Harpagoside

Harpagoside

Names
IUPAC name (1S,4aS,5R,7S,7aS)-1-(β-D-Glucopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl (2E)-3-phenylacrylate
Identifiers
CAS Number	19210-12-9
ChemSpider	4444874
Jmol interactive 3D	Image
PubChem	5281542
UNII	8KGS1DC5ZU
InChI 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 Key: KVRQGMOSZKPBNS-FMHLWDFHSA-N
SMILES C[C@@]1(C[C@H]([C@]2([C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)OC(=O)/C=C/c4ccccc4
Properties
Chemical formula	C24H30O11
Molar mass	494.49 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Harpagoside is a chemical compound classified as an iridoid glycoside.^[1] It is an chemical constituent of the plant Harpagophytum procumbens (devil’s claw).^[2]

In vitro, it inhibits NF-κB activation (a protein complex that controls transcription of DNA), suppresses lipopolysaccharide-induced iNOS, and inhibits COX-2 expression.^[2]

References

1. Milen I. Georgiev, Nina Ivanovska, Kalina Alipieva, Petya Dimitrov, Robert Verpoorte (2013). "Harpagoside: from Kalahari Desert to pharmacy shelf". Phytochemistry 92: 8–15. doi:10.1016/j.phytochem.2013.04.009.
2. Tom Hsun-Wei Huang, Van H Tran, Rujee K Duke, Sharon Tan, Sigrun Chrubasik, b, Basil D Roufogalis, Colin C Duke (2006). "Harpagoside suppresses lipopolysaccharide-induced iNOS and COX-2 expression through inhibition of NF-κB activation". Journal of Ethnopharmacology 104 (1–2): 149–155. doi:10.1016/j.jep.2005.08.055.