| Identification | Back Directory | [Name]
B-D-GLUCOPYRANOSE | [CAS]
60976-49-0 | [Synonyms]
eraniin
7:4®
GERANIIN
B-D-GLUCOPYRANOSE
b-D-Glucopyranose, cyclic 2®
5-(3,6-dihydro-2,9,10,11,11-pentahydroxy-3-oxo-2,6-Methano-2H-1-benzoxocin-5,7-dicarboxylate)cyclic 3,6-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate)1-(3,4,5-trihydroxybenzoate), stereoisoMer
β-D-Glucopyranose, cyclic 2→7:4→5-(3,6-dihydro-2,9,10,11,11-pentahydroxy-3-oxo-2,6-methano-2H-1-benzoxocin-5,7-dicarboxylate) cyclic 3,6-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate) 1-(3,4,5-trihydroxybenzoate), stereoisomer
beta-D-Glucopyranose cyclic 2-7:4-5-(3,6-dihydro-2,9,10,11,11-pentahydroxy-3-oxo-2,6-methano-2H-1-benzoxocin-5,7-dicarboxylate) cyclic 3,6-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate) 1-(3,4,5-trihydroxybenzoate) stereoisomer
3,4,4,6,7,15,16,17,18,19,20-undecahydroxy-2,9,13,22,27-pentaoxo-2,3,4,4a,9,11a,13,22,24,25,25a,27-dodecahydro-11H-3,5-epoxy-25,11-(epoxymethano)dibenzo[h,j]dibenzo[7,8:9,10][1,5]dioxacycloundecino[3,2-b][1,6]dioxacyclododecin-29-yl 3,4,5-trihydroxybenzoat | [Molecular Formula]
C6H12O6 | [MDL Number]
MFCD09038731 | [MOL File]
60976-49-0.mol | [Molecular Weight]
180.156 |
| Chemical Properties | Back Directory | [density ]
2.25 | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
DMSO : 100 mg/mL (104.97 mM; Need ultrasonic) | [form ]
powder | [pka]
6.35±0.70(Predicted) | [color ]
Light yellow | [Major Application]
food and beverages | [InChIKey]
JQQBXPCJFAKSPG-JAEVIPNINA-N | [SMILES]
O1[C@@]2(C([C@@H]3c4c1c(c(cc4C(=O)OC5C6OC(=O)c7c(c(c(c(c7)O)O)O)c8c(cc(c(c8O)O)O)C(=O)OCC(OC5OC(=O)c9cc(c(c(c9)O)O)O)C6OC(=O)C3=CC2=O)O)O)(O)O)O |
| Hazard Information | Back Directory | [Description]
Geraniin is a tannin that has been found in P. urinaria and has diverse biological activities.1,2,3 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; IC50s = 0.92 and 1.27 μM at pH 4.5 and 7.9, respectively), superoxide (IC50 = 2.65 μM), and hydroxyl radicals (IC50 = 1.44 μM) in cell-free assays.1 Geraniin inhibits herpes simplex virus 1 (HSV-1) and HSV-2 replication in plaque reduction assays (IC50s = 35 and 18.4 μM, respectively).2 It inhibits angiotensin-converting enzyme (ACE) in vitro (IC50 = 13.22 μM) and reduces both systolic and diastolic blood pressure in spontaneously hypertensive rats when administered at a dose of 5 mg/kg.1 Geraniin (5, 10, and 20 μM) induces apoptosis and halts the cell cycle at the S phase in A549 lung cancer cells.3 It reduces tumor growth in an A549 mouse xenograft model when administered at doses of 10 and 20 mg/kg. | [Chemical Properties]
It is a white powder, soluble in organic solvents such as methanol, ethanol, and DMSO. It comes from the whole herb of Phyllanthus urinaria L., a plant of the Euphorbiaceae family. | [Uses]
Geraniin protects PC12 cells against neuronal damage and may be used in the treatment of Alzheimer’s disease/ Also is an ACE inhibitor which is useful for hypertension treatment. | [Definition]
ChEBI: Geraniin is a tannin. | [in vivo]
Treatment with Geraniin prior to application of okadaic acid delays development of tumors compared with control group, reduces the percentage of tumor bearing mice from 80.0% to 40.0%, and reduces the average numbers of tumor per mouse from 3.8 to 1.1 in week 20. It is also showed that oral administration of Geraniin to rats (50 mg/kg/d or 100 mg/kg/d) inhibit the elevation of serum total cholesterol, lipid peroxide, free fatty acid, triglyceride, glutamic oxaloacetic transaminase and glutamic pyruvic transaminase induced by treatment with peroxidized oil[1]. | [References]
[1] SHYR-YI LIN . Antioxidant, anti-semicarbazide-sensitive amine oxidase, and anti-hypertensive activities of geraniin isolated from Phyllanthus urinaria[J]. Food and Chemical Toxicology, 2008, 46 7: Pages 2485-2492. DOI: 10.1016/j.fct.2008.04.007
[2] CHIEN-MIN YANG . The in vitro activity of geraniin and 1,3,4,6-tetra-O-galloyl-β-d-glucose isolated from Phyllanthus urinaria against herpes simplex virus type 1 and type 2 infection[J]. Journal of ethnopharmacology, 2007, 110 3: Pages 555-558. DOI: 10.1016/j.jep.2006.09.039
[3] JIA LI. Geraniin induces apoptotic cell death in human lung adenocarcinoma A549 cells in vitro and in vivo.[J]. Canadian journal of physiology and pharmacology, 2013, 91 12: 1016-1024. DOI: 10.1139/cjpp-2013-0140 |
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