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Homoplantaginin

$236

  • Brand : BIOFRON

  • Catalogue Number : BD-P0613

  • Specification : 98.0%(HPLC)

  • CAS number : 17680-84-1

  • Formula : C22H22O11

  • Molecular Weight : 462.4

  • PUBCHEM ID : 5318083

  • Volume : 25mg

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Catalogue Number

BD-P0613

Analysis Method

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

462.4

Appearance

Yellow cryst.

Botanical Source

This product is isolated and purified from the herbs of Saluia plebeia R. Br.

Structure Type

Category

SMILES

COC1=C(C=C2C(=C1O)C(=O)C=C(O2)C3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O

Synonyms

hispidulin-7-glucoside/4H-1-Benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-6-methoxy-/5-Hydroxy-2-(4-hydroxyphenyl)-6-methoxy-4-oxo-4H-chromen-7-yl β-D-glucopyranoside/HISPIDULOSIDE/Hispidulin 7-O-glucoside/Homoplantaginin

IUPAC Name

Applications

Anti-influenza effect of the major flavonoids from Salvia plebeia R.Br. via inhibition of influenza H1N1 virus neuraminidase.[Pubmed: 28504013]Nat Prod Res. 2017 May 15:1-5. METHODS AND RESULTS:To determine the compounds responsible for its anti-influenza activities, we isolated the three flavonoids, 6-hydroxyluteolin 7-O-β-d-glucoside (1), nepitrin (2), Homoplantaginin (3) from the MeOH extract of Salvia plebeia R.Br. and identified them by comparing the spectroscopic data with that reported in the literature. The contents of the three flavonoids in the whole extract were 108.74 ± 0.95, 46.26 ± 2.19, and 69.35 ± 1.22 mg/g for 6-hydroxyluteolin 7-O-β-d-glucoside, nepitrin, and Homoplantaginin, respectively, which demonstrates that they are the major constituents of this plant. The three flavonoids were evaluated for their inhibitory activities against influenza virus H1N1 A/PR/9/34 neuraminidase and H1N1-induced cytopathic effect (CPE) on Madin-Darby canine kidney (MDCK) cells. Our results demonstrated the following arrangement for their anti-influenza activities: nepitrin (2) > 6-hydroxyluteolin 7-O-β-d-glucoside (1) > Homoplantaginin (3).CONCLUSIONS: The potent inhibitory activities of these flavonoids against influenza suggested their potential to be developed as novel anti-influenza drugs in the future.

Density

1.6±0.1 g/cm3

Solubility

DMF

Flash Point

279.7±26.4 °C

Boiling Point

798.1±60.0 °C at 760 mmHg

Melting Point

256-258℃

InChl

InChl Key

GCLAFEGUXXHIFT-IWLDQSELSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:17680-84-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

22791168

Abstract

Recent data have indicated that inflammation plays an important role in the development of insulin resistance. The present study aims at examining the activity of homoplantaginin, a flavonoid from a traditional Chinese medicine Salvia plebeia R. BR., on palmitic acid (PA)-induced insulin sensitivity and the underlying mechanisms of its anti-infammatory properties in the endothelial cells. Pre-treatment of homoplantaginin on human umbilical vein endothelial cells (HUVECs) significantly inhibited PA induced tumour necrosis factor-α (TNF-α) and interleukin-6 (IL-6) mRNA expression, and inhibitory κB kinase beta (IKKβ) and nuclear factor-κB (NF-κB) p65 phosphorylation. To the PA-impaired insulin-dependent tyrosine phosphorylation of insulin receptor substrate-1 (IRS-1) and decrease in nitric oxide (NO) production, pretreatment of homoplantaginin could effectively reverse the effects of PA. Additionally, homoplantaginin significantly modulated the Ser/Thr phosphorylation of IRS-1, improved phosphorylation of Akt and endothelial nitric oxide synthase (eNOS), and increased NO production in the presence of insulin. Taken together, our results demonstrated that homoplantaginin ameliorates endothelial insulin resistance by inhibiting inflammation and modulating cell signalling via the IKKβ/IRS-1/pAkt/peNOS pathway, suggesting it may be used for the prevention and treatment of endothelial dysfunction associated with insulin resistance.

Title

Homoplantaginin Modulates Insulin Sensitivity in Endothelial Cells by Inhibiting Inflammation

Author

Feihua Wu 1 , Hui Wang, Juan Li, Jingyu Liang, Shiping Ma

Publish date

2012

PMID

6355761

Abstract

Palmitic acid (PA)-induced vascular endothelial inflammation plays a pivotal role in the occurrence and development of vascular diseases. The present study was conducted to examine the effect of homoplantaginin, a main flavonoid from a traditional Chinese medicine Salvia plebeia R. Br., on PA-treated human umbilical vein endothelial cells inflammation and the underlying molecular mechanism. Firstly, we found that homoplantaginin (0.1, 1, 10 μM) dose-dependently reduced expression of toll-like receptor-4 evoked by PA (100 μM). The inhibitory effect of homoplantaginin was further confirmed under lipopolysaccharide challenge. In addition, downstream adapted proteins including myeloid differentiation primary response gene 88, toll/interleukin-1 receptor-domain containing adaptor-inducing interferon-β and tumor necrosis factors receptor associated factor-6 were successfully inhibited by homoplantaginin under PA treatment. Also, we found that homoplantaginin tightly controlled PA-induced reactive oxygen species to prevent nucleotide-binding domain-like receptor 3 (NLRP3) inflammasome activation by suppressing reactive oxygen species-sensitive thioredoxin-interacting protein, NLRP3, and caspase-1. Meanwhile, protein and mRNA levels of inflammatory mediators (interleukin-1β, intercellular cell adhesion molecule-1, and monocyte chemotactic protein-1) were decreased by homoplantaginin. Furthermore, homoplantaginin restored PA-impaired nitric oxide generation. Taken together, these results indicated that homoplantaginin protected endothelial cells from ameliorating PA-induced endothelial inflammation via suppressing toll-like receptor-4 and NLRP3 pathways, and restoring nitric oxide generation, suggesting it may be a potential candidate for further development in the prevention and treatment of vascular diseases.

Title

Homoplantaginin Inhibits Palmitic Acid-induced Endothelial Cells Inflammation by Suppressing TLR4 and NLRP3 Inflammasome

Author

Baiqiu He 1 , Baobao Zhang, Feihua Wu, Liying Wang, Xiaoji Shi, Weiwei Qin, Yining Lin, Shiping Ma, Jingyu Liang

Publish date

2016 Jan 7.

PMID

27474945

Abstract

The purpose of the present paper was to study the pharmacokinetic characteristics of homoplantaginin, a major active ingredient of Salvia plebeia R.Br. In this study, the effective partition coefficient, in situ absorption in rat intestinal segments and in vitro biotransformation of homoplantaginin by rat intestinal bacteria were determined. In addition, homoplantaginin was administered to rats by intravenous, peritoneal injection and oral administration. The concentrations of homoplantaginin and hispidulin, a metabolite of homoplantaginin, were determined by a validated highperformance liquid chromatographic (HPLC) assay. After intravenous, peritoneal injection, the concentration of hispidulin could not be determined. In contrast, after oral administration, hispidulin and homoplantaginin were simultaneous quantified, homoplantaginin was rapidly absorbed (Tmax=16.00±8.94min), reaching a mean Cmax between 0.77 and 1.27nmol/mL. The absolute oral bioavailability was calculated to be only 0.75%, and the area under curve (AUC) of hispidulin was about 5.4 times than that of homoplantaginin. The poor oral bioavailability may be attributed to the biotransformation of homoplantaginin by rat intestinal bacteria.

KEYWORDS

Biotransformation; HPLC; Homoplantaginin; In situ single-pass intestinal perfusion; Pharmacokinetics.

Title

Pharmacokinetics of Homoplantaginin in Rats Following Intravenous, Peritoneal Injection and Oral Administration

Author

Youquan Cong 1 , Song Wu 2 , Jingjing Han 2 , Jun Chen 3 , Hang Liu 4 , Qiwen Sun 2 , Yu Wu 2 , Yun Fang 5

Publish date

2016 Sep 10