harpagide
(1S-(1alpha,4aalpha,5alpha,7alpha,7aalpha))-1,4a,5,6,7,7a-hexahydro-4a,5,7-trihydroxy-7-methylcyclopenta(c)pyran-1-yl beta-D-glucopyranoside
Identification
| Name | harpagide |
| CAS Number | 6926-08-5 |
| EINECS | 230-050-0 |
| FDA UNII | OF59XHX7SR |
| Molecular Formula | C15 H24 O10 |
| Molecular Weight | 364.34828000 |
| MDL Number | MFCD00017306 |
| Nikkaji Number | J3.360.256A |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 637.10 °C. @ 760.00 mm Hg (est) |
| Flash Point | 642.00 °F. TCC ( 339.10 °C. ) (est) |
| logP (o/w) | -3.690 (est) |
| Soluble in | water, 1e+006 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for harpagide usage levels up to | not for fragrance use. |
| Recommendation for harpagide flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
beta-D-
glucopyranoside
(1S-(1alpha,4aalpha,5alpha,7alpha,7aalpha))-1,4a,5,6,7,7a-
hexahydro-4a,5,7-trihydroxy-7-methylcyclopenta(c)pyran-1-yl beta-D-glucopyranoside
(1S,4aS,5R,7S,7aR)-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-4a,5,7-triol
PubMed:
Iridoid glycosides isolated from Scrophularia dentata Royle ex Benth. and their anti-inflammatory activity.
PubMed:
[Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens extract in beagle dog].
PubMed:
Chiroptical properties of ajugol investigated by quantum chemical calculation using time-dependent density functional theory.
PubMed:
Validated LC-MS method for simultaneous quantitation of catalpol and harpagide in rat plasma: application to a comparative pharmacokinetic study in normal and diabetic rats after oral administration of Zeng-Ye-Decoction.
PubMed:
Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens Thunb extract in rats.
PubMed:
Verbascum xanthophoeniceum-derived phenylethanoid glycosides are potent inhibitors of inflammatory chemokines in dormant and interferon-gamma-stimulated human keratinocytes.
PubMed:
A new flavonoid and other polar compounds from Galeopsis angustifolia Ehrh. ex Hoffm.
PubMed:
Devil's Claw-a review of the ethnobotany, phytochemistry and biological activity of Harpagophytum procumbens.
PubMed:
Phytochemical composition of polar fraction of Stachys germanica L. subsp. salviifolia (Ten.) Gams, a typical plant of Majella National Park.
PubMed:
[Determination of harpagide and harpagoside in Scrophulariae Radix by HPLC-UV].
PubMed:
Distribution of iridiod glucosides and anti-oxidant compounds in Spathodea campanulata parts.
PubMed:
Antiinflammatory activities of Hungarian Stachys species and their iridoids.
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:
Anti-inflammatory effect of Ajuga bracteosa Wall Ex Benth. mediated through cyclooxygenase (COX) inhibition.
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:
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:
Iridoid and aromatic glycosides from Scrophularia ningpoensis Hemsl. and their inhibition of [Ca2+](i) increase induced by KCl.
PubMed:
Cytotoxic activities of Stachys species.
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:
Effect of the major glycosides of Harpagophytum procumbens (Devil's Claw) on epidermal cyclooxygenase-2 (COX-2) in vitro.
PubMed:
Dermal and transcutaneous delivery of the major glycoside constituents of Harpagophytum procumbens (Devil's Claw) 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:
Antinociceptive and anti-inflammatory effects of saponin and iridoid glycosides from Verbascum pterocalycinum var. mutense Hub.-Mor.
PubMed:
Further flavonol and iridoid glycosides from Ajuga remota aerial parts.
PubMed:
Evaluation of antiprotozoal and antimycobacterial activities of the resin glycosides and the other metabolites of Scrophularia cryptophila.
PubMed:
Simultaneous determination of four active constituents in the roots of Scrophularia buergeriana by HPLC-DAD and LC-ESI-MS.
PubMed:
Liquid chromatography/electrospray ionization mass spectrometric characterization of Harpagophytum in equine urine and plasma.
PubMed:
Iridoid glycosides from Harpagophytum procumbens D.C. (devil's claw).
PubMed:
Monoterpenoids from Stachys glutinosa L.
PubMed:
A new phthalic acid ester from Ajuga bracteosa.
PubMed:
Proton and sodium cation affinities of harpagide: a computational study.
PubMed:
Rapid measurement and evaluation of the effect of drying conditions on harpagoside content in Harpagophytum procumbens (devil's claw) root.
PubMed:
LC-DAD-MS/SPE-NMR hyphenation. A tool for the analysis of pharmaceutically used plant extracts: identification of isobaric iridoid glycoside regioisomers from Harpagophytum procumbens.
PubMed:
A new iridoid diglycoside from Clerodendrum chinense.
PubMed:
Iridoids as allelochemicals and DNA polymerase inhibitors.
PubMed:
Iridoids from Scrophularia buergeriana attenuate glutamate-induced neurotoxicity in rat cortical cultures.
PubMed:
Benzoxazinoids and iridoid glucosides from four Lamium species.
PubMed:
Ionone, iridoid and phenylethanoid glycosides from Ajuga salicifolia.
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:
Four new neuroprotective iridoid glycosides from Scrophularia buergeriana roots.
PubMed:
Chemistry of plants from Crete: stachyspinoside, a new flavonoid glycoside and iridoids from Stachys spinosa.
PubMed:
Iridoids from Stachys grandidentata (Labiatae).
PubMed:
Fast repairing of oxidized OH radical adducts of dAMP and dGMP by phenylpropanoid glycosides from Scrophularia ningpoensis Hemsl.
PubMed:
Inhibition of TNF-alpha synthesis in LPS-stimulated primary human monocytes by Harpagophytum extract SteiHap 69.
PubMed:
Selective sequestration of iridoid glycosides from their host plants in Longitarsus flea beetles.
PubMed:
Iridoid glucosides from Caryopteris mongholica.
PubMed:
Iridoids from Caryopteris x clandonensis.
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:
Formation of nitrogen-containing metabolites from the main iridoids of Harpagophytum procumbens and H. zeyheri by human intestinal bacteria.
PubMed:
Two new pyridine monoterpene alkaloids by chemical conversion of a commercial extract of harpagophytum procumbens
PubMed:
Antiinflammatory effects of different extracts and harpagoside isolated from Scrophularia frutescens L.
PubMed:
Karsoside and scropolioside D, two new iridoid glycosides from Scrophularia ilwensis.
PubMed:
Vasoconstrictor activity of 8-O-acetylharpagide from Ajuga reptans.
PubMed:
Iridoids and an Alkaloid from Oxera morieri1.
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. II. Cardiovascular activity.
PubMed:
A drug used in traditional medicine. Harpagophytum procumbens DC. I. Scanning electron microscope observations.
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)].