Hypaphorine

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

Applications

Vaccaria hypaphorine impairs RANKL-induced osteoclastogenesis by inhibition of ERK, p38, JNK and NF-κB pathway and prevents inflammatory bone loss in mice. PUMID/DOI：DOI: 10.1016/j.biopha.2017.11.044 Biomed Pharmacother. 2018 Jan;97:1155-1163. Osteoclasts are sole bone-resorbing cells which exert a profound effect on skeletal metabolism. The search for medicines that affect the differentiation and function of osteoclasts is crucial in developing therapies for osteoclast-based diseases. Vaccaria hypaphorine, the main active compound of the traditionally used Chinese herb Vaccaria segetalis, has anti-inflammatory activity. The present study demonstrated for the first time that vaccaria hypaphorine could significantly inhibit the receptor activator of nuclear factor kappa B ligand (RANKL)-induced osteoclastic differentiation in vitro and alleviate lipopolysaccharide (LPS)-induced bone loss in vivo. Further study showed that vaccaria hypaphorine decreased osteoclastogenesis in a dose-dependent manner. Furthermore, vaccaria hypaphorine was confirmed to inhibit osteoclasts differentiation at early stage but not at later stage. Pit formation assay and F-actin ring staining showed that vaccaria hypaphorine inhibited the bone-resorbing activity of osteoclasts. Mechanistically, vaccaria hypaphorine impaired RANKL-induced osteoclastogenesis through reduction of extracellular signal-regulated kinases (ERK), p38, c-Jun N-terminal kinase (JNK) and NF-κB p65 phosphorylation. Taken together, our results provided evidences that vaccaria hypaphorine might be considered as potential therapeutic agent for treating osteoclast-based bone loss. Interactions of TLR4 and PPAR?, Dependent on AMPK Signalling Pathway Contribute to Anti-Inflammatory Effects of Vaccariae Hypaphorine in Endothelial Cells. PUMID/DOI：DOI: 10.1159/000478920 Cell Physiol Biochem. 2017;42(3):1227-1239. 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. Hypaphorine, an Indole Alkaloid Isolated from Caragana korshinskii Kom., Inhibites 3T3-L1 Adipocyte Differentiation and Improves Insulin Sensitivity in Vitro. PUMID/DOI：DOI: 10.1002/cbdv.201700038 Chem Biodivers. 2017 Jul;14(7). 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 ? (PPAR?) and CCAAT/enhancer binding protein (C/EBPa), 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. Major alkaloidal constituent from Impatiens niamniamensis seeds as antihyperglycemic agent PUMID/DOI：DOI: 10.1007/s00044-010-9401-7 Chand K, Akanksha, Rahuja N, et al. Major alkaloidal constituent from Impatiens niamniamensis, seeds as antihyperglycemic agent[J]. Medicinal Chemistry Research, 2011, 20(9):1505-1508. Hypaphorine, an α-N,N,N-trimethyltryptophan betaine, is isolated as major constituent from Impatiens niamniamensis seeds (Balsaminaceae) for the first time. The structure of the compound was established by spectroscopic data. This is the first report of its in vivo evaluation for antihyperglycemic activity. The ethanolic extract of the seeds showed mild antihyperglycemic activity at the dose of 200mg/kg body weight, whereas, hypaphorine showed significant activity in streptozotocin-induced diabetic rats at the dose of 50mg/kg body weight when compared to standard drug metformin (100mg/kg). Hypaphorine, an indole alkaloid from Erythrina velutina, induced sleep on normal mice. PUMID/DOI：DOI: 10.1016/j.bmcl.2008.06.002 Bioorg Med Chem Lett. 2008 Jul 15;18(14):3992-4. An indole alkaloid (hypaphorine (1)) was isolated from Brazilian medicinal plant, Erythrina velutina (Leguminosae). This compound was investigated for sleep promoting effects in mice, and the results showed that it significantly increased non-rapid eye movement (NREM) sleep time during the first hour after its administration. The NREM sleep time was enhanced by 33% in the experimental mice when compared to that of the controls. This study therefore confirmed its sleep promoting property.

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

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