SMB00416

Gentiopicroside

≥98% (HPLC)

• Synonyme(s) : (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one, (5R,6S)-5-Ethenyl-6-(-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-Pyrano[3,4-c]pyran-1-one, (5R-trans)-5-ethenyl-6-(-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one, Gentiopicrin, NSC606402
• Formule empirique (notation de Hill) : C₁₆H₂₀O₉
• CAS Number: 20831-76-9
• Poids moléculaire : 356.32
• Numéro CE : 244-070-2
• Numéro MDL: MFCD00075700
• Code UNSPSC : 12352205
• ID de substance PubChem : 329825007
• Nomenclature NACRES : NA.25

Propriétés

• Source biologique: plant (Gentiana macrophylla Pall)
• Niveau de qualité: 200
• Essai: ≥98% (HPLC)
• Forme: powder
• Application(s): metabolomics; vitamins, nutraceuticals, and natural products
• Température de stockage: 2-8°C
• Chaîne SMILES: C=C[C@H]1[C@H](O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C3C(OCC=C31)=O
• InChI: 1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1
• Clé InChI: DUAGQYUORDTXOR-GPQRQXLASA-N

Description

Description générale

Gentiopicroside (GPS) is a secoiridoid glycoside sourced from the dried roots of Gentiana rigescens.

Application

Gentiopicroside has been used as a reference standard for the quantification of iridoid glycoside in six Caucasian Gentians herb samples using high-performance liquid chromatography with diode array detection (HPLC-DAD) technique.

Actions biochimiques/physiologiques

Gentiopicroside is a potent anti-arthritic agent. It displays hepatoprotective effects in arthritic rats by improving oxidative stress and reducing inflammation in combination with leflunomide and/or methotrexate by regulating mRNA genes and pro-inflammatory cytokines. It also displays its efficacy by inhibiting reactive oxygen species (ROS)-Nuclear factor-kappa B (NF-κB)-NOD-like receptor protein 3 (NLRP3) inflammasome axis in adjuvant-induced arthritis (AIA) in vitro and in vivo models. Gentiopicroside exerts antiaging properties in yeast prolonging lifespan and inducing mitophagy and reducing oxidative stress. It prevents osteoporosis by regulating β-catenin-BMPsignaling and promoting osteogenesis in vitro.

Gentiopicroside is an important active component of secoiridoid glycosides from Gentiana macrophylla Pall that exhibit anti-inflammatory, antibacterial and liver protecting activities. Gentiopicroside protects chondrocytes from IL-1β-induced inflammation response.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable