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SMB00416

Sigma-Aldrich

Gentiopicroside

≥98% (HPLC)

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Synonym(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
Empirical Formula (Hill Notation):
C16H20O9
CAS Number:
Molecular Weight:
356.32
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

plant (Gentiana macrophylla Pall)

Quality Level

assay

≥98% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

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

InChI key

DUAGQYUORDTXOR-GPQRQXLASA-N

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This Item
SMB00313SML1572PHL89512
Gentiopicroside ≥98% (HPLC)

SMB00416

Gentiopicroside

Gastrodin ≥98% (HPLC)

SMB00313

Gastrodin

Gentiopicroside ≥98% (HPLC)

SML1572

Gentiopicroside

Gentiopicroside phyproof® Reference Substance

PHL89512

Gentiopicroside

biological source

plant (Gentiana macrophylla Pall)

biological source

plant (Gastrodia elata Blume)

biological source

-

biological source

-

form

powder

form

powder

form

powder

form

-

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

detection
metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

application(s)

food and beverages

Quality Level

200

Quality Level

-

Quality Level

100

Quality Level

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

General description

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.

Biochem/physiol Actions

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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
Daniil N Olennikov et al.
Metabolites, 9(11) (2019-11-11)
The members of Gentiana genus are widely distributed in the Caucasus region where they are used as phytoremedies, but they still have not been studied for their chemical composition and bioactivity. High-performance liquid chromatography with diode array and electrospray triple
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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