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Hypaphorine

$250

Brand : BIOFRON
Catalogue Number : BF-H4003
Specification : 98%(HPLC)
CAS number : 487-58-1
Formula : C14H18N2O2
Molecular Weight : 246.3
PUBCHEM ID : 442106
Volume : 25mg

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Catalogue Number

BF-H4003

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

246.3

Appearance

White crystalline powder

Botanical Source

Callerya speciosa,Abrus pulchellus subsp. cantoniensis,Caragana sinica,Hedysarum polybotrys,Vaccaria hispanica

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

C[N+](C)(C)C(CC1=CNC2=CC=CC=C21)C(=O)[O-]

Synonyms

(+)-Hypaphorine/Tryptophan, trimethylbetaine/(2S)-3-(1H-Indol-3-yl)-2-(trimethylammonio)propanoate/(S)-a-Carboxy-N,N,N-trimethyl-1H-indole-3-ethanaminium Inner Salt/1H-Indole-3-ethanaminium, α-carboxy-N,N,N-trimethyl-, inner salt, (αS)-/hypaphorine/tryptophan betaine/hypaphorin/1-Trimethylammonio-3-(3-indolyl)propionate/L-Hypaphorine/Glyyunnanenine

IUPAC Name

(2S)-3-(1H-indol-3-yl)-2-(trimethylazaniumyl)propanoate

Density

Solubility

Methanol; Water

Flash Point

Boiling Point

Melting Point

InChl

InChI=1S/C14H18N2O2/c1-16(2,3)13(14(17)18)8-10-9-15-12-7-5-4-6-11(10)12/h4-7,9,13,15H,8H2,1-3H3/t13-/m0/s1

InChl Key

AOHCBEAZXHZMOR-ZDUSSCGKSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:487-58-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

28683454

Abstract

Background /Aims: Accumulating evidence indicates that endothelial inflammation is one of the critical determinants in pathogenesis of atherosclerotic cardiovascular disease. Our previous studies had demonstrated that Vaccariae prevented high glucose or oxidative stress-triggered endothelial dysfunction in vitro. Very little is known about the potential effects of hypaphorine from Vaccariae seed on inflammatory response in endothelial cells.

METHODS:
In the present study, we evaluated the anti-inflammatory effects of Vaccariae hypaphorine (VH) on lipopolysaccharide (LPS)-challenged endothelial EA.hy926 cells. The inflammatory cytokines including tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), monocyte chemoattractant protein 1 (MCP-1) and vascular cellular adhesion molecule-1 (VCAM-1) were measured by real-time PCR (RT-PCR). The expressions of adenosine monophosphate-activated protein kinase (AMPK), acetyl-CoA carboxylase (ACC), toll-like receptor 4 (TLR4), peroxisome proliferator-activated receptor γ (PPARγ) were detected by Western blotting or immunofluorescence.

RESULTS:
We showed that LPS stimulated the expressions of TNF-α, IL-1β, MCP-1, VCAM-1 and TLR4, but attenuated the phosphorylation of AMPK and ACC as well as PPARγ protein levels, which were reversed by VH pretreatment. Moreover, we observed that LPS-upregulated TLR4 protein expressions were inhibited by PPARγ agonist pioglitazone, and the downregulated PPARγ expressions in response to LPS were partially restored by knockdown of TLR4. The negative regulation loop between TLR4 and PPARγ response to LPS was modulated by AMPK agonist AICAR (5-Aminoimidazole-4-carboxamide riboside or acadesine) or A769662.

CONCLUSIONS:
Taken together, our results suggested that VH ameliorated LPS-induced inflammatory cytokines production in endothelial cells via inhibition of TLR4 and activation of PPARγ, dependent on AMPK signalling pathway.

© 2017 The Author(s). Published by S. Karger AG, Basel.

KEYWORDS

AMPK; Endothelial inflammation; LPS; PPARγ; TLR4

Title

Interactions of TLR4 and PPARγ, Dependent on AMPK Signalling Pathway Contribute to Anti-Inflammatory Effects of Vaccariae Hypaphorine in Endothelial Cells.

Author

Sun H, Zhu X, Lin W, Zhou Y, Cai W, Qiu L.

Publish date

2017;

PMID

28420166

Abstract

Endothelial lesion response to injurious stimuli is a necessary step for initiating inflammatory cascades in blood vessels. Hypaphorine (Hy) from different marine sources is shown to exhibit anti-inflammatory properties. However, the potential roles and possible molecular mechanisms of Hy in endothelial inflammation have yet to be fully clarified. We showed that Hy significantly inhibited the positive effects of lipopolysaccharide (LPS) on pro-inflammatory cytokines expressions, including tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), monocyte chemoattractant protein 1 (MCP-1) and vascular cellular adhesion molecule-1 (VCAM-1), as well as induction of the phosphorylation of Akt and mTOR in HMEC-1 cells. The downregulated peroxisome proliferator-activated receptor γ (PPAR-γ) and upregulated toll-like receptor 4 (TLR4) expressions in LPS-challenged endothelial cells were prevented by Hy. Inhibition of both PI3K and mTOR reversed LPS-stimulated increases in TLR4 expressions and decreases in PPAR-γ levels. Genetic silencing of TLR4 or PPAR-γ agonist pioglitazone obviously abrogated the levels of pro-inflammatory cytokines in LPS-treated HMEC-1 cells. These results suggest that Hy may exert anti-inflammatory actions through the regulation of TLR4 and PPAR-γ dependent on PI3K/Akt/mTOR signal pathways. Hy may be considered as a therapeutic agent that can potentially relieve or ameliorate endothelial inflammation-associated diseases.

KEYWORDS

LPS; PPAR-γ; TLR4; endothelial cells; inflammation

Title

Hypaphorine Attenuates Lipopolysaccharide-Induced Endothelial Inflammation via Regulation of TLR4 and PPAR-γ Dependent on PI3K/Akt/mTOR Signal Pathway.

Author

Sun H1, Zhu X2, Cai W3, Qiu L4.

Publish date

2017 Apr 17;

PMID

28398659

Abstract

Obesity, a major health problem worldwide, is a complex multifactorial chronic disease that increases the risk for insulin resistance, type 2 diabetes, coronary heart disease, and hypertension. In this study, we assessed methods to isolate hypaphorine, a potent drug candidate for obesity and insulin resistance. Semi-preparative reversed-phase liquid chromatography (semi-preparative RPLC) was established as a method to separate three compounds, adenosine, l-tryptophan, and hypaphorine, from the crude extracts of Caragana korshinskii Kom. Due to its specific chemical structure, the effect of hypaphorine on differentiation and dexamethasone (DXM) induced insulin resistance of 3T3-L1 cells was investigated. The structures of the three compounds were confirmed by UV, 1 H-NMR, and 13 C-NMR analysis and compared with published data. The activity results indicated that hypaphorine prevented the differentiation of 3T3-L1 preadipocytes into adipocytes by down-regulating hormone-stimulated protein expression of peroxisome proliferator activated receptor γ (PPARγ) and CCAAT/enhancer binding protein (C/EBPα), and their downstream targets, sterol regulatory element binding protein 1 c (SREBP1c) and fatty acid synthase (FAS). Hypaphorine also alleviated DXM-induced insulin resistance in differentiated 3T3-L1 adipocytes via increasing the phosphorylation level of Akt2, a key protein in the insulin signaling pathway. Taken together, we suggest that the method can be applied to large-scale extraction and large-quantity preparation of hypaphorine for treatment of obesity and insulin resistance.

© 2017 Wiley-VHCA AG, Zurich, Switzerland.

KEYWORDS

3T3-L1 cells; Adipocyte differentiation; Hypaphorine; Insulin resistance; Isolation

Title

Hypaphorine, an Indole Alkaloid Isolated from Caragana korshinskii Kom., Inhibites 3T3-L1 Adipocyte Differentiation and Improves Insulin Sensitivity in Vitro.

Author

Luan G1,2, Tie F1,2, Yuan Z1,2, Li G1,3, He J3, Wang Z3, Wang H1,4.

Publish date

2017 Jul 18.