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(-)-Cubebin (CUB), isolated from seeds of Piper cubeba, was used as starting material to obtain the derivatives (-)-hinokinin (HK) and (-)-O-benzyl cubebin (OBZ). Using paw edema as the experimental model and different chemical mediators (prostaglandin and dextran), it was observed that both derivatives were active in comparison with both negative (5% Tween® 80 in saline) and positive (indomethacin) controls. The highest reduction in the prostaglandin-induced edema was achieved by OBZ (66.0%), while HK caused a 59.2% reduction. Nonetheless, the dextran-induced paw edema was not significantly reduced by either of the derivatives (HK or OBZ), which inhibited edema formation by 18.3% and 3.5%, respectively, in contrast with the positive control, cyproheptadine, which reduced the edema by 56.0%. The docking analysis showed that OBZ presented the most stable ligand-receptor (COX-2 - cyclooxygenase-2) interaction in comparison with CUB and HK.

Titel:	In vivo and in silico anti-inflammatory mechanism of action of the semisynthetic (-)-cubebin derivatives (-)-hinokinin and (-)-O-benzylcubebin.
Autor/in / Beteiligte Person:	Lima, TC ; Lucarini, R ; Volpe, AC ; de Andrade CQJ ; Souza, AMP ; Pauletti, PM ; Januário, AH ; Símaro, GV ; Bastos, JK ; Cunha, WR ; Borges, A ; da Silva Laurentiz R ; Conforti, VA ; Parreira, RLT ; Borges, CHG ; Caramori, GF ; Andriani, KF ; E Silva, MLA
Zeitschrift:	Bioorganic & medicinal chemistry letters, Jg. 27 (2017-01-15), Heft 2, S. 176-179
Veröffentlichung:	Oxford : Elsevier Science Ltd ; <i>Original Publication</i>: Oxford ; New York : Pergamon Press, c1991-, 2017
Medientyp:	academicJournal
ISSN:	1464-3405 (electronic)
DOI:	10.1016/j.bmcl.2016.11.081
Schlagwort:	4-Butyrolactone administration & dosage 4-Butyrolactone chemical synthesis 4-Butyrolactone chemistry 4-Butyrolactone pharmacology Animals Anti-Inflammatory Agents, Non-Steroidal administration & dosage Anti-Inflammatory Agents, Non-Steroidal chemical synthesis Anti-Inflammatory Agents, Non-Steroidal chemistry Benzodioxoles administration & dosage Benzodioxoles chemical synthesis Benzodioxoles chemistry Catalytic Domain Computer Simulation Cyclooxygenase 2 chemistry Cyclooxygenase 2 Inhibitors administration & dosage Cyclooxygenase 2 Inhibitors chemical synthesis Cyclooxygenase 2 Inhibitors chemistry Cyclooxygenase 2 Inhibitors pharmacology Cyproheptadine pharmacology Dextrans pharmacology Dinoprostone pharmacology Dioxoles administration & dosage Dioxoles chemical synthesis Dioxoles chemistry Edema chemically induced Furans administration & dosage Furans chemical synthesis Furans chemistry Indomethacin pharmacology Ligands Lignans administration & dosage Lignans chemical synthesis Lignans chemistry Lignans isolation & purification Male Mice Molecular Docking Simulation Polysorbates pharmacology Rats, Wistar Rutaceae chemistry 4-Butyrolactone analogs & derivatives Anti-Inflammatory Agents, Non-Steroidal pharmacology Benzodioxoles pharmacology Dioxoles pharmacology Furans pharmacology Lignans pharmacology
Sonstiges:	Nachgewiesen in: MEDLINE Sprachen: English Publication Type: Journal Article; Research Support, Non-U.S. Gov't Language: English [Bioorg Med Chem Lett] 2017 Jan 15; Vol. 27 (2), pp. 176-179. <i>Date of Electronic Publication: </i>2016 Nov 29. MeSH Terms: 4-Butyrolactone / analogs & derivatives ; Anti-Inflammatory Agents, Non-Steroidal / pharmacology ; Benzodioxoles / pharmacology ; Dioxoles / pharmacology ; Furans / pharmacology ; Lignans / pharmacology ; 4-Butyrolactone / administration & dosage ; 4-Butyrolactone / chemical synthesis ; 4-Butyrolactone / chemistry ; 4-Butyrolactone / pharmacology ; Animals ; Anti-Inflammatory Agents, Non-Steroidal / administration & dosage ; Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis ; Anti-Inflammatory Agents, Non-Steroidal / chemistry ; Benzodioxoles / administration & dosage ; Benzodioxoles / chemical synthesis ; Benzodioxoles / chemistry ; Catalytic Domain ; Computer Simulation ; Cyclooxygenase 2 / chemistry ; Cyclooxygenase 2 Inhibitors / administration & dosage ; Cyclooxygenase 2 Inhibitors / chemical synthesis ; Cyclooxygenase 2 Inhibitors / chemistry ; Cyclooxygenase 2 Inhibitors / pharmacology ; Cyproheptadine / pharmacology ; Dextrans / pharmacology ; Dinoprostone / pharmacology ; Dioxoles / administration & dosage ; Dioxoles / chemical synthesis ; Dioxoles / chemistry ; Edema / chemically induced ; Furans / administration & dosage ; Furans / chemical synthesis ; Furans / chemistry ; Indomethacin / pharmacology ; Ligands ; Lignans / administration & dosage ; Lignans / chemical synthesis ; Lignans / chemistry ; Lignans / isolation & purification ; Male ; Mice ; Molecular Docking Simulation ; Polysorbates / pharmacology ; Rats, Wistar ; Rutaceae / chemistry Contributed Indexing: Keywords: (−)-Cubebin; (−)-Hinokinin; (−)-O-benzylcubebin; Anti-inflammatory activity; Piper cubeba Substance Nomenclature: 0 (Anti-Inflammatory Agents, Non-Steroidal) ; 0 (Benzodioxoles) ; 0 (Cyclooxygenase 2 Inhibitors) ; 0 (Dextrans) ; 0 (Dioxoles) ; 0 (Furans) ; 0 (Ligands) ; 0 (Lignans) ; 0 (Polysorbates) ; 0 (o-benzyl cubebin) ; 26543-89-5 (hinokinin) ; 2YHB6175DO (Cyproheptadine) ; EC 1.14.99.- (Ptgs2 protein, mouse) ; EC 1.14.99.1 (Cyclooxygenase 2) ; J237078S8A (cubebin) ; K7Q1JQR04M (Dinoprostone) ; OL659KIY4X (4-Butyrolactone) ; XXE1CET956 (Indomethacin) Entry Date(s): Date Created: 20161214 Date Completed: 20171002 Latest Revision: 20171231 Update Code: 20231215

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In vivo and in silico anti-inflammatory mechanism of action of the semisynthetic (-)-cubebin derivatives (-)-hinokinin and (-)-O-benzylcubebin.