MMDBc0000014

Metabolite Identification

Common Name

Melibiose

Description

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 Œ≤-D-glucose and Œ≤-D-galactose by the Œ±-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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₁₂H₂₂O₁₁

Average Mass

342.2965

Monoisotopic Mass

342.116211546

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

13299-20-2

SMILES

Not Available

InChI Identifier

InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11+,12+/m1/s1

InChI Key

DLRVVLDZNNYCBX-CQHUIXDMSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Spleen
Urine

Tissue Locations

Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192361	Alpha-galactosidase A	Enzyme	P06280	Homo sapiens
MMDBp0193796	Maltase-glucoamylase, intestinal	Enzyme	O43451	Homo sapiens
MMDBp0194024	Neutral alpha-glucosidase C	Enzyme	Q8TET4	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	64	Human ; Human mucosa; Human supragingival plaque; Human saliva; Human subgingival plaque; Human feces; Human urine; Human sputum; Human stool; Human vaginal fluid	Microbial culture
Bacteria	Bacteroidetes	12	Human saliva; Human stool; Human feces; Human ; Human subgingival plaque	Microbial culture
Bacteria	Proteobacteria	6	Human ; Human feces; Human sputum; Human subgingival plaque	Microbial culture
Bacteria	Deinococcus-thermus	2		Microbial culture
Bacteria	Actinobacteria	2		Microbial culture
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food			FooDB	Ann R. Spevacek, Katy H. Benson, Charles W. Bamforth and Carolyn M. Slupsky. Beer metabolomics: molecular details of the brewing process and the differential effects of late and dry hopping on yeast purine metabolism. J. Inst. Brew. 2016; 122: 21-28
Food			FooDB	Ann R. Spevacek, Katy H. Benson, Charles W. Bamforth and Carolyn M. Slupsky. Beer metabolomics: molecular details of the brewing process and the differential effects of late and dry hopping on yeast purine metabolism. J. Inst. Brew. 2016; 122: 21-28

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	< 0.1	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	10585631
Human Urine	Detected but not Quantified			Adult (>18 years old)	Both	Bladder cancer	HMDB	28157703
Human Urine	Detected and Quantified	< 0.1	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	10585631
Human Spleen	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified						HMDB

External Links

Not Available

References

Synthesis Reference

Not Available

General References

Almeida IC, Milani SR, Gorin PA, Travassos LR: Complement-mediated lysis of Trypanosoma cruzi trypomastigotes by human anti-alpha-galactosyl antibodies. J Immunol. 1991 Apr 1;146(7):2394-400. [PubMed:1706399 ]
Sharma A, Ahmed H, Allen HJ: Isolation of a melibiose-binding protein from human spleen. Glycoconj J. 1995 Feb;12(1):17-21. doi: 10.1007/BF00731864. [PubMed:7795409 ]
Steuer MK, Steuer M, Bonkowsky V, Gabius HJ, Hofstadter F: Characterization of sugar receptor expression by neoglycoproteins in oral and oropharyngeal squamous cell carcinomas. Eur Arch Otorhinolaryngol. 1995;252(5):292-7. doi: 10.1007/BF00185392. [PubMed:7576587 ]
Vaughan HA, Loveland BE, Sandrin MS: Gal alpha(1,3)Gal is the major xenoepitope expressed on pig endothelial cells recognized by naturally occurring cytotoxic human antibodies. Transplantation. 1994 Oct 27;58(8):879-82. doi: 10.1097/00007890-199410270-00003. [PubMed:7524207 ]
Barboza Junior MS, Silva TM, Guerrant RL, Lima AA: Measurement of intestinal permeability using mannitol and lactulose in children with diarrheal diseases. Braz J Med Biol Res. 1999 Dec;32(12):1499-504. doi: 10.1590/s0100-879x1999001200008. [PubMed:10585631 ]
Furukawa K, Ying R, Nakajima T, Matsuki T: Hemagglutinins in fungus extracts and their blood group specificity. Exp Clin Immunogenet. 1995;12(4):223-31. [PubMed:8919354 ]
Gibbons RJ, Qureshi JV: Inhibition of adsorption of Streptococcus mutans strains to saliva-treated hydroxyapatite by galactose and certain amines. Infect Immun. 1979 Dec;26(3):1214-7. doi: 10.1128/iai.26.3.1214-1217.1979. [PubMed:528053 ]
Nicolopoulou A, Zoumbou K, Papageorgacopoulou N, Papapetropoulou M: Metabolic and compositional changes in Escherichia coli cells starved in seawater. Microbiol Res. 1994 Nov;149(4):343-50. doi: 10.1016/S0944-5013(11)80082-0. [PubMed:7842233 ]
Wu AM, Song SC, Chen YY, Gilboa-Garber N: Defining the carbohydrate specificities of aplysia gonad lectin exhibiting a peculiar D-galacturonic acid affinity. J Biol Chem. 2000 May 12;275(19):14017-24. doi: 10.1074/jbc.275.19.14017. [PubMed:10799474 ]
Rietra PJ, Van den Bergh FA, Tager JM: Properties of the residual alpha-galactosidase activity in the tissues of a Fabry hemizygote. Clin Chim Acta. 1975 Aug 4;62(3):401-13. doi: 10.1016/0009-8981(75)90092-3. [PubMed:809216 ]
Colby SM, Harrington DJ, Russell RR: Identification and genetic characterisation of melibiose-negative isolates of Streptococcus mutans. Caries Res. 1995;29(5):407-12. doi: 10.1159/000262100. [PubMed:8521444 ]
Tomita K, Nagura T, Okuhara Y, Nakajima-Adachi H, Shigematsu N, Aritsuka T, Kaminogawa S, Hachimura S: Dietary melibiose regulates th cell response and enhances the induction of oral tolerance. Biosci Biotechnol Biochem. 2007 Nov;71(11):2774-80. doi: 10.1271/bbb.70372. Epub 2007 Nov 7. [PubMed:17986780 ]
Hugouvieux-Cotte-Pattat N, Charaoui-Boukerzaza S: Catabolism of raffinose, sucrose, and melibiose in Erwinia chrysanthemi 3937. J Bacteriol. 2009 Nov;191(22):6960-7. doi: 10.1128/JB.00594-09. Epub 2009 Sep 4. [PubMed:19734309 ]
Xu W, Yu S, Liu Q, Zhang T, Jiang B, Mu W: Enzymatic Production of Melibiose from Raffinose by the Levansucrase from Leuconostoc mesenteroides B-512 FMC. J Agric Food Chem. 2017 May 17;65(19):3910-3918. doi: 10.1021/acs.jafc.7b01265. Epub 2017 May 5. [PubMed:28453942 ]

Showing metabocard for Melibiose (MMDBc0000014)

MOL for #<Metabolite:0x00007fdb70375598>

3D MOL for #<Metabolite:0x00007fdb70375598>

3D SDF for #<Metabolite:0x00007fdb70375598>

3D-SDF for #<Metabolite:0x00007fdb70375598>

PDB for #<Metabolite:0x00007fdb70375598>

3D PDB for #<Metabolite:0x00007fdb70375598>

SMILES for #<Metabolite:0x00007fdb70375598>

INCHI for #<Metabolite:0x00007fdb70375598>

Structure for #<Metabolite:0x00007fdb70375598>

3D Structure for #<Metabolite:0x00007fdb70375598>