| Identification | Back Directory | [Name]
LUFFARIELLOLIDE | [CAS]
111149-87-2 | [Synonyms]
LUFFARIELLOLIDE
4-[(3E,7E)-4,8-Dimethyl-10-(2,6,6-trimethyl-1-cyclohexenyl)-3,7-decadienyl]-5-hydroxyfuran-2(5H)-one
3-[(3E,7E)-4,8-dimethyl-10-(2,6,6-trimethylcyclohexen-1-yl)deca-3,7-dienyl]-2-hydroxy-2H-furan-5-one
4-[(3E,7E)-4,8-Dimethyl-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,7-decadienyl]-5-hydroxy-2(5H)-furanone
2(5H)-Furanone, 4-[(3E,7E)-4,8-dimethyl-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,7-decadien-1-yl]-5-hydroxy- | [Molecular Formula]
C25H38O3 | [MDL Number]
MFCD00211056 | [MOL File]
111149-87-2.mol | [Molecular Weight]
386.57 |
| Chemical Properties | Back Directory | [Boiling point ]
541.7±50.0 °C(Predicted) | [density ]
1.006±0.06 g/cm3(Predicted) | [solubility ]
DMSO: soluble; Ethanol: soluble | [form ]
Pale yellow oil. | [pka]
9.98±0.40(Predicted) | [InChI]
InChI=1S/C25H38O3/c1-18(11-7-13-21-17-23(26)28-24(21)27)9-6-10-19(2)14-15-22-20(3)12-8-16-25(22,4)5/h10-11,17,24,27H,6-9,12-16H2,1-5H3/b18-11+,19-10+ | [InChIKey]
JPWPYTMXSXYUPG-QZPYEDBESA-N | [SMILES]
O1C(O)C(CC/C=C(\C)/CC/C=C(\C)/CCC2C(C)(C)CCCC=2C)=CC1=O |
| Hazard Information | Back Directory | [Uses]
Luffariellolide is a natural sesterterpenoid which reversibly inhibits secretory phospholipase A2 isoforms from bee venom (IC50 = 230 nM) and snake venom, reducing inflammation. It blocks the production of platelet-activating factor in stimulated neutrophils (IC50 = 5 μM). Luffariellolide is also a structural mimic of all-trans retinoic acid (RA) and, at 1 μM, acts as an agonist for the RA receptors RAR α, β, and γ but not for other nuclear receptors. In RA-sensitive cancer cell lines, luffariellolide induces the expression of RAR target genes and inhibits cell growth. It also inhibits the activation of hypoxia-inducible factor by hypoxia (IC50 = 3.6 μM).[Cayman Chemical] | [Uses]
Luffariellolide is an anti-inflammatory PLA2?inhibitor. | [Definition]
ChEBI:Luffariellolide is a diterpene lactone. |
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