Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C12H16O6 |
| Molecular Weight | 256.2518 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@@H](OC2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI
InChIKey=NEZJDVYDSZTRFS-RMPHRYRLSA-N
InChI=1S/C12H16O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9-,10+,11-,12-/m1/s1
| Molecular Formula | C12H16O6 |
| Molecular Weight | 256.2518 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Phenyl-β-D-glucopyranoside is a component of Phellodendron amurense. It was discovered, that phenyl-β-D-glucopyranoside might be beneficial for the prevention and treatment of anti-inflammatory diseases, due to its inhibition of the nuclear translocation of nuclear factor-κB (NF-κB), which is one of the most important transcription factors involved in the inflammatory process. In addition, Phenyl-β-D-glucopyranoside attenuated proinflammatory cytokines, including tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), IL-6 in a concentration-dependent manner. Furthermore, phenyl-β-D-glucopyranoside abolished increased adhesion, ninjurin 1 (Ninj1) expression, and matrix metalloproteinase (MMP) activity induced by endotoxin treatment.
Approval Year
Sample Use Guides
In Vitro Use Guide
Curator's Comment: Phenyl-β-D-glucopyranoside not only inhibited nitric oxide (NO) production but also significantly inhibited the expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) without inducing cytotoxicity. Phenyl-β-D-glucopyranoside also attenuated proinflammatory cytokines, including tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β) and other inflammation-related genes, such as IL-6 in a concentration-dependent manner. Furthermore, phenyl-β-D-glucopyranoside abolished increased adhesion, ninjurin 1 (Ninj1) expression, and matrix metalloproteinase (MMP) activity induced by endotoxin treatment. Finally, phenyl-β-D-glucopyranoside inhibited the nuclear translocation of nuclear factor-κB (NF-κB), which is one of the most important transcription factors involved in the inflammatory process.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:59:56 GMT 2025
by
admin
on
Mon Mar 31 18:59:56 GMT 2025
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| Record UNII |
4W3PGI3766
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID40883677
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215-978-6
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1464-44-4
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65080
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4W3PGI3766
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admin on Mon Mar 31 18:59:56 GMT 2025 , Edited by admin on Mon Mar 31 18:59:56 GMT 2025
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PRIMARY |