We Offer Worldwide Shipping
Login Wishlist

Harpagoside

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-H2008

  • Specification : 98%

  • CAS number : 19210-12-9

  • Formula : C24H30O11

  • Molecular Weight : 494.49

  • PUBCHEM ID : 5281542

  • Volume : 20mg

In stock

Quantity
Checkout Bulk Order?

Catalogue Number

BF-H2008

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

494.49

Appearance

White crystalline powder

Botanical Source

Scrophularia ningpoensis,Gentiana macrophylla

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)OC(=O)C=CC4=CC=CC=C4

Synonyms

8'-CINNAMOYLHARPAGIDE/1-(Hexopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl 3-phenylacrylate/2-Propenoic acid, 3-phenyl-, 1-(hexopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta[c]pyran-7-yl ester/Harpagosid/8-O-E CINNAMOYL HARPAGIDE/Harpogoside

IUPAC Name

[(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate

Density

1.5±0.1 g/cm3

Solubility

Methanol

Flash Point

244.3±26.4 °C

Boiling Point

720.7±60.0 °C at 760 mmHg

Melting Point

120ºC (dec.)

InChl

InChI=1S/C24H30O11/c1-23(35-16(27)8-7-13-5-3-2-4-6-13)11-15(26)24(31)9-10-32-22(20(23)24)34-21-19(30)18(29)17(28)14(12-25)33-21/h2-10,14-15,17-22,25-26,28-31H,11-12H2,1H3/b8-7+/t14-,15-,17-,18+,19-,20-,21+,22+,23+,24-/m1/s1

InChl Key

KVRQGMOSZKPBNS-FMHLWDFHSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:19210-12-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29355053

Abstract

Background: Harpagoside (HAR) is an active component of Scrophularia ningpoensis (SN), which has anti-inflammatory and anti-immune effects. SN is used widely in China to treat various diseases. Recently, SN has been used as a traditional Chinese medicine injection and used clinically. However, allergic responses to these injections are frequently reported.
Aim: We examined whether the main component of SN, HAR, is associated with the allergic reaction to SN.
Methods: This study assessed the effects of HAR in mice and mast cell activation to characterize its anaphylactic effects and underlying mechanisms. Mice hindpaw swelling, serum allergy factor detection, enzyme-linked immunosorbent assays, and degranulation assays were performed to measure allergic mediators both in vivo and in vitro.
Results: The present study indicated that HAR induced paw swelling, interleukin-6, inositol triphosphate, tumor necrosis factor-α, and histamine increases in mice. Our in vitro data also showed that HAR induced β-hexosaminidase, inositol triphosphate, and interleukin-6 release, leading to mast cell degranulation. In contrast, neither C48/80 nor HAR induced local anaphylaxis in STOCK KitW-sh/HNihrJaeBsmJNju mice.
Conclusions: HAR is a potential sensitization compound in SN, and these results provide information for the safe clinical use of SN.

KEYWORDS

IgE-independent; Scrophularia ningpoensis; anaphylactoid reaction; harpagoside; mast cell.

Title

Harpagoside-induced Anaphylactic Reaction in an IgE-independent Manner Both in Vitro and in Vivo

Author

Delu Che 1 , Jiao Cao 1 , Rui Liu 1 , Jue Wang 1 , Yajing Hou 1 , Tao Zhang 1 , Nan Wang 1

Publish date

2018 Apr

PMID

27082319

Abstract

There is growing evidence in support of the involvement of inflammatory response in the pathogenesis of osteoarthritis (OA). Harpagoside, one of the bioactive components of Harpagophytum procumbens (Hp), has been shown to possess anti-inflammatory properties. Here we used an in vitro model of inflammation in OA to investigate the potential of harpagoside to suppress the production of inflammatory cytokines/chemokines such as IL-6 and matrix degrading proteases. We further investigated the likely targets of harpagoside in primary human OA chondrocytes. OA chondrocytes were pre-treated with harpagoside before stimulation with IL-1β. mRNA expression profile of 92 cytokines/chemokines was determined using TaqMan Human Chemokine PCR Array. Expression levels of selected mRNAs were confirmed using TaqMan assays. Protein levels of IL-6 and MMP-13 were assayed by ELISA and immunoblotting. Total protein levels and phosphorylation of signaling proteins were determined by immunoblotting. Cellular localization of IL-6 and c-Fos was performed by immunofluorescence and confocal microscopy. DNA binding activity of c-FOS/AP-1 was determined by ELISA. Harpagoside significantly altered the global chemokine expression profile in IL-1β-stimulated OA chondrocytes. Expression of IL-6 was highly induced by IL-1β, which was significantly inhibited by pre-treatment of OA chondrocytes with harpagoside. Harpagoside did not inhibit the IL-1β-induced activation of NF-κB and C/EBPβ transcription factors but suppressed the IL-1β-triggered induction, phosphorylation, and DNA binding activity of c-FOS, one of the main components of AP-1 transcription factors. Further, harpagoside significantly inhibited the expression of MMP-13 in OA chondrocytes under pathological conditions. siRNA-mediated knockdown of IL-6 resulted in suppressed expression and secretion of MMP-13 directly linking the role of IL-6 with MMP-13 expression. Taken together, the present study suggests that harpagoside exerts a significant anti-inflammatory effect by inhibiting the inflammatory stimuli mediated by suppressing c-FOS/AP-1 activity in OA chondrocytes under pathological conditions. © 2016 Orthopaedic Research Society. Published by Wiley Periodicals, Inc. J Orthop Res 35:311-320, 2017.

KEYWORDS

IgE-independent; Scrophularia ningpoensis; anaphylactoid reaction; harpagoside; mast cell.

Title

Harpagoside Suppresses IL-6 Expression in Primary Human Osteoarthritis Chondrocytes

Author

Abdul Haseeb 1 , Mohammad Yunus Ansari 1 , Tariq M Haqqi 1

Publish date

2017 Feb

PMID

29614669

Abstract

Vascular dementia (VaD) is the second most common dementia worldwide. Unlike Alzheimer’s disease, VaD does not yet have effective therapeutic drugs. Harpagoside is the most important component extracted from Harpagophytum procumbens, a traditional Chinese medicine that has been widely used. The neuroprotective effects of harpagoside have been studied in Aβ- and MPTP-induced neurotoxicity. However, whether harpagoside is protective against VaD is not clear. In this study, with the use of chronic cerebral hypoperfusion rats, a well-known VaD model, we demonstrated that chronic administration (two months) of harpagoside was able to restore both the spatial learning/memory and fear memory impairments. Importantly, the protective effects of harpagoside were not due to alterations in the physiological conditions, metabolic parameters, or locomotor abilities of the rats. Meanwhile, we found that harpagoside suppressed the overactivation of PTEN induced by CCH by enhancing PTEN phosphorylation. Furthermore, harpagoside elevated the activity of Akt and inhibited the activity of GSK-3β, downstream effectors of PTEN. Overall, our study suggested that harpagoside treatment might be a potential therapeutic drug targeting the cognitive impairments of VaD.

KEYWORDS

Chronic cerebral hypoperfusion; GSK-3β; PTEN; harpagoside; memory.

Title

Harpagoside Rescues the Memory Impairments in Chronic Cerebral Hypoperfusion Rats by Inhibiting PTEN Activity

Author

Chen Chen 1 , Haifeng Zhang 1 , Hongliang Xu 1 , Rui Xue 2 , Yake Zheng 1 , Tianwen Wu 1 , Yajun Lian 1

Publish date

2018


Description :

Harpagoside is isolated from Harpagophytum procumbens (Hp). Harpagoside has inhibitory effects on COX-1 and COX-2 activity and inhibits NO production[1].