6926-08-5

Usage

Uses

Used in Pharmaceutical Industry:
Harpagide is used as an anti-inflammatory agent for its potential to alleviate inflammation and associated pain. It is particularly useful in the development of treatments for various inflammatory conditions due to its strong anti-inflammatory properties.
Used in Herbal Medicine:
In the field of herbal medicine, Harpagide is used as a key component in formulations aimed at reducing inflammation and pain. Its natural origin and potent effects make it a valuable addition to herbal remedies for a range of conditions.
Used in Nutraceutical Industry:
Harpagide is also used in the nutraceutical industry as an ingredient in dietary supplements and functional foods. Its anti-inflammatory properties make it a popular choice for products designed to support joint health, reduce inflammation, and promote overall well-being.

InChI:InChI=1/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3/t6-,7-,8-,9+,10-,11?,12+,13+,14+,15-/m1/s1

Upstream product

• 20770-66-5 Pentaacetylantirrhinosid 
• 20770-66-5 penta-O-acetylantirrhinoside 
• 133561-41-8 8-O-cis-cinnamoyl-6-O-β-D-glucosylharpagide 
• 133561-42-9 trans-6'-O-p-coumaroylharpagide 
• 19210-12-9 8-O-cis-cinnamoylharpagide 
• 19210-12-9 harpagoside 
• 87686-74-6 8-O-4-hydroxycinnamoylharpagide 

Relevant academic research and scientific papers

Iridoids As Allelochemicals and DNA Polymerase Inhibitors

Growth inhibitory activities and nutritional indices of catalpol (1), 8-O-acetylharpagide (2), and harpagide (3) were determinated in larvae and adults of Tribolium castaneum, respectively. Compound 1 produced a series of allelochemical effects probably related with the DNA synthesis. This iridoid possessed the highest inhibitory activity against DNA polymerase. Molecular orbital calculations suggest that a π-π charge transfer recognition model could explain the action of iridioids toward nucleic acid synthesis.

Effect of an 8-Hydroxymethyl Substituent on the Base-Catalyced Ring Opening of 7,8-Epoxyiridoid Glucosides

Base-catalyzed ring opening of 7,8-epoxyiridoids has been found to be dependent on the substitution pattern at C-8.Epoxyiridoids 5, 6, and 10 (CH3-8) react in barium or sodium hydroxide solutions through a normal SN2 process, yielding the expected 7α,8β-diols while for iridoids 3 and 4 (CH2OH-8) the stereochemistry of the final diol function is reversed (7β,8α).This abnormal SN2 process is explained by a preliminary "epoxide migration" from carbons 7,8 to 8,10 followed by normal oxirane cleavage.Participation of the CH2OH-8 substituent in the cleavage reaction is proved by the behavior of the hexa-O-methyl derivative 3 which gives the normal 7α,8β-diol.Four new nonnatural iridoid glucosides (9, 11, 14, 16) are also described and spectroscopically (1H and 13C NMR) characterized.

Use of harpagid-related compounds for prevention and treatment of osteoporosis, arthritis and ruptured disc and pharmaceutical composition containing the same

In the present invention, it is discovered that a compound of formula (I) has a potent effect for treatment of osteoporosis, arthritis and ruptured disc: in which R1 represents hydrogen atom or alkyl group and R2 represents hydrogen atom r cinnamoyl group. Therefore, the compound of formula (I) can be used for prevention and treatment of osteoporosis, arthritis and ruptured disc. Thus, the present invention provides a pharmaceutical preparation containing as an effective component a compound of formula (I) in combination with a pharmaceutically acceptable auxiliary, diluent, isotonic agent, preservative, lubricant and solubilizing aid, which is formulated in the form of a pharmaceutically acceptable preparation and has a potent effect for osteoporosis, arthritis and ruptured disc.

IRIDOID GLUCOSIDES FROM ROGERIA ADENOPHYLLA

Three new harpagide derivatives have been isolated from the aerial parts of Rogeria adenophylla (Pedaliaceae).Their structures have been established as 8-O-cis-cinnamoylharpagide, 8-O-cis-cinnamoyl-6-O-β-D-glucosyl-harpagide and 6'-O-p-coumaroyl harpagide respectively, the p-coumaroyl moiety of the latter existing in either the trans or cis configuration.In addition, harpagide, harpagoside, 8-O-trans-p-coumaroylharpagide, procumbide and verbascoside have been isolated and identified.

Chemistry and Stereochemistry of Iridoids, V. - Crystal and Molecular Structure of Hexaacetylleonuride - Stereochemical Correlations of Some Iridoid Glucosides

Leonuride (ajugol, 1a) and myoporoside (2) are C-6 epimers, the configurations of which are specified differently in the literature.By X-ray structure analysis of hexaacetylleonuride (1d) the absolute configuration of leonuride (1a) is fixed, to which the configurations of catalpol (3a), antirrhinoside (6a), and harpagide (7a) as well as procumbide (14a) and 6-epi-harpagide (15a) are linked by chemical correlation.

New Iridoid Glucosides from Harpagophytum procumbres DC.

Three new iridoid glucosides, 8-O-(p-coumaroyl)-harpagide, 6'-O-(p-coumaroyl)-procumbide and procumboside, have been isolated from the roots of Harpagophytum procumbers DC., together with three known iridoid glucosides, harpagide, harpagoside, and procumbide.Procumboside is a novel iridoid glucoside having an ether linkage between C-3 and C-6.