WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 600140
Description: Harpagoside is an anti-inflammatory small molecule natural product originally isolated from the Harpagophytum procumbens (DevilÂ’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. (Source: http://www.scbt.com/datasheet-203073-harpagoside.html)
MedKoo Cat#: 600140
Chemical Formula: C24H30O11
Exact Mass: 494.17881
Molecular Weight: 494.49
Elemental Analysis: C, 58.29; H, 6.12; O, 35.59
Synonym: SMR001233395; Eharpagoside; AC1NQYLY; Prestwick3000988
IUPAC/Chemical Name: [(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
InChi Key: KVRQGMOSZKPBNS-FMHLWDFHSA-N
InChi Code: 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
SMILES Code: O=C(O[C@@]1(C)C[C@@H](O)[C@@]2(O)[C@]1([H])[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C2)/C=C/C4=CC=CC=C4
1: Cheng J, Di LQ, Shan JJ, Zhao XL, Kang A, Bi XL, Li JS. [Studies on effects of Achyranthes bidentata on tongsaimai pellets main active ingredients chlorogenic acid, isoliquiritin, harpagoside and glycyrrhizin in vivo pharmacokinetics]. Zhongguo Zhong Yao Za Zhi. 2014 Apr;39(8):1502-8. Chinese. PubMed PMID: 25039191.