Handelin

• CAT Number: I017709
• CAS Number: 62687-22-3
• Molecular Formula: C32H40O8
• Molecular Weight: 552.66
• Purity: ≥95%
• Synonyms: [(1’R,2’R,3S,3aR,4S,5’S,6R,6aR,9’R,9aR,9bR,10’R,11’R)-2′,6-dihydroxy-2′,6,9,11′-tetramethyl-6′-methylidene-2,7′-dioxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-3,15′-8-oxatetracyclo[9.2.2.01,10.05,9]pentadec-12-ene]-4-yl] acetate
• InChI: InChI=1S/C32H40O8/c1-15-7-8-19-21(15)24-22(20(38-17(3)33)13-29(19,5)36)32(27(35)40-24)14-31-12-11-28(32,4)25(31)23-18(9-10-30(31,6)37)16(2)26(34)39-23/h7,11-12,18-25,36-37H,2,8-10,13-14H2,1,3-6H3/t18-,19+,20-,21-,22+,23+,24+,25+,28+,29+,30+,31-,32+/m0/s1
• InChIKey: SZQWAXGDCUONOB-RJRCOPBWSA-N
• SMILES: CC1=CCC2C1C3C(C(CC2(C)O)OC(=O)C)C4(CC56C=CC4(C5C7C(CCC6(C)O)C(=C)C(=O)O7)C)C(=O)O3

Handelin is a guaianolide dimer from Chrysanthemum boreale that has potent anti-inflammatory activity by down-regulating NF-κB signaling and pro-inflammatory cytokine production[1].
Handelin (Compound 1; 10-40 μM; RAW 264.7 cells) treatment suppresses the LPS-induced (1 μg/mL) overexpression of iNOS and COX-2 protein levels in a concentration-dependent manner. Handelin also suppresseS the induction of pro-inflammatory cytokines TNF-α and IL-1β in LPS-stimulated RAW 264.7 cells. Handelin also suppresses the activation of mitogen-activated protein kinases, including ERK and JNK signaling[1].
Handelin (Compound 1; 10-40 μM; RAW 264.7 cells) treatment significantly reduces the iNOS and COX-2 mRNA levels in LPS- stimulated RAW 264.7 cells. The transcriptional activity of NF-κB stimulated with LPS is also suppressed by Handelin. In addition, the LPS-stimulated upregulation of miRNA-155 expression is suppressed by Handelin[1].
Handelin (Compound 1; 10-20 mg/kg; oral administration; for 30 mintues; male Sprague-Dawley rats) treatment inhibits acute inflammation in carrageenan-induced paw edema model. The serum level of IL-1β is also inhibited by Handelin in a carrageenan-induced paw edema model [1].

Reference

[1]. Y Pyee, et al. Suppression of inflammatory responses by handelin, a guaianolide dimer from Chrysanthemum boreale, via downregulation of NF-κB signaling and pro-inflammatory cytokine production. J Nat Prod. 2014 Apr 25;77(4):917-24.
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