Structural revision of clusianone and 7-epi-clusianone and anti-HIV activity of polyisoprenylated benzophenones |
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Authors: | Anna Lisa Piccinelli Mariano Barrios Chica Bruno Pagano Vincenzo Barone |
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Institution: | a Dipartimento di Scienze Farmaceutiche, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano, Salerno, Italy b Institute for Pharmacy and Food (IFAL), University of Havana, Ave. 23, 21425 Lisa, C. Habana, Cuba c Escuela de Quimica de la Universidad Nacional de Costa Rica, San Josè, Costa Rica, USA d Department of Cellular and Molecular Medicine, Infectious Diseases. St George'S Hospital Medical School, Cranmer Terrace, Tooting, SW17 0RE London, UK e Dipartimento di Chimica, Università Federico II, Complesso Universitario Monte Sant'Angelo, Via Cintia, I-80126 Napoli, Italy |
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Abstract: | For the first time, the tautomeric pairs of clusianone and 7-epi-clusianone were isolated from the same source, Clusia torresii fruits. An extensive NMR spectroscopic study is described to establish 1H and 13C chemical shift assignments and the C-7 relative configuration of these epimers and to clarify contradictory NMR spectroscopic data previously reported. Quantum mechanical computations than pointed out the relationship between indirect coupling constants and the equilibrium between the B-ring chair and twist-boat forms of the bicyclo-3.3.1.]-nonane system. Clusianone, 7-epi-clusianone and polyisoprenylated benzophenones 18,19-dihydroxyclusianone, propolone A and nemorosone were screened for their activity against HIV infection in C8166 cells. All compounds inhibited infection with selectivity index values ranging from 2.25 to 15.6. Only clusianone derivatives inhibited infection by binding to viral protein gp120 and prevented its interaction with cellular receptor CD4 as detected by ELISA using recombinant proteins. |
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Keywords: | Clusia torresii Clusianone and 7-epi-clusianone NMR Quantum mechanical calculations Anti-HIV |
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