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Gentiopicroside

$78

  • Brand : BIOFRON

  • Catalogue Number : BF-G3006

  • Specification : 98%

  • CAS number : 20831-76-9

  • Formula : C16H20O9

  • Molecular Weight : 356.32

  • PUBCHEM ID : 88708

  • Volume : 25mg

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Catalogue Number

BF-G3006

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

356.32

Appearance

Off-white crystalline powder

Botanical Source

Lamiophlomis rotata,Gentiana scabra,Gentiana macrophylla,Aconitum tanguticum,Gentiana waltonii

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

C=CC1C(OC=C2C1=CCOC2=O)OC3C(C(C(C(O3)CO)O)O)O

Synonyms

(5R,6S)-6-{[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-on/Gentiop icroin/(5R,6S)-5-ethenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one/(5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl β-D-glucopyranoside/(5R-trans)-5-Ethenyl-6-(b-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one/Gentiopicroside/β-D-Glucopyranoside de (5R,6S)-5-ethenyl-1-oxo-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yle/(5R,6S)-1-Oxo-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-6-yl β-D-glucopyranoside/(5R,6S)-6-{[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one/(5R-trans)-5-Ethenyl-6-(β-d-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one/(5R,6S)-1-Oxo-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyr-6-yl-β-D-glucopyranoside/1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(β-D-glucopyranosyloxy)-5,6-dihydro-, (5R,6S)-/GENTIOPICRIN

IUPAC Name

(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

Density

1.5±0.1 g/cm3

Solubility

Methanol; Acetontrile; Water; DMSO

Flash Point

247.1±25.0 °C

Boiling Point

667.8±55.0 °C at 760 mmHg

Melting Point

191°C

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:20831-76-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30308492

Abstract

Background/aims: Gentiopicroside is promising as an important secoiridoid compound against pain. The present study aimed to investigate the analgesic effect and the probable mechanism of Gentiopicroside on Diabetic Peripheral Neuropathy (DPN), and to figure out the association among Gentiopicroside, dyslipidemia and PPAR- γ/AMPK/ACC signaling pathway.
Methods: DPN rat models were established by streptozotocin and RSC96 cells were cultured. Hot, cold and mechanical tactile allodynia were conducted. Blood lipids, nerve blood flow, Motor Nerve Conduction Velocity (MNCV) and Sensory Nerve Conduction Velocity (SNCV) were detected. Gene and protein expression of PPAR- γ/AMPK/ACC pathway was analyzed by reverse transcription-quan titative polymerase chain reaction (RT-qPCR) and Westernblot. Besides, PPAR-γ antagonist GW9662 and agonist rosiglitazone, AMPK antagonist compound C and activator AICAR as well as ACC inhibitor TOFA were used to further confirm the relationship between PPAR-γ and AMPK.
Results: The results demonstrated that Gentiopicroside markedly ameliorated hyperalgesia with prolonged paw withdrawal latency to heat and cold stimuli and fewer responses to mechanical allodynia compared with DPN model group. Gentiopicroside regulated dyslipidemia, enhanced nerve blood flow and improved MNCV as well as SNCV. Gentiopicroside suppressed ACC expression through the activation of AMPK and PPAR-γ mediated the activation of AMPK and subsequent inhibition of ACC expression.
Conclusion: In conclusion, the present study demon strated that Gentiopicroside exerted nerve-protective effect and attenuated experimental DPN by restoring dyslipidmia and improved nerve blood flow through regulating PPAR-γ/AMPK/ACC signal pathway. These results provided a promising potential treatment of DPN.

KEYWORDS

AMPK; Diabetic peripheral neuropathy (DPN); Gentiopicroside; PPAR-γ.

Title

Gentiopicroside Ameliorates Diabetic Peripheral Neuropathy by Modulating PPAR- Γ/AMPK/ACC Signaling Pathway

Author

Yi Lu 1 , Jiayin Yao 2 , Chulian Gong 3 , Bao Wang 1 , Piao Zhou 1 , Shaoli Zhou 3 , Xinhua Yao 1

Publish date

2018

PMID

29428661

Abstract

Gentiopicroside, a main active component from the traditional Chinese herb medicine Gentiana manshurica Kitag, has been shown to possess anti-arthritis effect. However, the molecular mechanism of gentiopicroside on the osteoclast formation remains unclear. The present study was designed to investigate the effects and mechanisms of gentiopicroside on receptor activator of nuclear factor-κB ligand (RANKL)-induced osteoclastogenesis. The results showed that pre-treatment with gentiopicroside significantly inhibited RANKL-induced osteoclast formation from mouse bone marrow macrophages (BMMs). In addition, we observed that gentiopicroside efficiently suppressed osteoclastogenesis-related marker genes expression in RANKL-stimulated BMMs. Mechanistically, gentiopicroside suppressed RANKL-induced the activation of JNK and NF-κB signaling pathways in BMMs. Taken together, the present study demonstrated that gentiopicroside inhibits RANKL-induced osteoclastogenesis through the inactivation of JNK and NF-κB signaling pathways. Thus, gentiopicroside may be a promising agent for the treatment of osteoporosis.

KEYWORDS

AMPK; Diabetic peripheral neuropathy (DPN); Gentiopicroside; PPAR-γ.

Title

Gentiopicroside Inhibits RANKL-induced Osteoclastogenesis by Regulating NF-κB and JNK Signaling Pathways

Author

Fangqing Chen 1 , Lin Xie 2 , Ran Kang 2 , Rongrong Deng 2 , Zhipeng Xi 2 , Daoxi Sun 2 , Jin Zhu 3 , Liming Wang 4

Publish date

2018 Apr

PMID

29338075

Abstract

Background and purpose: Regulating P2X7 receptor-mediated activation of NLRP3 inflammasomes could be a therapeutic strategy to treat alcoholic hepatosteatosis. We investigated whether this process was modulated by gentiopicroside, the main active secoiridoid glycoside from Gentiana manshurica Kitagawa.
Experimental approach: In vivo models of acute and chronic alcoholic hepatosteatosis were established by intragastrically administered ethanol or using chronic plus binge ethanol feeding of Lieber-DeCarli liquid diet to male C57BL/6 mice. In vitro, HepG2 cells were treated with ethanol. RAW 264.7 macrophages and murine bone marrow-derived macrophages (BMDMs) were stimulated with LPS and ATP.
Key results: In both the acute and chronic alcohol-induced mouse hepatosteatosis models, gentiopicroside decreased serum aminotransferases and triglyceride accumulation. Up-regulated SREBP1, down-regulated PPARα and phosphorylated acetyl-CoA carboxylase caused by acute and chronic alcohol feeding were modulated by gentiopicroside, through the elevation of LKB1 and AMPK. Suppression of P2X7 receptor-NLRP3 activation by gentiopicroside inhibited IL-1β production. In ethanol-exposed HepG2 cells, gentiopicroside reduced lipogenesis and promoted lipid oxidation via activation of P2X7 receptor-NLRP3 inflammasomes. Genetic or pharmacological blockade of P2X7 receptors enhanced AMPK activity and reduced SREBP1 expression in ethanol-treated HepG2 cells. Gentiopicroside down-regulated P2X7 receptor-mediated inflammatory responses in LPS/ATP-stimulated RAW 264.7 macrophages and BMDMs. IL-1β from macrophages accelerated lipid accumulation in hepatocytes. Depleting macrophages by clodronate liposomes ameliorated alcoholic hepatosteatosis, and it was further alleviated by gentiopicroside.
Conclusions and implications: Activation of LKB1/AMPK signalling by gentiopicroside was mediated by the P2X7 receptor-NLRP3 inflammasome, suggesting the therapeutic value of blocking P2X7 receptors in the treatment of alcoholic hepatosteatosis.
© 2018 The British Pharmacological Society.

Title

Liver Kinase B1/AMP-activated Protein Kinase-Mediated Regulation by Gentiopicroside Ameliorates P2X7 Receptor-Dependent Alcoholic Hepatosteatosis

Author

Xia Li 1 , Yu Zhang 1 , Quan Jin 1 , Kai-Li Xia 1 , Min Jiang 1 , Ben-Wen Cui 1 , Yan-Ling Wu 1 , Shun-Zong Song 1 , Li-Hua Lian 1 , Ji-Xing Nan 1 2

Publish date

018 May


Description :

Gentiopicroside, a naturally occurring iridoid glycoside, inhibits P450 activity, with an IC50 and a Ki of 61 µM and 22.8 µM for CYP2A6; Gentiopicroside has antianti-inflammatoryand antioxidative effects.