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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 720.66 °C. @ 760.00 mm Hg (est)
|
| Flash Point: | 472.00 °F. TCC ( 244.30 °C. ) (est)
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| logP (o/w): | -1.591 (est) |
| Soluble in: |
| | water, 3.649e+004 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
| Alfa Biotechnology |
| For experimental / research use only. |
| Harpagoside 98%
|
| BOC Sciences |
| For experimental / research use only. |
| Harpagoside
|
| Carbosynth |
| For experimental / research use only. |
| Harpagoside
|
| Changsha Organic Herb |
| Devils Caw Extract
|
| Coompo |
| For experimental / research use only. |
| Harpagoside from Plants ≥98%
Odor: characteristic Use: Harpagoside inhibited lipopolysaccharide-induced mRNA levels and protein expression of cyclooxygenase-2 and inducible nitric oxide in HepG2 cells. These inhibitions appeared to correlate with the suppression of NF-kappaB activation by harpagoside, as pre-treating cells with harpagoside blocked the translocation of NF-kappaB into the nuclear compartments and degradation of the inhibitory subunit IkappaB-alpha. Furthermore, harpagoside dose-dependently inhibited LPS-stimulated NF-kappaB promoter activity in a gene reporter assay in RAW 264.7 cells, indicating that harpagoside interfered with the activation of gene transcription. These results suggest that the inhibition of the expression of cyclooxygenase-2 and inducible nitric oxide by harpagoside involves suppression of NF-kappaB activation, thereby inhibiting downstream inflammation and subsequent pain events.
Bioassays indicated that at 3 mM concentration, Harpagoside showed moderate inhibition of seed germination. These compounds also reduced root length when they were assayed on pregerminated seeds at 1 mM to 0.001 mM concentration range.
Harpagide (1) and harpagoside (2) are two iridoid glycosides existing in many medicinal plants. Although they are believed to be the main bioactive compounds related to the anti-inflammatory efficacy of these plants, the mechanisms of their anti-inflammatory activities remain unclear. The results of our present study showed that 1 and 2 had no effects on inhibitions of cyclooxygenase (COX)-1/2 enzyme activity, tumor necrosis factor-a (TNF-a) release, and nitric oxide (NO) production in vitro. However, the hydrolyzed products of 1 and 2 with β-glucosidase treatment showed a significant inhibitory effect on COX-2 activity at 2.5100 M in a concentration-dependent manner. Our further study revealed that the hydrolyzed 2 product was structurally the same as the hydrolyzed 1 product (H-harpagide (3)). The structure of 3 was 2-(formylmethyl)-2,3,5-trihydroxy-5-methylcyclopentane carbaldehyde, with a backbone similar to prostaglandins and COX-2 inhibitors such as celecoxib. All of them have a pentatomic ring with two adjacent side chains. The result of molecular modeling and docking study showed that 3 could bind to the COX-2 active domain well through hydrophobic and hydrogen-bonding interactions, whereas 1 and 2 could not, implying that the hydrolysis of the glycosidic bond of 1 and 2 is a pre-requisite step for their COX-2 inhibitory activity. |
| ExtraSynthese |
| For experimental / research use only. |
| Harpagoside (HPLC) ≥99 %
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| Santa Cruz Biotechnology |
| For experimental / research use only. |
| Harpagoside
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| Sigma-Aldrich |
| For experimental / research use only. |
| Harpagoside
analytical standard |
Safety Information:
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
|
Not determined
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| Dermal Toxicity: |
|
Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for harpagoside usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for harpagoside flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5281542 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| [(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 |
| Chemidplus:0019210129 |
References:
| | [(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 |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 5281542 |
| Pubchem (sid): | 135046693 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| [(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 | | | hapagoside | | | harpogoside | | 2- | propenoic acid, 3-phenyl-, (1S,4aS,5R,7S,7aS)-1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta[c]pyran-7-yl ester, (2E)- |
Articles:
| PubMed:What the devil is in your phytomedicine? Exploring species substitution in Harpagophytum through chemometric modeling of (1)H-NMR and UHPLC-MS datasets. |
| PubMed:[Studies on effects of Achyranthes bidentata on tongsaimai pellets main active ingredients chlorogenic acid, isoliquiritin, harpagoside and glycyrrhizin in vivo pharmacokinetics]. |
| PubMed:Iridoid glycosides isolated from Scrophularia dentata Royle ex Benth. and their anti-inflammatory activity. |
| PubMed:Network pharmacology analyses of the antithrombotic pharmacological mechanism of Fufang Xueshuantong Capsule with experimental support using disseminated intravascular coagulation rats. |
| PubMed:Iridoid glycosides from Alonsoa meridionalis. |
| PubMed:Harpagoside: from Kalahari Desert to pharmacy shelf. |
| PubMed:[HPLC fingerprint of scrophulariae radix from southwest China]. |
| PubMed:Verbascum xanthophoeniceum-derived phenylethanoid glycosides are potent inhibitors of inflammatory chemokines in dormant and interferon-gamma-stimulated human keratinocytes. |
| PubMed:Preparative isolation and purification of harpagoside and angroside C from the root of Scrophularia ningpoensis Hemsley by high-speed counter-current chromatography. |
| PubMed:Devil's Claw-a review of the ethnobotany, phytochemistry and biological activity of Harpagophytum procumbens. |
| PubMed:Anatomical study of secondary tuberized roots of Harpagophytum procumbens DC and quantification of harpagoside by high-performance liquid chromatography method. |
| PubMed:Effect of silymarin and harpagoside on inflammation reaction of BEAS-2B cells, on ciliary beat frequency (CBF) of trachea explants and on mucociliary clearance (MCC). |
| PubMed:[Determination of harpagide and harpagoside in Scrophulariae Radix by HPLC-UV]. |
| PubMed:Harpagoside attenuates MPTP/MPP⁺ induced dopaminergic neurodegeneration and movement disorder via elevating glial cell line-derived neurotrophic factor. |
| PubMed:Antiinflammatory activities of Hungarian Stachys species and their iridoids. |
| PubMed:Development of an in-line HPLC fingerprint ion-trap mass spectrometric method for identification and quality control of Radix Scrophulariae. |
| PubMed:Metabolic differentiations and classification of Verbascum species by NMR-based metabolomics. |
| PubMed:Effects of β-glucosidase hydrolyzed products of harpagide and harpagoside on cyclooxygenase-2 (COX-2) in vitro. |
| PubMed:The interaction potential of herbal medicinal products: a luminescence-based screening platform assessing effects on cytochrome P450 and its use with devil's claw (Harpagophyti radix) preparations. |
| PubMed:[Simultaneous determination of five constituents in Scrophularia ningpoensis by HPLC]. |
| PubMed:Simultaneous chemical fingerprinting and quantitative analysis of crude and processed Radix Scrophulariae from different locations in China by HPLC. |
| PubMed:Harpagoside variation is positively correlated with temperature in Scrophularia ningpoensis Hemsl. |
| PubMed:Effect of isolated fractions of Harpagophytum procumbens D.C. (devil's claw) on COX-1, COX-2 activity and nitric oxide production on whole-blood assay. |
| PubMed:Morroniside cinnamic acid conjugate as an anti-inflammatory agent. |
| PubMed:Inhibitory effects of devil's claw (secondary root of Harpagophytum procumbens) extract and harpagoside on cytokine production in mouse macrophages. |
| PubMed:A new iridoid glycoside from Scrophularia ningpoensis. |
| PubMed:Estimation of the relative antiinflammatory efficacies of six commercial preparations of Harpagophytum procumbens (Devil's Claw). |
| PubMed:Effects of Devil's Claw (Harpagophytum procumbens) on the multidrug transporter ABCB1/P-glycoprotein. |
| PubMed:The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells. |
| PubMed:Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis. |
| PubMed:A novel ex vivo skin model for the assessment of the potential transcutaneous anti-inflammatory effect of topically applied Harpagophytum procumbens extract. |
| PubMed:[Determination of five compounds in Scrophularia ningpoensis by HPLC-UV-ELSD]. |
| PubMed:[Study on preparation and quantity determination of Scrophularia ningpoensis dispensing granules]. |
| PubMed:An in vivo microdialysis measurement of harpagoside in rat blood and bile for predicting hepatobiliary excretion and its interaction with cyclosporin A and verapamil. |
| PubMed:Iridoid and aromatic glycosides from Scrophularia ningpoensis Hemsl. and their inhibition of [Ca2+](i) increase induced by KCl. |
| PubMed:Validated HPTLC methods for the determination of salicin in Salix sp. and of harpagoside in Harpagophytum [corrected] procumbens. |
| PubMed:Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae). |
| PubMed:Analysis of iridoids from Harpagophytum and eleutherosides from Eleutherococcus senticosus in horse urine. |
| PubMed:Cognitive-enhancing and antioxidant activities of iridoid glycosides from Scrophularia buergeriana in scopolamine-treated mice. |
| PubMed:Effect of the major glycosides of Harpagophytum procumbens (Devil's Claw) on epidermal cyclooxygenase-2 (COX-2) in vitro. |
| PubMed:Optimization of solid-phase extraction for the liquid chromatography-mass spectrometry analysis of harpagoside, 8-para-coumaroyl harpagide, and harpagide in equine plasma and urine. |
| PubMed:Abietane lactones and iridoids from Goldfussia yunnanensis. |
| PubMed:Simultaneous determination of harpagoside and cinnamic acid in rat plasma by high-performance liquid chromatography: application to a pharmacokinetic study. |
| PubMed:Simultaneous determination of harpagoside and cinnamic acid in rat plasma by liquid chromatography electrospray ionization mass spectrometry and its application to pharmacokinetic studies. |
| PubMed:Simultaneous determination of four active constituents in the roots of Scrophularia buergeriana by HPLC-DAD and LC-ESI-MS. |
| PubMed:Patient-perceived benefit during one year of treatment with Doloteffin. |
| PubMed:Evidence of effectiveness of herbal antiinflammatory drugs in the treatment of painful osteoarthritis and chronic low back pain. |
| PubMed:Screening of plant extracts for antimicrobial activity against bacteria and yeasts with dermatological relevance. |
| PubMed:Structural revision of some recently published iridoid glucosides. |
| PubMed:Reverse-phase high pressure liquid chromatographic analysis of harpagoside, scorodioside and verbascoside from Scrophularia scorodonia: quantitative determination of harpagoside. |
| PubMed:Herbal medicine for low back pain: a Cochrane review. |
| PubMed:Preparative isolation and purification of harpagoside from Scrophularia ningpoensis hemsley by high-speed counter-current chromatography. |
| PubMed:Liquid chromatography/electrospray ionization mass spectrometric characterization of Harpagophytum in equine urine and plasma. |
| PubMed:Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L. |
| PubMed:Iridoid glycosides from Harpagophytum procumbens D.C. (devil's claw). |
| PubMed:Herbal medicine for low back pain. |
| PubMed:High anti-inflammatory activity of harpagoside-enriched extracts obtained from solvent-modified super- and subcritical carbon dioxide extractions of the roots of Harpagophytum procumbens. |
| PubMed:Harpagoside suppresses lipopolysaccharide-induced iNOS and COX-2 expression through inhibition of NF-kappa B activation. |
| PubMed:The commercial harvest of devil's claw (Harpagophytum spp.) in southern Africa: the devil's in the details. |
| PubMed:Hydrophilic solutes in modified carbon dioxide extraction-prediction of the extractability using molecular dynamic simulation. |
| PubMed:Fast HPLC for quality control of Harpagophytum procumbens by using a monolithic silica column: method transfer from conventional particle-based silica column. |
| PubMed:Rapid measurement and evaluation of the effect of drying conditions on harpagoside content in Harpagophytum procumbens (devil's claw) root. |
| PubMed:Comparison between HPLC and HPTLC-densitometry for the determination of harpagoside from Harpagophytum procumbens CO(2)-extracts. |
| PubMed:A 1-year follow-up after a pilot study with Doloteffin for low back pain. |
| PubMed:Downregulation of iNOS expression in rat mesangial cells by special extracts of Harpagophytum procumbens derives from harpagoside-dependent and independent effects. |
| PubMed:Quality control of Harpagophytum procumbens and its related phytopharmaceutical products by means of NIR-FT-Raman spectroscopy. |
| PubMed:Harpgophytum procumbens for osteoarthritis and low back pain: a systematic review. |
| PubMed:[Devil's claw extract as an example of the effectiveness of herbal analgesics]. |
| PubMed:Evaluation of acute and chronic treatments with Harpagophytum procumbens on Freund's adjuvant-induced arthritis in rats. |
| PubMed:Effectiveness of Harpagophytum extracts and clinical efficacy. |
| PubMed:Treatment of patients with arthrosis of hip or knee with an aqueous extract of devil's claw (Harpagophytum procumbens DC.). |
| PubMed:New and known iridoid- and phenylethanoid glycosides from Harpagophytum procumbens and their in vitro inhibition of human leukocyte elastase. |
| PubMed:The quality of clinical trials with Harpagophytum procumbens. |
| PubMed:Screening pharmaceutical preparations containing extracts of turmeric rhizome, artichoke leaf, devil's claw root and garlic or salmon oil for antioxidant capacity. |
| PubMed:Scropolioside-D2 and harpagoside-B: two new iridoid glycosides from Scrophularia deserti and their antidiabetic and antiinflammatory activity. |
| PubMed:[Establishment of a TLC identification method for xuanshen(radix scrophulariae)]. |
| PubMed:A randomized double-blind pilot study comparing Doloteffin and Vioxx in the treatment of low back pain. |
| PubMed:Four new neuroprotective iridoid glycosides from Scrophularia buergeriana roots. |
| PubMed:[TLC analysis of harpagoside in devil claw extract and its tablets]. |
| PubMed:Comparison of outcome measures during treatment with the proprietary Harpagophytum extract doloteffin in patients with pain in the lower back, knee or hip. |
| PubMed:[Pain management with herbal antirheumatic drugs]. |
| PubMed:Antiviral activity of seven iridoids, three saikosaponins and one phenylpropanoid glycoside extracted from Bupleurum rigidum and Scrophularia scorodonia. |
| PubMed:De novo regeneration of Scrophularia yoshimurae Yamazaki (Scrophulariaceae) and quantitative analysis of harpagoside, an iridoid glucoside, formed in aerial and underground parts of in vitro propagated and wild plants by HPLC. |
| PubMed:Fast repairing of oxidized OH radical adducts of dAMP and dGMP by phenylpropanoid glycosides from Scrophularia ningpoensis Hemsl. |
| PubMed:Investigations on the pharmacokinetic properties of Harpagophytum extracts and their effects on eicosanoid biosynthesis in vitro and ex vivo. |
| PubMed:Reports of equivalence trials should not mask negative or mediocre results. |
| PubMed:Inhibition of TNF-alpha synthesis in LPS-stimulated primary human monocytes by Harpagophytum extract SteiHap 69. |
| PubMed:Seasonal variations in the harpagoside content of Scrophularia scorodonia L. |
| PubMed:Efficacy and tolerance of Harpagophytum procumbens versus diacerhein in treatment of osteoarthritis. |
| PubMed:Harpagophytum procumbens in the treatment of knee and hip osteoarthritis. Four-month results of a prospective, multicenter, double-blind trial versus diacerhein. |
| PubMed:Isoangoroside C, a phenylpropanoid glycoside from Scrophularia scorodonia roots. |
| PubMed:Effects of some iridoids from plant origin on arachidonic acid metabolism in cellular systems. |
| PubMed:Physicochemical properties of harpagoside and its in vitro release from Harpagophytum procumbens extract tablets. |
| PubMed:Iridoids from plantago lagopus. |
| PubMed:Formation of nitrogen-containing metabolites from the main iridoids of Harpagophytum procumbens and H. zeyheri by human intestinal bacteria. |
| PubMed:Effectiveness of Harpagophytum extract WS 1531 in the treatment of exacerbation of low back pain: a randomized, placebo-controlled, double-blind study. |
| PubMed:Two new pyridine monoterpene alkaloids by chemical conversion of a commercial extract of harpagophytum procumbens |
| PubMed:An analytical study, anti-inflammatory and analgesic effects of Harpagophytum procumbens and Harpagophytum zeyheri. |
| PubMed:Antiinflammatory effects of different extracts and harpagoside isolated from Scrophularia frutescens L. |
| PubMed:Effectiveness of Harpagophytum procumbens in treatment of acute low back pain. |
| PubMed:[Quality evaluation of Harpagophyton capsules]. |
| PubMed:Anti-inflammatory and analgesic effects of an aqueous extract of Harpagophytum procumbens. |
| PubMed:A drug used in traditional medicine: Harpagophytum procumbens DC. IV. Effects on some isolated muscle preparations. |
| PubMed:A drug used in traditional medicine: Harpagophytum procumbens DC. III. Effects on hyperkinetic ventricular arrhythmias by reperfusion. |
| PubMed:A drug used in traditional medicine: Harpagophytum procumbens DC. II. Cardiovascular activity. |
| PubMed:A drug used in traditional medicine. Harpagophytum procumbens DC. I. Scanning electron microscope observations. |
| PubMed:[Iridoids from Verbascum sinuatum.]. |
| PubMed:[Biological analysis of Harpagophytum procumbens D.C. II. Pharmacological analysis of the effects of harpagoside, harpagide and harpagogenine on the isolated guinea-pig ileum (author's transl)]. |
| PubMed:[Antiphlogistic, analgesic and spasmolytic effect of harpagoside, a glycoside from the root of Harpagophytum procumbens DC]. |
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