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SMB00416

Sigma-Aldrich

Gentiopicroside

≥98% (HPLC)

Sinonimo/i:

(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

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About This Item

Formula empirica (notazione di Hill):
C16H20O9
Numero CAS:
Peso molecolare:
356.32
Numero CE:
Numero MDL:
Codice UNSPSC:
12352205
ID PubChem:
NACRES:
NA.25

Origine biologica

plant (Gentiana macrophylla Pall)

Livello qualitativo

Saggio

≥98% (HPLC)

Forma fisica

powder

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Temperatura di conservazione

2-8°C

Stringa SMILE

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
DUAGQYUORDTXOR-GPQRQXLASA-N

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Descrizione generale

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

Applicazioni

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.

Azioni biochim/fisiol

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


Certificati d'analisi (COA)

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Sigma-Aldrich

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Zhijie Wan et al.
Life sciences, 265, 118689-118689 (2020-11-02)
This study aimed to examine whether gentiopicroside (GPS) could exert hepatoprotective effects on leflunomide (LEF)- and/or methotrexate (MTX)-treated arthritic rats through anti-inflammatory and antioxidant pathways. We observed the external symptoms of joints, analysed serum indicators, measured haematological parameters and mRNA
Na Jia et al.
Journal of ethnopharmacology, 189, 1-9 (2016-05-18)
The flowers of Gentiana macrophylla have been usually applied to cure the joint inflammation and rheumatoid arthritis in Traditional Chinese Medicine. This work aimed to investigate the anti-rheumatoid arthritic effect and possible mechanism of iridoid glycosides from G. macrophylla (GMI)
Huaji Jiang et al.
Journal of cellular and molecular medicine, 25(23), 10825-10836 (2021-11-17)
Osteoporosis is characterized by increased bone fragility, and the drugs used at present to treat osteoporosis can cause adverse reactions. Gentiopicroside (GEN), a class of natural compounds with numerous biological activities such as anti-resorptive properties and protective effects against bone
Meiling Wang et al.
Frontiers in pharmacology, 11, 515-515 (2020-06-02)
Rheumatoid arthritis (RA) is among the most prevalent forms of autoimmunity. Gentiopicroside (Gent) is an iridoid glucoside derived from the Gentiana Macrophylla Pall which is used in traditional Chinese medicine to treat RA. The present study was designed to explore
Qian Liu et al.
Oxidative medicine and cellular longevity, 2020, 9125752-9125752 (2020-08-25)
Gentiopicroside (GPS), an antiaging secoiridoid glycoside, was isolated from Gentiana rigescens Franch, a traditional Chinese medicine. It prolonged the replicative and chronological lifespans of yeast. Autophagy, especially mitophagy, and antioxidative stress were examined to clarify the mechanism of action of

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