Name | Yejunualactone |
Synonyms | HANDELIN handelin Yejuhualactone Yejunualactone YEJUHUALACTONE 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 Spiro[azuleno[4,5-b]furan-3(2H),10'-[4H-6a,9]ethanoazuleno[4,5-b]furan]-2,2'(3'H)-dione, 4-(acetyloxy)-3a,3'a,4,5,5',6,6',6a,7,9',9a,9'a,9b,9'b-tetradecahydro-6,6'-dihydroxy-6,6',9,9'-tetramethyl-3'-methylene-, (3R,3aR,3'aS,4S,6R,6'R,6aR,6'aR,9'R,9aR,9'aS,9bR,9'bS)- |
CAS | 62687-22-3 |
Molecular Formula | C32H40O8 |
Molar Mass | 552.66 |
Density | 1.34±0.1 g/cm3 (20 ºC 760 Torr) |
Melting Point | 212°C |
Boling Point | 731.0±60.0 °C(Predicted) |
Specific Rotation(α) | +47.8 (c, 1.3 in Py) |
Solubility | Almost insoluble (0.083g/L) (25°C) |
Appearance | White to off-white (Solid) |
pKa | 14.34±0.70(Predicted) |
Storage Condition | 2-8℃ |
MDL | MFCD11656142 |
Physical and Chemical Properties | White powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from wild chrysanthemum. |
Reference Show more | 1. [IF=6.762] Caiping Tian et al."Multiplexed Thiol Reactivity Profiling for Target Discovery of Electrophilic Natural Products."Cell Chem Biol. 2017 Nov;24:1416 2. [IF=3] Qu Lala et al."Phenotypic assessment and ligand screening of ETA/ETB receptors with label-free dynamic mass redistribution assay."N-S Arch Pharmacol. 2020 Jun;393(6):937-950 |
biological activity | Handelin is a guaiacol lactone dimer from Chrysanthemum boreale, it has powerful anti-inflammatory activity by down-regulating NF-κB signaling and the production of pro-inflammatory cytokines. |
Cell Line: | RAW 264.7 cells RAW 264.7 cells |
Concentration: | 10 μM, 20 μM, 40 μM 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. 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. Inhibited acute inflammation in carrageenan-induced paw. The serum level of IL-1β was also inhibited. |
Animal Model: | Male Sprague-Dawley (SD) rats (150-170 g, 5 weeks old) injected with carrageenan |
Dosage: | 10 mg/kg, 20 mg/kg |
Administration: | Oral administration; for 30 mintues |
Use | The Wild chrysanthemum lactone has the function of clearing away heat and toxic, detumescence and lowering blood pressure. for content determination/identification/pharmacological experiments. |