| Stereochemistry | ABSOLUTE |
| Molecular Formula | C24H30O11 |
| Molecular Weight | 494.4884 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]1(C[C@@H](O)[C@]2(O)C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]12)OC(=O)\C=C\C4=CC=CC=C4
InChI
InChIKey=KVRQGMOSZKPBNS-FMHLWDFHSA-N
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
| Molecular Formula | C24H30O11 |
| Molecular Weight | 494.4884 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
Harpagoside is an anti-inflammatory small molecule natural product originally isolated from the Harpagophytum procumbens (Devil's Claw) root, but can be isolated from other plants such as Crophularia ningpoensis Hemsl (Figwort). Treatment of HepG2 cells with Harpagoside demonstrated suppression of NF-κB nuclear translocation and degradation of IκB-α, blocking NF-κB activation. Multiple anti-inflammatory cellular effects were correlated with this blockade, as Harpagoside was observed to inhibit the expression of inflammation-mediating enzymes cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS), and to reduce lipopolysaccharide-induced mRNA levels. The suppression of NF-κB activation is indicated as the mechanism beneath the anti-inflammatory effects of Harpagoside. Harpagoside is widely used as a folk remedy to treat rheumatic complaints.
Approval Year
PubMed
Patents
Sample Use Guides
Devil's claw has been studied for low back pain, muscle pain, and osteoarthritis using daily doses of crude tuber up to 9 g, 1 to 3 g of extract, or harpagoside 50 to 100 mg.
Route of Administration:
Oral
