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62687-22-3

62687-22-3 structure
62687-22-3 structure
  • Name: handelin
  • Chemical Name: 6,6'-dihydroxy-6,6',9,9'-tetramethyl-3'-methylene-2,2'-dioxo-2',3a,3',3a',4,5,5',6,6a,6',7,9a,9b,9',9a',9b'-hexadecahydro-4'H-spiro[azuleno[4,5-b]furan-3,10'-[6a,9]ethanoazuleno[4,5-b]furan]-5-yl acetate
  • CAS Number: 62687-22-3
  • Molecular Formula: C32H40O8
  • Molecular Weight: 552.655
  • Catalog: Biochemical Plant extracts
  • Create Date: 2018-08-29 09:51:35
  • Modify Date: 2025-08-21 18:14:27
  • 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].
Name 6,6'-dihydroxy-6,6',9,9'-tetramethyl-3'-methylene-2,2'-dioxo-2',3a,3',3a',4,5,5',6,6a,6',7,9a,9b,9',9a',9b'-hexadecahydro-4'H-spiro[azuleno[4,5-b]furan-3,10'-[6a,9]ethanoazuleno[4,5-b]furan]-5-yl acetate
Synonyms (2'R,5R,6S,9'S,9bS)-2',6-Dihydroxy-2',6,9,11'-tetramethyl-6'-methylene-2,7'-dioxo-3a,4,5,6,6a,7,9a,9b-octahydrospiro[azuleno[4,5-b]furan-3,12'-[8]oxatetracyclo[9.2.2.0.0]pentadec[14]en]-5-y l acetate
(1'R,2'R,3R,3aR,4S,5'S,6R,6aR,9'S,9aR,9bR,10'S)-2',6-Dihydroxy-2',6,9,11'-tetramethyl-6'-methylene-2,7'-dioxo-3a,4,5,6,6a,7,9a,9b-octahydrospiro[azuleno[4,5-b]furan-3,12'-[8]oxatetracyclo[9.2.2.0.0]pentadec[14]en]-4-yl acetate
(2'R,5R,6S,9'S,9bS)-2',6-Dihydroxy-2',6,9,11'-tetramethyl-6'-methylene-2,7'-dioxo-3a,4,5,6,6a,7,9a,9b-octahydrospiro[azuleno[4,5-b]furan-3,12'-[8]oxatetracyclo[9.2.2.0.0]pentadec[14]en]-5-yl acetate
Description 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].
Related Catalog
In Vitro 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]. RT-PCR[1] Cell Line: RAW 264.7 cells Concentration: 10 μM, 20 μM, 40 μM Incubation Time: 5 hours Result: iNOS and COX-2 mRNA levels were significantly reduced. The transcriptional activity of NF-κB stimulated with LPS was also suppressed and the LPS-stimulated upregulation of miRNA-155 expression was also suppressed. Western Blot Analysis[1] Cell Line: RAW 264.7 cells Concentration: 10 μM, 20 μM, 40 μM Incubation Time: Result: Suppressed the LPS-induced overexpression of iNOS and COX-2 protein levels in a concentration-dependent manner. Suppressed the induction of pro-inflammatory cytokines TNF-α and IL-1β, and also also suppressed the activation of mitogen-activated protein kinases, including ERK and JNK signaling in LPS-stimulated RAW 264.7 cells.
In Vivo 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]. Animal Model: Male Sprague-Dawley (SD) rats (150-170 g, 5 weeks old) injected with carrageenan[1] Dosage: 10 mg/kg, 20 mg/kg Administration: Oral administration; for 30 mintues Result: Inhibited acute inflammation in carrageenan-induced paw. The serum level of IL-1β was also inhibited.
References

[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.
Density 1.3±0.1 g/cm3
Boiling Point 731.0±60.0 °C at 760 mmHg
Molecular Formula C32H40O8
Molecular Weight 552.655
Flash Point 236.3±26.4 °C
Exact Mass 552.272339
PSA 119.36000
LogP 2.36
Vapour Pressure 0.0±5.4 mmHg at 25°C
Index of Refraction 1.615
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